2021/12/13 更新

写真a

タカイシ カズト
髙石 和人
TAKAISHI Kazuto
所属
自然科学学域 准教授
職名
准教授
外部リンク

学位

  • 博士(薬学) ( 京都大学 )

研究分野

  • ナノテク・材料 / 構造有機化学、物理有機化学

  • ナノテク・材料 / 有機合成化学

学歴

  • 京都大学    

    2005年4月 - 2008年3月

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  • 岡山大学   大学院自然科学研究科  

    2003年4月 - 2005年3月

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  • 岡山大学   農学部  

    1999年4月 - 2003年3月

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経歴

  • 岡山大学 大学院自然科学研究科   准教授

    2020年4月 - 現在

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  • 岡山大学 大学院自然科学研究科   講師

    2015年4月 - 2020年3月

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  • 成蹊大学 理工学部   助教

    2012年4月 - 2015年3月

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  • 理化学研究所   特別研究員

    2011年4月 - 2012年3月

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  • 理化学研究所   基礎科学特別研究員

    2008年4月 - 2011年3月

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論文

  • Circularly Polarized Luminescence Liquids Based on Siloxybinaphthyls: Best Binaphthyl Dihedral Angle in the Excited State 査読

    Kazuto Takaishi, Tomoki Matsumoto, Miyu Kawataka, Tadashi Ema

    Angewandte Chemie - International Edition   60 ( 18 )   9968 - 9972   2021年4月

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    担当区分:筆頭著者   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    A series of axially chiral 1,1′-binaphthyls with trialkylsiloxy (OSiR3) groups were synthesized. Among them, 1 a–c possessing OSiR3 groups at the 7,7′-positions and methyl groups at the 2,2′-positions were liquids at room temperature, and the neat liquids showed circularly polarized luminescence (CPL) (R=Bu; Φfl,liquid=0.21, |glum,liquid|=1.6×10−3). The |glum,liquid| value is the highest of pure liquids. These compounds remained liquid over a broad range of temperatures, down to −50 °C. Time-dependent DFT calculations indicated that in the excited state, the binaphthyls adopt a transoid conformation with a small angle between the electric and magnetic transition dipole moments (θμ,m=77°), which is a key factor in their CPL activity. The best binaphthyl dihedral angle in the excited state is approximately 110°.

    DOI: 10.1002/anie.202101226

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  • C-Methylenation of anilines and indoles with CO2 and hydrosilane using a pentanuclear zinc complex catalyst 査読

    Kazuto Takaishi, Hiroyasu Kosugi, Ritsuki Nishimura, Yuya Yamada, Tadashi Ema

    Chemical Communications   2021年

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    担当区分:筆頭著者   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/D1CC03675K

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  • Chiral exciplex dyes showing circularly polarized luminescence: extension of the excimer chirality rule 査読

    Kazuto Takaishi, Sho Murakami, Kazuhiro Iwachido, Tadashi Ema

    Chemical Science   2021年

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    担当区分:筆頭著者   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/D1SC04403F

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  • Aggregation‐Induced Circularly Polarized Luminescence from Boron Complexes with a Carbazolyl Schiff Base 査読 国際誌

    Chihiro Maeda, Shuichi Nomoto, Kazuto Takaishi, Tadashi Ema

    Chemistry – A European Journal   26 ( 57 )   13016 - 13021   2020年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    A variety of carbazolyl-appended Schiff bases were readily synthesized from 1-formylcarbazoles and aniline derivatives. Boron complexation of the resulting ligands allowed for facile preparation of new carbazole-based BODIPY analogues showing solid-state fluorescence. Furthermore, some dyes were converted into chiral compounds through the Et2 AlCl-mediated incorporation of a binaphthyl unit. The chiral dyes showed aggregation-induced fluorescence and circularly polarized luminescence (CPL) with the ΦF and glum of up to 0.22 and -3.5×10-3 , respectively, in the solid state. The solid-state fluorescence and CPL were well characterized by the crystal packing analyses and DFT calculations.

    DOI: 10.1002/chem.202001463

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  • Tetrameric and Hexameric Porphyrin Nanorings: Template Synthesis and Photophysical Properties 査読 国際誌

    Chihiro Maeda, Shoki Toyama, Naoki Okada, Kazuto Takaishi, Seongsoo Kang, Dongho Kim, Tadashi Ema

    Journal of the American Chemical Society   142 ( 37 )   15661 - 15666   2020年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    Hexameric and tetrameric porphyrin nanorings, Z6·T6 and Z4·T4, were synthesized in 53% and 14% yields, respectively, by the Sonogashira-type self-oligomerization of porphyrin monomer 1 using hexadentate template T6 and tetrapyridylporphyrin template T4. Template-free nanorings Z6 and Z4 were also prepared. The femtosecond transient absorption measurements revealed fast excitation energy hopping (EEH) along these nanorings with hopping rates of 2-5 ps. Treatment of Z6 with chiral template CT6 gave Z6·CT6 showing circular dichroism (CD) and circularly polarized luminescence (CPL) in the absorption and fluorescence regions of Z6, respectively, which indicates chirality transfer from CT6 to Z6.

    DOI: 10.1021/jacs.0c07707

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  • Synthesis and Chiroptical Properties of Chiral Carbazole-Based BODIPYs. 査読 国際誌

    Chihiro Maeda, Keita Suka, Keiji Nagahata, Kazuto Takaishi, Tadashi Ema

    Chemistry (Weinheim an der Bergstrasse, Germany)   26 ( 19 )   4261 - 4268   2020年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    A series of carbazole-based boron dipyrromethenes (BODIPYs) 2 a-g bearing binaphthyl units have been synthesized by the Et2 AlCl-mediated reaction of the corresponding BODIPY difluorides 1 a-g with 1,1'-binaphthalene-2,2'-diol. Substituents such as halogen, nitrile, and amino groups were tolerated under the reaction conditions, and the reaction of the phenylethynyl-substituted 1 h gave (R,R)-3 h bearing two binaphthyl units. The chiroptical properties of these dyes with different substituents were investigated by UV/Vis, CD, fluorescence, and circularly polarized luminescence (CPL) spectroscopy. The CD spectra showed Cotton effects in the absorption region of the BODIPY moieties. In addition, they showed CPL both in solution and in the solid state. Interestingly, several dyes recorded higher glum values in the solid state, probably due to intermolecular interactions. Because (R,R)-3 h recorded relatively low glum values, the diastereomer (R,S)-3 h was prepared. The (R,S) diastereomer showed intense CPL, which suggests a synergetic effect of the two binaphthyl groups. Finally, chiral carbazole-based BODIPY dimers have been synthesized for the first time and their chiroptical properties were investigated. They showed redshifted fluorescence and CPL, which reached the near-IR (NIR) region in the solid state.

    DOI: 10.1002/chem.201904954

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  • Solvent-Induced Sign Inversion of Circularly Polarized Luminescence: Control of Excimer Chirality by Hydrogen Bonding 査読

    Kazuto Takaishi, Kazuhiro Iwachido, Tadashi Ema

    Journal of the American Chemical Society   142 ( 4 )   1774 - 1779   2020年1月

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    担当区分:筆頭著者   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    DOI: 10.1021/jacs.9b13184

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  • Macrocyclic multinuclear metal complexes acting as catalysts for organic synthesis 査読

    Bikash Dev Nath, Kazuto Takaishi, Tadashi Ema

    Catalysis Science & Technology   2020年

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry ({RSC})  

    DOI: 10.1039/C9CY01894H

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  • Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore 査読

    Kazuto Takaishi, Sakiko Hinoide, Tomoki Matsumoto, Tadashi Ema

    Journal of the American Chemical Society   141 ( 30 )   11852 - 11857   2019年7月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    DOI: 10.1021/jacs.9b06240

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  • Organic Monolithic Natural Hyperbolic Material 査読

    Yeon Ui Lee, Olivier P. M. Gaudin, KwangJin Lee, Eunyoung Choi, Virginie Placide, Kazuto Takaishi, Tsuyoshi Muto, Pascal André, Atsuya Muranaka, Masanobu Uchiyama, Fabrice Mathevet, Tetsuya Aoyama, JeongWeon Wu, Anthony D’Aléo, Jean-Charles Ribierre

    ACS Photonics   6 ( 7 )   1681 - 1689   2019年7月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    DOI: 10.1021/acsphotonics.9b00185

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  • Unexpected Macrocyclic Multinuclear Zinc and Nickel Complexes that Function as Multitasking Catalysts for CO 2 Fixations 査読

    Kazuto Takaishi, Bikash Dev Nath, Yuya Yamada, Hiroyasu Kosugi, Tadashi Ema

    Angewandte Chemie International Edition   58 ( 29 )   9984 - 9988   2019年7月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/anie.201904224

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  • Evolving Fluorophores into Circularly Polarized Luminophores with a Chiral Naphthalene Tetramer: Proposal of Excimer Chirality Rule for Circularly Polarized Luminescence 査読

    Kazuto Takaishi, Kazuhiro Iwachido, Ryosuke Takehana, Masanobu Uchiyama, Tadashi Ema

    Journal of the American Chemical Society   141 ( 15 )   6185 - 6190   2019年4月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    DOI: 10.1021/jacs.9b02582

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  • Hemisquaramide Tweezers as Organocatalysts: Synthesis of Cyclic Carbonates from Epoxides and CO2 査読

    Kazuto Takaishi, Takafumi Okuyama, Shota Kadosaki, Masanobu Uchiyama, Tadashi Ema

    Organic Letters   21 ( 5 )   1397 - 1401   2019年3月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    DOI: 10.1021/acs.orglett.9b00117

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  • Chiroptical and catalytic properties of doubly binaphthyl-strapped chiral porphyrins 査読 国際誌

    Chihiro Maeda, Kanae Ogawa, Kosuke Sadanaga, Kazuto Takaishi, Tadashi Ema

    Chemical Communications   55 ( 8 )   1064 - 1067   2019年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry ({RSC})  

    Doubly (R)-binaphthyl-strapped porphyrins with methylene chains were synthesized. The CD spectra showed the positive Cotton effect around the Soret bands, and several porphyrins showed CPL. In addition, we found that the chiral porphyrins were applicable to kinetic resolution of epoxide with CO2.

    DOI: 10.1039/C8CC09114E

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  • Synthesis of chiral carbazole-based BODIPYs showing circularly polarized luminescence 査読 国際誌

    Chihiro Maeda, Keiji Nagahata, Kazuto Takaishi, Tadashi Ema

    Chemical Communications   55 ( 21 )   3136 - 3139   2019年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry ({RSC})  

    Chiral carbazole-based BODIPYs with a binaphthyl unit were synthesized via an Al-mediated reaction. Et2AlCl was found to be a convenient reagent for the reaction to give the chiral BODIPYs in high yields. It has been shown for the first time that these chiral carbazole-based BODIPYs show circularly polarized luminescence (CPL) both in solution and in the solid state.

    DOI: 10.1039/C9CC00894B

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  • Cross-Coupling Approach to an Array of Macrocyclic Receptors Functioning as Chiral Solvating Agents 査読

    Tadashi Ema, Takayuki Yamasaki, Sagiri Watanabe, Mahoko Hiyoshi, Kazuto Takaishi

    The Journal of Organic Chemistry   83 ( 18 )   10762 - 10769   2018年9月

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    Copyright © 2018 American Chemical Society. Chiral macrocyclic receptors 1 with multiple hydrogen-bonding sites in the cavity were synthesized and used as NMR chiral solvating agents (CSAs). The Suzuki-Miyaura cross-coupling reaction gave rapid access to a series of variants 1b-p of unsubstituted parent compound 1a. Among them, 1d with the 4-cyanophenyl group at the 3,3′-positions of the binaphthyl moiety was the most excellent CSA for a benchmark analyte compound, 2-chloropropionic acid (CPA); both of the quartet and doublet signals of CPA were split most completely in CDCl3. Binding constants (Ka) determined in CDCl3by NMR titrations indicated that (R)-1d was the most enantioselective (Ka(S)/Ka(R) = 5.4). Interestingly, the Kavalue of (R)-1d for (S)-CPA (5900) was greater than that of (R)-1a for (S)-CPA (3080), which strongly suggests an attractive interaction between the 4-cyanophenyl group of (R)-1d and (S)-CPA. The X-ray crystal structure of 1d indicates that one of the two H atoms meta to the cyano group is directed toward the cavity. DFT calculations suggested that this H atom of the 4-cyanophenyl group of (R)-1d forms a weak hydrogen bond with the Cl atom of (S)-CPA (C-H···Cl-C hydrogen bond).

    DOI: 10.1021/acs.joc.8b01327

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    その他リンク: http://orcid.org/0000-0003-4979-7375

  • Simultaneous Edge-on to Face-on Reorientation and 1D Alignment of Small π-Conjugated Molecules Using Room-Temperature Mechanical Rubbing 査読

    Jean Charles Ribierre, Jean Charles Ribierre, Toshihiko Tanaka, Li Zhao, Yuki Yokota, Yuki Yokota, Shinya Matsumoto, Shinya Matsumoto, Daisuke Hashizume, Kazuto Takaishi, Tsuyoshi Muto, Benoît Heinrich, Stéphane Méry, Fabrice Mathevet, Toshinori Matsushima, Toshinori Matsushima, Toshinori Matsushima, Masanobu Uchiyama, Masanobu Uchiyama, Chihaya Adachi, Chihaya Adachi, Chihaya Adachi, Tetsuya Aoyama

    Advanced Functional Materials   28 ( 19 )   2018年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim In this study, room-temperature mechanical rubbing is used to control the 3D orientation of small π-conjugated molecular systems in solution-processed polycrystalline thin films without using any alignment substrate. High absorption dichroic ratio and significant anisotropy in charge carrier mobilities (up to 130) measured in transistor configuration are obtained in rubbed organic films based on the ambipolar quinoidal quaterthiophene (QQT(CN)4). Moreover, a solvent vapor annealing treatment of the rubbed film is found to improve the optical and charge transport anisotropy due to an increased crystallinity. X-ray diffraction and atomic force microscopy measurements demonstrate that rubbing does not only lead to an excellent 1D orientation of the QQT(CN)4 molecules over large areas but also modifies the orientation of the crystals, moving molecules from an edge-on to a face-on configuration. The reasons why a mechanical alignment technique can be used at room temperature for such a polycrystalline film are rationalized, by the plastic characteristics of the QQT(CN)4 layer and the role of the flexible alkyl side chains in the molecular packing. This nearly complete conversion from edge-on to face-on orientation by mechanical treatment in polycrystalline small-molecule-based thin films opens perspectives in terms of fundamental research and practical applications in organic optoelectronics.

    DOI: 10.1002/adfm.201707038

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  • Binaphthyl–Bipyridyl Cyclic Dyads as a Chiroptical Switch 査読

    Kazuto Takaishi, Makoto Yasui, Tadashi Ema

    Journal of the American Chemical Society   140 ( 16 )   5334 - 5338   2018年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society ({ACS})  

    A series of chiral cyclic dyads, axially chiral binaphthyls linked to a 3,3′-bipyridyl, was synthesized. The dyad 2 bearing methoxy groups exhibited ON/OFF properties in circularly polarized luminescence (CPL), yielding a |glum| of 1.6 × 10-3 or 0 without any change in fluorescence. This type of CPL switch is unprecedented. Regioisomer 4 exhibited a dextro/levo rotation switching ability in [α]D. X-ray structures as well as experimental and theoretical analyses suggested that the switching properties depended on conformational changes.

    DOI: 10.1021/jacs.8b01860

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    その他リンク: http://orcid.org/0000-0003-4979-7375

  • Calix[4]pyrroles as macrocyclic organocatalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide 査読

    Chihiro Maeda, Sota Sasaki, Kazuto Takaishi, Tadashi Ema

    Catalysis Science & Technology   8 ( 16 )   4193 - 4198   2018年

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    掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry ({RSC})  

    © 2018 The Royal Society of Chemistry. Calix[4]pyrrole 1, calix[4]arene 2, or porphyrin 3 together with tetrabutylammonium iodide (TBAI) catalyzed the conversion of epoxides and CO2into cyclic carbonates. Among them, meso-octamethylcalix[4]pyrrole 1a, which was synthesized easily in one step by the acid-catalyzed condensation of pyrrole with acetone, was found to be a very active and robust organocatalyst. DFT calculations suggested that 1a adopts a 1,3-alternate conformation to stabilize the anionic species generated during the catalysis. In the key transition state of the epoxide ring-opening step, one pyrrolic NH group and the tetrabutylammonium (TBA) cation activate the epoxide by hydrogen bonding while another NH group on the opposite side guides the I-anion, which is located away from the TBA cation, to the backside attack on the epoxide.

    DOI: 10.1039/C8CY00941D

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  • Intense excimer CPL of pyrenes linked to a quaternaphthyl 査読

    Kazuto Takaishi, Ryosuke Takehana, Tadashi Ema

    Chemical Communications   54 ( 12 )   1449 - 1452   2018年

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    担当区分:筆頭著者   記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry ({RSC})  

    (R,R,R)-Quaternaphthyls possessing eight and six pyrenes (compounds 4 and 3) displayed intense excimer-CPL. The glum values in solution and in the solid state were +0.034-0.037 and +0.0053-0.0056, respectively. The glum values of 3 and 4 were indistinguishable, indicating that the pyrenes of 3 and 4 assumed the same conformation, even in excited states. The intense CPL was caused by conformationally rigid pyrenes arranged via the cumulative steric effects along the quaternaphthyl axis.

    DOI: 10.1039/C7CC09187G

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  • Palladium Complexes of Carbazole-Based Chalcogenaisophlorins: Synthesis, Structure, and Solid-State NIR Absorption Spectra 査読

    Chihiro Maeda, Kazuto Takaishi, Tadashi Ema

    ChemPlusChem   82 ( 12 )   1368 - 1371   2017年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley-Blackwell  

    Annulation reactions of the butadiyne-bridged carbazole dimer 1 produced carbazole-based chalcogenaisophlorins 2-4, which were transformed into the corresponding palladium complexes 2Pd-4Pd. The structures were characterized by NMR spectroscopy and X-ray diffraction analysis. Metallation fixed the structures which displayed weak antiaromatic character derived from the 20 isophlorin framework. These complexes showed weak near-infrared (NIR) absorption typical for antiaromatic porphyrinoids in solution. In addition, 2Pd and 3Pd showed relatively strong solid-state NIR absorption. X-ray diffraction analyses of 2Pd and 3Pd revealed trimeric and dimeric stacked layered structures, respectively, and DFT calculations suggest that the solid-state NIR absorption is ascribed to intermolecular charge transfer.

    DOI: 10.1002/cplu.201700470

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  • Induction of oxidative stress by anticancer drugs in the presence and absence of cells

    Chikako Yokoyama, Yuto Sueyoshi, Mika Ema, Yumi Mori, Kazuto Takaishi, Hisashi Hisatomi

    ONCOLOGY LETTERS   14 ( 5 )   6066 - 6070   2017年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPANDIDOS PUBL LTD  

    Reactive oxygen species (ROS) are generated in the cell through multiple mechanisms. Intracellular ROS are rapidly detoxified by various enzymatic and non-enzymatic mechanisms; however, disruption of the oxidant-antioxidant balance causes oxidative stress and elicits cell damage. The oxidative stress induced by chemotherapy is known to cause side effects in patients with cancer. However, few studies have examined whether anticancer drugs induce oxidative stress in cancer cells. Furthermore, the precise mechanism by which anticancer drugs induce the generation of ROS remains unclear. In the present study, to investigate whether anticancer drugs induce oxidative stress, DLD-1 human colorectal cancer cells were treated with 20 different anticancer drugs and then stained with CellROX (R) ROS detection reagent. Furthermore, an oxygen radical absorbance capacity assay in the presence of copper was performed to estimate the oxidative activities of the anticancer drugs in the absence of cells. The data of the present study using assay methods in the presence and absence of cells suggest that nimustine, actinomycin D, doxorubicin, mitomycin C, mitoxantrone, carmofur, gemcitabine, mercaptopurine, camptothecin, paclitaxel, vinblastine, and vinorelbine are able to induce oxidative stress.

    DOI: 10.3892/ol.2017.6931

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  • Quasi-Phase Diagrams at Air/Oil Interfaces and Bulk Oil Phases for Crystallization of Small-Molecular Semiconductors by Adjusting Gibbs Adsorption

    Satoshi Watanabe, Takahisa Ohta, Rota Urata, Tetsuya Sato, Kazuto Takaishi, Masanobu Uchiyarna, Tetsuya Aoyama, Masashi Kunitake

    LANGMUIR   33 ( 36 )   8906 - 8913   2017年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The temperature and concentration dependencies of the crystallization of two small-molecular semiconductors were clarified by constructing quasi-phase diagrams at air/oil interfaces and in bulk oil phases. A quinoidal quaterthiophene derivative with four alkyl chains (QQT(CN)-4) in 1,1,2,2-tetrachroloethane (TCE) and a thienoacene derivative with two alkyl chains (C8-BTBT) in o-dichlorobenzene were used. The apparent crystal nucleation temperature (T-n) and dissolution temperature (T-d) of the molecules were determined based on optical microscopy examination in closed glass capillaries and open dishes during slow cooling and heating processes, respectively. Tn and Td were considered estimates of the critical temperatures for nuclear formation and crystal growth, respectively. The Tn values of QQT(CN)-4 and C8-BTBT at the air/oil interfaces were higher than those in the bulk oil phases, whereas the Td values at the air/oil interfaces were almost the same as those in the bulk oil phases. These Gibbs adsorption phenomena were attributed to the solvophobic effect of the alkyl chain moieties. The temperature range between Tn and Td corresponds to suitable supercooling conditions for ideal crystal growth based on the suppression of nucleation. The Tn values at the water/oil and oil/glass interfaces did not shift compared with those of the bulk phases, indicating that adsorption did not occur at the hydrophilic interfaces. Promotion and inhibition of nuclear formation for crystal growth of the semiconductors were achieved at the air/oil and hydrophilic interfaces, respectively.

    DOI: 10.1021/acs.langmuir.7b01603

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  • Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide

    Tadashi Ema, Maki Yokoyama, Sagiri Watanabe, Sota Sasaki, Hiromi Ota, Kazuto Takaishi

    ORGANIC LETTERS   19 ( 15 )   4070 - 4073   2017年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Among chiral macrocycles 1 synthesized, lm with the 3,5-bis(trifluoromethypphenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of lm revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of epoxides. A catalytic cycle proposed was supported by DFT calculations.

    DOI: 10.1021/acs.orglett.7b01838

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  • Polymerization of 2,5-Diaminoterephthalic acid-Type Monomers for the Synthesis of Polyamides Containing Ladder Unit

    Akihiro Yokoyama, Jinya Kuramochi, Ryohei Kiyota, Kazuki Kishimoto, Kazuto Takaishi, Tsutomu Yokozawa

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   55 ( 14 )   2365 - 2372   2017年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY  

    To synthesize ladder-type polyamides by construction of two amide bonds successively, 2,5-diaminoterephthalic acid derivatives bearing anthranilic acid ester and isatoic anhydride moieties were synthesized and their polymerization was investigated. Polymerization of the methyl ester monomer proceeded in the presence of lithium hexamethyldisilazide (LiHMDS) as a base in tetrahydrofuran (THF). However, mass spectroscopic analysis of the product suggested that not only the bis(trimethylsilyl)amide anion of LiHMDS but also the methoxide anion eliminated at the second amide-linkage formation reaction decomposed the isatoic anhydride unit of the growing oligomer by nucleophilic attack to disturb the polymerization. To reduce the nucleophilicity of the eliminated anion, methyl ester of the monomer was changed to phenyl ester and its polymerization was studied. The reaction conditions were optimized, and the best result was obtained when the polymerization was conducted in the presence of 1.0 equivalent of LiHMDS without additives in THF at 50 degrees C. (C) 2017 Wiley Periodicals, Inc.

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  • Helical Oligonaphthodioxepins Showing Intense Circularly Polarized Luminescence (CPL) in Solution and in the Solid State

    Kazuto Takaishi, Takahiro Yamamoto, Sakiko Hinoide, Tadashi Ema

    CHEMISTRY-A EUROPEAN JOURNAL   23 ( 39 )   9249 - 9252   2017年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    A series of oligonaphthodioxepins was synthesized, revealing a helically arranged octamer, (R,R,R,R,R,R,R)-3, which showed intense circularly polarized luminescence (CPL) both in solution and in the solid state. The fluorescence quantum yields (Phi(FL)) in solution and in the solid state were 0.90 and 0.22, respectively, and the glum values in solution and in the solid state were vertical bar 2.2 x 10 (-3) 3 and + 7.0 x 10 (-3) , respectively. This is one of the highest solid-state CPL glum values yet reported. The high FFL and glum values were due to the rigidity, as well as to the fact that (R, R, R, R, R, R, R)-3 was a non-planar molecule. Moreover, (R, R, R, R, R, R, R)-3 was highly stable both chemically and stereochemically.

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  • Microcrystallization of a Solution-Processable Organic Semiconductor in Capillaries for High-Performance Ambipolar Field Effect Transistors

    Satoshi Watanabe, Takuma Fujita, Jean-Charles Ribierre, Kazuto Takaishi, Tsuyoshi Muto, Chihaya Adachi, Masanobu Uchiyama, Tetsuya Aoyama, Mutsuyoshi Matsumoto

    ACS APPLIED MATERIALS & INTERFACES   8 ( 27 )   17574 - 17582   2016年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    We report on the use of microcrystallization in capillaries to fabricate patterned crystalline microstructures of the low-bandgap ambipolar quinoidal quaterthiophene derivative (QQT(CN)(4)) from a chloroform solution. Aligned needle -shaped QQT(CN)(4) crystals were formed in thin film microstructures using either open-or closed capillaries made of polydimethylsiloxane (PDMS). Their charge transport properties were evaluated in a bottom-gate top-contact 10(-5) transistor configuration. Hole and electron mobilities were found to be as high as 0.17 and 0.083 cm(2) V-1 s(-1), respectively, approaching the values previously obtained in individual QQT(CN)(4) single crystal microneedles. It was possible to control the size of the needle crystals and the microline arrays by adjusting the structure of the PDMS mold and the concentration of QQT(CN)(4) solution. These results demonstrate that the microcrystallization in capillaries technique can be used to simultaneously pattern organic needle single crystals and control the microcrystallization processes. Such a simple and versatile method should be promising for the future development of high-performance organic electronic devices.

    DOI: 10.1021/acsami.5b12713

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  • Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads

    Kazuto Takaishi, Jun Suzuki, Tatsuya Yabe, Hikaru Asano, Michihiro Nishikawa, Daisuke Hashizume, Atsuya Muranaka, Masanobu Uchiyama, Akihiro Yokoyama

    ORGANIC LETTERS   17 ( 16 )   4098 - 4101   2015年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    An axially chiral binaphthyl-bipyridyl cyclic dyad in which the two units are connected by short -CH2O- linkers Was synthesized. Experimental and theoretical analyses indicate that the (R)-binaphthyl unit in the dyad induces (R)-chirality in the bipyridyl unit, both in the solid state and in solution. It is shown that vibrational circular dichroism (VCD) is useful to determine the twisting pattern of 2,2'-bipyridyl compounds. The dyad shows crystallization-induced emission enhancement (CIEE).

    DOI: 10.1021/acs.orglett.5b02041

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  • Ambipolar organic field-effect transistors based on solution-processed single crystal microwires of a quinoidal oligothiophene derivative

    J. C. Ribierre, L. Zhao, S. Furukawa, T. Kikitsu, D. Inoue, A. Muranaka, K. Takaishi, T. Muto, S. Matsumoto, D. Hashizume, M. Uchiyama, P. Andre, C. Adachi, T. Aoyama

    CHEMICAL COMMUNICATIONS   51 ( 27 )   5836 - 5839   2015年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    A simple and versatile solution-processing method based on molecular self-assembly is used to fabricate organic single crystal microwires of a low bandgap quinoidal oligothiophene derivative. Individual single crystal microwire transistors present well-balanced ambipolar behaviour with hole and electron mobilities as high as 0.4 and 0.5 cm(2) V-1 s(-1), respectively.

    DOI: 10.1039/c4cc09608h

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  • Thin reduced graphene oxide interlayer with a conjugated block copolymer for high performance non-volatile ferroelectric polymer memory

    Dhinesh Babu Velusamy, Richard Hahnkee Kim, Kazuto Takaishi, Tsuyoshi Muto, Daisuke Hashizume, Soyoon Lee, Masanobu Uchiyama, Tetsuya Aoyama, Jean-Charles Ribierre, Cheolmin Park

    ORGANIC ELECTRONICS   15 ( 11 )   2719 - 2727   2014年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE BV  

    Polymer ferroelectric-gate field effect transistors (Fe-FETs) employing ferroelectric polymer thin films as gate insulators are highly attractive as a next-generation non-volatile memory. For minimizing gate leakage current of a device which arises from electrically defective ferroelectric polymer layer in particular at low operation voltage, the materials design of interlayers between the ferroelectric insulator and gate electrode is essential. Here, we introduce a new solution-processed interlayer of conductive reduced graphene oxides (rGOs) modified with a conjugated block copolymer, poly(styrene-block-paraphenylene) (PS-b-PPP). A FeFET with a solution-processed p-type oligomeric semiconducting channel and ferroelectric poly(vinylidene fluoride-co-trifluoroethylene) (PVDF-TrFE) insulator exhibited characteristic source-drain current hysteresis arising from ferroelectric polarization switching of a PVDF-TrFE insulator. Our PS-b-PPP modified rGOs (PMrGOs) with conductive moieties embedded in insulating polymer matrix not only significantly reduced the gate leakage current but also efficiently lowered operation voltage of the device. In consequence, the device showed large memory gate voltage window and high ON/OFF source-drain current ratio with excellent data retention and read/write cycle endurance. Furthermore, our PMrGOs interlayers were successfully employed to FeFETs fabricated on mechanically flexible substrates with promising non-volatile memory performance under repetitive bending deformation. (C) 2014 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.orgel.2014.07.035

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  • Helical π-systems of bidipyrrin-metal complexes

    Hiromitsu Maeda, Takuma Nishimura, Akira Tsujii, Kazuto Takaishi, Kazuto Takaishi, Masanobu Uchiyama, Masanobu Uchiyama, Atsuya Muranaka, Atsuya Muranaka

    Chemistry Letters   43 ( 7 )   1078 - 1080   2014年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Various metal-bridged single and double helical complexes of π-conjugated ligand molecules, bidipyrrins, were prepared. The introduction of terminal end units enabled the formation of chiral single and double helices; their spectroscopic properties and temperature-dependent behaviors were examined. © 2014 The Chemical Society of Japan.

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  • Oligonaphthofurans: Fan-shaped and three-dimensional π-compounds

    Kentaro Nakanishi, Daisuke Fukatsu, Kazuto Takaishi, Kazuto Takaishi, Taiki Tsuji, Keita Uenaka, Kouji Kuramochi, Takeo Kawabata, Kazunori Tsubaki

    Journal of the American Chemical Society   136 ( 19 )   7101 - 7109   2014年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Using a bottom-up method, we prepared a series of oligonaphthofurans composed of alternating naphthalene rings and furan rings. The largest compound (compound 25) contained 8 naphthalene units and 7 furan units. DFT calculations revealed that these compounds were fan-shaped molecules and each naphthalene ring was oriented in an alternate mountain-valley fold conformation because of steric repulsion by the hydrogens at the peri-positions. We investigated the optical properties that derived from their fan-shaped and mountain-valley sequences. As the number of aromatic rings of the oligonaphthofurans increased, the peaks of the longest wavelength absorptions in the UV-vis spectra (HOMO-LUMO energy gap) of these compounds steadily red-shifted, although the shapes of spectra were not sustained because of the decreasing molar absorption coefficients (εs) of their λmax. We compared our results with those reported for other types of oligoaromatic compounds such as acenes 1, ethene-bridged p-phenylenes 2, rylenes 3, oligofurans 4, and oligonaphthalenes 5. The slopes of the plots between the transition energies (HOMO-LUMO energy gap) of the oligoaromatic compounds and the reciprocal of the number of aromatic rings indicated that the efficiency of π conjugation of the oligonaphthofurans was comparable with that of linear and rigid acenes and rylenes. The higher-order compounds 22 and 25 aggregated even under high dilution conditions (∼10-6 M). © 2014 American Chemical Society.

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  • Non-volatile organic memory with sub-millimetre bending radius 査読

    Richard Hahnkee Kim, Hae Jin Kim, Insung Bae, Sun Kak Hwang, Dhinesh Babu Velusamy, Suk Man Cho, Kazuto Takaishi, Tsuyoshi Muto, Daisuke Hashizume, Masanobu Uchiyama, Pascal Andre, Fabrice Mathevet, Benoit Heinrich, Tetsuya Aoyama, Dae-Eun Kim, Hyungsuk Lee, Jean-Charles Ribierre, Cheolmin Park

    NATURE COMMUNICATIONS   5   2014年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:NATURE PUBLISHING GROUP  

    High-performance non-volatile memory that can operate under various mechanical deformations such as bending and folding is in great demand for the future smart wearable and foldable electronics. Here we demonstrate non-volatile solution-processed ferroelectric organic field-effect transistor memories operating in p- and n- type dual mode, with excellent mechanical flexibility. Our devices contain a ferroelectric poly(vinylidene fluoride-co-trifluoroethylene) thin insulator layer and use a quinoidal oligothiophene derivative (QQT(CN)4) as organic semiconductor. Our dual-mode field-effect devices are highly reliable with data retention and endurance of > 6,000 s and 100 cycles, respectively, even after 1,000 bending cycles at both extreme bending radii as low as 500 mu m and with sharp folding involving inelastic deformation of the device. Nano-indentation and nano scratch studies are performed to characterize the mechanical properties of organic layers and understand the crucial role played by QQT(CN)4 on the mechanical flexibility of our devices.

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  • Crystal structure of N-isopropylanthranilic acid trimer

    Akihiro Yokoyama, Natsumi Kawano, Yuka Wada, Michihiro Nishikawa, Kazuto Takaishi, Tsutomu Yokozawa

    X-ray Structure Analysis Online   30   35 - 36   2014年1月

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    The crystal structure of N-isopropylanthranilic acid trimer was characterized by a single-crystal X-ray diffraction method to study the conformation of oligo(o-benzamide). The compound crystallized in a triclinic space group, P1, with a = 7.720(4)Å, b = 9.006(4)Å, c = 20.131(9)Å, α = 92.459(7)°, β = 95.299(7)°, γ = 91.099(7)°, V = 1391.9(11)Å3, and Z = 2. In the crystal structure, one of the amide linkages adopts a cis conformation, while the other adopts a trans conformation. © 2014, The Japan Society for Analytical Chemistry.

    DOI: 10.2116/xraystruct.30.35

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  • Binaphthyl-based chiral macrocyclophanes with variously sized cavities: D-n-symmetrical structure constructed from unidirectionally-inclined rod segments

    Kazuto Takaishi, Tatsuya Yabe, Masanobu Uchiyama, Akihiro Yokoyama

    TETRAHEDRON   70 ( 3 )   730 - 734   2014年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    As new and chiral macrocyclophanes with unique structures, variously sized Pn and Mn (n=2-7=number of 'rod' segments) with D-2-D-7 symmetry were constructed by alternating connection of axially chiral binaphthyls and linear biphenyls via -CH2O- moieties, so that the macrocycle consists of multiple rod-like naphthalene biphenyl naphthalene units linked together at the binaphthyl bonds. The dihedral angle of the two naphthalene rings of binaphthyl is restricted to around 90 degrees, and the calculated values of strain energy difference per naphthalene biphenyl unit in P2-P7 are almost independent of the macrocycle size, presumably owing to the flexibility of the -CH2O- connectors. (C) 2013 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2013.11.081

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  • Chiroptical Control in Helical Receptor-Anion Complexes

    Hiromitsu Maeda, Tomohiro Shirai, Yuya Bando, Kazuto Takaishi, Masanobu Uchiyama, Atsuya Muranaka, Tsuyoshi Kawai, Masanobu Naito

    ORGANIC LETTERS   15 ( 23 )   6006 - 6009   2013年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Dimers of appropriately arranged anion-responsive pi-conjugated moieties form helical structures by interaction with chiral anions. Terphenyl-bridged dimers of dipyrrolyldiketone boron complexes show chirality induced by binding L-amino acid anions, as observed by circular dichroism (CD) and circularly polarized luminescence (CPL). The preferred configurations of helical structures depend on the geometries of the terphenyl spacer moieties.

    DOI: 10.1021/ol402895r

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  • Chirality induction by formation of assembled structures based on anion-responsive π-conjugated molecules

    Hiromitsu Maeda, Wataru Hane, Yuya Bando, Yoshitaka Terashima, Yohei Haketa, Hiroshi Shibaguchi, Tsuyoshi Kawai, Masanobu Naito, Masanobu Naito, Kazuto Takaishi, Kazuto Takaishi, Masanobu Uchiyama, Masanobu Uchiyama, Atsuya Muranaka, Atsuya Muranaka

    Chemistry - A European Journal   19 ( 48 )   16263 - 16271   2013年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Anion-responsive π-conjugated compounds having chiral alkyl chains were synthesized. Circular dichroism (CD) and circularly polarized luminescence (CPL) were observed in the solution-state assemblies of the chiral anion receptors and those of their anion complexes as salts of a planar triazatriangulenium cation. The CD and CPL spectral patterns of the ion-pair-based assemblies were completely opposite to those of the anion-free assemblies, and this suggests that anion binding and subsequent ion pairing change the chirality of the assembly modes. Opposite signs of the circular dichroism (CD) and circularly polarized luminescence (CPL) spectral patterns of ion-pair-based assemblies and anion-free assemblies of anion-responsive π-conjugated compounds bearing chiral alkyl chains (see figure) suggest that anion binding and subsequent ion pairing change the chirality of the assembly modes. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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  • Ion-based materials derived from positively and negatively charged chloride complexes of π-conjugated molecules

    Bin Dong, Bin Dong, Tsuneaki Sakurai, Yuya Bando, Shu Seki, Kazuto Takaishi, Kazuto Takaishi, Masanobu Uchiyama, Masanobu Uchiyama, Atsuya Muranaka, Atsuya Muranaka, Hiromitsu Maeda

    Journal of the American Chemical Society   135 ( 39 )   14797 - 14805   2013年10月

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    掲載種別:研究論文(学術雑誌)  

    Oriented salts from planar charged species were prepared by combining positively and negatively charged receptor-anion complexes with similar geometries using dicationic and electronically neutral π-conjugated receptors. Phenylene-or pyrimidine-bridged bis(imidazolium) dicationic anion receptors formed monocationic receptor-Cl- complexes that were accompanied by a free Cl-. This free Cl- was subsequently captured by pyrrole-based neutral anion receptors to form negatively charged receptor-Cl- complexes. The ion pair of the resulting positively and negatively charged planar receptor-Cl- complexes could produce a supramolecular octane gel, adopting a lamellar self-organized structure in its xerogel state. On the other hand, the solid-state ion pairs had hexagonal columnar mesophases, which formed via alternate stacking of the positively and negatively charged planar receptor-Cl- complexes. By use of the flash-photolysis time-resolved microwave conductivity technique, the one-dimensional charge-carrier transporting property, with a mobility of 0.05 cm2 V-1 s-1, was determined for the newly prepared solid-state ion pairs. © 2013 American Chemical Society.

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  • Formation and Geometrical Control of Polygon-Like Metal-Coordination Assemblies

    Hiromitsu Maeda, Ryo Akuta, Yuya Bando, Kazuto Takaishi, Masanobu Uchiyama, Atsuya Muranaka, Norimitsu Tohnai, Shu Seki

    CHEMISTRY-A EUROPEAN JOURNAL   19 ( 35 )   11676 - 11685   2013年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Polygon-like [2+2]- and [3+3]-type metal complexes were prepared from dipyrrin dimers connected by acute-angled spacers. The electrical conduction depends strongly on the packing alignment of the compounds, revealing the presence of effective hopping pathways for holes with relatively high mobility up to 0.11cm(2)V(-1)s(-1) along the aligned axis of [3+3]-type metal-bridged assemblies. These observations correlated with the geometrical control of the -conjugated metal complexes in the cyclic structures, which enables their ordered arrangement in the assemblies.

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    researchmap

  • Formation of Cyclic and Polymeric Structures from Zwitterions

    Harunobu Komatsu, Wataru Oi, Kazumasa Naritani, Kazuto Takaishi, Masanobu Uchiyama, Atsuya Muranaka, Hiromitsu Maeda

    CHEMISTRY-A EUROPEAN JOURNAL   19 ( 22 )   6956 - 6960   2013年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Covalent linkages: Zwitterion-based covalent linkages were observed in cyclic oligomers and in dispersed polymers based on monomers. Addition of acids and bases promoted transitions between monomeric species and the oligomeric and/or polymeric states. Exchange of constituent monomer units in the cyclic oligomers was observed in the solution state, whereas the polymers obtained as precipitates from CH3CN were not converted to the cyclic oligomers (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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  • Two double helical modes of bidipyrrin-ZnII complexes

    Hiromitsu Maeda, Takuma Nishimura, Ryo Akuta, Kazuto Takaishi, Masanobu Uchiyama, Atsuya Muranaka

    Chemical Science   4 ( 3 )   1204 - 1211   2013年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    This paper reports the formation and properties of covalently strapped double helices of bidipyrrin-ZnII complexes, where four dipyrrin chromophores interact with one another by strong exciton coupling. Thorough experimental examination, UV/vis, CD and 1H NMR spectra, and theoretical studies suggest the existence of two modes of the double helix depending on the dihedral angles between two of the dipyrrin units at the pyrrole α-α bond. In fact, the changes of the modes were observed according to the lengths of straps as well as the temperatures. © 2013 The Royal Society of Chemistry.

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  • Light-driven Supramolecular Chiral Materials: Photoinduced Control of Liquid- crystalline Helical Structures and Non-destructive Erasable Molecular Memory for Photonic Applications

    Masuki Kawamoto, Natsuki Shiga, Kazuto Takaishi, Takafumi Sassa, Takashi Yamashita, Yoshihiro Ito

    LIQUID CRYSTALS XVII   8828   2013年

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    記述言語:英語   掲載種別:研究論文(国際会議プロシーディングス)   出版者・発行元:SPIE-INT SOC OPTICAL ENGINEERING  

    Light-driven supramolecular chiral materials containing an azobenzene moiety as a photoresponsive part and binaphthyl moiety as a chiral part were designed. We found that the dynamic molecular twisting motion of the binaphthyl moiety could be achieved by irradiation of UV or visible light to cause photoisomerization of the azobenzene moiety. The twisting motion induced by the photochromic reaction gave rise to large change in the molecular structure and the value of optical rotation. The chiral materials were demonstrated to behave uniquely as photomodulation of liquid-crystalline helical structures and non-destructive erasable chiroptical memory through photoinduced switching of the dihedral angle of the binaphthyl moiety.

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  • Exciton diffusion in near-infrared absorbing solution-processed organic thin films

    H. -Y. Shin, J. H. Woo, M. J. Gwon, M. Barthelemy, M. Vomir, T. Muto, K. Takaishi, M. Uchiyama, D. Hashizume, T. Aoyama, D. -W. Kim, S. Yoon, J. -Y. Bigot, J. W. Wu, J. C. Ribierre

    PHYSICAL CHEMISTRY CHEMICAL PHYSICS   15 ( 8 )   2867 - 2872   2013年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    We report on singlet-singlet annihilation and exciton diffusion in as-prepared p-type and annealed n-type thin films of the low-bandgap quinoidal quaterthiophene [QQT(CN)4] using ultrafast transient absorption measurements. The decay dynamics of exciton populations are well described by a one-dimensional diffusion-limited bimolecular recombination, indicating that the singlet excitons migrate preferentially along the stacking direction. Our results show that the exciton diffusion constants in QQT(CN)4 films do not vary significantly upon thermal annealing. Exciton diffusion lengths are measured to be as high as 4 and 5 nm in as-prepared and annealed QQT(CN)4 films, respectively. We also observe an influence of the excitation densities on the singlet exciton diffusion, which is attributed to phonon scattering. Because of the possibility of patterning p-n regions in QQT(CN)4 films by thermal nanolithography techniques, this study provides important insight not only into the photophysical properties of quinoidal oligothiophene derivatives but also for their future integration into high-performance p-n nanostructured near infrared light-sensing devices.

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  • Fusion of Photochromic Reaction and Synthetic Reaction: Photoassisted Cyclization to Highly Strained Chiral Azobenzenophanes

    Kazuto Takaishi, Masuki Kawamoto, Atsuya Muranaka, Masanobu Uchiyama

    ORGANIC LETTERS   14 ( 13 )   3252 - 3255   2012年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A method for synthesizing highly strained cyclic structures by combining photochromic and synthetic reactions is described. Tightly linked azobenzene binaphthyl dyads (R)-4 and (R)-6 could not be obtained by conventional cyclization, but continuous application of photoirradiation, which induced (E)->(Z) isomerization of the azobenzene moiety, allowed the cyclization reaction to proceed, affording the desired chiral azobenzenophanes.

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  • Photoinversion of Cisoid/Transoid Binaphthyls

    Kazuto Takaishi, Atsuya Muranaka, Masuki Kawamoto, Masanobu Uchiyama

    ORGANIC LETTERS   14 ( 1 )   276 - 279   2012年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Axially chiral binaphthyl-azobenzene cyclic dyads in which the two moieties are connected by two linkers of different lengths were synthesized. In the case of benzylated-binaphthyl analogue 2b, photoirradiation resulted in a dramatic change of the CD spectrum and optical rotation. Experimental and theoretical analyses indicated that the dihedral angle of the two naphthalene rings is strongly coupled to the azobenzene photoisomerization; cis-azobenzene induces a transoid-binaphthyl structure, while trans-azobenzene Induces a cisold-binaphthyl structure.

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  • Optical and Charge Transport Properties of an Ambipolar Quinoidal Oligothiophene Derivative

    J. C. Ribierre, K. Takaishi, L. Mager, T. Fujihara, T. Muto, M. Uchiyama, T. Aoyama

    MOLECULAR CRYSTALS AND LIQUID CRYSTALS   566   2 - 7   2012年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:TAYLOR & FRANCIS LTD  

    We report on the charge transport and absorption properties of a low bandgap quinoidal oligothiophene derivative [QQT(CN)4]. Organic field-effect transistors based on QQT(CN)4 thin films show an ambipolar p-type dominant behavior and can be converted to n-type by thermal annealing at 100 degrees C for 30 minutes. Absorption spectra and atomic force microscopy measurements carried out in both neat films and polymer blends provide new important insights into the role of the degree of aggregation and the intermolecular interactions on the semiconducting and photophysical properties of this organic electronic material.

    DOI: 10.1080/15421406.2012.701107

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  • Asymmetric Induction in the Preparation of Helical Receptor-Anion Complexes: Ion-Pair Formation with Chiral Cations

    Yohei Haketa, Yuya Bando, Kazuto Takaishi, Masanobu Uchiyama, Atsuya Muranaka, Masanobu Naito, Hiroshi Shibaguchi, Tsuyoshi Kawai, Hiromitsu Maeda

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   51 ( 32 )   7967 - 7971   2012年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Asymmetry through ion pairing: Upon addition of chloride and bromide ions, as chiral ammonium salts, to solutions of pyrrole-based π-conjugated linear oligomers, helical structures form with asymmetric induction, which is guided by the formation of diastereomeric ion pairs with chiral counter cations (see picture). These ions pairs exhibit circular dichroism (CD) and strong circularly polarized luminescence (CPL) with glumvalues of greater than 0.1. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

    DOI: 10.1002/anie.201202196

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  • Planar Chirality of Twisted trans-Azobenzene Structure Induced by Chiral Transfer from Binaphthyls

    Kazuto Takaishi, Atsuya Muranaka, Masuki Kawamoto, Masanobu Uchiyama

    JOURNAL OF ORGANIC CHEMISTRY   76 ( 18 )   7623 - 7628   2011年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The absolute configuration of a binaphthylazobenzene dyad 2b, which has a chiral axis and a chiral plane, was determined by comparing the experimental circular dichroism (CD) spectra with the theoretical CD spectra calculated by the time-dependent (TD)-DFT method. The CD signals of the trans-azobenzene moiety indicated that the two benzene rings of this moiety are twisted unidirectionally. It is suggested that these dyads with shorter linkers may be suitable for use as chiroptical switches.

    DOI: 10.1021/jo201578z

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  • Flexible organic field-effect transistors and complementary inverters based on a solution-processable quinoidal oligothiophene derivative

    J. C. Ribierre, K. Takaishi, T. Muto, T. Aoyama

    OPTICAL MATERIALS   33 ( 9 )   1415 - 1418   2011年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE BV  

    We report on the fabrication and characterization of ambipolar organic field-effect transistors based on the solution-processable quinoidal oligothiophene [QQT(CN)4] and using a new fluorinated polymer (AL-X601) with a dielectric constant of 3.1 as dielectric material layer. As-prepared devices show ambipolar transport with hole and electron field-effect mobilities of 6 x 10(-2) and 5 x 10(-3) cm(2)/V s respectively as well as an on and off state current ratio higher than 10(3). Influence of a thermal annealing on the device performances was investigated and was found to lead to a majority carrier type conversion from a p-type to an n-type dominant behavior. QQT(CN)4 based field-effect transistors and complementary inverters fabricated on flexible substrates and using Al-X601 as gate dielectric material show high performance and good mechanical stability. (C) 2011 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.optmat.2011.03.015

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  • Influence of gate dielectric on the ambipolar characteristics of solution-processed organic field-effect transistors

    J. C. Ribierre, S. Ghosh, K. Takaishi, T. Muto, T. Aoyama

    JOURNAL OF PHYSICS D-APPLIED PHYSICS   44 ( 20 )   2011年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:IOP PUBLISHING LTD  

    Solution-processed ambipolar organic field-effect transistors based on dicyanomethylene-substituted quinoidal quaterthiophene derivative [QQT(CN) 4] are fabricated using various gate dielectric materials including cross-linked polyimide and poly-4-vinylphenol. Devices with spin-coated polymeric gate dielectric layers show a reduced hysteresis in their transfer characteristics. Among the insulating polymers examined in this study, a new fluorinated polymer with a low dielectric constant of 2.8 significantly improves both hole and electron field-effect mobilities of QQT(CN)4 thin films to values as high as 0.04 and 0.002 cm(2) V(-1) s(-1). These values are close to the best mobilities obtained in QQT(CN)4 devices fabricated on SiO(2) treated with octadecyltrichlorosilane. The influence of the metal used for source/drain metal electrodes on the device performance is also investigated. Whereas best device performances are achieved with gold electrodes, more balanced electron and hole field-effect mobilities could be obtained using chromium.

    DOI: 10.1088/0022-3727/44/20/205102

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  • Synthesis and Conformation of Substituted Chiral Binaphthyl-Azobenzene Cyclic Dyads with Chiroptical Switching Capabilities

    Kazuto Takaishi, Masuki Kawamoto

    MOLECULES   16 ( 2 )   1603 - 1624   2011年2月

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    記述言語:英語   出版者・発行元:MDPI AG  

    Optically active binaphthyl-azobenezene cyclic dyads were synthesized to develop a photochromic switching molecule. Azobenezene moieties were cis-trans isomerized by photoirradiation. As a reflection of the structural change, the specific optical rotation and circular dichroism underwent significant shifts. Under certain conditions, the positive-negative and zero-positive (or zero-negative) signals were reversed. Optical rotation may potentially be applied in noise-cancelling nondestructive photoswiches. The conformations were studied by experimental and theoretical methods. The results revealed that the helical chirality, (P) or (M), of the cis-azobenzene moiety was induced by intramolecular axial chirality. The twist direction depended on the axial chirality as well as the azobenzene linkage position to the binaphthyls, but was independent of the identity of substituted groups. 2,2'-Linked-(R)-binaphthyl was found to induce cis-(P)-azobenzene, whereas symmetrically 7,7'-linked-(R)-binaphthyl was found to induce cis-(M)-azobenzene.

    DOI: 10.3390/molecules16021603

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  • Helical Chirality of Azobenzenes Induced by an Intramolecular Chiral Axis and Potential as Chiroptical Switches

    Kazuto Takaishi, Masuki Kawamoto, Kazunori Tsubaki, Taniyuki Furuyama, Atsuya Muranaka, Masanobu Uchiyama

    CHEMISTRY-A EUROPEAN JOURNAL   17 ( 6 )   1778 - 1782   2011年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    The cis and trans forms of the azobenzene skeleton differ significantly in length and therefore are frequently used as photochromic parts for changing absorption and fluorescence properties, in addition to association constants when they are hosts.Although optically active compounds with azobenzene adducts have been reported,few studies have examined the asymmetry of the azobenzene moiety itself. Haberhauer and Kallweit have investigated the twisting direction of the cis-azobenzene moiety by studying the helical chirality linked to a chiral cyclic imidazole tetrapeptide, possessing four asymmetric centers.The axially chiral binaphthyl is rigid in the rod direction, but around the axis has a wide and flexible asymmetric field. Thus, binaphthyl skeletons have been employed in asymmetric organocatalysis,molecular recognition,and chiral doping of liquid crystals. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

    DOI: 10.1002/chem.201003087

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  • Multibridged Chiral Naphthalene Oligomers with Continuous Extreme-Cisoid Conformation

    Kazuto Takaishi, Masuki Kawamoto, Kazunori Tsubaki

    ORGANIC LETTERS   12 ( 8 )   1832 - 1835   2010年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Axially chiral 2,2'-methylenedioxy-bridged-1,1'-binaphthyls, quaternaphthalenes, and octinaphthalenes were synthesized and their optical properties researched. 2,2'-Methylenedioxy bridges led to a continuous extremely cisoid conformation and subsequent extensive conjugation in the rod direction. Therefore, the absorption and fluorescence regions were red-shifted as the number of naphthalene rings increased. These oligonaphthalenes fluoresced in both solution and the solid state. Furthermore, DFT calculations showed that the LUMO and HOMO of these bridged oligonaphthalenes were spread over a wide range.

    DOI: 10.1021/ol100582v

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  • Non-destructive erasable molecular switches and memory using light-driven twisting motions

    Masuki Kawamoto, Natsuki Shiga, Kazuto Takaishi, Takashi Yamashita

    CHEMICAL COMMUNICATIONS   46 ( 44 )   8344 - 8346   2010年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Novel types of chiroptical switches and memory with non-destructive readout that are entirely optically controlled for molecular devices in solution and neat films.

    DOI: 10.1039/c0cc02685a

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  • Synthesis and properties of S,R-alternating octinaphthalenes

    Kazuto Takaishi, Daisuke Sue, Shunsuke Kuwahara, Nobuyuki Harada, Takeo Kawabata, Kazunori Tsubaki

    TETRAHEDRON   65 ( 31 )   6135 - 6140   2009年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    (S,R,S,R,S,R,S)- and (S,R,S,S,S,R,S)-octinaphthalenes were synthesized by oxidative coupling of (S,R,S)-quaternaphthalene, and differences due to axis chirality of (S,R.S,R,S,R,S)-, (S,R,S,S,S,R,S)-, (S,S,S,R,S,S,S)-, and (S,S,S,S,S,S,S)-octinaphthalenes were compared using the R(f) values on TLC, specific optical rotations, (1)H NMR chemical shifts of the hydroxy groups, and CD spectra. A clear CD additivity was found in the Delta(epsilon) values of the (1)L(a) transition around 290 nm, which are proportional to the difference between the numbers of S and R binaphthalene units. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2009.05.040

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  • Photoswitching of Dextro/Levo Rotation with Axially Chiral Binaphthyls Linked to an Azobenzene

    Kazuto Takaishi, Masuki Kawamoto, Kazunori Tsubaki, Tatsuo Wada

    JOURNAL OF ORGANIC CHEMISTRY   74 ( 15 )   5723 - 5726   2009年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    To examine the reversible photoisomerization and subsequent change of asymmetric field, we synthesized optically active 3,3'-disubstituted-1,1'-binaphthyls with an azobenzene moiety. Reflecting the structural change, the specific rotation and circular dichroism underwent significant variations, Under certain conditions, the positive-negative signals were reversible. Furthermore, the magnitude of these changes showed a 3,3'-substituent dependency. Dibenzyloxy or bis(diphenylmethyloxy) derivatives were better suited for sign interconversion of the optical properties. in contrast, the hydroxy group(s) lacked both optical signals and durability.

    DOI: 10.1021/jo901030s

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  • Synthesis of Chiral Dotriacontanaphthalenes: How Many Naphthalene Units Are We Able To Elaborately Connect?

    Daisuke Sue, Kazuto Takaishi, Takunori Harada, Reiko Kuroda, Takeo Kawabata, Kazunori Tsubaki

    JOURNAL OF ORGANIC CHEMISTRY   74 ( 10 )   3940 - 3943   2009年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    (S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S,S)-dotriacontanaphthalenes 32A-E alternately possessing butoxy and methoxy side chains were precisely constructed through a bottom-up synthesis, and their absolute configurations and fluorescence quantum yields were determined.

    DOI: 10.1021/jo900463t

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  • Synthesis and biological evaluation of alkoxycoumarins as novel nematicidal constituents

    Kazuto Takaishi, Minoru Izumi, Naomichi Baba, Kazuyoshi Kawazu, Shuhei Nakajima

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   18 ( 20 )   5614 - 5617   2008年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    We synthesized all of the monomethoxycoumarins, 5-alkoxycoumarins and their derivatives, and investigated their nematicidal activity against the phytopathogenic nematode, Bursaphelenchus xylophilus. Among the compounds, 5-ethoxycoumarin showed the highest nematicidal activity. Furthermore, 5-ethoxycoumarin was comparatively harmless against both the brine shrimps, Artemia salina, and the Japanese killifish, Oryzias latipes. (C) 2008 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.bmcl.2008.08.102

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  • Three-component cascade energy transfer with use of oligonaphthalene skeletons

    Kazunori Tsubaki, Kazuto Takaishi, Daisuke Sue, Kazunari Matsuda, Yoshihiko Kanemitsu, Takeo Kawabata

    JOURNAL OF ORGANIC CHEMISTRY   73 ( 11 )   4279 - 4282   2008年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Three oligonaphthalenes with zinc porphyrin and free-base porphyrin moieties were synthesized, in which cascade energy transfer (from naphthalene to free-base porphyrin via zinc porphyrin) was observed when the zinc and free-base porphyrins were close to each other.

    DOI: 10.1021/jo800642u

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  • Synthesis and determination of the absolute configuration of chiral tetracosanaphthalenes

    Kazunori Tsubaki, Kazuto Takaishi, Daisuke Sue, Takeo Kawabata

    Journal of Organic Chemistry   72 ( 11 )   4238 - 4241   2007年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    (Chemical Equation Presented) Tetracosanaphthalenes with diethylaminocarbonylmethoxy side chains were constructed by bottom-up synthesis, and their absolute configurations were determined by an exciton chirality method. © 2007 American Chemical Society.

    DOI: 10.1021/jo070343g

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  • Synthesis and optical properties of the helical oligonaphthalenes

    Kazuto Takaishi, Kazunori Tsubaki, Hiroyuki Tanaka, Masaya Miura, Takeo Kawabata

    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN   126 ( 9 )   779 - 787   2006年9月

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    記述言語:英語   出版者・発行元:PHARMACEUTICAL SOC JAPAN  

    We have developed an efficient synthesis method for optically active oligonaphthalenes (from 2 mer to 16 mer), which are connected at their 1,4-positions, under oxidative homo coupling with a stoichiometric amount of CuCl2 and amines. The absolute configuration of the newly formed axis bond was determined based on the CD spectra of oligonaphthalenes with 1) two pyrene rings on the central naphthalenes or 2) two tetraphenylporphyrins (TPP) on the top and bottom naphthalenes. The fluorescence quantum yields increased as the number of naphthalene units increased in methoxy derivatives 10-12, and the intramolecular energy transfer quantum yields of bispyrene derivatives 7-9 were around 20% regardless of the number of naphthalene units. Furthermore, the hexadecanaphthalene derivative 4b with two TPPs exhibited a clear exciton coupling over an interchromophore distance to ca. 66 angstrom.

    DOI: 10.1248/yakushi.126.779

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  • Bottom-up synthesis of optically active oligonaphthalenes: Three different pathways for controlling axial chirality

    Kazunori Tsubaki, Hiroyuki Tanaka, Kazuto Takaishi, Masaya Miura, Hiroshi Morikawa, Takumi Furuta, Kiyoshi Tanaka, Kaoru Fuji, Takahiro Sasamori, Norihiro Tokitoh, Takeo Kawabata

    JOURNAL OF ORGANIC CHEMISTRY   71 ( 17 )   6579 - 6587   2006年8月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    The oxidative homocoupling of optically active binaphthalenes 1a-d with a stoichiometric amount of CuCl2 and amines afforded quaternaphthalenes 2a-d in up to 93% de. The high diastereoselectivities were achieved through three different pathways ( epimerization of the axis together with diastereoselective crystallization, thermodynamic, and kinetic control pathways). The type of side chains on the naphthalene influenced which pathway dominates. Three pathways were applicable to octinaphthalenes ( 8a-d) and hexadecanaphthalene 10a with 46-99% de. The absolute configuration of the newly formed axial bond was determined by ( 1) X-ray crystallographic analysis, ( 2) transformation to known compounds 15 and 16, ( 3) CD spectra of oligonaphthalenes with two pyrene rings as exciton parts, and ( 4) the shift values in C-13 NMR spectra of C-13-enriched derivatives 29-31 toward chiral shift reagent Eu(+tfc)(3).

    DOI: 10.1021/jo060974v

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  • Long-range exciton-coupled circular dichroism: Application for determination of the absolute configuration of oligonaphthalenes

    Kazunori Tsubaki, Kazuto Takaishi, Hiroyuki Tanaka, Masaya Miura, Takeo Kawabata

    ORGANIC LETTERS   8 ( 12 )   2587 - 2590   2006年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Hexadecanaphthalenes (S, S, S, S, S, S, S, S, S, S, S, S, S, S, S)-4b and ( S, S, S, S, S, S, S, R, S, S, S, S, S, S, S)-4b that possess two tetraphenylporphyrins (TPP) on the upper and lower naphthalene rings were synthesized. Long-range exciton-coupled CD in the Soret region of TPP (about 66 angstrom) was observed.

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  • Synthesis and antinematodal activity of 3-n-alkylphenols

    K Takaishi, Y Alen, K Kawazu, N Baba, S Nakajima

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   68 ( 11 )   2398 - 2400   2004年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:TAYLOR & FRANCIS LTD  

    Several 3-alkylphenols including 3-undecylphenol, which was isolated from a Sumatran rainforest plant, were synthesized to investigate their antinernatodal activity against the phytopathogenic nematodes, Bursapherencus xylophilus. A three-step synthesis involving the treatment of 2-cyclohexen-1-one with the Grignard reagent, oxidation of the resulting 1-alkyl-2-cyclohexen-1-ol and subsequent aromatization of 3-alkyl-2-cyclohexen-1-one successfully afforded such phenols. Among the 3-alkylphenols, 3-nonylphenol showed the highest activity, while 3-decylphenol and 3-undecylphenol also showed high activity.

    DOI: 10.1271/bbb.68.2398

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  • 溶媒によって円偏光発光性の符号が切り替わるビナフチル–ピレン–サンドイッチ型色素の開発

    高石 和人

    Jasco Report   63   13 - 16   2021年1月

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    担当区分:筆頭著者  

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  • 溶媒によって性質が激変するキラル発光色素の創製

    高石 和人

    化学と工業   73   798 - 799   2020年10月

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  • キラルナフタレン多量体から成る円偏光発光色素の合成 招待

    高石 和人

    有機合成化学協会誌   78   846 - 855   2020年9月

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  • 任意の発光色素を円偏光発光色素に変化させる手法

    高石 和人

    化学と工業   73   261 - 261   2020年9月

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  • 軸性キラリティーを有するナフタレン多量体のキラル光学特性制御

    高石 和人

    有機合成化学協会誌   76   885 - 893   2018年9月

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  • 振動円二色性(VCD)スペクトルによる軸不斉2,2'-ビピリジルの絶対配置の決定

    村中 厚哉, 高石 和人, 内山 真伸

    Jasco report   58 ( 2 )   1 - 5   2016年6月

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    記述言語:日本語   出版者・発行元:ジャスコレポート社  

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    高石 和人

    ファルマシア   51   58 - 58   2015年1月

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  • 光学活性オリゴナフタレンの合成と軸性不斉の決定 査読

    須江大輔, 椿一典, 高石和人, 川端猛夫

    第128日本薬学会年会 ,神奈川   2008年3月

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  • 基礎有機化学会 野副記念奨励賞

    2021年9月  

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  • 岡山県産業振興財団 科学技術賞

    2021年7月  

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    2021年4月  

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    2021年3月  

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  • Thieme Chemistry Journals Award

    2021年1月  

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  • Chemist Award BCA

    2020年12月  

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    2020年6月  

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    2020年6月  

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  • 日本化学会第100春季年会 若い世代の特別講演証

    2020年3月  

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    2018年12月  

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    2018年7月  

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    2016年4月  

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    2015年7月  

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  • 第2回ホストゲスト化学シンポジウム Impressive Presentation Award

    2007年  

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担当授業科目

  • 反応有機化学 (2021年度) 後期  - 月1,月2

  • 合成化学実験3 (2021年度) 第3学期  - 火5,火6,火7,火8,金5,金6,金7,金8

  • 合成化学実験3 (2021年度) 第3学期  - 火5,火6,火7,火8,金5,金6,金7,金8

  • 合成有機化学演習 (2021年度) 通年  - その他

  • 実践応用化学 (2021年度) 前期  - その他

  • 応用化学ゼミナール1 (2021年度) 前期  - その他

  • 応用化学ゼミナール2 (2021年度) 後期  - その他

  • 応用化学特別研究 (2021年度) 通年  - その他

  • 技術表現法 (2021年度) 3・4学期  - 月5,月6,月7,月8

  • 技術表現法 (2021年度) 3・4学期  - 月5~6

  • 有機化学3 (2021年度) 第1学期  - 月1,月2,木1,木2

  • 有機化学4 (2021年度) 第1学期  - 月1,月2,木1,木2

  • 有機反応機構論 (2021年度) 後期  - その他

  • 物理有機化学 (2021年度) 第4学期  - 火1,火2

  • 物理有機化学 (2021年度) 第4学期  - 火1,火2

  • 反応有機化学 (2020年度) 後期  - 月1,月2

  • 合成化学実験3 (2020年度) 第3学期  - 火4,火5,火6,火7,金4,金5,金6,金7

  • 合成化学実験3 (2020年度) 第3学期  - 火4,火5,火6,火7,金4,金5,金6,金7

  • 合成有機化学演習 (2020年度) 通年  - その他

  • 実践応用化学 (2020年度) 前期  - その他

  • 応用化学ゼミナール1 (2020年度) 前期  - その他

  • 応用化学ゼミナール2 (2020年度) 後期  - その他

  • 応用化学特別研究 (2020年度) 通年  - その他

  • 技術表現法 (2020年度) 3・4学期  - 月5,月6

  • 技術表現法 (2020年度) 3・4学期  - 月5,月6

  • 有機化学3 (2020年度) 第1学期  - 月1,月2,木1,木2

  • 有機化学4 (2020年度) 第1学期  - 月1,月2,木1,木2

  • 有機反応機構論 (2020年度) 後期  - その他

  • 物理有機化学 (2020年度) 第4学期  - 火1,火2

  • 物理有機化学 (2020年度) 第4学期  - 火1,火2

▼全件表示