Updated on 2022/11/02

写真a

 
OKAMOTO Hideki
 
Organization
Faculty of Natural Science and Technology Associate Professor
Position
Associate Professor
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Degree

  • Dr.Science ( Okayama University )

Research Interests

  • Organic photochemistry

  • Functional chemistry

  • Chemiluninecence

  • 発光センサー

  • 機能化学

  • 化学発光

  • 有機光化学

  • Luminescent sensor

Research Areas

  • Nanotechnology/Materials / Functional solid state chemistry

  • Life Science / Bioorganic chemistry

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

Research History

  • Okayama University   The Graduate School of Natural Science and Technology   Associate Professor   Associate professor

    2009

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    Country:Japan

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  • Kyushu University   Institute for Materials Chemistry and Engineering

    2008.10 - 2010.3

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  • Okayama University   The Graduate School of Natural Science and Technology   Assistant Professor

    2007.4 - 2009.4

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    Country:Japan

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  • Wuerzburg University   在外研究員

    1999.10 - 2000.9

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    Country:Germany

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  • Okayama University   Faculty of Science   Research Assistant

    1988.4 - 2007.3

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    Country:Japan

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Professional Memberships

Committee Memberships

  • 日本化学会   代表正会員  

    2009 - 2014   

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    Committee type:Academic society

    日本化学会

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Papers

  • Photochemical synthesis and device application of acene–phenacene hybrid molecules, dibenzo[n]phenacenes (n = 5–7) Reviewed

    Yanting Zhang, Ritsuko Eguchi, Shino Hamao, Kenta Goto, Fumito Tani, Minoru Yamaji, Yoshihiro Kubozono, Hideki Okamoto

    Chemical Communications   57 ( 39 )   4768 - 4771   2021

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>Dibenzo[<italic>n</italic>]phenacenes (<bold>DBnP</bold>, <italic>n</italic> = 5–7) were applied to the active layers of p-channel FETs and their effective mobilities were evaluated to demonstrate that <italic>C</italic>2h-symmetrical <bold>DB6P</bold> showed superior performance to the <italic>C</italic>2v-symmetrical homologues.</p>

    DOI: 10.1039/d1cc01294k

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  • Synthesis of [7]phenacene incorporating tetradecyl chains in the axis positions and its application in field-effect transistors Reviewed International coauthorship International journal

    Hideki Okamoto, Shino Hamao, Keiko Kozasa, Yanan Wang, Yoshihiro Kubozono, Yong-He Pan, Yu-Hsiang Yen, Germar Hoffmann, Fumito Tani, Kenta Goto

    Journal of Materials Chemistry C   8 ( 22 )   7422 - 7435   2020

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>Ditetradecyl-substituted [7]phenacene was prepared and applied in thin-film FET devices, displaying higher mobility compared to parent [7]phenacene.</p>

    DOI: 10.1039/d0tc00272k

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  • Synthesis of the extended phenacene molecules, [10]phenacene and [11]phenacene, and their performance in a field-effect transistor Reviewed International coauthorship International journal

    Hideki Okamoto, Shino Hamao, Ritsuko Eguchi, Hidenori Goto, Yasuhiro Takabayashi, Paul Yu-Hsiang Yen, Luo Uei Liang, Chia-Wei Chou, Germar Hoffmann, Shin Gohda, Hisako Sugino, Yen-Fa Liao, Hirofumi Ishii, Yoshihiro Kubozono

    Scientific Reports   9 ( 1 )   4009 - 4009   2019.12

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Springer Science and Business Media LLC  

    DOI: 10.1038/s41598-019-39899-4

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    Other Link: http://www.nature.com/articles/s41598-019-39899-4

  • Solvent-induced multicolour fluorescence of amino-substituted 2,3-naphthalimides studied by fluorescence and transient absorption measurements Reviewed

    Mayu Fujii, Misa Namba, Minoru Yamaji, Hideki Okamoto

    PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES   15 ( 7 )   842 - 850   2016

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

    A series of amino-2,3-naphthalimide derivatives having the amino functionality at 1-, 5-and 6-positions (1ANI, 5ANI and 6ANI, respectively) were prepared, and their photophysical properties were systematically investigated based on the measurements of steady-state absorption and fluorescence spectra, fluorescence lifetimes as well as transient absorption spectra. The ANIs efficiently fluoresced in solution, and the emission spectra appreciably shifted depending on the solvent polarity. 1ANI displayed only a slight fluorescence red-shift upon increasing the solvent polarity. In contrast, 5ANI and 6ANI showed marked positive solvatofluorochromism with large Stokes shifts displaying multicolour fluorescence; the fluorescence colours of 5ANI and 6ANI varied from violet-blue in hexane to orange-red in methanol. 5ANI and 6ANI, thus, serve as micro-environment responding fluorophores. In methanol, the intensity of the fluorescence emission band of 5ANI and 6ANI significantly reduced. Based on the fluorescence quantum yields and lifetimes, and transient absorption measurements, it has been revealed that internal conversion from the S-1 state of ANIs to the ground state was accelerated by the protic medium, resulting in a reduction in their fluorescence efficiency, while intersystem crossing from the S1 state to a triplet state was not responsible for the decrease of fluorescence intensity.

    DOI: 10.1039/c6pp00048g

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  • Efficient Synthetic Photocyclization for Phenacenes Using a Continuous Flow Reactor Reviewed

    Hideki Okamoto, Takamitsu Takane, Shin Gohda, Yoshihiro Kubozono, Kaori Sato, Minoru Yamaji, Kyosuke Satake

    CHEMISTRY LETTERS   43 ( 7 )   994 - 996   2014.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:CHEMICAL SOC JAPAN  

    The continuous flow reaction technique has been applied to the photocyclization of 1,2-diarylethenes, the so-called Mallory reaction, to afford phenacenes in high chemical yields and efficiencies (114-288 mg h(-1)). The present technique will allow us to produce several grams of phenacenes at a time.

    DOI: 10.1246/cl.140182

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  • An Extended Phenacene-type Molecule, [8] Phenacene: Synthesis and Transistor Application Reviewed

    Hideki Okamoto, Ritsuko Eguchi, Shino Hamao, Hidenori Goto, Kazuma Gotoh, Yusuke Sakai, Masanari Izumi, Yutaka Takaguchi, Shin Gohda, Yoshihiro Kubozono

    SCIENTIFIC REPORTS   4   5330-1-5330-8   2014.6

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:NATURE PUBLISHING GROUP  

    A new phenacene-type molecule, [8] phenacene, which is an extended zigzag chain of coplanar fused benzene rings, has been synthesised for use in an organic field-effect transistor (FET). The molecule consists of a phenacene core of eight benzene rings, which has a lengthy pi-conjugated system. The structure was verified by elemental analysis, solid-state NMR, X-ray diffraction (XRD) pattern, absorption spectrum and photoelectron yield spectroscopy (PYS). This type of molecule is quite interesting, not only as pure chemistry but also for its potential electronics applications. Here we report the physical properties of [8] phenacene and its FET application. An [8] phenacene thin-film FET fabricated with an SiO2 gate dielectric showed clear p-channel characteristics. The highest m achieved in an [8] phenacene thin-film FET with an SiO2 gate dielectric is 1.74 cm(2) V-1 s(-1), demonstrating excellent FET characteristics; the average mu was evaluated as 1.2(3) cm(2) V-1 s(-1). The mu value in the [8] phenacene electric-double-layer FET reached 16.4 cm(2) V-1 s(-1), which is the highest reported in EDL FETs based on phenacene-type molecules; the average m was evaluated as 8(5) cm(2) V-1 s(-1). The mu values recorded in this study show that [8] phenacene is a promising molecule for transistor applications.

    DOI: 10.1038/srep05330

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  • Transistor application of alkyl-substituted picene Reviewed

    Hideki Okamoto, Shino Hamao, Hidenori Goto, Yusuke Sakai, Masanari Izumi, Shin Gohda, Yoshihiro Kubozono, Ritsuko Eguchi

    SCIENTIFIC REPORTS   4   5408-1-5408-6   2014.5

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:NATURE PUBLISHING GROUP  

    Field-effect transistors (FETs) were fabricated with a thin film of 3,10-ditetradecylpicene, picene-(C14H29)(2), formed using either a thermal deposition or a deposition from solution (solution process). All FETs showed p-channel normally-off characteristics. The field-effect mobility, m, in a picene-(C14H29)(2) thin-film FET with PbZr0.52Ti0.48O3 (PZT) gate dielectric reached similar to 21 cm(2) V-1 s(-1), which is the highest mu value recorded for organic thin-film FETs; the averagem mu value (&lt;mu &gt;) evaluated from twelve FET devices was 14(4) cm(2)V(-1) s(-1). The, m. values for picene-(C14H29)(2) thin- film FETs with other gate dielectrics such as SiO2, Ta2O5, ZrO2 and HfO2 were greater than 5 cm(2) V-1 s(-1), and the lowest absolute threshold voltage, vertical bar V-th vertical bar, (5.2 V) was recorded with a PZT gate dielectric; the average jVthj for PZT gate dielectric is 7(1) V. The solution-processed picene-(C14H29)(2) FET was also fabricated with an SiO2 gate dielectric, yielding mu = 3.4 x 10(-2) cm(2) V-1 s(-1). These results verify the effectiveness of picene-(C14H29)(2) for electronics applications.

    DOI: 10.1038/srep05048

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  • S-2 fluorescence from picene vapor Reviewed

    Takao Itoh, Minoru Yamaji, Hideki Okamoto

    CHEMICAL PHYSICS LETTERS   570   26 - 28   2013.5

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:ELSEVIER SCIENCE BV  

    Fluorescence, fluorescence excitation and absorption spectra of picene have been measured in the vapor phase. It is shown that picene vapor exhibits weak fluorescence from the S-2(pi, pi*) state in addition to strong S-1(pi, pi*) fluorescence. The S-2/S-1 fluorescence yield ratio is evaluated to be approximately 1.3 x 10(-2) following the excitation into the S-3 state. It is shown that the relative S-2 fluorescence quantum yield increases with increasing excitation energy, while the S-1 fluorescence yield is nearly invariant. Mechanism of the appearance of the S-2 fluorescence of picene vapor is discussed. (c) 2013 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.cplett.2013.03.055

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  • Photochemical synthesis and electronic spectra of fulminene ([6]phenacene) Reviewed

    Hideki Okamoto, Minoru Yamaji, Shin Gohda, Kaori Sato, Hisako Sugino, Kyosuke Satake

    RESEARCH ON CHEMICAL INTERMEDIATES   39 ( 1 )   147 - 159   2013.1

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    Authorship:Lead author, Corresponding author   Language:English   Publisher:SPRINGER  

    Facile synthesis of fulminene ([6]phenacene) was achieved through the Mallory reaction of 1-(1-naphthyl)-2-(1-phenanthryl)ethene or the 9-fluorenone-sensitized photo-ring-closure of 1-(1-naphthyl)-2-(1-phenanthryl)ethane. The electronic spectral properties of fulminene were investigated for the first time using photoluminescence as well as transient absorption spectroscopy. The spectral features were compared with those of a series of lower phenacene homologs such as phenanthrene ([3]phenacene), chrysene ([4]phenacene), and picene ([5]phenacene). For the [n]phenacene series, both the fluorescence and phosphorescence bands linearly red-shifted with an increase in the number of the benzene rings (n). Trends in the energy levels of the excited singlet (E (S)) and the triplet (E (T)) states were expressed as E (s) = -2.6n + 89.1 (kcal mol(-1)) and E (T) = -1.8n + 66.2 (kcal mol(-1)), respectively. In the case of fulminene, laser flash photolysis displayed a transient spectrum with an absorption maximum (lambda (max) (T-T) ) at 675 nm, which was assigned as the triplet fulminene excited state. The lambda (max) (T-T) values for the [n]phenacene series showed a linear correlation as a function of the ring number n, given by an equation, lambda (max) (T-T) = 60n + 318 (nm).

    DOI: 10.1007/s11164-012-0639-1

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  • Fabrication of high performance/highly functional field-effect transistor devices based on [6]phenacene thin films Reviewed

    Ritsuko Eguchi, Xuexia He, Shino Hamao, Hidenori Goto, Hideki Okamoto, Shin Gohda, Kaori Sato, Yoshihiro Kubozono

    PHYSICAL CHEMISTRY CHEMICAL PHYSICS   15 ( 47 )   20611 - 20617   2013

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

    Field-effect transistors (FETs) based on [6]phenacene thin films were fabricated with SiO2 and parylene gate dielectrics. These FET devices exhibit field-effect mobility in the saturation regime as high as 7.4 cm(2) V-1 s(-1), which is one of the highest reported values for organic thin-film FETs. The two- and four-probe mobilities in the linear regime display nearly similar values, suggesting negligible contact resistance at 300 K. FET characteristics were investigated using two-probe and four-probe measurement modes at 50-300 K. The two-probe mobility of the saturation regime can be explained by the multiple shallow trap and release model, while the intrinsic mobility obtained by the four-probe measurement in the linear regime is better explained by the phenomenon of transport with charge carrier scattering at low temperatures. The FET device fabricated with a parylene gate dielectric on polyethylene terephthalate possesses both transparency and flexibility, implying feasibility of practical application of [6] phenacene FETs in flexible/transparent electronics. N-channel FET characteristics were also achieved in the [6] phenacene thin-film FETs using metals that possess a small work function for use as source/drain electrodes.

    DOI: 10.1039/c3cp53598c

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  • Facile Synthesis of Picene from 1,2-Di(1-naphthyl)ethane by 9-Fluorenone-Sensitized Photolysis Reviewed

    Hideki Okamoto, Minoru Yamaji, Shin Gohda, Yoshihiro Kubozono, Noriko Komura, Kaori Sato, Hisako Sugino, Kyosuke Satake

    ORGANIC LETTERS   13 ( 10 )   2758 - 2761   2011.5

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    A facile formation of picene was achieved by photosensitization of 1,2-di(1-naphthyl)ethane using 9-fluorenone as a sensitizer. This sensitized photoreaction is the first photochemical cyclization of ethylene-bridged naphthalene moieties to afford the picene skeleton. 5,8-Dibromopicene, prepared by this procedure using 1,2-di[1-(4-bromonaphthyl)]ethane as the substrate, was readily converted to novel functionalized picenes by conventional substitution and cross-coupling reactions.

    DOI: 10.1021/ol200874q

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  • Superconductivity in alkali-metal-doped picene Reviewed

    Ryoji Mitsuhashi, Yuta Suzuki, Yusuke Yamanari, Hiroki Mitamura, Takashi Kambe, Naoshi Ikeda, Hideki Okamoto, Akihiko Fujiwara, Minoru Yamaji, Naoko Kawasaki, Yutaka Maniwa, Yoshihiro Kubozono

    NATURE   464 ( 7285 )   76 - 79   2010.3

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    Efforts to identify and develop new superconducting materials continue apace, motivated by both fundamental science and the prospects for application. For example, several new superconducting material systems have been developed in the recent past, including calcium-intercalated graphite compounds(1), boron-doped diamond(2) and-most prominently-iron arsenides such as LaO(1-x)F(x)FeAs (ref. 3). In the case of organic superconductors, however, no new material system with a high superconducting transition temperature (T(c)) has been discovered in the past decade. Here we report that intercalating an alkali metal into picene, a wide-bandgap semiconducting solid hydrocarbon, produces metallic behaviour and superconductivity. Solid potassium-intercalated picene (K(x)picene) shows T(c) values of 7K and 18 K, depending on the metal content. The drop of magnetization in Kxpicene solids at the transition temperature is sharp (&lt;2 K), similar to the behaviour of Ca-intercalated graphite(1). The Tc of 18K is comparable to that of K-intercalated C(60) (ref. 4). This discovery of superconductivity in K(x)picene shows that organic hydrocarbons are promising candidates for improved T(c) values.

    DOI: 10.1038/nature08859

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  • Air-assisted high-performance field-effect transistor with thin films of picene Reviewed

    Hideki Okamoto, Naoko Kawasaki, Yumiko Kaji, Yoshihiro Kubozono, Akihiko Fujiwara, Minoru Yamaji

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   130 ( 32 )   10470 - +   2008.8

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    A field-effect transistor (FET) with thin films of picene has been fabricated on SiO(2) gate dielectric. The FET showed p-channel enhancement-type FET characteristics with the field-effect mobility, mu, of 1.1 cm(2) V(-1) s(-1) and the on-off ratio of &gt;10(5). This excellent device performance was realized under atmospheric conditions. The p increased with an increase in temperature, and the FET performance was improved by exposure to air or O(2) for a long time. This result implies that this device is an air (O(2))-assisted FET. The FET characteristics are discussed on the basis of structural topography and the energy diagram of picene thin films.

    DOI: 10.1021/ja803291a

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  • Fluorescence response of a 4-trifluoroacetylaminophthalimide to iodide ions upon 254 nm irradiation in MeCN Reviewed

    Hideki Okamoto, Hiroyuki Konishi, Mami Kohno, Kyosuke Satake

    ORGANIC LETTERS   10 ( 14 )   3125 - 3128   2008.7

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    The title trifluoroacetylaminophthalimide derivative produced a violet fluorescence (lambda(FL)(max) 392 nm) in MeCN, and it displayed a green emission (lambda(FL)(max) 506 nm) after irradiation at 254 nm in the presence of iodide ions. The corresponding amidate ion of the trifluoroacetamide was identified as the green fluorescence emitter. The deprotonation reaction may be caused by proton-abstracting solvated electrons generated by a photochemical charge-transfer-to-solvent process from I(-) to MeCN.

    DOI: 10.1021/ol801184x

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  • Photoreaction of a 2,11-diaza[3.3]paracyclophane derivative: Formation of octahedrane by photochemical dimerization of benzene Reviewed

    Hideki Okamoto, Kyosuke Satake, Hiroyuki Ishida, Masaru Kimura

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   128 ( 51 )   16508 - 16509   2006.12

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    DOI: 10.1021/ja067350r

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  • Triplet-sensitized photolysis of the photoisomer of a 2,11-diaza[3,3](9,10)anthracenoparacyclophane: An adiabatic cycloreversion and a [2 pi a+2 pi a+2 sigma s] rearrangement in a triplet state of the biplanophane system Reviewed

    H Okamoto, M Yamaji, K Satake, S Tobita, M Kimura

    JOURNAL OF ORGANIC CHEMISTRY   69 ( 23 )   7860 - 7868   2004.11

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

    The triplet-sensitized photoreactions of the title biplanophane system 6, the photoisomer of a 2,11diaza[3,31(9,10)anthracenoparacyclophane derivative 5, were investigated by stationary and laserflash photolyses using xanthone (XT) and benzophenone (BP) as triplet sensitizers. Vaen photoisomer 6 underwent XT-sensitized irradiation, a triplet cyclophane 5 and a novel polycyclic product 7 were obtained via an adiabatic cycloreversion and a formal [2pia + 2 pia + 2sigmas] rearrangement, respectively. The maximum quantum yield for the formation of cyclophane 5 (0.69) and the upper-limit efficiency for the formation of polycycle 7 (0.31) were determined by laser photolysis techniques. For BP-sensitized photolysis of photoisomer 6, oxetane 8, in addition to triplet cyclophane 5 and polycycle 7, was formed by a Paterno-Biichi reaction. The quenching rate constant (k(q)) of triplet BP by photoisomer 6 (3.4 x 10(8) dm(3) Mol(-1) s(-1)) was found to be 1 order of magnitude smaller than that for XT (5.0 x 10(9) dm(3) mol(-1) s(-1)). On the basis of the relationship between k(q) and the triplet donor-acceptor energy gap, the triplet energy level of photoisomer 6 was estimated to be similar to71 kcal mol(-1). The photochemical and the photophysical processes involved in the sensitized photolyses are summarized in an energetic reaction diagram and discussed in detail.

    DOI: 10.1021/jo048757m

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  • Evaluation of Effective Field-Effect Mobility in Thin-Film and Single-Crystal Transistors for Revisiting Various Phenacene-Type Molecules

    Yanting Zhang, Ritsuko Eguchi, Shino Hamao, Hideki Okamoto, Hidenori Goto, Yoshihiro Kubozono

    ACS OMEGA   7 ( 6 )   2022.2

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    The magnitude of the field-effect mobility mu of organic thin-film and single-crystal field-effect transistors (FETs) has been over-estimated in certain recent studies. These reports set alarm bells ringing in the research field of organic electronics. Herein, we report a precise evaluation of the mu values using the effective field-effect mobility, mu(eff), a new indicator that is recently designed to prevent the FET performance of thin-film and single-crystal FETs based on various phenacene molecules from being overestimated. The transfer curves of a range of FETs based on phenacene are carefully categorized on the basis of a previous report. The exact evaluation of the value of mu(eff) depends on the exact classification of each transfer curve. The transfer curves of all our phenacene FETs could be successfully classified based on the method indicated in the aforementioned report, which made it possible to evaluate the exact value of mu(eff) for each FET. The FET performance based on the values of mu(eff) obtained in this study is discussed in detail. In particular, the mu(eff) values of single-crystal FETs are almost consistent with the mu values that were reported previously, but the mu(eff) values of thin-film FETs were much lower than those previously reported for mu, owing to a high absolute threshold voltage, vertical bar V-th vertical bar. The increase in the field-effect mobility as a function of the number of benzene rings, which was previously demonstrated based on the mu values of single-crystal FETs with phenacene molecules, is well reproduced from the mu(eff) values. The FET performance is discussed based on the newly evaluated mu(eff) values, and the future prospects of using phenacene molecules in FET devices are demonstrated.

    DOI: 10.1021/acsomega.1c06932

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  • Solid-state photoluminescence of biaryls: Relationship between photophysical feature and crystal structure Reviewed International journal

    Minoru Yamaji, Hideki Okamoto, Kenta Goto, Fumito Tani

    Journal of Photochemistry and Photobiology A: Chemistry   421   113518 - 113518   2021.12

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    DOI: 10.1016/j.jphotochem.2021.113518

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  • Fabrication of ring oscillators using organic molecules of phenacene and perylenedicarboximide Reviewed International coauthorship International journal

    Niko Fioravanti, Luca Pierantoni, Davide Mencarelli, Claudio Turchetti, Shino Hamao, Hideki Okamoto, Hidenori Goto, Ritsuko Eguchi, Akihiko Fujiwara, Yoshihiro Kubozono

    RSC Advances   11 ( 13 )   7538 - 7551   2021

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>A ring oscillator consisting of p-channel and n-channel organic FETs.</p>

    DOI: 10.1039/d1ra00511a

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  • Synthesis and photophysical properties of blue-color emitting compounds having multi N-methylanthranillic (MANT) chromophore Reviewed International journal

    Minoru Yamaji, Kanae Sano, Hideki Okamoto, Ichiro Matsuo

    Journal of Photochemistry and Photobiology A: Chemistry   400   112650 - 112650   2020.9

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    © 2020 Elsevier B.V. We prepared various compounds having the N-methylaminoanthranyl (MANT) moiety tethered with oligomethylene chains, and investigated the photophysical features in solution and the solid state based on the fluorescence quantum yields and lifetimes, and quantum chemical calculation. The molar absorption coefficient and fluorescence quantum yield were enhanced by an increase of the number of the MANT chromophore, resulting in an increase of the brightness as emission probes. Solid-state blue emission at room temperature was observed with moderate fluorescence quantum yields. The fluorescence rates in the solid state were found to be similar those in solution. From the results of the transient absorption measurements, the photophysical deactivation pathways in the solution were discussed. The studied multi-MANT compounds could be applicable to emissive photonic crystals and an exciton generating source for blue-color OLED.

    DOI: 10.1016/j.jphotochem.2020.112650

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  • Facile synthesis of picenes incorporating imide moieties at both edges of the molecule and their application to n-channel field-effect transistors Reviewed International journal

    Yuxin Guo, Kaito Yoshioka, Shino Hamao, Yoshihiro Kubozono, Fumito Tani, Kenta Goto, Hideki Okamoto

    RSC Advances   10 ( 52 )   31547 - 31552   2020

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry (RSC)  

    <p>Picenediimide derivatives serve as the active layer of <italic>n</italic>-channel thin-film field-effect transistors displaying a maximum charge carrier mobility as high as 2.0 × 10−1 cm2 V−1 s−1.</p>

    DOI: 10.1039/d0ra06629j

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  • Low-voltage organic thin-film transistors based on [n]phenacenes Reviewed International coauthorship International journal

    Afra Al Ruzaiqi, Hideki Okamoto, Yoshihiro Kubozono, Ute Zschieschang, Hagen Klauk, Peter Baran, Helena Gleskova

    Organic Electronics   73   286 - 291   2019.10

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    DOI: 10.1016/j.orgel.2019.06.021

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  • Fluorescence properties of amido-substituted 2,3-naphthalimides: Excited-state intramolecular proton transfer (ESIPT) fluorescence and responses to Ca2+ ions Reviewed International journal

    Lei Wang, Mayu Fujii, Misa Namba, Minoru Yamaji, Hideki Okamoto

    Tetrahedron Letters   60 ( 43 )   151189 - 151189   2019.10

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.tetlet.2019.151189

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  • Distinctive effects on fluorescence quantum yields of 4-substituted N-methylphthalimides by inclusion complexation with β-cyclodextrins Reviewed

    Yoshimi Sueishi, Yuki Matsumoto, Junko Sohama, Yoshihiro Osawa, Hideki Okamoto

    Journal of Inclusion Phenomena and Macrocyclic Chemistry   93 ( 3-4 )   275 - 281   2019.4

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Springer Science and Business Media LLC  

    DOI: 10.1007/s10847-018-00877-4

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    Other Link: http://link.springer.com/article/10.1007/s10847-018-00877-4/fulltext.html

  • Transistor Application and Intercalation Chemistry of π-Conjugated Hydrocarbon Molecules

    Yoshihiro Kubozono, Shino Hamao, Takahiro Mikami, Yuma Shimo, Yasuhiko Hayashi, Hideki Okamoto

    Physics and Chemistry of Carbon-Based Materials   229 - 252   2019

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    DOI: 10.1007/978-981-13-3417-7_8

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  • Fabrication of flexible high-performance organic field-effect transistors using phenacene molecules and their application toward flexible CMOS inverters Reviewed International coauthorship International journal

    Emanuela Pompei, Claudio Turchetti, Shino Hamao, Akari Miura, Hidenori Goto, Hideki Okamoto, Akihiko Fujiwara, Ritsuko Eguchi, Yoshihiro Kubozono

    Journal of Materials Chemistry C   7 ( 20 )   6022 - 6033   2019

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    <p>The transport properties of 3,10-ditetradecylpicene ((C14H29)2-picene) and [6]phenacene thin-film field-effect transistors (FETs) on Si and plastic substrates are reported, in which SiO2 and parylene are used as gate dielectrics, respectively.</p>

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  • Blue fluorescence from N,O-coordinated BF2 complexes having aromatic chromophores in solution and the solid state Reviewed International journal

    Minoru Yamaji, Kazuhiro Tomonari, Keisuke Ikuma, Kenta Goto, Fumito Tani, Hideki Okamoto

    Photochemical & Photobiological Sciences   18 ( 12 )   2884 - 2892   2019

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    <p>
    <italic>N</italic>,<italic>O</italic>-Coordinated BF2 complexes (Ar@HCs) having aromatic (Ar) and heterocycle (HC) moieties were prepared, and their photophysical properties were investigated in solution and the solid state along with their crystal structures.</p>

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  • Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state Reviewed International journal

    Minoru Yamaji, Hideki Okamoto

    Journal of Photochemistry and Photobiology A: Chemistry   360   204 - 209   2018.6

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    DOI: 10.1016/j.jphotochem.2018.04.017

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  • Synthesis of isomeric coumarin-fluorene hybrids by photocyclization and the photophysical features Reviewed International journal

    Minoru Yamaji, Hideki Okamoto, Kenta Goto, Shin-ichiro Kato, Fumito Tani, Yosuke Nakamura

    Tetrahedron Letters   59 ( 13 )   1216 - 1219   2018.3

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    DOI: 10.1016/j.tetlet.2018.02.033

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  • Excited-state intramolecular proton transfer (ESIPT) fluorescence from 3-amidophthalimides displaying RGBY emission in the solid state Reviewed

    Hideki Okamoto, Kazumasa Itani, Minoru Yamaji, Hiroyuki Konishi, Hiromi Ota

    Tetrahedron Letters   59 ( 4 )   388 - 391   2018.1

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    DOI: 10.1016/j.tetlet.2017.12.049

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  • Fluorescence behaviour of 2-, 3- and 4-amino-1,8-naphthalimides: effects of the substitution positions of the amino functionality on the photophysical properties Reviewed International journal

    Lei Wang, Mayu Fujii, Minoru Yamaji, Hideki Okamoto

    Photochemical & Photobiological Sciences   17 ( 10 )   1319 - 1328   2018

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    <p>2-Amino-1,8-naphthalimide showed blue fluorescence independent of the microenvironment of the solvents whereas the corresponding 3- and 4-amino derivatives displayed marked positive solvatofluorochromism.</p>

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  • Blue Fluorescence from BF2 Complexes of N,O-Benzamide Ligands: Synthesis, Structure, and Photophysical Properties Reviewed

    Minoru Yamaji, Shin-ichiro Kato, Kazuhiro Tomonari, Michitaka Mamiya, Kenta Goto, Hideki Okamoto, Yosuke Nakamura, Fumito Tani

    Inorganic Chemistry   56 ( 20 )   12514 - 12519   2017.10

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  • Synthesis, structure, and photoreactions of fluorinated 2,11-diaza[32]paracyclophane: Photochemical formation of cage-diene type benzene dimer Reviewed

    Hideki Okamoto, Tetsuya Kozai, Zenji Okabayashi, Teruo Shinmyozu, Hiromi Ota, Kiichi Amimoto, Kyosuke Satake

    Journal of Physical Organic Chemistry   30 ( 9 )   e3726 - e3726   2017.9

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    DOI: 10.1002/poc.3726

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  • Convenient Phenacene Synthesis by Sequentially Performed Wittig Reaction and Mallory Photocyclization Using Continuous-Flow Techniques Reviewed

    Hideki Okamoto, Haruhiko Takahashi, Takamitsu Takane, Yasuhiro Nishiyama, Kiyomi Kakiuchi, Shin Gohda, Minoru Yamaji

    SYNTHESIS-STUTTGART   49 ( 13 )   2949 - 2957   2017.7

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    Various phenacenes possessing chrysene, picene, and fulminene frameworks were prepared by using a continuous-flow synthetic protocol in which Wittig reaction affording diarylethenes and their Mallory photocyclization producing phenacene skeletons were sequentially performed. The Wittig reaction solution, containing the diarylethene obtained from an arylaldehyde and an arylmethyltriphenylphosphonium salt, was mixed with an iodine solution in the flow system and, subsequently, the solution was subjected to the photoreaction. Desired phenacenes were obtained with high to moderate chemical yield. For the present protocol, isolation of the intermediary diarylethene, which is the key precursor of the phenacene, is unnecessary. The approach provides a convenient method to supply a variety of phenacene samples, which are needed for initial systematic surveys in material science.

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  • Adsorption of Phenacenes on a Metallic Substrate: Revisited Reviewed

    Song-Wen Chen, I-Chen Sang, Hideki Okamoto, Germar Hoffmann

    The Journal of Physical Chemistry C   121 ( 21 )   11390 - 11398   2017.6

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    DOI: 10.1021/acs.jpcc.7b01806

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  • Systematic investigations on fused pi-system compounds of seven benzene rings prepared by photocyclization of diphenanthrylethenes Reviewed

    Shota Fujino, Minoru Yamaji, Hideki Okamoto, Toshiki Mutai, Isao Yoshikawa, Hirohiko Houjou, Fumito Tani

    PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES   16 ( 6 )   925 - 934   2017.6

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    We studied the photoproducts of 1-(n-phenanthryl)-2-(m-phenanthryl) ethenes (nEm; n, m = 1, 3 and 9) for understanding photocyclization patterns based on NMR spectroscopy. The crystal structures of the photoproducts were analyzed by X-ray crystallography, and the photophysical features of the photocyclized molecules were investigated based on emission and transient absorption measurements. Phenanthrene derivatives substituted at the 1-and 3-positions were prepared for synthesizing nEm by photocyclization of stilbene derivatives. We obtained four types of primary photoproducts (n@ m) from the corresponding nEm. Two of them were found to have racemic molecular structures in the single crystal determined by X-ray crystallography. Besides the primary photoproducts, two types of secondary photoproducts (n@mPP) were isolated. Fluorescence quantum yields and lifetimes of the obtained photoproducts were determined in solution whereas the definite fluorescence quantum yields were obtained in the powder. Observation of the triplet-triplet absorption spectra in solution by laser photolysis techniques showed that intersystem crossing to the triplet state competes with the fluorescence process.

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  • Photochemical synthesis and photophysical properties of coumarins bearing extended polyaromatic rings studied by emission and transient absorption measurements Reviewed

    Minoru Yamaji, Yuma Hakoda, Hideki Okamoto, Fumito Tani

    PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES   16 ( 4 )   555 - 563   2017.4

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    We prepared a variety of coumarin derivatives having expanded pi-electron systems along the direction crossing the C-3-C-4 bond of the coumarin skeleton via a photochemical cyclization process and investigated their photophysical features as a function of the number (n) of the added benzene rings based on emission and transient absorption measurements. Upon increasing n, the fluorescence quantum yields of the pi-extended coumarins increased. Expanding the p-electron system on the C-3-C-4 bond of the coumarin skeleton was found to be efficient for increasing the fluorescence ability more than that on the C-7-C-8 bond. Introducing the methoxy group at the 7-position was also efficient for enhancing the fluorescence quantum yield and rate of the expanded coumarins. The non-radiative process from the fluorescence state was not substantially influenced by the expanded pi-electron system. The competitive process with the fluorescence was found to be intersystem crossing to the triplet state based on the observations of the triplet-triplet absorption. The effects of the expanded pi-electron systems on the fluorescence ability were investigated with the aid of TD-DFT calculations.

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  • Chemical analysis of superconducting phase in K-doped picene Reviewed

    Takashi Kambe, Saki Nishiyama, Huyen L. T. Nguyen, Takahiro Terao, Masanari Izumi, Yusuke Sakai, Lu Zheng, Hidenori Goto, Yugo Itoh, Taiki Onji, Tatsuo C. Kobayashi, Hisako Sugino, Shin Gohda, Hideki Okamoto, Yoshihiro Kubozono

    JOURNAL OF PHYSICS-CONDENSED MATTER   28 ( 44 )   2016.11

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    Potassium-doped picene (K(3.0)picene) with a superconducting transition temperature (TC) as high as 14 K at ambient pressure has been prepared using an annealing technique. The shielding fraction of this sample was 5.4% at 0 GPa. The TC showed a positive pressure-dependence and reached 19 K at 1.13 GPa. The shielding fraction also reached 18.5%. To investigate the chemical composition and the state of the picene skeleton in the superconducting sample, we used energy-dispersive x-ray (EDX) spectroscopy, MALDI-time-of-flight (MALDI-TOF) mass spectroscopy and x-ray diffraction (XRD). Both EDX and MALDI-TOF indicated no contamination with materials other than K-doped picene or K-doped picene fragments, and supported the preservation of the picene skeleton. However, it was also found that a magnetic K-doped picene sample consisted mainly of picene fragments or K-doped picene fragments. Thus, removal of the component contributing the magnetic quality to a superconducting sample should enhance the volume fraction.

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  • Recent progress on carbon-based superconductors Reviewed

    Yoshihiro Kubozono, Ritsuko Eguchi, Hidenori Goto, Shino Hamao, Takashi Kambe, Takahiro Terao, Saki Nishiyama, Lu Zheng, Xiao Miao, Hideki Okamoto

    Journal of Physics: Condensed Matter   28 ( 33 )   334001 - 334001   2016.8

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    DOI: 10.1088/0953-8984/28/33/334001

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  • Synthesis and photophysical properties of difluoroboronated beta-diketones with the fluorene moiety that have high fluorescence quantum yields Reviewed

    Yurie Suwa, Minoru Yamaji, Hideki Okamoto

    TETRAHEDRON LETTERS   57 ( 15 )   1695 - 1698   2016.4

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    Difluoroboronate beta-diketones, compounds 1 having the fluorene moiety and the phenyl groups as well as the ligating precursors of the corresponding beta-diketones, compounds 2 were synthesized. The photophysical features of compounds 1 were investigated based on the measurements of fluorescence yields and lifetimes, and transient absorption. Compounds 1 are significantly fluorescent with quantum yields of ca. 0.95 in acetonitrile and ca. 0.90 in chloroform. Fluorescence from compounds 1 was observed also in the solid state. Observation of extremely weak triplet-triplet absorption spectra of compounds I verifies the large fluorescence quantum yields. (C) 2016 Elsevier Ltd. All rights reserved.

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  • Synthesis and transistor application of the extremely extended phenacene molecule, [9] phenacene Reviewed

    Yuma Shimo, Takahiro Mikami, Shino Hamao, Hidenori Goto, Hideki Okamoto, Ritsuko Eguchi, Shin Gohda, Yasuhiko Hayashi, Yoshihiro Kubozono

    SCIENTIFIC REPORTS   6   2016.2

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    the widespread interest in the chemistry, physics and materials science of such molecules and their potential applications. In particular, extended phenacene molecules, consisting of coplanar fused benzene rings in a repeating W-shaped pattern have attracted much attention because field-effect transistors (FETs) using phenacene molecules show promisingly high performance. Until now, the most extended phenacene molecule available for transistors was [8] phenacene, with eight benzene rings, which showed very high FET performance. Here, we report the synthesis of a more extended phenacene molecule, [9] phenacene, with nine benzene rings. Our synthesis produced enough [9] phenacene to allow the characterization of its crystal and electronic structures, as well as the fabrication of FETs using thin-film and single-crystal [9] phenacene. The latter showed a field-effect mobility as high as 18 cm(2) V-1 s(-1), which is the highest mobility realized so far in organic single-crystal FETs.

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  • Photochemically-assisted synthesis and photophysical properties of difluoroboronated beta-diketones with fused four-benzene-ring chromophores, chrysene and pyrene Reviewed

    Michitaka Mamiya, Yurie Suwa, Hideki Okamoto, Minoru Yamaji

    PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES   15 ( 7 )   928 - 936   2016

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    We investigated the photophysical properties of difluoroboronated beta-diketones (BF2DK) with chrysene and pyrene skeletons (ChB and PyB, respectively) in solution and in the solid state. Acetylchrysenes, as the key precursors to ChBs, were photochemically prepared from the corresponding (acetylphenyl) naphthylethenes by means of a modified photocyclization method. The absorption and emission spectra of the BF(2)DKs were obtained in chloroform and acetonitrile, and the quantum yields and lifetimes of the fluorescence were determined. Excimeric fluorescence from PyB was absent even in highly concentrated solution. Based on the Lippert-Mataga analysis of the absorption and fluorescence features, the photophysical properties of the ChBs were discussed in comparison with those of PyB. The fluorescence states of the studied BF(2)DKs are shown to be of a charge-transfer character. The fluorescence quantum yields decrease with increasing the solvent polarity due to the enhanced internal conversion process. The fluorescence quantum yields in the solid state of the studied BF(2)DKs were determined, and it was found that PyB is fluorescent, whereas the fluorescence quantum yields of the ChBs depend on the substituted position of the chrysene moiety.

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  • Preparation and photophysical properties of fluorescent difluoroboronated beta-diketones having phenanthrene moieties studied by emission and transient absorption measurements Reviewed

    Michitaka Mamiya, Yurie Suwa, Hideki Okamoto, Minoru Yamaji

    PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES   15 ( 2 )   278 - 286   2016

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    Six difluoroboronated beta-diketones having the phenanthrene skeleton (Phe@Ar) are prepared. Based on the measurements of the fluorescence quantum yields, lifetimes and transient absorption, the photophysical features of Phe@Ar are studied in comparison with those of difluoroboronated diketones having phenyl, naphthyl and anthryl moieties. beta-Diketones having 1-, 2-, 3- and 9-phenanthryl moieties (PheDKAr) were prepared as the precursor to Phe@Ar. 1-Acetylphenanthrene was synthesized by the photocyclization method as the key building block of PheDKAr having the 1-phenanthryl moiety. The counter aromatic moieties (Ar) of the prepared PheDKAr are varied with phenyl, furyl and thienyl rings (Ar = Ph, F and T, respectively) to investigate the effects of p-conjugation on the fluorescence properties. The prepared Phe@Ars are fluorescent with appreciable fluorescence quantum yields which depend on the substitution position of the phenanthrene moiety. 3-Phe@Ph having the 3-phenanthryl moiety provides the largest fluorescence quantum yield (0.81) in acetonitrile among the Phe@Ars whereas 2-Phe@Ph having the 2-phenanthryl moiety shows the smallest fluorescence quantum yield (0.07) in acetonitrile. All the Phe@Ars show fluorescence also in the solid state, and the fluorescence spectra and quantum yields were determined. Transient absorption measurement using laser flash photolysis of the Phe@Ars revealed the triplet formation. DFT and TD-DFT calculations of Phe@Ars rationalize the dependency of the fluorescence quantum yields on the substitution position of the phenanthrene skeleton in terms of difference in the oscillator strength for the HOMO-LUMO transition.

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  • Photophysical and Photochemical Processes of Excited Singlet and Triplet [3(n)]Cyclophanes (n=2-6) Studied by Emission Measurements and Steady-State and Laser Flash Photolyses Reviewed

    Minoru Yamaji, Hideki Okamoto, Yuhko Hakoshima, Teruo Shinmyozu

    JOURNAL OF PHYSICAL CHEMISTRY A   119 ( 10 )   1867 - 1874   2015.3

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    Photophysical and photochemical features of [3n]cyclophanes (3nCPs) (n = 2-6) in solution were investigated by emission and transient absorption measurements. The studied 3nCPs show excimer fluorescence without locally excited fluorescence whereas some of them emit excimer phosphorescence in rigid glass at 77 K. The probability of excimeric phosphorescence from transannular pi-electron systems was shown to strictly depend on the symmetric molecular structures. A feature of intersystem crossing from an excimeric fluorescence state to the excimeric triplet state was observed. Transient absorption spectra obtained upon laser flash photolysis of 3nCP revealed formation of the triplet excimer states. Triplet sensitization of 33CP using xanthone as the sensitizer demonstrated formation of triplet 33CP via triplet energy transfer whereas from the xanthone ketyl radical formation, it was inferred that triplet xanthone undergoes H atom abstraction from 32CP, providing a benzylic 32CP radical as the counter species. Based on kinetic and spectroscopic data obtained upon laser flash photolysis, differences in photochemical reactions of triplet xanthone between 32CP and 33CP were discussed.

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  • Transistors fabricated using the single crystals of [8]phenacene Reviewed

    Yuma Shimo, Takahiro Mikami, Hiroto T. Murakami, Shino Hamao, Hidenori Goto, Hideki Okamoto, Shin Gohda, Kaori Sato, Antonio Cassinese, Yasuhiko Hayashi, Yoshihiro Kubozono

    JOURNAL OF MATERIALS CHEMISTRY C   3 ( 28 )   7370 - 7378   2015

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    Field-effect transistors (FETs) with single crystals of a new phenacene-type molecule, [8]phenacene, were fabricated and characterized. This new molecule consists of a phenacene core of eight benzene rings, with an extended p-conjugated system, which was recently synthesized for use in an FET by our group. The FET characteristics of an [8]phenacene single-crystal FET with SiO2 gate dielectrics show typical p-channel properties with an average field-effect mobility, &lt;mu &gt;, as high as 3(2) cm(2) V-1 s(-1) in two-terminal measurement mode, which is a relatively high value for a p-channel single-crystal FET. The hmi was determined to be 6(2) cm(2) V-1 s(-1) in four-terminal measurement mode. Low-voltage operation was achieved with PbZr0.52Ti0.48O3 (PZT) as the gate dielectric, and an electric-double-layer (EDL) capacitor. The &lt;mu &gt; and average values of absolute threshold voltage, &lt;vertical bar V-th vertical bar &gt;, were 1.6(4) cm(2) V-1 s(-1) and 5(1) V, respectively, for PZT, and 4(2) x 10(-1) cm(2) V-1 s(-1) and 2.38(4) V, respectively, for the EDL capacitor; these values were evaluated in two-terminal measurement mode. The inverter circuit was fabricated using [8]phenacene and N, N'-1H, 1H-perfluorobutyldicyanoperylene-carboxydi-imide single-crystal FETs. This is the first logic gate circuit using phenacene molecules. Furthermore, the relationship between mu and the number of benzene rings was clarified based on this study and the previous studies on phenacene single-crystal FETs.

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  • Photochemical synthesis of diphenylphenanthrenes, and the photophysical properties studied by emission and transient absorption measurements Reviewed

    Minoru Yamaji, Yuuma Hakoda, Ami Horimoto, Hideki Okamoto

    Rapid communications in Photoscience   4   73 - 75   2014

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  • Characteristics of [6]phenacene thin film field-effect transistor Reviewed

    Noriko Komura, Hidenori Goto, Xuexia He, Hiroki Mitamura, Ritsuko Eguchi, Yumiko Kaji, Hideki Okamoto, Yasuyuki Sugawara, Shin Gohda, Kaori Sato, Yoshihiro Kubozono

    APPLIED PHYSICS LETTERS   101 ( 8 )   2012.8

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    Transistor characteristics are studied for field-effect transistors (FETs) with thin films of [6]phenacene, which has six benzene rings and W-shape structure. The molecular alignment preferable for FET transport is found to be formed in [6]phenacene thin films. The transistor shows clear p-channel FET characteristics with field-effect mobility mu as high as 3.7 cm(2) V-1 s(-1). The similar O-2 sensing properties to picene FET are observed in [6]phenacene thin film FET. The bias stress properties are observed in [6]phenacene thin film FET. The pulse-voltage application suppresses the bias-stress effect and it enables a continuous O-2 sensing in [6]phenacene FET. (C) 2012 American Institute of Physics. [http://dx.doi.org/10.1063/1.4747201]

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  • Unprecedented Temperature-dependent Formation of 3-and 7-Methyl-3H-azepine Derivatives by the Reaction of o-Nitrotoluene with Tributylphosphine in Nucleophilic Media Reviewed

    Siti Mariyah Ulfa, Hideki Okamoto, Kyosuke Satake

    CHEMISTRY LETTERS   41 ( 4 )   400 - 402   2012.4

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    The reaction of o-methylphenylnitrene in the presence of alcohol and amine was expected to give isomeric pairs of 3- and 7-methyl-3H-azepine derivatives. The formation ratio between these isomers was found to be obviously influenced by reaction temperature, that is, reaction at 150 degrees C gave 7-methyl-3H-azepine derivative, however, it became minor under 70 degrees C in both media. The ratio between 3- and 7-methyl derivatives is explained by a scheme of kinetic- and thermodynamic-controlled product distribution from o-methylphenylnitrene to 3- and 7-methyldehydroazepine intermediates which are trapped by nucleophilic media to give 3- and 7-methyl-3H-azepine derivatives.

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  • Studies on interactions of excited cadmium and mercury atoms with secondary and tertiary alkyl- and silylamines in gas phase

    Shunzo Yamamoto, Eriko Kainaga, Omar Ahmed, Hideki Okamoto, Yoshimi Sueishi

    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY   228 ( 1 )   38 - 43   2012.1

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    The Cd(P-3(1))- and Hg(P-3(1))-photosensitized emissions of some secondary and tertiary alkyl- and silylamines have been investigated under conditions of steady illumination at 493 and 298 K, respectively. The emission bands were observed at around 440 nm in the cadmium-photosensitized reactions of these amines. In contrast, no appreciable emission bands were observed in the mercury-photosensitized reactions of these amines. However, upon addition of tert-butyl alcohol to the amine-mercury system, an emission band evolved at around 350 nm in the mercury-photosensitization. The peak-wavelengths for secondary and tertiary alkyl- and silylamines are slightly shorter than the values predicted from the correlations between the peak wavelength and the first ionization energy obtained in the cadmium- and mercury-photosensitized luminescence of ammonia and primary amines. The quenching efficiencies of the cadmium and mercury resonance lines by secondary alkyl- and silylamines are higher than those by tertiary alkyl- and silylamines. These observations suggest that the steric hindrance by the alkyl and silyl groups to the approach of the nitrogen atom in the amines to excited cadmium and mercury atoms seems to be an important factor for the stabilization of the exciplexes and the quenching of the resonance lines. The behavior of silylamines is similar to that of alkylamines in cadmium- and mercury-photosensitized reactions. (C) 2011 Elsevier B.V. All rights reserved.

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  • Fluorescence response of 3-trifluoroacetylaminophthalimide to a Li+-I- ion pair induced by 254 nm photolysis in acetonitrile

    Hideki Okamoto, Hiroyuki Konishi, Kyosuke Satake

    CHEMICAL COMMUNICATIONS   48 ( 17 )   2346 - 2348   2012

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    A 3-trifluoroacetylaminophthalimide selectively distinguished LiI from other alkaline-metal iodides and lithium halides by a marked fluorescence colour change, from orange-yellow to sky-blue, subsequent to 254 nm photolysis.

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  • STERIC EFFECT ON THE FORMATION OF 3H-AZEPINE DERIVATIVES FROM o-ALKYLPHENYLNITRENE AND ALCOHOL AS A NUCLEOPHILIC MEDIA

    Siti Mariyah Ulfa, Hideki Okamoto, Kyosuke Satake

    HETEROCYCLES   83 ( 6 )   1259 - 1265   2011.6

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    The cause of regioselectivity for the formation of 3-alkyl- and/or 7-alkyl-3H-azepine derivatives via the intramolecular insertion reaction of o-alkylphenylnitrene, which is generated by an action of Buy on o-alkylnitrobenzene, in the presence of alcohol found to be elucidated by the steric effects of an alcohol adduct on the dehydroazepine intermediate. Observed selectivity is confirmed both by changing the bulkiness of the o-alkyl group of phenylnitrene and that of alcohol as a nucleophile.

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  • Phthalide-derived novel fluoroionophores incorporating picolylamino receptors: synthesis and response to metal cations Reviewed

    Hideki Okamoto, Ayako Matsui, Kyosuke Satake

    ANALYST   136 ( 15 )   3164 - 3169   2011

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    Phthalide derivatives incorporating mono- and di-picolylamino functionalities at the 6-position have been prepared as novel fluoroionophores and their fluorescence responses to metal cations have been investigated. These phthalides not only exhibited efficient fluorescence in an aqueous medium but also displayed fluorescence on-off response upon addition of transition-metal cations, namely Cu(2+). The 6-aminophthalide fluorophore served as the core of the fluorescent probes although it has rarely been applied to a chemosensor. To the best of our knowledge, these modified phthalides are the first 6-aminophthalide-derived fluorometric probes for metal cations, namely Cu(2+).

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  • Metal-intercalated aromatic hydrocarbons: a new class of carbon-based superconductors Reviewed

    Yoshihiro Kubozono, Hiroki Mitamura, Xuesong Lee, Xuexia He, Yusuke Yamanari, Yosuke Takahashi, Yuta Suzuki, Yumiko Kaji, Ritsuko Eguchi, Koki Akaike, Takashi Kambe, Hideki Okamoto, Akihiko Fujiwara, Takashi Kato, Taichi Kosugi, Hideo Aoki

    PHYSICAL CHEMISTRY CHEMICAL PHYSICS   13 ( 37 )   16476 - 16493   2011

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    New carbon-based superconductors are synthesized by intercalating metal atoms into the solid-phase hydrocarbons picene and coronene. The highest reported superconducting transition temperature, T-c, of a hydrocarbon superconductor is 18 K for K(3)picene. The physics and chemistry of the hydrocarbon superconductors are extensively described for Axpicene (A: alkali and alkali earth-metal atoms) for x = 0-5. The theoretical picture of their electronic structure is also reviewed. Future prospects for hydrocarbon superconductors are discussed from the viewpoint of combining electronics with condensed-matter physics: modification of the physical properties of hydrocarbon solids is explored by building them into a field-effect transistor. The features of other carbon-based superconductors are compared to clarify the nature of hydrocarbon superconductors.

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  • Quantitative analysis of O-2 gas sensing characteristics of picene thin film field-effect transistors Reviewed

    Xuesong Lee, Yasuyuki Sugawara, Akio Ito, Shuhei Oikawa, Naoko Kawasaki, Yumiko Kaji, Ryoji Mitsuhashi, Hideki Okamoto, Akihiko Fujiwara, Kenji Omote, Takashi Kambe, Naoshi Ikeda, Yoshihiro Kubozono

    ORGANIC ELECTRONICS   11 ( 8 )   1394 - 1398   2010.8

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    O-2 gas sensing behaviors are studied in picene thin film field-effect transistors (FETs) with hydrophobic polymer (Cytop(TM) or polystyrene) coated SiO2 gate dielectrics. Picene thin film FETs show a rapid reduction of hysteresis in transfer curves recorded in forward and reverse measurement modes, compared to a picene FET with hexamethydisilazane-coated SiO2. The picene FETs show very sensitive O-2 gas sensing effects down to similar to 10 ppm. A quantitative analysis is presented of the gate voltage (V-G) dependent mobility induced by O-2 exposure, i.e., the suppression of drain current at high V-G. (C) 2010 Elsevier B.V. All rights reserved.

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  • Flexible picene thin film field-effect transistors with parylene gate dielectric and their physical properties Reviewed

    Naoko Kawasaki, Wolfgang L. Kalb, Thomas Mathis, Yumiko Kaji, Ryoji Mitsuhashi, Hideki Okamoto, Yasuyuki Sugawara, Akihiko Fujiwara, Yoshihiro Kubozono, Bertram Batlogg

    APPLIED PHYSICS LETTERS   96 ( 11 )   113305   2010.3

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    Flexible picene thin film field-effect transistors (FETs) have been fabricated with parylene gate dielectric on polyethylene terephthalate substrates. The picene thin film FETs show p-channel output/transfer characteristics and the field-effect mobility mu reaches similar to 1 cm(2) V(-1) s(-1) in vacuum. The FET shows a clear O(2) gas sensing effect and negligible hysteresis in the transfer curves, indicating a possible application of the transistor as O(2) selective gas sensor. Furthermore, it has been found that the parylene gate dielectric can eliminate a reduction in on-state drain current caused by continuous bias-voltage application which is observed if a SiO(2) gate dielectric is used.

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  • Linear response of multiphoton reaction: Three-photon Cycloreversion of anthracene biplanemer in solution by intense femtosecond laser pulses Reviewed

    Yatsuhashi, T., Nakahagi, Y., Okamoto, H., Nakashima, N.

    Journal of Physical Chemistry A   114 ( 39 )   10475 - 10480   2010

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    DOI: 10.1021/jp1041475

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  • Low voltage operation in picene thin film field-effect transistor and its physical characteristics Reviewed

    Yumiko Kaji, Naoko Kawasaki, Xuesong Lee, Hideki Okamoto, Yasuyuki Sugawara, Shohei Oikawa, Akio Ito, Hiroyuki Okazaki, Takayoshi Yokoya, Akihiko Fujiwara, Yoshihiro Kubozono

    APPLIED PHYSICS LETTERS   95 ( 18 )   183302/1-183302/3   2009.11

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    Low voltage operation of picene thin film field-effect transistor (FET) has been realized with 40 nm thick SiO(2) gate dielectrics coated by two polymers, Cytop (TM) and polystyrene. The picene FETs operated in low absolute gate voltage vertical bar V(G)vertical bar below 15 V for Cytop (TM) coated SiO(2) and 30 V for polystyrene coated SiO(2) gate dielectrics, and they showed a significant O(2) gas sensing effect down to similar to 10 ppm. Photoemission spectrum clarified that O(2) molecules penetrate into the thin films at O(2)/picene mole ratio of 1: 1. X-ray diffraction pattern of picene thin films showed highly oriented growth on the polymer-coated SiO(2).

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  • High-performance C-60 and picene thin film field-effect transistors with conducting polymer electrodes in bottom contact structure Reviewed

    Yumiko Kaji, Ryoji Mitsuhashi, Xuesong Lee, Hideki Okamoto, Takashi Kambe, Naoshi Ikeda, Akihiko Fujiwara, Minoru Yamaji, Kenji Omote, Yoshihiro Kubozono

    ORGANIC ELECTRONICS   10 ( 3 )   432 - 436   2009.5

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    C-60 and picene thin film field-effect transistors (FETs) in bottom contact structure have been fabricated with poly(3,4-ethylenedioxythiophene): poly(styrenesulfonate) (PED-OT:PSS) electrodes for a realization of mechanical flexible organic FETs. The C-60 thin film FETs showed n-channel enhancement-type characteristics with the field-effect mobility mu value of 0.41 cm(2\) V-1 s(-1), while the picene thin film FET showed p-channel enhancement-type characteristics with the p of 0.61 cm(2) V-1 s(-1). The p values recorded for C-60 and picene thin film FETs are comparable to those for C-60 and picene thin film FETs with Au electrodes. (C) 2009 Elsevier B.V. All rights reserved.

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  • Trap states and transport characteristics in picene thin film field-effect transistor Reviewed

    Naoko Kawasaki, Yoshihiro Kubozono, Hideki Okamoto, Akihiko Fujiwara, Minoru Yamaji

    APPLIED PHYSICS LETTERS   94 ( 4 )   043310/1-043310/3   2009.1

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    Transport characteristics and trap states are investigated in picene thin film field-effect transistor under O(2) atmosphere on the basis of multiple shallow trap and release (MTR) model. The channel transport is dominated by MTR below 300 K. It has been clarified on the basis of MTR model that the O(2)-exposure induces a drastic reduction in shallow trap density to increase both the field-effect mobility mu and on-off ratio. We also found that the O(2)-exposure never caused an increase in hole carrier density. Actually, a very high mu value of 3.2 cm(2) V(-1) s(-1) is realized under 500 Torr of O(2).

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  • Photochemistry of nitrogen-bridged cyclophanes: 2,11-Diaza[3 2]anthracenoparacyclophane and 2,11-diaza[32] paracyclophane systems Invited Reviewed

    Hideki Okamoto, Minoru Yamaji, Kyosuke Satake

    Synlett   ( 13 )   1931 - 1945   2008.8

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    This account provides an overview of the photochemical properties of cyclophanes possessing nitrogen atoms in the bridge chains, namely 2,11-diaza[32]anthracenoparacyclophane and 2,11-diaza[3 2]paracyclophane systems. Although the photoreactions of aromatic molecules that are bound by a linker or fixed in a cyclophane structure have been widely investigated, much less attention has been paid to the photochemistry of aromatic rings incorporated in a nitrogen-bridged cyclophane. During the course of our work on the photoreactions of cyclophanes possessing nitrogen atoms in their bridge chains, the nitrogen-bridged cyclophanes were found to display photoproperties significantly different from those of the nonbridged aromatic chromophores or the corresponding carbonbridged cyclophane analogues. The 2,11-diaza[32]anthracenoparacyclophane system displayed an efficient photochemical cycloaddition-adiabatic cycloreversion cycle in the excited singlet state, while in the triplet state, the photoisomer underwent a novel rearrangement and adiabatic cycloreversion. Upon photolysis of the 2,11-diaza[32]paracyclophane system, an octahedrane cage was formed. This is the first reported octahedrane formation to occur by the photochemical dimerization of benzene. Thus, the title cyclophane systems display a variety of photoprocesses involving cycloaddition, adiabatic cycloreversion accompanied by photoinduced chemiluminescence, novel rearrangements, and previously unknown benzene dimerization. 1 Introduction 2 Photochemistry of the 2,11-Diaza[32]anthracenoparacyclophane System 2.1 General Comments on the Photochemical Cycloaddition and Cycloreversion of Aromatic Molecules in the Singlet State 2.2 Intramolecular Photochemical Cycloaddition and Cycloreversion of the 2,11-Diaza[32] anthracenoparacyclophane System 2.3 General Introduction to the Photochemistry of Aromatic Molecules in the Triplet State 2.4 Photoproperties of the 2,11-Diaza[32]anthracenoparacyclo-phane System in the Triplet State 3 Photochemistry of the 2,11-Diaza[32]paracyclophane System 3.1 General Remarks on the Photoreactions of Cyclophanes Containing Two Benzene Rings 3.2 Construction of the 2,11-Diaza[32]paracyclophane Skeleton 3.3 Photoreactions of the 2,11-Diaza[32]paracyclophane System 4 Summary.

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  • A convenient synthesis of trifluoroacetamide derivatives of diaza[3(2)]cyclophanes and triaza[3(3)]cyclophanes Reviewed

    Hideki Okamoto, Hiroyuki Takemura, Kyosuke Satake

    SYNTHESIS-STUTTGART   44 ( 1 )   39 - 44   2008.1

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    The diaza[3(2)]cyclophane skeleton has been constructed by the bis-N-alkylation of 1,4-bis[(4-nitrophenylsulfonylamin o)methyl] benzene with 1,4-bis(halomethyl)benzene in the presence of sodium hydride. The 4-nitrophenylsulfonyl (Ns) amides in the bridge chains of the cyclophane were effectively deprotected by sodium ethanethiolate and the resulting free amine moieties were reprotected as the trifluoroacetamide under mild conditions to afford 3,7-bis(trifluoroacetyl)-3,7-diaza-1,5(1,4)-dibenzenacyclooctaphane in 26% overall yield. This Ns-amide method has also been applied for the preparation of a higher homologue, the trifluoroacetamide derivative of triaza[3(3)]cyclophane, 3,5,7-tris(trifluoroacetyl)-3,7, 10-triaza- 1,5(1,3,5)-dibenzenabicyclo[3.3.3]undecaphane, in 18% overall yield. Thus, the present procedure provides a convenient synthetic route to azacyclophane derivatives possessing trifluoroacetamide groups in the bridge chains.

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  • Fluorescence properties of 3-and 4-trifluoroacetylamino-1,8-naphthalimides: Solvent-controlled switching of fluorescence color and response to metal-cations Reviewed

    Hideki Okamoto, Kyosuke Satake, Masaru Kimura

    ARKIVOC   8   112 - 123   2007

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    The effects of solvents and metal cations on the fluorescence spectra of 3- ( 1) and 4- ( 2) trifluoroacetylamino-1,8-naphthalimides were investigated. In MeCN, these naphthalimides displayed a violet similar to blue fluorescence based on their neutral amide form ( 1, 2). Whereas in DMSO, they gave off a yellow similar to orange emission due to their amide anions (1(-), 2(-)). In MeOH, naphthalimide 2 emitted a dual fluorescence (lambda(FL) 436 and 556 nm) to display a white luminescence. Naphthalimides 1, 2 are essentially insensitive to metal cations in their neutral amide form. In contrast, the fluorescence of the amide anions 1-, 2- was quenched by metal cations. The efficiency of the quenching correlated with the Lewis acidity of the metal cations; a stronger Lewis acid tended to display a more effective fluorescence quenching. Therefore, the fluorescence color and the sensitivity to metal cations of the naphthalimides were effectively switched by the solvent.

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  • Novel parallel reaction between a [1,5] sigmatropic alkylthio shift and a [1,5] sigmatropic hydrogen shift observed in a 2H-azepine ring Reviewed

    Yasuhiro Kubota, Kyosuke Satake, Hideki Okamoto, Masaru Kimura

    ORGANIC LETTERS   8 ( 24 )   5469 - 5472   2006.11

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    Although heating 2-methoxy-2H-azepine results in a [1,5] sigmatropic hydrogen shift, heating 2-propylthio-2H-azepine results in not only a [1,5] sigmatropic hydrogen shift but also a [1,5] sigmatropic propylthio shift. Kinetic measurements reveal that migratory aptitudes increase in the order of MeO &lt; H, PrS. These [1,5] sigmatropic shifts are discussed on the basis of ab initio DFT calculations.

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  • Invariom structure refinement, electrostatic potential and toxicity of 4-O-methylalpinumisoflavone, O,O-dimethylalpinumisoflavone and 5-O-methyl-4-O-(3-methylbut-2-en-1-yl)alpinum-isoflavone Reviewed

    Robert Kingsford-Adaboh, Birger Dittrich, Christian B. Huebschle, Winfred S. K. Gbewonyo, Hideki Okamoto, Masaro Kimura, Hiroyuki Ishida

    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE   62   843 - 849   2006.10

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    The accurate X-ray single-crystal structures of the isoflavone compounds 4-O-methylalpinumisoflavone, O, O-dimethylalpinumisoflavone and 5-O-methyl-4-O-( 3-methylbut-2-en-1-yl) alpinumisoflavone {alpinumisoflavone = 5-hydroxy7-( 4-hydroxyphenyl)-2,2-dimethyl-2H, 6H-benzo[ 1,2-b: 5,4-b']dipyran-6-one} from data sets measured at cryogenic temperature have been obtained from invariom modelling using theoretically predicted Hansen and Coppens multipole-model form factors, which describe the aspherical electron density distribution. Molecular dipole moments and electrostatic potentials obtained from invariom modelling are discussed and compared with results from ab initio theoretical calculations. All three studied compounds are solvent extracts of root bark or seed powder of Millettia thonningii ( leguminosae), a plant molluscicide and cercaricide used in Franco West Africa as medication against various diseases. The compounds' toxicities to brine shrimp have been determined and their different potencies tentatively related to conformation differences, intramolecular contacts, dipole moments and electrostatic potential features.

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  • Formation of 4H-azepine by the electrophilic reaction of a 2-methoxyazepinium ion and analysis of the sigmatropic isomerization Reviewed

    Christopher E. J. Cordonier, Kyosuke Satake, Hideki Okamoto, Masaru Kimura

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 17 )   3803 - 3807   2006.8

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    2-Aryl-2H-, 3-aryl-3H-, and 4-aryl-4H-azepine were formed by the novel, electrophilic, pi(LUMO)-controlled reaction of the 2-methoxyazepinium ion, generated in situ by the reaction of TiCl4 with 2,7-dialkoxy-2H-azepine and an aryl compound, for which the kinetic parameters of the sigmatropic hydrogen rearrangement of the 4H-azepine was measured. The substitution and hydrogen shift of the azepinium ion were analyzed with DFT studies. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

    DOI: 10.1002/ejoc.200600257

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  • Crystal structure of 4 '-O-methylalpinumisoflavone at 90K Reviewed

    R. Kingsford-Adaboh, E. Ahiano, B. Dittrich, H. Okamoto, M. Kimura, H. Ishida

    CRYSTAL RESEARCH AND TECHNOLOGY   41 ( 7 )   728 - 733   2006.7

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    4'-O-Methylalpinumisoflavone crystals which hitherto had been difficult to crystallize for X-ray diffraction analyses have been obtained from a demethylated product of O,O- dimethylalpinumisoflavone. The structural and conformational features of the crystal measured at 90 K are reported and compared with previously reported work of O,O-dimethylalpinumisoflavone and 5-O-methyl-4'-O-(3-methyl-but-2-en-1-yl) alpinumisoflavone. Each of these compounds is characterized by a six membered ring that is further fused to a benzopyrone isoflavone moiety resulting in a tricyclic ring system. This six membered ring shows a half-chair conformation in all the molecules studied, with the ring in the title compound showing the least Cremer-Pople puckering amplitude Q and shorter inter and intramolecular contacts. (C) 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

    DOI: 10.1002/crat.200510656

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  • An azacrowned phthalimide as a metal-ion sensitive and solvatofluorochromic fluorophore: Fluorescence properties and a mimic integrated logic operation Reviewed

    H Okamoto, M Kohno, K Satake, M Kimura

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 12 )   2180 - 2187   2005.12

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    The novel azacrowned phthalimide 1 has been prepared and its fluorescence properties have been investigated by addition of EtOH and Ag+. The phthalimide 1 showed appreciable solvatofluorochromism; its fluorescence maxima (lambda(FL)) appeared in the wavelength region between 458 (in Et2O) and 544 nm (in EtOH). In benzene, the phthalimide 1 gave off blue emission (lambda(FL) 466 nm) while it emitted green fluorescence (lambda(FL) 497 nm) upon addition of 250 mM of EtOH. Both the blue and the green emissions were quenched by Ag+. Potential logic operations of the phthalimide 1 were examined using fluorescence outputs at 450 (Out(1)) and 515 nm (Out(2)) and two input stimuli, EtOH (In,) and Ag+ (In-2). The Out, was on in the absence of these inputs while its intensity was reduced (off) by either or both of the inputs to serve as a NOR operator. The Out(2) was off without the inputs; in contrast, the intensity of Out(2) was enhanced (on) by In-2. The enhanced Out(2) was switched off by In-2. The Obt(2), thus, corresponds to an INHIBIT operation responding to the input signals. The crowned phthalimide 1 mimics a two-input-two-output combinational logic gate with a single fluorophore and a single ion-sensing unit.

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  • Electrophilic behavior of the pi delocalized azepinium ion: Friedel-crafts reactions with benzenes and five-membered aromatic heterocycles Invited

    Y Kubota, K Satake, H Okamoto, M Kimura

    ORGANIC LETTERS   7 ( 23 )   5215 - 5218   2005.11

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    Although the reactivity of tropylium ion with aromatic substrates is low, the reaction of azepinium ion with aromatic substrates such as benzene, phenol, furan, and thiophene resulted in the formation of 2-aryl-2H-azepine as a major product. An exceptional result in the formation of ring-contracted product was observed in the reaction with pyrrole.

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  • Preparation of an azacrowned isoluminol and its chemiluminescence initiated by alkali-metal iodides in acetonitrile Reviewed

    H Okamoto, M Kimura

    CHEMISTRY LETTERS   34 ( 10 )   1452 - 1453   2005.10

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    The novel azacrowned isoluminol has been prepared as the first luminol analogue possessing an azacrown ionophore. The crowned isoluminol displayed flash chemiluminescence upon addition of alkali-metal iodides in acetonitrile containing alkaline hydrogen peroxide and the chemiluminescence intensity varied depending on the metal cations studied; K+ &gt;&gt; Na+ &gt; Li+.

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  • Reaction of 2-methoxy-3H-azepine with NBS: Efficient synthesis of 2-substituted 2H-azepines

    CEJ Cordonier, K Satake, M Atarashi, Y Kawamoto, H Okamoto, M Kimura

    JOURNAL OF ORGANIC CHEMISTRY   70 ( 9 )   3425 - 3436   2005.4

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    The reaction of 2-methoxy-3H-azepines, in the presence or absence of a nucleophile, with N-bromosuccinimide (NBS) gave a regioselective 1,4-adduct from which the corresponding 2H-azepine derivatives were formed via base-promoted hydrogen bromide elimination, generally in moderate to quantitative yield. Competitive formation of 4-bromo-2-methoxy-3H-azepine by electrophilic substitutuion or 3H-azepin-2-yl 2H-azepin-2-yl ether by transetherification was minimized at lower reaction temperatures. Quantitative substitution of 2-(2',4',6'-trichlorophenoxy)2H-azepine derivatives, formed in moderate yield from the respective 3H-azepine and NBS in the presence of 2,4,6-trichlorophenol (TCP), by various nucleophiles gave the corresponding 2-substituted 2H-azepine. Among these nucleophiles were alkanethiol and alkylamine that are not tolerated in the reaction of 3H-azepine and NBS.

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  • Synthesis of a delocalized azepinium ion and investigation of its electrophilic character Invited

    K Satake, Y Kubota, CEJ Cordonier, H Okamoto, M Kimura

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   43 ( 6 )   736 - 738   2004

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    DOI: 10.1002/anie.200352794

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  • Nucleophilic reactions of 5-tert-butyl-2-methoxy-3H-azepine with alkoxides and alkyllithium reagents Reviewed

    Y Kubota, K Satake, R Ikui, H Okamoto, N Kimura

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   76 ( 4 )   805 - 811   2003.4

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    The reaction of 5-tert-butyl-2-methoxy-3H-azepine (2a) with sodium alkoxides gave 2-alkoxy-3H-azepine derivatives 3-6 by nucleophilic transetherification. The treatment of 2a with tert-butyllithium also yielded 2,5-di-tert-butyl-3H-azepine (7): however, the reaction of 2a and methyllithium gave the expected 5-tert-butyl-2-methyl-3H-azepine (8) along with unexpected 5-tert-butyl-2,2-dimethyl-2,3-dihydro-1H-azepine (9). but also 5,5'-di(tert-butyl)-2,2'-methylenedi(3H-azepine) (11), the structure of which was found to be tautomerized 5-tert-butyl-2-(5-tert-butyl-2,3-dihydro-1H-azepine-2-ylidenemethyl)-3H-azepine (12). The energy profile for the observed tautomerization is discussed based on ab initio DFT calculations and kinetic measurements.

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  • Photochemistry of N-isopropoxy-substituted 2(1H)-pyridone and 4-p-tolylthiazole-2(3H)-thione: Alkoxyl-radical release (spin-trapping, EPR, and transient spectroscopy) and its significance in the photooxidative induction of DNA strand breaks Reviewed

    W Adam, J Hartung, H Okamoto, S Marquardt, WM Nau, U Pischel, CR Saha-Moller, K Spehar

    JOURNAL OF ORGANIC CHEMISTRY   67 ( 17 )   6041 - 6049   2002.8

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    UVA-irradiation of the photo-Fenton reagents N-isopropoxypyridone 2b and N-isopropoxythiazole-2(3H)-thione 3b releases radicals which induce strand breaks. Transient spectroscopy establishes N-O bond scission [Phi(N-O) = (75 8)% for 2b and (65 7)% 3b] as the dominating primary photochemical process to afford the DNA-damaging radicals. Product studies and laser-flash experiments reveal that the thiazolethione 3b leads primarily to the disulfide 5, from which through C-S bond breakage, the bithiazyl 6, the thiazole 7, and the isothiocyanate 8 are derived. Upon irradiation of pyridone 2b (300 nm) in aqueous media, a mixture of isopropoxyl and 2-hydroxyprop-2-yl radicals is formed, as confirmed by trapping with 5,5-dimethyl-1-pyrroline N-oxide (DMPO) and EPR spectroscopy. In contrast, the photolysis of the thiazolethione 3b (350 nm) affords exclusively the DMPO adducts of the isopropoxyl radicals. Control experiments disclose that the thiazolethione-derived photoproduct disulfide 5, or the intermediary thiyl radicals B, scavenge the carbon-centered 2-hydroxyprop-2-yl radicals, which are generated from the isopropoxyl radicals by hydrogen shift. With supercoiled pBR 322 DNA in a 60:40 mixture of H2O-MeCN, the pyridone 2b and the thiazolethione 3b display moderate strand-break activity (17% open-circular DNA for 2b and 12% for 3b). In pure water, however, the pyridone 2b photoinduces substantially more DNA cleavage (32% open-circular DNA), which is attributed to the peroxyl radicals generated from the 2-hydroxyprop-2-yl radicals by oxygen trapping. The lower strand-break activity of the thiazolethione 3b derives presumably from isopropoxyl radicals, because only these are detected in the photolysis of this photo-Fenton reagent.

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  • Nucleophilic substitution reaction of 5-t-butyl-2methoxy-3H-azepine with alkoxides and alkyllithium reagents: A formation of bis(5-t-butyl-3H-azepin-2-yl)methane having a vinamidine conjugation Reviewed

    K Satake, Y Kubota, H Okamoto, M Kimura

    HETEROCYCLES   57 ( 2 )   223 - 228   2002.2

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    Reaction of 5-t-butyl-2-methoxy-3H-azepine (2) with nuclephiles (alkoxides or t-butyllithium) gave respective substitution product at 2-position of the ring. Unexpectedly, when methyllithium was used as a nucleophile, bis(5-t-butyl-3H-azepin-2-yl)methane (7), the structure of which found to be tautomeric vinamidine (7a,b), was formed. Tautomerization between 7 and 7a,b was characterized spectroscopically and theoretically based on the levels of B3LYP/631G(d).

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  • Photochromic properties of a 2,11-diaza[3,3]paracyclo(9,10)anthracenophane derivative having ethylenediamine host function on its bridge chains Reviewed

    Hideki Okamoto, Yukari Nakatsu, Masaru Kimura, Kyosuke Satake

    ITE Lett. Batter. New Technol. Med.   2002

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  • Preparation of a crown-ether-modified lophine peroxide as a guest-sensitive novel chemiluminophore and modulation of its chemiluminescence by metal cations Reviewed

    H Okamoto, M Owari, M Kimura, K Satake

    TETRAHEDRON LETTERS   42 ( 42 )   7453 - 7455   2001.10

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    A guest-sensitive chemiluminophore, a novel crown-ether-modified lophine peroxide 1. has been prepared. and its chemiluminescent behavior has been investigated in the presence of alkaline and alkaline earth metal cations. In the presence of Na+, the lambda (max) of the chemiluminescence of peroxide 1 was blue-shifted (505 nm) compared to the case without a metal cation (566 nm). The chemiluminescent intensity was enhanced by addition of Na+ while that of Mg2+ decreased the intensity. (C) 2001 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(01)01572-6

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  • N-hydroxy-4-(4-chlorophenyl)th iazole-2(3H)-thione as a photochemical hydroxyl-radical source: Photochemistry and oxidative damage of DNA (Strand breaks) and 2 '-deoxyguanosine (8-oxodG formation) Reviewed

    W Adam, J Hartung, H Okamoto, CR Saha-Moller, K Spehar

    PHOTOCHEMISTRY AND PHOTOBIOLOGY   72 ( 5 )   619 - 624   2000.11

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    On irradiation of N-hydroxythiazole-2(3H)-thione 3 at 300 nm, the photoproducts disulfide 4, bisthiazole 5 and thiazole 6 are formed. During this photolysis, hydroxyl radicals are released, which have been detected by spin trapping with 5,5-dimethyl-1-pyrroline N-oxide (DMPO), coupled with electron paramagnetic resonance spectroscopy. In the presence of supercoiled pBR322 DNA, irradiation of thiazolethione 3 induces strand breaks through the photogenerated hydroxyl-radicals, as confirmed by control experiment with the hydroxyl-radical scavenger isopropanol, Singlet oxygen appears not to be Involved, as attested by the lack of a D2O isotope effect. During the photoreaction of thiazolethione 3 in the presence of 2'-deoxyguanosine (dG), the latter is photooxidized (ca 10% conversion after 2 h of irradiation) to the 7,8-dihydro-8-oxo-2'-deoxyguanosine as the main oxidation product. The dG conversion levels off after complete consumption of thiazolethione 3 and is suppressed by the addition of the hydroxyl-radical scavenger 2,6-di-tert-butyleresol or DMPO, Since the photoproducts 4-6 are ineffective as sensitizers for the photooxidation of dG and DNA, the hydroxyl radicals released in the photolysis of thiazolethione 3 are the oxidizing species of DNA and dG, These results suggest that the thiazolethione 3 may serve as a novel and effective photochemical hydroxyl-radical source for photobiological studies.

    DOI: 10.1562/0031-8655(2000)072<0619:NHCTHT>2.0.CO;2

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  • Sensitized irradiation of anthracene-benzene biplanemers: Formation of adducts of a benzvalene or a Dewar benzene with anthracene Reviewed

    Masaru Kimura, Hideki Okamoto, Zhi Zhi Hu, Setsuo Kashino

    ITE Lett. Batter. New Technol. Med.   2000

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  • Circular polarization of photochemiluminescence from the photoisomer of a conformationally fixed 2,11-diaza[3.3](9,10)anthracenoparacyclophane derivative Reviewed

    Hideki Okamoto, Harry P. J. M. Dekkers, Kyosuke Satake, Masaru Kimura

    Chemical Communications   ( 9 )   1049 - 1050   1998.5

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    The conformation of 2,11-diaza[3.3](9,10)anthracenoparacyclophane 1, which underwent photointerconversion with isomer 2, was fixed with the aid of a chiral camphanic auxiliary to have molecular chirality, and the photochemiluminescence from the modified 2a was circularly polarized reflecting the chirality of the emitting state.

    DOI: 10.1039/a801296b

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  • Adiabatic photocycloreversion of bridged benzene-anthracene biplanemers: Controlling of the efficiency of the excited product formation by auxiliary substituents on the side-chains Reviewed

    Hideki Okamoto, Kyosuke Satake, Masaru Kimura

    Chemistry Letters   ( 9 )   873 - 874   1997

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    The efficiency for excited product formation in the adiabatic photocycloreversion of bridged biplanemer 1 was controlled by the size of its side-chain substituents which changed the interchromophore distance in the photoproduct 2.

    DOI: 10.1246/cl.1997.873

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  • Rearrangement of bicyclo[2.2.2]octa-2,5-diene and bicyclo[3.2.2]nona-6,8-diene under the conditions of bromination Reviewed

    Kyosuke Satake, Kazuyuki Hikasa, Hajime Itoh, Hideki Okamoto, Masaru Kimura, Shiro Morosawa

    Bulletin of the Chemical Society of Japan   69 ( 2 )   453 - 457   1996

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    A reaction of electrophilic bromination of norbornadiene homologs such as bicyclo[2.2.2]octa-2,5-diene (4) and bicyclo[3.2.2]nona-6,8-diene (7) with bromine gave hitherto unknown skeleton rearranged dibromides. The rearrangement may proceed via a bromonium cation of starting diene to give bicyclo[3.2.1]octene or bicyclo[3.3.1]nonene skeleton in respective cases. The observed rearrangement reactions are also confirmed in 6,7-bis(methoxycarbonyl) derivatives of bicyclodiene 7 under similar conditions.

    DOI: 10.1246/bcsj.69.453

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  • A new ring contraction rearrangement of 2,5-and 3,6-di-tert-butyl-3H-azepines to pyridine derivatives Reviewed

    Kyosuke Satake, Koichi Takaoka, Michiaki Hashimoto, Hideki Okamoto, Masaru Kimura, Shiro Morosawa

    Chemistry Letters   ( 12 )   1129 - 1130   1996

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    A new ring contraction reaction giving pyridine derivatives from 3,6-and 2,5-di-tert-butyl-3H-azepines was observed by a successive treatment with bromine and aqueous K2CD3. A plausible mechanism via azatropilium cation for the rearrangement was discussed based on the product's distribution from respective 3H-azepines.

    DOI: 10.1246/cl.1996.1129

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  • Characterization of a Longicyclic (2,2,2,2) Conjugated π System in 1,4-Difluorobenzene-Naphthalene Biplanemer

    OKAMOTO Hideki, SATAKE Kyosuke, KIMURA Masaru

    Bull. Chem. Soc. Jpn.   68 ( 12 )   3557 - 3562   1995.12

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    The electronic absorption spectrum of a 1,4-difluorobenzene–naphthalene biplanemer 1 exhibited a characteristic absorption band around 290 nm. This was attributable to intramolecular charge transfer interaction between the longicyclic conjugated π system and the benzene chromophore. The oxidation potential of 1 was 1.70 V (vs. Ag/AgCl), which was lower than those of the related compounds in which one of the double bonds of 1 was hydrogenated. Thermally, the biplanemer 1 underwent facile Cope rearrangement, followed by dehydrofluorination, to give 1-(4-fluorophenyl)naphthalene and 2-(3-fluorophenyl)naphthalene.

    DOI: 10.1246/bcsj.68.3557

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  • Synthesis and Adiabatic Photochemistry of a 1,4-Difluorobenzene-Naphthalene Biplanemer. Reviewed

    Okamoto Hideki, Kimura Masaru, Satake Kyosuke, Morosawa Shiro

    Bull. Chem. Soc. Jpn.   66 ( 8 )   2436 - 2439   1993

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    A naphtalene-1,4-difluorobenzene biplanemer 1a has been prepared through the electrolytic oxidative didecarboxylation. The direct irradiation of 1a gave 1,4-difluorobenzene and excited naphthalene in both a singlet state (Φf = 0.098) and a triplet state (Φp = 0.029) at 77 K in EPA. In the triplet-sensitized reaction, the biplanemer 1a underwent intramolecular [2π+2π] cycloaddition to give a cage compound instead of the formation of the triplet naphthalene.

    DOI: 10.1246/bcsj.66.2436

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  • Detection and thermal properties of 1,4-Difluorobenzene-naphthoquinone Biplanemer: A new longicyclic π system Reviewed

    Masaru Kimura, Koji Sirasu, Hideki Okamoto, Kyosuke Satake, Shiro Morosawa

    Tetrahedron Letters   33 ( 46 )   6975 - 6978   1992.11

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    9,10-difluorotetracyclo[6.4.21,8.29,12.02,7]hexadeca-2,4,6,10,13,15-hexaene-3, 6-dione is thermally labile and shows a notably clear, long wave-length CT absorption. © 1992.

    DOI: 10.1016/S0040-4039(00)60910-3

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  • The Base-Catalyzed H/D-Exchange of Anisole Moiety of Ruthenium Complex in Cooperation with Demethylation by Hydroxide Anion in Methanol-d4

    Kimura Masaru, Morita Mitsunobu, Mitani Hideo, Okamoto Hideki, Satake Kyosuke, Morosawa Shiro

    Bulletin of the Chemical Society of Japan   65 ( 9 )   2557 - 2559   1992

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    [Ru(&eta;5-C5H5)(&eta;6-arene A)]BF4 (arene A = nitrobenzene, m- or p-nitrotoluene, anisole, phenetole, m- or p-methylanisole) were quantitatively converted to pure [Ru(&eta;5-C5H5)(&eta;6-arene B)]BF4 (arene B = phenoxido-2d m- or p-monodeuterated methylphenoxido) in the presence of excess KOH in CD3OD, whereas [Ru(&eta;5-C5H5)(&eta;6-anisole)] BF4 was quantitatively obtained by treatment [Ru(&eta;5-C5H5)(&eta;6-nitrobenzene)] BF4 with 1 equivalent KOH or CH3OK.

    DOI: 10.1246/bcsj.65.2557

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  • Synthesis and characterization of 2H-, 3H- and 4H-azepine: The first observation of the thermal distribution equilibrium of azepines Reviewed

    Kyosuke Satake, Ryoichi Okuda, Michiaki Hashimoto, Yasushi Fujiwara, Izumi Watadani, Hideki Okamoto, Masaru Kimura, Shiro Morosawa

    Journal of the Chemical Society, Chemical Communications   ( 17 )   1154 - 1156   1991

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    Demethoxycarbonylation of methyl 2,5,-di-tert-butyl-1H-azepine-1- carboxylate using 1,8-diazabicyclo[5.4.0]undec-7-ene gives exclusively two isomers of 3H-azepine derivatives, while methyl 3,6-di-tert-butyl-1H-azepine-1- carboxylate gives a mixture of 2H-, 3H- and 4H-azepine derivatives under the same conditions because of a 1,5-hydrogen shift in the resulting triene system.

    DOI: 10.1039/C39910001154

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  • A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties Reviewed

    Masaru Kimura, Hideki Okamoto, Hisatoshi Kura, Ayumi Okazaki, Eiji Nagayasu, Kyosuke Satake, Shiro Morosawa, Masayoshi Fukazawa, Hamzer Abdel-Halim, D. O. Cowan

    Journal of Organic Chemistry   53 ( 17 )   3908 - 3911   1988.8

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    Electronic oxidative bisdecarboxylation of photoadducts of 2,5-dihalo-1,2-dihydrophthalic anhydride and anthracene gave the corresponding energy-rich heterodimers 12 and 13. The quantum yields of the formation of the excited anthracene from 12 and 13 by the irradiation of 280-nm light were 0.65 and 0.25, respectively. We assumed that the heterodimers of 12 and 13 form biradicaloid intermediates during thermal retro [4πs + 4πs] cycloaddition and consumed their stored energy without any visible light. However, we observed emission light from 340 to 460 nm through a glass filter and the formation of anthracene using Nd-YAG laser IR light (1.06 μm) by the multiphoton absorption, when fine powders of 12 and 13 were used. © 1988, American Chemical Society. All rights reserved.

    DOI: 10.1021/jo00252a004

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  • Synthesis and photochemistry of 3, 6-difluoro-10,11-benzopentacyclo-[6,4,0.0&lt;sup&gt;2.7&lt;/sup&gt;,0&lt;sup&gt;3.12&lt;/sup&gt;.0&lt;sup&gt;6.9&lt;/sup&gt;]dodeca-4,10-diene Reviewed

    Masaru Kimura, Hisatoshi Kura, Kastumi Nukada, Hideki Okamoto, Kyosuke Satake, Shiro Morosawa

    Journal of the Chemical Society, Perkin Transactions 1   ( 12 )   3307 - 3310   1988

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    9,12-Difluoro-and 9,12-dichlorotetracyclo[6.4.2.2&lt
    sup&gt
    9.12&lt
    /sup&gt
    .0&lt
    sup&gt
    2.7&lt
    /sup&gt
    ] hexadeca-2,4,6,13,15-pentaene-10,11 -dicarboxylic anhydrides (2a) and (2b) were prepared by 4π&lt
    inf&gt
    s&lt
    /inf&gt
    + 4π&lt
    inf&gt
    s&lt
    /inf&gt
    is photocycloaddition between cis-3,6-difluoro-or cis-3,6-dichloro-1,2-dihydrophthalic anhydride and naphthalene, respectively. 12, 15-Difluoro-and 12, 15-dichlorohexacyclo [8.6.0.0&lt
    sup&gt
    2.15&lt
    /sup&gt
    .0&lt
    sup&gt
    3.8&lt
    /sup&gt
    .0&lt
    sup&gt
    9.12&lt
    /sup&gt
    .0&lt
    sup&gt
    11.16&lt
    /sup&gt
    ] hexadeca-3,5,7-triene-13,14-dicar-boxylic anhydrides (6a) and (6b) were obtained by 2π&lt
    inf&gt
    s&lt
    /inf&gt
    + 2π&lt
    inf&gt
    s&lt
    /inf&gt
    is intramolecular photocycloaddition of adducts (2a) and (2b), respectively. 12,15-Difluorohexacyclo[8.6.0.0&lt
    sup&gt
    2.15&lt
    /sup&gt
    .0&lt
    sup&gt
    3.8&lt
    /sup&gt
    .0&lt
    sup&gt
    9.12&lt
    /sup&gt
    .0&lt
    sup&gt
    11.16&lt
    /sup&gt
    ]hexadeca-3,5,7,13-tetraene (7a) has been synthesized by the electro-oxidative decarboxylation of anhydride (6a) and the excited singlet naphthalene has been observed on irradiation of adduct (7a), and is presumably formed via an adiabatic pathway. © 1988, The Royal Society of Chemistry.

    DOI: 10.1039/P19880003307

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  • Physics and Chemistry of Carbon-Based Materials

    Hideki Okamoto( Role: Contributor ,  Organic Chemistry of π-Conjugated Polycyclic Aromatic Hydrocarbons: Acenes and Phenacenes)

    Springer  2019.4 

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  • Light-Active Functional Organic Materials

    Hideki Okamoto, Yoshihiro Kubozono( Role: Contributor ,  10. Photochemical Synthesis of Phenacenes and Their Application to Organic Semiconductors)

    Jenny Stanford Publishing  2019.3 

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  • 光化学フロンティア : 未来材料を生む有機光化学の基礎

    水野, 一彦, 宮坂, 博, 池田, 浩( Role: Contributor ,  第5章光化学反応の有機合成への応用,5.2 ベンゼン類,かご型化合物の合成など)

    化学同人  2018.12  ( ISBN:9784759814194

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  • 光フロー反応を用いた高次フェナセンの効率的合成と有機半導体トランジスタへの応用

    岡本秀毅, 久保園芳博( Role: Contributor ,  第3章高移動度な有機半導体材料の開発 3節光フロー反応を用いた高次フェナセンの効率的合成と有機半導体トランジスタへの応用)

    技術情報協会  2017.10 

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  • 光と生命の事典

    日本光生物学協会光と生命の事典編集委員会, 日本光生物学協会( Role: Contributor ,  第1章光と生命の基礎,「光吸収による電子励起状態の生成」)

    朝倉書店  2016.2  ( ISBN:9784254171617

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  • 光化学の事典 = Encyclopedia of photochemistry

    光化学協会光化学の事典編集委員会, 伊藤, 紳三郎, 宍戸, 昌彦, 堀江, 一之, 真嶋, 哲朗( Role: Contributor ,  光と化学の基礎II-有機化学-様々な光化学反応(16),「脱離反応」)

    朝倉書店  2014.6  ( ISBN:9784254140965

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  • New Trends in Structural Organic Chemistry

    Research Signpost, Kerala  2005 

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MISC

  • N-Hをプロトンドナーとする励起状態分子内プロトン移動(ESIPT)蛍光色素の最近の展開 Invited

    岡本秀毅

    光化学   52   124 - 130   2021.12

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  • Organic field-effect transistors based on newly synthesized dibenzo[n]phenacenes (n = 5 - 7)

    ZHANG Yanting, EGUCHI Ritsuko, HAMAO Shino, GOTO Kenta, TANI Fumito, YAMAJI Minoru, KUBOZONO Yoshihiro, OKAMOTO Hideki

    応用物理学会春季学術講演会講演予稿集(CD-ROM)   68th   2021

  • フェナセン系薄膜電界効果トランジスタの論理回路応用

    三上隆弘, 江口律子, 下侑馬, 浜尾志乃, 後藤秀徳, 岡本秀毅, 林靖彦, 久保園芳博

    応用物理学会春季学術講演会講演予稿集(CD-ROM)   63rd   2016

  • フェナセン単結晶を用いた高性能電界効果トランジスタの作製及びその伝導特性

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    応用物理学会秋季学術講演会講演予稿集(CD-ROM)   76th   2015

  • フェナセン系薄膜電界効果トランジスタのデバイス構造の改変による伝導特性制御と論理回路応用

    三上隆弘, 下侑馬, 浜尾志乃, 江口律子, 後藤秀徳, 岡本秀毅, 久保園芳博, 林靖彦

    応用物理・物理系学会中国四国支部合同学術講演会講演予稿集   2015   2015

  • 多環フェナセン単結晶電界効果トランジスタの伝導特性と論理回路応用

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    応用物理・物理系学会中国四国支部合同学術講演会講演予稿集   2015   2015

  • フェナセン単結晶FETの特性と論理回路応用

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    日本化学会中国四国支部大会講演要旨集   2015   2015

  • 高性能フェナセン薄膜FETの開発と論理回路応用

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  • フェナセン系薄膜電界効果トランジスタの伝導特性評価と論理回路応用

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  • ベンゼンクロモフォアを持つシクロファンの光反応

    岡本秀毅

    光化学   45   2 - 8   2014.4

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  • 芳香族有機分子による超伝導体の開発

    久保園芳博, 神戸高志, 岡本秀毅, 藤原明比古

    ファインケミカル   40 ( 2 )   5 - 13   2011.1

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  • 22pGS-9 N-channel characteristics of picene thin film field-effect transistors

    Kawasaki N., Kaji Y., Komura N., Okamoto H., Kambe T., Ikeda N., Kubozono Y., Fujiwara A.

    Meeting abstracts of the Physical Society of Japan   65 ( 1 )   901 - 901   2010.3

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  • ピセン超伝導のメカニズム

    久保園芳博, 岡本秀毅, 神戸高志, 藤原明比古

    化学   65   52 - 57   2010

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  • 芳香族分子ピセン結晶における超伝導の発見(最近の研究から)

    久保園芳博, 神戸高志, 岡本秀毅, 藤原明比古

    日本物理学会誌   65   978 - 983   2010

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  • 27aYD-1 Carrier transport in heterojunction devices of C_<60>/picene and PCBH/picene

    Kawai N., Nagata T., Hamao S., Takahashi Y., Okamoto H., Takaguchi Y., Kubozono Y., Kambe T., Ikeda N.

    Meeting abstracts of the Physical Society of Japan   64 ( 2 )   769 - 769   2009.8

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  • 29pYG-6 Superconductivity of alkaline doped aromatic hydrocarbon

    Mitsuhashi R., Kubozono Y., Kawasaki N., Kambe T., Ikeda N., Okamoto H., Yamanari Y., Suzuki Y., Fujiwara A., Maniwa Y.

    Meeting abstracts of the Physical Society of Japan   64 ( 1 )   643 - 643   2009.3

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  • 29pYG-6 Superconductivity of alkaline doped aromatic hydrocarbon

    Mitsuhashi R., Kubozono Y., Kawasaki N., Kambe T., Ikeda N., Okamoto H., Yamanari Y., Suzuki Y., Fujiwara A., Maniwa Y.

    Meeting abstracts of the Physical Society of Japan   64 ( 1 )   847 - 847   2009.3

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    Language:Japanese   Publisher:The Physical Society of Japan (JPS)  

    CiNii Article

    CiNii Books

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  • 22aTB-10 Interface trap and hysteresis of transfer characteristics in picene field-effect transistor

    Kawasaki N., Kubozono Y., Fujiwara A., Okamoto H.

    Meeting abstracts of the Physical Society of Japan   63 ( 2 )   760 - 760   2008.8

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  • Preparation of a crown-ether modified isoluminol derivative and its chemiluminescence properties in an organic medium

    Hideki Okamoto, Masaru Kimura

    Bioluminescence & Chemiluminescence, Progress and Perspectives   183 - 186   2005

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Article, review, commentary, editorial, etc. (international conference proceedings)   Publisher:WORLD SCIENTIFIC PUBL CO PTE LTD  

    DOI: 10.1142/9789812702203_0043

    Web of Science

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  • 金属イオンの指令で光増感反応を制御する

    岡本秀毅

    化学と工業   2003

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  • バイプレンマー類の光化学発光とフォトクロミズム

    木村勝, 岡本秀毅

    ファインケミカル   28, 26-32   1999

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Presentations

  • ビアリル分子の固体発光と結晶構造の関連性について

    山路 稔, 岡本秀毅, 五島健太, 谷 文都

    2020年光化学討論会  2021.9.16 

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    Event date: 2021.9.14 - 2021.9.16

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • スルホンアミドをプロトンドナーとするフタルイミド類のESIPT蛍光特性

    多月あおい, 伊谷一将, 山路 稔, 岡本秀毅

    2020年光化学討論会 

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    Event date: 2021.9.14 - 2021.9.16

    Language:Japanese   Presentation type:Poster presentation  

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  • Organic field-effect transistors based on newly synthesized dibenzo[n]phenacenes (n = 5 - 7)

    Y. Zhang, R. Eguchi, S. Hamao, K. Goto, F. Tani, M. Yamaji, Y. Kubozono, H. Okamoto

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    Event date: 2021.3.16 - 2021.3.19

    Language:English   Presentation type:Oral presentation (general)  

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  • 分子⻑軸の両端にイミド部位を持つπ拡張フェナセン誘導体の合成研究

    吉岡海渡, 岡本秀毅

    2020日本化学会中国四国支部大会島根大会 

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    Event date: 2020.11.28 - 2020.11.29

    Language:Japanese   Presentation type:Poster presentation  

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  • Photochemical Synthesis of Picenes Incorporating Imide Moieties at the both Edges of the Molecule and their Application to n-Channel Field-Effect Transistors

    Yuxin Guo, Kaito Yoshioka, Shino Hamao, Yoshihiro Kubozono, Fumito Tani, Kenta Goto, Hideki Okamoto

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    Event date: 2020.10.20 - 2020.10.22

    Language:English   Presentation type:Poster presentation  

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  • 長鎖アルキル基を有するπ拡張フェナセンの合成: 高性能FET材料の開拓

    小笹景子, 浜尾志乃, 久保園芳博, 谷 文都, 五島健太, 岡本秀毅

    第10回CSJ化学フェスタ2020 

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    Event date: 2020.10.20 - 2020.10.22

    Language:Japanese   Presentation type:Poster presentation  

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  • 分子長軸の両端にイミド基を持つフェナセン誘導体の蛍光の溶媒応答

    𠮷岡海渡, 山路 稔, 五島健太, 谷 文都, 岡本秀毅

    2020年光化学討論会 

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    Event date: 2020.9.14 - 2020.9.16

    Language:Japanese  

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  • 炭素架橋および窒素架橋[3.3](ナフタレノファン類の合成,構造及び光反応

    大熊由貴子, 山本昌典, 太田弘道, 山路 稔, 岡本秀毅

    2020年Web光化学討論会 

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    Event date: 2020.9.9 - 2020.9.11

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  • 両端にドナーおよびアクセプター置換基を有する[7]ヘリセン誘導体の合成および電子スペクトル

    中塚智子, 岡本秀毅

    2020年Web光化学討論会 

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    Event date: 2020.9.9 - 2020.9.11

    Language:Japanese   Presentation type:Poster presentation  

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  • マルチクロモファー化による芳香族分子の発光特性への影響

    山路 稔, 岡本秀毅, 加藤真一郎

    2020年Web光化学討論会 

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    Event date: 2020.9.9 - 2020.9.11

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • ピセンジイミド誘導体の合成とn-型半導体特性

    𠮷岡海渡, 郭玉鑫, 浜尾志乃, 久保園芳博, 岡本秀毅

    日本化学会第100春季年会 

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    Event date: 2020.3.22 - 2020.3.25

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  • 高性能FET材料開拓を目指した長鎖アルキル基を有するπ拡張フェナセンの合成

    小笹景子, 浜尾志乃, 久保園芳博, 岡本秀毅

    日本化学会第100春季年会 

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    Event date: 2020.3.22 - 2020.3.25

    Language:Japanese   Presentation type:Poster presentation  

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  • 炭素架橋および窒素架橋[3.3](1,4)ナフタレノファンの合成と光反応

    大熊由貴子, 山本昌典, 山路 稔, 太田弘道, 岡本秀毅

    日本化学会第100春季年会 

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    Event date: 2020.3.22 - 2020.3.25

    Language:Japanese  

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  • 両末端にドナーおよびアクセプター置換基を有する[7]ヘリセン誘導体の合成

    中塚智子, 岡本秀毅

    日本化学会第100春季年会 

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    Event date: 2020.3.22

    Language:Japanese   Presentation type:Poster presentation  

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  • Blue Fluorescence from N,O-Coordinated BF2 Complexes with Aromatic Chromophores in Solution and Solid State

    Minoru Yamaji, Hideki Okamoto, Kenta Goto, Fumito Tani

    The 18th Asian Chemical Congress 

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    Event date: 2019.12.8 - 2019.12.12

    Language:English   Presentation type:Oral presentation (general)  

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  • Excited State Intramolecular Proton Transfer (ESIPT) Fluorescence Behavior of Amido-substituted Phthalimides and Naphthalimides

    Hideki Okamoto, Kazumasa Itani, Mayu Fujii, Lei Wang, Minoru Yamaji

    The 18th Asian Chemical Congress 

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    Event date: 2019.12.8 - 2019.12.12

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • Fluorescence behavior of amide derivatives of 2,3-naphthalimides and their responses to metal ions

    Lei Wang, Mayu Fujii, Misa Namba, Minoru Yamaji, Hideki Okamoto

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    Event date: 2019.11.16 - 2019.11.17

    Language:English   Presentation type:Oral presentation (general)  

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  • [3.3](1,4)ナフタレノファン類の合成と光反応

    大熊由貴子, 山本昌典, 岡本秀毅

    2020日本化学会中国四国支部大会島根大会 

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    Event date: 2019.11.16 - 2019.11.17

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  • 空間を通したドナー-アクセプター型[7]ヘリセン誘導体の合成研究

    中塚智子, 岡本秀毅

    2019年日本化学会中国四国支部大会徳島大会 

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    Event date: 2019.11.16 - 2019.11.17

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  • 末端にイミドを導入したピセン誘導体の合成研究

    𠮷岡海渡, 郭玉鑫, 浜尾志乃, 久保園芳博, 岡本秀毅

    第30回基礎有機化学討論会 

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    Event date: 2019.9.25 - 2019.9.27

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  • 高性能有機半導体材料の開拓を指向する3,12-ジテトラデシル[7]フェナセンの合成

    小笹景子, 浜尾志乃, 久保園芳博, 郷田慎, 岡本秀毅

    第30回基礎有機化学討論会 

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    Event date: 2019.9.25 - 2019.9.27

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  • Blue fluorescence from N,O-coordinated BF2 complexes having aromatic chromophores in solution and solid state

    Minoru Yamaji, Hideki Okamoto, Kenta Goto, Fumito Tani

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    Event date: 2019.9.10 - 2019.9.12

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  • Synthesis of Diimide Derivatives of Picene as New n-Type OFET Materials Through Photocyclization

    Yuxin Guo, Kaito Yoshioka, Shino Hamao, Yoshihiro Kubozono, Hideki Okamoto

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    Event date: 2019.9.10 - 2019.9.12

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  • Photochemical reactions of nitrogen-bridged [3.3](1,4)naphthalenophanes: Formation of naphthalene dimers and their structures Invited

    Hideki Okamoto

    The 12th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules 

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    Event date: 2019.8.30 - 2019.9.3

    Language:English   Presentation type:Oral presentation (invited, special)  

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  • Synthesis, Electronic Spectra, and Transistor Application of π-Extended Phenacenes Invited

    Hideki Okamoto, Yoshihiro Kubozono, Minoru Yamaji

    International Conference on Photocatalysis and Photoenergy 2019 

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    Event date: 2019.5.22 - 2019.5.25

    Language:English   Presentation type:Oral presentation (invited, special)  

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  • Fluorescence Behavior of Amino-substituted Phthalimides and The Related Compounds: Potential Probe for Micro-environment and Ionic Species Invited

    Hideki Okamoto

    9th Annual Basic Science International Conference 2019 

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    Event date: 2019.3.20 - 2019.3.21

    Language:English   Presentation type:Oral presentation (invited, special)  

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  • N-H型ESIPT蛍光を示す3-アミド置換フタルイミドの発光特性に及ぼすスルホンアミド置換基の効果

    伊谷一将, 山路 稔, 岡本秀毅

    日本化学会第99春季年会 

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    Event date: 2019.3.16 - 2019.3.19

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • Synthesis and Fluorescence Properties of Amino-substituted 1,8-Naphthalimides

    Lei Wang, Minoru Yamaji, Hideki Okamoto

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    Event date: 2018.11.17 - 2019.11.18

    Language:English   Presentation type:Poster presentation  

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  • Fluorescence Properties of Amino-substituted Phthalimides and the Related Compounds Invited

    Hideki Okamoto

    International Conference on Novel Functional Materials(ICNFM2018) 

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    Event date: 2018.9.16 - 2018.9.19

    Language:English   Presentation type:Oral presentation (invited, special)  

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  • π共役拡張フェナセンの光環化による合成と電子スペクトル特性

    岡本秀毅, 久保園芳博, 浜尾志乃, 郷田 慎, 杉野久子, 山路 稔

    2018年光化学討論会 

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    Event date: 2018.9.5 - 2018.9.7

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  • Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state

    Minoru Yamaji, Hideki Okamoto, Kenta Goto, Fumito, Tani

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    Event date: 2018.9.5 - 2018.9.7

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • フタルイミド誘導体のESIPT蛍光特性に及ぼすアミド置換基の効果

    伊谷一将, 山路 稔, 岡本秀毅

    2018年光化学討論会 

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    Event date: 2018.9.5 - 2018.9.7

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  • Preparation of Amino-substituted 1,8-Naphthalimide Derivatives and Their Fluorescence Properties

    Lei Wang, Minoru Yamaji, Hideki Okamoto

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    Event date: 2018.9.5 - 2018.9.7

    Language:English   Presentation type:Poster presentation  

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  • Photochemical synthesis and electronic spectra of extremely π-extended phenacenes Invited

    Hideki Okamoto

    The 11th Japan-Taiwan Bilateral Symposium on Architecture of Functional Organic Molecules 

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    Event date: 2018.8.25 - 2018.8.29

    Language:English   Presentation type:Oral presentation (invited, special)  

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  • Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state

    Minoru Yamaji, Hideki Okamoto, Kenta Goto, Fumito Tani

    The 11th Japan-Taiwan Bilateral Symposium on Architecture of Functional Organic Molecules 

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    Event date: 2018.8.25 - 2018.8.29

    Language:English   Presentation type:Oral presentation (invited, special)  

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  • 連続光フロー反応によるフェナセンの簡便合成と機能化フェナセンへの展開

    2017年日本化学会中国四国支部大会鳥取大会 

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    Event date: 2017.11.11 - 2017.11.12

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  • Fluorescence manipulation of amino- and amido-substituted phthalimides and naphthalimides based on ICT and ESIPT features Invited International conference

    Hideki Okamoto

    SYMPOSIUM ON ORGANIC AND APPLIED CHEMISTRY 2021  2021.12.22  Department of Chemistry,Faculty of Mathematics and Natural Sciences, Brawijaya University

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    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Online  

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  • Photochemical synthesis of phenacenes and the application to OFET devices

    The 2nd OU-SKKU Bilateral Symposium on Photofunctional Materials and Nanointerfaces  2019.11.25 

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  • 含窒素架橋を持つシクロファンの光化学反応 Invited

    岡本秀毅

    徳島大学ポストLEDフォトニクス研究所セミナー  2019.6.24 

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    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • Synthesis and photophysics of difluoroboron complexes

    The 10th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules  2017 

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  • Photochemistry of fluorine-substituted 2,11-diaza[32]paracyclophane

    The 10th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules  2017 

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  • 3-アミド置換フタルイミドの固体状態でのESIPT機構によるRGBY発光

    第28回基礎有機化学討論会  2017 

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  • Wittig反応-Mallory光環化シーケンシャルフロー合成によるフェナセン骨格の簡便かつ系統的な構築

    第28回基礎有機化学討論会  2017 

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  • ジフェニルフェナンスリルエテンから光環化反応により生成するベンゼン環7つからなる縮環化合物の研究

    2017年光化学討論会  2017 

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  • 固体中における3-アミド置換フタルイミドのESIPT蛍光

    2017年光化学討論会  2017 

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  • 3-アミド置換フタルイミドのESIPT機構を用いた蛍光カラーチューニング

    2017年日本化学会中国四国支部大会鳥取大会  2017 

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  • Synthesis of π-extended phenacenes by photocyclization of diarylethenes and their transistor application

    2017 Global Research Efforts on Energy and Nanomaterials (GREEN 2017)  2017 

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  • 光縮環法で作成したフェナセンをクロモファーとするボロンジケトン錯体の合成と光物理特性の研究

    2016年光化学討論会  2016 

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  • アミノナフタルイミド誘導体の合成と蛍光ソルバトクロミズム分子としての評価

    日本化学会第96春季年会  2016 

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  • 芳香核上にメトキシ基をもつ2.11-ジアザ[3.3]パラシクロファンの合成研究

    日本化学会第96春季年会  2016 

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  • Preparation of Extremely -Extended Phenacenes and Their Application to Organic Field-Effect Transistor

    日本化学会第96春季年会  2016 

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  • 架橋鎖に窒素原子を持つ[3.3](1,4)ナフタレノファンの光反応と生成物の構造

    日本化学会第96春季年会  2016 

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  • アミノ置換2,3-ナフタルイミドの蛍光挙動:媒体環境に応答するマルチカラー発光

    2016年光化学討論会  2016 

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  • アミノナフタルイミド誘導体の合成及び蛍光特性の評価

    第27回基礎有機化学討論会  2016 

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  • ベンゼン環上に置換基を有するアザシクロファンの合成と光化学特性に関する研究

    第27回基礎有機化学討論会  2016 

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  • 窒素架橋を有するナフタレノファンの光反応:分子内ナフタレン光二量化反応と生成物の構造

    第27回基礎有機化学討論会  2016 

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  • アミノナフタルイミド誘導体の合成および蛍光特性の評価

    第37回光化学若手の会  2016 

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  • マロリー光環化反応によるピセン骨格の形成に関する研究

    第37回光化学若手の会  2016 

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  • メトキシ置換ジアザ[3.3]パラシクロファンの合成研究

    第37回光化学若手の会  2016 

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  • Facile Synthesis of pi-extended phenacenes by the Mallory photocyclization and their application to organic field-effect transistor

    The 11th Korea-Japan Symposium on Frontier Photoscience  2016 

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  • Photochemical Synthesis and Photophysical features of Condensed Coumarin Derivatives Studied by Emission Measurements, Steady State and Laser Flash Photolyses

    26th IUPAC Symposium on Photochemistry  2016 

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  • Facile Synthesis of pi-extended phenacenes by the Mallory photocyclization and their application to organic field-effect transistor

    26th IUPAC Symposium on Photochemistry  2016 

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  • 置換基を有するアザシクロファンの光反応

    2016年日本化学会中国四国支部大会香川大会  2016 

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  • Wittig反応-Mallory光環化シーケンシャル合成によるフェナセン骨格の簡便な構築

    2016年日本化学会中国四国支部大会香川大会  2016 

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  • アミノ及びアミド置換ナフタルイミド誘導体の合成と蛍光特性の評価

    2016年日本化学会中国四国支部大会香川大会  2016 

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  • ベンゼンおよびナフタレンをコアにもつアザシクロファンの光化学反応

    2015年日本化学会中国四国支部大会  2015 

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  • 光フロー反応による高次フェナセンの効率的合成とOFETへの応用

    2015年日本化学会中国四国支部大会有機エレクトロニクスシンポジウム  2015 

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  • Preparation of Extremely -Extended Phenacenes by Mallory Homologation Strategy and Their Application to Organic Field-Effect Transistor

    International Symposium on Construction and Application of Functional Molecules/Systems  2015 

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  • 光フロー反応を用いるフェナセンの効率的合成

    近畿化学協会第68回フローマイクロ合成研究会  2015 

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  • ジピコリルアミノメチルレセプターを持つアントラセンジカルボイミドとアントラセンジカルボヒドラジドの合成および金属イオンに対する蛍光,化学発光応答

    2015年光化学討論会  2015 

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  • Fluorescence Properties of Trifluoroacetamido-substituted Phthalimides: Response to Halide and Alkali-Metal Ions Induced by 254-nm Photolysis

    The 11th Korea-Japan Symposium on Frontier Photoscience–2015  2015 

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  • ベンゼンおよびナフタレンをコアに持つアザシクロファンの合成

    日本化学会第95春季年会  2015 

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  • フロー法によるMallory光環化反応の効率化と置換ピセンの合成への展開

    日本化学会第95春季年会  2015 

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  • Photochemistry of Nitrogen-bridged Paracyclophanes: One-step Formation of Benzene Dimers

    Symposium on New ChemistryBased on Cyclophane and pi-Electronic molecules  2015 

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  • 窒素架橋を持つ[3.3]パラシクロファンの光化学反応:ベンゼン二量体の生成

    第3回有機光化学研究会  2015 

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  • 高性能フェナセン薄膜 FET の開発と論理回路応用

    2015年日本化学会中国四国支部大会  2015 

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  • アミノナフタルイミド誘導体の合成と蛍光特性

    2015年日本化学会中国四国支部大会  2015 

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  • メトキシ置換 2,11-ジアザ [3.3]パラシクロファンの合成研究

    2015年日本化学会中国四国支部大会  2015 

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  • 連続フローリアクタを利用したマロリー光環化による化学修飾フェナセンの合成

    2015年日本化学会中国四国支部大会  2015 

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  • Synthesis of Phenacenes by Photochemical Cyclization Reactions of Diarylethanes and Diarylethenes

    The 8th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules  2014 

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  • Synthesis of Phenacenes by Mallory Reaction: Comparison of Efficiencies by Batch and Flow Photolyses

    The 10th Korea-Japan Symposium on Frontier Photoscience–2014 (KJFP2014)  2014 

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  • Efficient Synthetic Flow Photoreaction: Facile Preparation of Phenacenes and Their Application to OFET

    The 10th Korea-Japan Symposium on Frontier Photoscience–2014 (KJFP2014)  2014 

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  • Mallory環化によるフェナセン類の合成:バッチ法とフロー法による反応効率の比較

    日本化学会第94春季年会  2014 

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  • テトラアザ[34](1,2,4,5)シクロファン誘導体の合成

    大阪府立大学21世紀科学研究機構分子エレクトロニックデバイス研究所第16回研究会  2014 

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  • フロー法によるMallory光環化反応の効率化と置換ピセンの合成

    大阪府立大学21世紀科学研究機構分子エレクトロニックデバイス研究所第16回研究会  2014 

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  • 光環化反応によるフェナセンの合成と高性能OFETへの展開

    大阪府立大学21世紀科学研究機構分子エレクトロニックデバイス研究所第16回研究会  2014 

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  • 光でつくるフェナセン:合成と電子材料への展開

    第15回日本写真学会アンビエント技術研究会  2014 

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  • 光縮環法を用いたアシルフェナセンの合成と光物理・光化学的性質の研究

    2014年光化学討論会  2014 

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  • ジアザパラシクロファンの光化学反応におけるベンゼンの二量化反応

    2014年光化学討論会  2014 

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  • Photophysical and Photochemical Processes of Excited Singlet and Triplet [3n]Cyclophanes (n = 2–6) Studied by Emission Measurements, Steady-state and Laser Flash Photolyses

    The 8th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules  2014 

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  • ベンゼン環上にフッ素置換基を持つジアザパラシクロファンの光化学反応

    2013年光化学討論会  2013 

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  • アレーン置換ジベンゾクリセンの電気化学的および分光学的特性

    第37回有機電子移動化学討論会  2013 

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  • Fluorescence properties of trifluoroacetamide substituted phthalimides

    The 9th Korea-Japan Symposium on Frontier Photoscience–2013 (KJFP2013)  2013 

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  • Photochemical Synthesis of [n]Phenacenes: 9-Fluorenone Sensitized Photocyclization of 1,2-Diarylethane

    The 9th Korea-Japan Symposium on Frontier Photoscience–2013 (KJFP2013)  2013 

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  • オキシカルボニル基を有するアゼピン誘導体の1,5-シグマトロピー転位

    2013年日本化学会中国四国支部大会  2013 

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  • トリフルオロアセトアミド置換フタルイミドの蛍光特性

    2013年日本化学会中国四国支部大会  2013 

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  • ピセンジカルボン酸エステルの簡便な合成と官能基変換

    2013年日本化学会中国四国支部大会  2013 

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  • フッ素置換アザシクロファンの光化学反応によるカゴ型ジエン生成とその構造及び反応性

    2013年日本化学会中国四国支部大会  2013 

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  • Mallory環化によるフェナセンの合成:光フローリアクタを用いる合成の効率化

    2013年光化学討論会  2013 

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  • Photoreaction of Fluorinated 2,11-Diaza[3.3]paracyclophane: Formation of Cage Diene Type Benzene Dimer

    The 9th Korea-Japan Symposium on Frontier Photoscience–2013 (KJFP2013)  2013 

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  • 2,11-ジアザ[3.3]パラシクロファンの光化学反応:p,p’-ジベンゼン骨格の生成

    2012年光化学討論会  2012 

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  • ジアザ[3.3]パラシクロファンの光化学反応によるp,p'-ジベンゼンの生成とその構造

    日本化学会第92春季年会  2012 

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  • ジアザ[3.3]パラシクロファンの光化学反応

    日本化学会第92春季年会  2012 

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  • 3-および4-アミノフタルイミドのペルフルオログルタリルアミド誘導体のアミド‐アミダート平衡に基づく蛍光特性操作

    2012年光化学討論会  2012 

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  • プロパン鎖でリンクさせたトリフルオロアセチルアミノフタルイミド二量体のハロゲン化物イオンおよび金属イオンに対する蛍光応答

    2012年光化学討論会  2012 

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  • ジピコリルアミノメチルレセプターを有する新規化学発光プローブの合成および金属イオン種に対する化学発光応答

    2012年日本化学会西日本大会  2012 

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  • 3,10-ピセンジカルボン酸エステルの簡便な合成

    2012年日本化学会西日本大会  2012 

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  • ベンゼン環上に置換基を有する 2,11-ジアザ[3.3]パラシクロファン誘導体の合成

    2012年日本化学会西日本大会  2012 

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  • 2 位に置換基を導入した2H-アゼピン誘導体の合成と反応

    2012年日本化学会西日本大会  2012 

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  • 2-アルキルアミノ-3H-アゼピン類の合成および反応性

    2012年日本化学会西日本大会  2012 

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  • 2-メトキシ-3H-アゼピン誘導体とグリニャール試薬の反応

    第23回基礎有機化学討論会  2012 

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  • 光化学反応によるフルミネン([6]フェナセン)の合成および電子スペクトル

    第23回基礎有機化学討論会  2012 

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  • ジアザ[3.3]パラシクロファンの合成,構造および光化学反応

    第23回基礎有機化学討論会  2012 

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  • Photochemical Synthesis and Properties of [n]Phenacenes (n= 3–6)

    7th Asian Photochemistry Conference 2012  2012 

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  • ジピコリルアミノメチルレセプターを有するアントラセンジカルボヒドラジドの合成および金属イオン種に対する化学発光応答

    2011年光化学討論会  2011 

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  • Preparation of Anthracenedicarboxylic-acid-derived Fluorescence and Chemiluminescence Probes Incorporating Dipicolylaminomethyl Receptors and Their Luminescence Responses to Metal Cations

    XXVth International Conference on Photochemistry  2011 

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  • アミンおよびアルコール存在下でのo-アルキルフェニルナイトレンの反応における温度依存性

    日本化学会第91春季年会  2011 

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  • ジピコリルアミノレセプターで修飾されたアントラセンジカルボン酸類縁体をルミノフォアとして用いるPETプローブの構築と発光特性

    日本化学会第91春季年会  2011 

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  • ベンゼン環上にメチル基を有するジアザ[3.3]パラシクロファン類の合成と光化学反応

    2011年光化学討論会  2011 

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  • 分子内電荷移動型蛍光色素を用いるマルチセンシングプローブの構築

    第5回有機π電子系シンポジウム  2011 

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  • 2-メトキシ-3H-アゼピン誘導体とアミン類の求核置換反応による2-アルキルアミノ-3H-アゼピン類の合成

    2011年日本化学会西日本大会  2011 

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  • メタノール存在下,p-トリメチルシリルニトロベンゼンとトリブチルホスフィンの反応

    2011年日本化学会西日本大会  2011 

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  • o-アルキルフェニルナイトレンの反応により得られる3-および7-アルキル-3H-アゼピンの生成比に与える温度効果

    第41回 複素環化学討論会  2011 

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  • ヘキサフルオロ[33](1,3,5)シクロファンの光化学反応:かご型ジエンの単離と反応

    2011年光化学討論会  2011 

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  • ニトロベンゼン誘導体から5-ホルミルペンタジエン酸の簡便合成法の開発

    2010年日本化学会西日本大会  2010 

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  • 2-置換2H-アゼピン誘導体の光および熱反応性

    2010年日本化学会西日本大会  2010 

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  • ジナフチルエタンの光化学反応:芳香族カルボニル化合物存在下での光照射によるピセン骨格生成

    2010年光化学討論会  2010 

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  • トリフルオロアセトアミド置換キノリン誘導体の亜鉛イオン及び 銅イオンに対する蛍光応答性スイッチング

    日本化学会第90春季年会  2010 

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  • アルコール及びアミン存在下におけるフェニルニトレンの反応

    日本化学会第90春季年会  2010 

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  • Facile Reaction Path to 3H-Azepine from Alkylphenylnitrene

    2010 PACIFICHEM  2010 

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  • Photo- and thermal reaction of 2-alkoxy and 2-alkylthio 2H-azepines

    2010 PACIFICHEM  2010 

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  • ジナフチルエタンの光増感反応によるピセン骨格生成

    第4回有機π電子系シンポジウム  2010 

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  • 3-メチル-3H-アゼピン誘導体の合成および理論計算と核磁気共鳴スペクトルよる配座解析

    2010年日本化学会西日本大会  2010 

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  • アントラセンジカルボキシイミドフルオロフォアを用いたPET センサーの合成と発光挙動

    2010年日本化学会西日本大会  2010 

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  • トリフルオロアセトアミド置換キノリンの蛍光挙動:アミド-アミデート平衡を利用した金属イオン応答スイッチング

    2010年日本化学会西日本大会  2010 

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  • フェムト秒レーザーパルスによるアントラセン光二量体の3光子分解反応

    2009年光化学討論会  2009 

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  • Fluorescence behavior of 3-trifluoroacetylamino derivative of phthalimide: Photochemically induced response to Li+/I- ion pair

    XXIVth International Conference on Photochemistry  2009 

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  • トリフルオロアセチルアミノフタルイミド誘導体の蛍光挙動:LiIに対する選択的光応答

    日本化学会第89春期年会  2009 

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  • 新規なアルキル置換3H-アゼピン類の合成ならびに反応性

    日本化学会第89春期年会  2009 

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  • 両端にホルミル基とカルボキシル基を持つブタジエン誘導体の簡便合成

    日本化学会西日本大会  2009 

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  • [3.3]パラシクロファンの光化学反応

    日本化学会西日本大会  2009 

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  • 2H-アゼピンの光反応挙動

    日本化学会西日本大会  2009 

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  • フェニルニトレンから誘導されるデヒドロアゼピンとアルコールの反応の立体効果

    第39回複素環化学討論会  2009 

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  • トリフルオロアセタミド置換フタルイミドの蛍光挙動:ハロゲン化物イオン及びイオンペアへの光応答

    2009年光化学討論会  2009 

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  • Fluorescence properties of 4-acetylamino derivatives of phthalimide: A potential halide-ion recognition probe

    XXIIth IUPAC Symposium on Photochemistry  2008 

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  • 1-ニトロナフタレン類とトリブチルホスフィンとの反応によるベンゾ縮環アゼピンの合成

    2008年日本化学会西日本大会  2008 

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  • 2-Alkoxy-2H-Azepineの合成及びその化学反応性

    2008年日本化学会西日本大会  2008 

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  • ピコリルアミノレセプターを持つフタリドの合成と金属イオンへの蛍光応答

    2008年光化学討論会,  2008 

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  • 4-アミノフタルイミドのトリフルオロアセトアミド誘導体のヨウ化物イオンに対するケイ光応答

    2008年光化学討論会,  2008 

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  • Friedel-Crafts Reaction of Delocalized Azepinium Ions with Benzene and Five-Membered Aromatic Heterocycles

    23rd European Colloquium on Heterocyclic Chemistry (ECHC08)  2008 

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  • ハロゲン化物イオンを見分けるプローブ:4-トリフルオロアセチルアミノフタルイミドのケイ光挙動

    第4回分子情報ダイナミクス研究会  2008 

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  • Preparation and photoproperties of (aza)n[3n]cyclophanes (n = 2,3)

    ICP2007―XXIII International Conference on Photochemistry  2007 

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  • 1,8-ナフタルイミドのトリフルオロアセトアミド誘導体の蛍光挙動

    光化学若手の会  2007 

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  • ゼオライト細孔中の共存カチオンによる4-acetylbiphenylの光物性への影響

    日本化学会内87春季年会  2007 

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  • 固体型色素増感太陽電池に用いる光増感シアニン色素の合成と評価

    2007年日本化学会西日本大会  2007 

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  • ニトロ基を持つアリール化合物類とトリブチルホスフィンとの反応性の検討

    2007年日本化学会西日本大会  2007 

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  • Exploration of a Shortcut Approach to Diazepine Derivatives from Nitropyridines

    2007年日本化学会西日本大会  2007 

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  • モノアザトリエン共役をもつアゼピン誘導体の光反応挙動の研究

    2007年日本化学会西日本大会  2007 

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  • 4-(トリフルオロアセチルアミノ)フタルイミド誘導体のハロゲン化物イオン対するケイ光応答

    2007年日本化学会西日本大会  2007 

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  • 2H-及び3H-Azepine誘導体の合成及びその化学反応性の検討

    2007年日本化学会西日本大会  2007 

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  • ゼオライト細孔内における4-acetylbiphenylの光物性に対する共存金属イオンの効果

    2007年光化学討論会  2007 

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  • ジアザ[32]-およびトリアザ[33]シクロファンのトリフルオロアセトアミド誘導体の合成と光反応挙動

    2007年光化学討論会  2007 

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  • Photochemistry of nitrogen-bridged cylophanes(依頼講演)

    3rd International Workshop on Molecular Information and Dynamics  2007 

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  • A Trifruoroacetamide Derivative of 1,8-Naphthalimide As Solvent And Metal-Ion Sensitive Fluorophore

    XXIst IUPAC Symposium on Photochemistry  2006 

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  • アゼピニウムイオンのフリーデル・クラフツ反応および反応生成物の挙動について

    日本化学会西日本大会  2006 

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  • ジアザパラシクロファン誘導体の合成と光反応:ベンゼン光二量化の新しい反応モード

    2006年光化学討論会  2006 

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  • ジアザシクロファン類の光反応(依頼講演)

    第28回光化学若手の会  2006 

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  • 両末端にソルバトフルオロクロミズム性色素を持つポダンドのケイ光挙動

    2005年光化学討論会  2005 

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  • 1,8-ナフタルイミドトリフルオロアセトアミド誘導体のケイ光特性:自発的プロトン解離に基づく発光挙動

    2005年光化学討論会  2005 

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  • 溶媒駆動によるケイ光操作

    第27回光化学若手の会  2005 

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  • クラウン化アミノフタルイミド誘導体の蛍光特性とロジックゲート動作

    日本化学会第85春季年会  2005 

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  • 1,8-ナフタルイミドアセトアミド誘導体のケイ光特性:アルコール中における白色LED類似の発光スペクトル

    第20回シクロファン研究会  2005 

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  • アザクラウン化イソルミノールの合成と化学発光挙動

    化学発光生物発光研究会第23回学術講演会  2005 

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  • 2個の化学発光部位を有するイミダゾール類の化学発光

    2005年光化学討論会  2005 

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  • Photochemistry via a Triplet Exciplex between an Aromatic Triplet and a Ground-State Ketone

    XXth IUPAC Symposium on Photochemistry  2004 

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  • 新規なアザトロピリウムイオンと芳香族化合物の求電子反応

    第34回複素環化学討論会  2004 

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  • 三重項励起錯体を経由するジナフチルエタンの光化学反応過程の研究

    2004年光化学討論会  2004 

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  • ヘキサプリズマン骨格合成-[4 + 4]光環化付加の反応条件の最適化-

    2004年光化学討論会  2004 

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  • アザクラウン化フタルイミドの合成とケイ光挙動:ソルバトフルオロクロミズムと金属イオン応答を示すケイ光センサー

    2004年光化学討論会  2004 

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  • Preparation of a crown-ether modified isoluminol derivative and its chemiluminescence properties in an organic medium

    13th International Symposium on Bioluminescence and Chemiluminescence  2004 

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  • 2,11-ジアザ[3,3](9,10)アントラセノパラシクロファン誘導体の光化学

    第18回シクロファン研究会  2003 

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  • 2,11-ジアザ[3,3](9,10)アントラセノパラシクロファン光異性体の三重項光増感反応

    2003年光化学討論会  2003 

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  • 共役アゼピニウムイオンの合成と求電子反応性

    第33回複素環化学討論会  2003 

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  • Preparation and chemiluminescent properties of an isoluminol having an azacrown ether function

    XXIst International Conference on Photochemisry  2003 

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  • 化学発光を操作するための新しい試み

    第25回光化学若手の会in筑波  2003 

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  • クラウンエーテルで機能化したイソルミノール誘導体の合成と化学発光挙動

    日本化学会第83春季年会  2003 

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  • アントラセノパラシクロファン誘導体の光反応:アントラセンとベンゼンクロモフォア間の[4+4]光付加・解離過程

    第24回光化学若手の会in大阪  2002 

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  • 2-メトキシ-3H-アゼピン誘導体と臭素およびNBSとの反応

    日本化学会第81春季年会  2002 

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  • 2-アルコキシ-及び2-アルキルチオ-2H-アゼピン類の合成と反応性

    日本化学会第81春季年会  2002 

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  • クラウンエーテル機能をもつ2,4,5-トリフェニルイミダゾール誘導体の金属イオンによる化学発光特性モジュレーション

    日本化学会第81春季年会  2002 

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  • 2H-アゼピン環で観測される水素原子及びアルキルチオ基の[1,5]シグマトロピー転位

    第32回複素環化学討論会  2002 

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  • 化学発光操作の新しい手法:クラウン機能化ロフィンペルオキシドの化学発光挙動

    2002年日本化学会西日本大会  2002 

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  • エチレンジアミンホスト機能を持つパラシクロアントラセノファン誘導体のフォトクロミズム

    2002年光化学討論会  2002 

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  • Chemiluminescence of a lophine peroxide having a crown-ether function: A novel guest-sensitive chemiluminophore

    XIXth IUPAC Symposium on PhotochemistryJuly  2002 

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  • クラウンエーテルで機能化されたロフィンペルオキシドの生成とその化学発光制御

    日本化学会第79春季年会  2001 

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  • N-Hydroxy- and N-Alkoxythiazole-2(3H)-thiones as Novel Photo-Fenton Reagents: Photo-induced Oxyl-radical Release and DNA Strand Breaks

    光化学討論会  2001 

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  • Reaction of 2-methoxy-5-tert-butyl-3H-azepine with sodium alkoxyde and alkyllithium

    18th International Congress of Heterocyclic Chemistry  2001 

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  • [3.3]パラシクロ(9,10)アントラセノファン誘導体とその光異性体の発光挙動

    1999年光化学討論会  1999 

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Awards

  • 岡山工学振興会科学技術賞

    2015  

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    Country:Japan

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  • 有機合成化学協会中国四国支部奨励賞

    2007  

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    Country:Japan

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  • ITE Research Award

    2003  

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Research Projects

  • Development of high-performance semiconductor molecules utilizing molecular and electronic skeletons of phenacenes

    Grant number:20K05648  2020.04 - 2023.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

    岡本 秀毅, 山路 稔

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    Grant amount:\4290000 ( Direct expense: \3300000 、 Indirect expense:\990000 )

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  • 光縮環法を駆使した有機超伝導・半導体創製から有機EL発光素子開発への展開

    Grant number:18H02043  2018.04 - 2021.03

    日本学術振興会  科学研究費助成事業 基盤研究(B)  基盤研究(B)

    山路 稔, 岡本 秀毅

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    Grant amount:\17290000 ( Direct expense: \13300000 、 Indirect expense:\3990000 )

    我々は前駆体に光を照射するだけでベンゼン環がジグザグに配列した高純度なフェナセン類を簡便に合成する方法を見いだした。通常の有機合成では作成が難しいフェナセン類もこの光反応を用いれば容易に合成が可能な化合物もあり、この方法により創製された化合物で新しい物性発現が期待される。目的のフェナセンをこの光反応で作製するときに重要な点は主に二つある。一つは前駆体の設計である。光励起状態で環化反応が進行するため、励起状態のある程度の寿命が(数ナノ秒以上)必要なため、励起状態の短寿命化を避けるような分子設計が必要である。もう一つは光環化反応の高効率化である。ベンゼン環数が6以上のフェナセンを光縮環法で作成する場合、基本的にベンゼン環数が3-5個であるフェナセン誘導体(本研究では基本ユニットと呼ぶ)を組み合わせて作成しなければならない。このため高次フェナセンを効率良く作成するためには、大量の基本ユニットを準備する必要がある。基本ユニットはこれまでのバッジ処理による光縮環では効率が大きくない(約50%)ことが問題であった。我々はこの基本ユニット作成効率の向上のため、マイクロ流路光反応装置を考案し、作成効率を100%近くまで向上させることに成功している。このように作成したフェナセン部位を発光性分子のクロモファーに導入すると、発光量子収支が向上するという知見を得ている。これらの実績を踏まえて今年度は以下の成果を得た。
    我々は窒素と酸素原子で配位したジフロロボロン錯体を新規に創製し、固体と溶液状態で発光効率が全く異なることを発見している。今年度は、この錯体のクロモファーをフェナセンに置換した配位子を作製し、その光物性と結晶構造との関連性を研究した。固体、溶液中いずれも高効率で青色発光を示し、結晶構造との関連性を明らかにした。有機ELデバイスの青色発光層への応用の可能性を示すことが出来た。

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  • フェナセンを拡張πモチーフとして活用する有機エレクトロニクスへの挑戦

    Grant number:17K05976  2017.04 - 2021.03

    日本学術振興会  科学研究費助成事業 基盤研究(C)  基盤研究(C)

    岡本 秀毅, 山路 稔

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    Grant amount:\4680000 ( Direct expense: \3600000 、 Indirect expense:\1080000 )

    (1)長鎖アルキル基を持つπ拡張フェナセンのFET挙動:分子長軸方向に長鎖アルキル鎖を有する[7]フェナセン(C14[7]フェナセン)の構造解析と薄膜電界効果型トランジスタ(FET)挙動の詳細を検討した.薄膜中でC14[7]フェナセンは,FET動作に有効な配列を持ち,長鎖アルキル鎖を持たない母体[7]フェナセンに比べて高い電荷移動度を示した.長鎖アルキル鎖によって,薄膜中においてFET動作に有利なC14[7]フェナセンの分子配列が実現されたためと考えられる.また,走査型トンネル顕微鏡(STM)で金属表面に吸着されたC14[7]フェナセンの分子構造と分子配列の詳細を観測することにも成功した.
    (2)フェナセンFETの評価:低電圧で駆動する[5]~[7]フェナセンのp-型FETを構築できることを示した.これらのデバイス中で,π系が拡張するに従って移動度は向上する傾向が観測された.これは,フェナセンの分子間π系相互作用が高まるためと考えられる.
    (3)イミド部位を持つピセンの合成とFET挙動:分子の両末端にイミド部位を導入したピセン誘導体(PicDI)を4ステップで簡便に合成した.固体中での分子間相互作用を制御する目的で,イミド部位のアルキル鎖長を変えた誘導体を合成した.フェナセン分子の短軸方向にイミドを持つ誘導体の合成例はあるが,長軸方向にイミド部位をを持つ誘導体の合成は初めてである.溶液中でPicDIはアルキル鎖長に依存しない電子スペクトルを示したが,固体中では,アルキル鎖長の違いによって異なる電子的挙動を示した.PicDIの薄膜FETはn-型で作動し,イミド部位のアルキル鎖がオクチル基の場合に最も高い電荷移動度を観測した.

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  • Studies of condensed aromatic compounds having super- and semi-conductivity produced by efficient photochemical methods.

    Grant number:26288032  2014.04 - 2017.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)  Grant-in-Aid for Scientific Research (B)

    Yamaji Minoru, KUBOZONO YOSHIHIRO

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    Grant amount:\16900000 ( Direct expense: \13000000 、 Indirect expense:\3900000 )

    Organic synthesis of fused aromatic compounds of a large number of the benzene ring requires multistep synthetic procedures whereas photocyclization process of corresponding ethene precursors is a facile procedure for synthesizing them. In advance of the main study, we made a flowphotoreactor that achieves efficient photocyclization. By using this instrument, we synthesized small phenacene derivatives, such as phenanthrene, chrysene and picene, with the bromomethyl and formyl groups at various substituted positions used as the basic chromophores for the following photocyclization of diarylethenes. We prepared various diarylethenes, and carried out their photocyclization to obtain a variety of cyclized aromatic compound. Photophysical properties of compounds were studied based on emission and transient absorption measurements as well as the single crystal structures by X-ray crystallography. The electronic properties as semiconductor and electroluminescence devices were examined.

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  • Photochemical conversion of small aromatic chromophores into polycyclic frameworks

    Grant number:24550054  2012.04 - 2015.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

    OKAMOTO Hideki, YAMAJI Minoru

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    Grant amount:\5590000 ( Direct expense: \4300000 、 Indirect expense:\1290000 )

    Photochemical conversion of small aromatic chromophores, e.g. benzene, naphthalene, phenanthrene, etc., into polycyclic frameworks have been investigated.
    (1) For the photoreaction of azacyclophanes incorporating two benzene chromophores, benzene photodimerization took place to afford various polycyclic skeletons. Depending on the substituents on the benzene rings, we have observed formation of p,p'-dibenzene, octahedrane, and cage diene benzene dimers. Relative energies of the benzene dimer were evaluated by theoretical calculation to have insight into the substituent effects.
    (2) Diarylethenes, incorporating benzene, naphthalene, or phenanthrene chromophores, were converted into polycyclic aromatic frameworks, namely phenacenes in which the benzene rings were fused in a zigzag array. By applying a continuous flow photoreaction technique, various phenacenes were successfully synthesized with high chemical yield.

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  • Research for fused aromatic molecules potential for super- and semi-conductors prepared by the photosensitizing condensation method

    Grant number:23350059  2011.04 - 2014.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)  Grant-in-Aid for Scientific Research (B)

    YAMAJI Minoru, OKAMOTO Hideki, KUBOZONO Yoshihiro

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    Grant amount:\19110000 ( Direct expense: \14700000 、 Indirect expense:\4410000 )

    Chemical formation of fused aromatic compounds requires a variety of steps and efforts. We have found a new method for synthesizing pure condensed aromatic compounds by UV light irradiation in solution. With this method, we have prepared polyaromatic fuzed compounds and five-membered aromatic compounds containing oxygen, nitrogen and sulfur atoms. Photophysical and photochemical properties of these compounds have been revealed for utilizing them as efficient luminescent materials. For the aim of applying them to electronic materials such as an electron transfer layer in field-effect transistors (FET), the electron mobility was measured. The photochemical mechanism of the photocondensation method was investigated by using laser flash photolysis techniques.

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  • Study on aromatic hydrocarbon superconductors

    Grant number:22244045  2010.04 - 2015.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (A)  Grant-in-Aid for Scientific Research (A)

    KUBOZONO YOSHIHIRO, KAMBE Takashi, IWASA Yoshihiro, OKAMOTO Hideki

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    Grant amount:\46540000 ( Direct expense: \35800000 、 Indirect expense:\10740000 )

    The first discovery of superconductivity in solids of metal doped aromatic hydrocarbons was made for K-doped picene (Kxpicene). Its superconducting transition temperatures (Tc's) were 7 and 18 K. During this project, we pursued to make new superconductors using aromatic hydrocarbons. Various techniques such as high-temperature annealing method, liquid ammonia method, and electrochemical process were used for metal doping. The superconducting phases of Kxpicene and Rbxpicene exhibiting more than 10% superconducting fraction were successfully prepared in this project. The zero-resistance was confirmed in Kxpicene. With applying pressure, the Tc of 7 K phase of Kxpicene monotonically decreased, while the Tc's of 14 and 18 K phases increased, implying that 14 and 18 K phases are non-BCS type. Furthermore, superconductors were fabricated by doping various types of phenacene molecules with metals. The chemical composition and crystal structures of superconducting phases were investigated.

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  • Development of Luminescent Chemosensors Displaying Switching of Analyte-sensitivity

    Grant number:21550134  2009 - 2011

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

    OKAMOTO Hideki

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    Grant amount:\4810000 ( Direct expense: \3700000 、 Indirect expense:\1110000 )

    Luminescent material displaying a specific response, such as changes in luminescence intensity and color, toward an analyte is useful to detect the analyte(referenced as chemosensor). Most conventional chemosensors respond to one analyte. Thus, when we detect two(or more) analytes, we need to use plural receptors responding to each analyte. In the present study, we have developed intelligent chemosensors which display switching of responses to analytes. By utilizing amide functionalities, which shows amide. amidate equilibrium, analyte sensitivity of luminescent sensors to various ionic species and ion pairs were able to be controlled.

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  • Construction of multi-color, multi-sensing fluorescent probes with a single chromophore

    Grant number:19550141  2007 - 2008

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

    OKAMOTO Hideki

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    Grant amount:\3900000 ( Direct expense: \3000000 、 Indirect expense:\900000 )

    トリフルオロアセチルアミノ基を持つフタルイミドおよび, ナフタルイミド誘導体はアミドプロトンの解離により単一クロモフォアでマルチカラー発光を示すことを見いだした. このプロトン解離は, I-と紫外光照射でも誘起される意外な現象を発見し, I-検出および生成したアミドアニオンの陽イオンへの応答により, マルチセンシングの可能性が示された. また, 6-アミノフタリドにピコリルアミノレセプターを導入し, アミノフタリド色素を持つ初めてのセンサーを合成することができた.

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  • ホスト機能をもつ外部指令感応型化学発光性色素の構築とその発光制御

    Grant number:13740398  2001 - 2002

    日本学術振興会  科学研究費助成事業 若手研究(B)  若手研究(B)

    岡本 秀毅

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    Grant amount:\2200000 ( Direct expense: \2200000 )

    1.「化学発光物質にホスト機能を導入し,ゲストを指令物質として能動的に化学発光を制御する」という新しい概念に基づき,外部指令感応型化学発光性色素の設計と発光操作に関する研究を行った.
    2.化学発光性色素としてロフィンペルオキシドおよびイソルミノール用い,それぞれをアザ-15-クラウン-5-エーテルで修飾してホスト機能を持つ化学発光物質を合成した.クラウンホスト機能を持つ化学発光物質は本研究で初めて合成された.
    3.クラウン機能化ロフィンペルオキシド(化合物1)は塩基の添加により黄色の化学発光を示した.アルカリあるいはアルカリ土類金属イオンの存在下に化合物1の化学発光挙動を検討したところ,発光強度は金属イオンのない場合に比べて,ナトリウムイオン存在下で約150%,マグネシウムイオン存在下では70%で,金属イオンの指令に応答して化合物1の化学発光強度が変化することがわかった.化合物1の発光強度は,リチウム,カリウム,カルシウム,バリウムイオンにほとんど影響を受けず,ナトリウムとマグネシウムイオンに対して特異的に応答することを見いだした.また,化合物1の化学発光の発光極大はナトリウムイオンにより約50nm短波長へシフトすることも観測され,発光強度のみならず発光波長も指令物質により操作できる可能性を見いだした
    4.クラウン機能化ロフィンペルオキシド(化合物2)は塩基性過酸化水素中,アルカリ金属イオンヨウ化物の添加で,青色の化学発光を示した.化合物2においては化学発光強度に対する金属イオンの効果は化合物1より顕著で,カリウムイオンに対して特異的に応答し,リチウムあるいはナトリウムイオンに比べ発光強度が600〜700%へ増大した.
    5.本研究で,当初計画した分子設計により外部指令に応答する化学発光性色素の構築とゲストによる化学発光操作が可能であることが明らかとなった.

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  • バイプレンマーを用いた光応答性光信号放出システムの構築

    Grant number:08740546  1996

    日本学術振興会  科学研究費助成事業 奨励研究(A)  奨励研究(A)

    岡本 秀毅

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    Grant amount:\1000000 ( Direct expense: \1000000 )

    バイプレンマー(芳香族化合物の4+4型付加体)の光化学発光を利用した光応答性光信号放出システムの構築に関して以下の知見を得た.
    1.合成と光反応
    アントラセンとベンゼンをC-N-C3原子の架橋鎖で結合することでバイプレンマー型1とシクロファン型2の光相互変換が可能であった.1のC-S-C3原子又はC-C2原子架橋誘導体では光相互変換が起こらず表題分子素子として作用しない.ナフタレンとアントラセンを2と同様にシクロファン型に結合させた誘導体4では相当するバイプレンマー3を与えるが,3→4の光反応過程に副生成物が存在し光機能素子としては有望でない.ベンゼンとナフタレンの組合せではシクロファン→バイプレンマーの光変換が起こらず表題システムとして作用しない.
    2.光化学発光挙動
    (1)1の光反応で光化学発光が起こることを初めて見いだし,表題分子素子として有望であることが判った.1の光化学発光量子収率は当初予想していなかった側鎖置換基の立体効果を鋭敏に反映し発光効率が制御できた.置換基の嵩高さが増すほど励起生成物生成の効率が高まった.この置換基効果は2→1の逆反応もコントロールできることが知られており,バイプレンマーの光情報素子としての光応答性を制御する重要な因子となることを明らかにした.
    (2)1の光化学発光は直線偏光の励起に対し完全に直交していることが判明し,1の光化学発光による偏光面変換素子の可能性が示された.また1の側鎖上に光学活性な置換基を導入するとC_2対称の分子不斉を持つ1'となり,1'とその光異性体2'の分子不斉に基づく円偏光の偏光面変換の可能性についても現在検討中である.
    (3)C_2対称の1',2'は光化学発光性を保っているのみならず,1'と2'で円2色性,偏光度が変化し,複数の光物性を同時に制御できる多機能記憶-光物性読出素子として有望なモデルとなることが判った.

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  • ヘテロダイマーの固相化学発光反応に及ぼす結晶構造の影響の解明

    Grant number:06854034  1994

    日本学術振興会  科学研究費助成事業 奨励研究(A)  奨励研究(A)

    岡本 秀毅

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    Grant amount:\900000 ( Direct expense: \900000 )

    表題化合物1のエステル誘導体1a;(CO_2Et)_2、カルボン酸1b;(CO_2H)の固相熱分解により化学発光を確認した。モノエステル1c;(CO_2Me)、ハロゲン誘導体1d;(ハロゲン=F or Cl)では化学発光は観測されなかった。固相熱分解を示差走査熱分析(DSC)により追跡しフリードマン法により熱力学解析した結果、次の二点が明らかになった。i)化学発光性の1abでは非化学発光性の1cdよりエネルギー放出量が約10kcalmol^<-1>大きい。ii)活性化エネルギーは1bで反応率に依らず一定、1cでは反応の進行と共に小さくなった。結晶の1aではDSCで二つのピークを示し、低温ピーク、高温ピークはそれぞれ1b、1cと同様の挙動を示した。粉末の1aは化学発光はなくなり、1cと同様のDSC挙動を示した。以上より非化学発光性の1c、粉末の1aはゆるい結晶構造を有し、反応のエネルギーが結晶格子の構造変化に消費され発光はない、一方、1b、結晶の1aは強固な結晶構造を持ち、放出されたエネルギーが構造変化に使われず効率よく光エネルギーへ変換されると結論できる。1は熱的に不安定であるが、1aについてX線構造解析に成功した。1aの結晶中ではエステル基が柱のように配向し個々の分子が独立した結晶構造を形成する。当初、近隣分子士志の相互作用により生成系に安定な励起錯体を形成可能な構造があると予想したが、隣接分子同士の振動、衝突あるいは電子的相互作用によるエネルギー消費が少ない構造を持つことがわかった。本研究により1の固相化学発光において、強固な結晶構造が反応エネルギーを保存し、また、近接分子との相互作用を抑制することにより、光エネルギーへ変換する場を形成していることが明らかになった。DSC法を化学発光反応に初めて適用しエネルギー変換場としての結晶の影響解明に有効であることを示した。

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  • Measurement of Quantity of Heat and Thermodynamical Prameters for the Chemiluminescent Cycloreversion specific in the Solid State

    Grant number:05453022  1993 - 1995

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for General Scientific Research (B)  Grant-in-Aid for General Scientific Research (B)

    KIMURA Masaru, OKAMOTO Hideki, SATAKE Kyousuke

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    Grant amount:\5000000 ( Direct expense: \5000000 )

    We have investigated a thermally forbidden ring fission or ring opening reaction of biplanemers ([4+4] heterodimers of arenes) 1, lophine peroxides 2 and cyclobuta [b] pyroles 3 which are an energy rich system. The chemiluminescent thermal cycloreversion of 9-anthracenecarboxylic acid-benzene biplanemer and the chemiluminescent multiphoton cycloreversion of anthracene- p-difluoro-benzene biplanemer with Nd-Yag IR laser light gave off chemiluminescent light only in the solid phase. As there has not been any attempt to reveal the determinants in the solid state for the chemiluminescence from thermodynamical view points, this prompted us to collect the thermodynamic parameters by differential scanning calorimetry (DSC). In the cases of 1, two substantial exothermal processes are superimposed for the chemiluminescent crystals, whereas one main exothermal process is observed for a nonchemiluminescent powder sample. The thermodynamic parameters for the thermal cycloreversions were collected. Higher activation energy is characteristic of the chemiluminescent process prepared in the solid phase. Efficient chemiluminescence was observed in the thermal reaction of lophineperoxides 2 in both solid and liquid phases. Virtually same activation energies were obtained. The kinetic and thermochemical study of thermal ring opening reaction of 3,5- and 2,4-di-tert-butyl-3a, 5a-dihydro-3H-cyclobuta- [b] pyroles 3a and 3b to the corresponding di-tert-butyl substituted azepines was performed in the solid state, and provided activation energies 12 kcal/mol and 24 kcal/mol, respectively.

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  • 光環化付加反応に対する過塩素酸リチウムの特殊効果並びに高圧効果

    Grant number:04640502  1992

    日本学術振興会  科学研究費助成事業 一般研究(C)  一般研究(C)

    木村 勝, 岡本 秀毅, 佐竹 恭介

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    Grant amount:\1900000 ( Direct expense: \1900000 )

    トランスケイヒ酸骨格の典型的な光化学反応形式はシス体への異性化と[2+2]型の光2量化反応である。この光2量化反応のトポロジー規制効果をみるために、トランスケイヒ配部をポリエチレングリコール鎖の両末端につけた1__〜を合成し、鎖=Rの長さをかえたリアルカリカチオンの取り込み能を利用することでトポロジー効果を観察した。1__〜の三重項増感反応で、LiclO_4を加えた場合β-トルキシル酸のクラウン誘導体とともにアリールテトラリン骨格も得られた。特にアリールテトラリン2__<_>はこれまでケイヒ酸の反応から得られたという報告がない。反応形式は光ディールズアルダーで、スチレン骨格では酸化的に認められる特異反応である。1__〜がL_1^*との光照射下での相互作用で酸化的に2__<_>を形成したと考え1__〜の酸化電位と2__<_>の生成の関係をつかむため、Y_<ANACO>ポーラログラフィクアナライザーで酸化電位を測定した。1_a、1_b、1_cの酸化電位は1.6V、1.4V、1.45Vで、2__<_>の生成は1aが最もよい。これから特に1__〜の酸化過程が2__<_>の生成に重要なものとは思われなかった。この点について検討中である。

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  • イテロダイマ-を用いるIR多光子吸収による化学発光と断熱的光化学過程の研究

    Grant number:01540378  1989

    日本学術振興会  科学研究費助成事業 一般研究(C)  一般研究(C)

    木村 勝, 平塚 浩士, 岡本 秀毅

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    Grant amount:\1700000 ( Direct expense: \1700000 )

    分子間光化学反応過程のうち、特別なものとして着目されている断熱的光化学過程の研究、化学発光過程の研究を行ってきた。今回酵素原子の関与しないIR多光子吸収による化学発光に関する研究をまとめた。研究に必要な材料1_<a,b,c>の合成、さらに高エネルギ-貯蔵化合物3、4の合成に至り64年度の目標の第一段階を達成した。1、2、3の断熱的光化学過程での三重項状態発生も低温マトリックスを用いて観測し、瞬間マルケ測光システムによる発光の測定も可能となった。さらに3、4を用いての光によるヘキサプリズマン合成を試みたが、直接照射、増感反応を温度、溶媒また圧力などをかえて行ったが目的のヘキサプリズマン骨格合成には至っていない。特に圧力150Paにまで上げてみたが逆〔4π+4π〕光付加反応が起こるのみであった。この点に関しては今進行中である。化学発光に関して興味深い発見は1_bをルブレン存在下熱を加えるとルブレンからのものと思われる発光が認められたことがある。特に溶液中ではこのような発光は全く認められず、固体状態からのみ認められたことは発光機構を知る上で重要な発見といわなければならない。
    以上、今年度は1、2、3、4などの高歪物質を合成する新しい手法を開発し、その歪化合物を使っての光および熱の反応を行いほぼ実施計画を予定通り終了出来た。

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