研究者詳細 - 西原　康師

論文 - 西原　康師

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Transistor Application of Phenacene Molecules and Their Characteristics

Yoshihiro Kubozono, Xuexia He, Shino Hamao, Kazuya Teranishi, Hidenori Goto, Ritsuko Eguchi, Takashi Kambe, Shin Gohda, Yasushi Nishihara

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY 2014 ( 24 ) 3806 - 3819 2014年8月

記述言語：英語出版者・発行元：WILEY-V C H VERLAG GMBH

The characteristics of field-effect transistors (FETs) fabricated from thin films and single crystals of phenacene molecules are fully reported in this review together with the electronic and crystal structures of phenacenes. Phenacene molecules possess a low HOMO level and a wide band gap. The highest mobility observed in the phenacene thin-film FETs is 7.4 cm(2)V(-1)s(-1) for [6]phenacene, and in single-crystal FETs the highest value is 6.3 cm(2)V(-1)s(-1) for [7]phenacene. The phenacene thin-film FETs show O-2-sensing properties unlike their single-crystal FETs. The bias-stress effect is fully investigated for phenacene single-crystal FETs. Furthermore, the low-voltage operation of phenacene single-crystal FETs with electric-double-layer (EDL) capacitors is reported. The temperature dependence of phenacene single-crystal FETs is reported to clarify the transport mechanism, which is suggestive of band-like transport.

DOI： 10.1002/ejic.201402168

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New Entry to the Synthesis of α-Iminonitriles by Lewis Acid Mediated Isomerization of Cyano-Substituted Iminoisobenzofurans Prepared by Palladium-Catalyzed Three-Component Coupling of Arynes, Isocyanides, and Cyanoformates

Jing Li, Shintaro Noyori, Kiyohiko Nakajima, Yasushi Nishihara

Organometallics 33 ( 13 ) 3500 - 3507 2014年7月

Synthesis of 2,9-dialkylated phenanthro[1,2-b:8,7-b ']dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide 査読

Keita Hyodo, Hikaru Nonobe, Shuhei Nishinaga, Yasushi Nishihara

TETRAHEDRON LETTERS 55 ( 29 ) 4002 - 4005 2014年7月

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

Phenanthro[1,2-b:8,7-b']dithiophene (PDT) was prepared via Suzuki-Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b']dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki-Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents. (C) 2014 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2014.05.035

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Synthesis of Methoxy-Substituted Picenes: Substitution Position Effect on Their Electronic and Single-Crystal Structures

Hiroki Mori, Xi-chao Chen, Ning-hui Chang, Shino Hamao, Yoshihiro Kubozono, Kiyohiko Nakajima, Yasushi Nishihara

JOURNAL OF ORGANIC CHEMISTRY 79 ( 11 ) 4973 - 4983 2014年6月

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 series of picenes having methoxy groups was synthesized through Pd-catalyzed Suzuki-Miyaura couplings or Wittig reaction/intramolecular cyclization sequences, and their physicochemical properties and single-crystal structures were evaluated. The substitution position effects between the outer 1,12-, 2,11-, and 4,9-position and the inner 3,10-position are quite different; the former showed the same electronic structure as that of picene, but the latter results in a HOMO geometry different from those of picene and other methoxy picenes. In addition, crystal structures of four types of methoxy-substituted picenes 4a-c,e strongly depend on their substitution position and number of methoxy groups, which dramatically changes the structures from the fully anisotropic 1D pi-stacked structure to a unique 3D herringbone structure due to steric hindrance of methoxy groups. The calculations of transfer integrals based on their single-crystal structures reveal that the methoxy picenes have intermolecular overlaps less effective than that of the parent nonsubstituted picene. These results are attributed not only to the packing structure but also to electronic structures such as the HOMO distribution. The preliminary OFET of the representative 4c,e showed hole mobilities significantly lower than that of picene due to their less effective intermolecular overlaps, as predicted by the calculated transfer integrals.

DOI： 10.1021/jo500543h

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Palladium- Catalyzed Direct Thiolation of Aryl C similar to H Bonds with Disulfides 査読

Masayuki Iwasaki, Miki Iyanaga, Yuta Tsuchiya, Yugo Nishimura, Wenjuan Li, Zhiping Li, Yasushi Nishihara

CHEMISTRY-A EUROPEAN JOURNAL 20 ( 9 ) 2459 - 2462 2014年2月

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 catalytic variant of the direct thiolation of arenes, bearing directing groups, with disulfides or thiols has been developed under palladium and copper co-catalysis. Both sulfenyl moieties of the disulfide could be incorporated into the thiolated products, therefore, the reactions reached completion with only half an equivalent of disulfide, with respect to the starting arene. Experimental evidence suggested that the reaction proceeds through a Pd-II/Pd-IV mechanism.

DOI： 10.1002/chem.201304717

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Palladium-Catalyzed Regio- and Stereoselective Chlorothiolation of Terminal Alkynes with Sulfenyl Chlorides 査読

Masayuki Iwasaki, Tomoya Fujii, Arisa Yamamoto, Kiyohiko Nakajima, Yasushi Nishihara

CHEMISTRY-AN ASIAN JOURNAL 9 ( 1 ) 58 - 62 2014年1月

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

Chlorothiolation of terminal alkynes with sulfenyl chlorides yields anti-adducts without transition-metal catalysts. In sharp contrast, transition-metal-catalyzed chlorothiolation has not been developed to date, possibly because organosulfur compounds can poison catalyst. Herein, the regio- and stereoselective palladium-catalyzed chlorothiolation of terminal alkynes with sulfenyl chlorides is described. syn-Chlorothiolation offers a complementary synthetic route to chloroalkenyl sulfides. 2-Chloroalkenyl sulfides can easily be transformed into various sulfur-containing products, most of which are often found in natural products and pharmaceuticals.

DOI： 10.1002/asia.201301295

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Diborylation of Alkynyl MIDA Boronates and Sequential Chemoselective Suzuki-Miyaura Couplings: A Formal Carboborylation of Alkynes 査読

Keita Hyodo, Masato Suetsugu, Yasushi Nishihara

ORGANIC LETTERS 16 ( 2 ) 440 - 443 2014年1月

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

Platinum-catalyzed diborylation of phenylethynyl MIDA boronate with B-pin-B-pin proceeds to yield 1,1,2-triboryl-2-phenylethene with two different classes of the boron functionalities. Sequentially, the obtained 1,1,2-triboryl-2-phenylethene are subjected to Suzuki-Miyaura coupling to introduce a series of aryl groups chemoselectively to afford 1,1-boryl-2,2-diarylethenes.

DOI： 10.1021/ol403326z

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Selective Synthesis of Multisubstituted Olefins Utilizing gem- and vic-Diborylated Vinylsilanes Prepared by Silylborylation of an Alkynylboronate and Diborylation of Alkynylsilanes 査読

Jiao Jiao, Keita Hyodo, Hao Hu, Kiyohiko Nakajima, Yasushi Nishihara

JOURNAL OF ORGANIC CHEMISTRY 79 ( 1 ) 285 - 295 2014年1月

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 synthesis of a series of gem- and vic-diborylated vinylsilanes was accomplished via highly selective transition-metal-catalyzed syn-dimetalation to the alkynylmetal species. This protocol served as a general synthetic method toward regio- and stereodefined multisubstituted olefins. The key steps are the diastereoselective Suzuki-Miyaura cross-coupling reactions of gem- and vic-diborylated vinylsilanes, in which the two boron groups showed discrete reactivities to afford diverse precursors of multisubstituted olefins.

DOI： 10.1021/jo4024057

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The origin of exo-selectivity in methyl cyanoformate addition onto the C=C bond of norbornene in Pd-catalyzed cyanoesterification” 査読

奥田靖浩, Szilagyi, R. K, 森聖治, 西原康師

Dalton Trans. 43 ( 25 ) 9537 - 9548 2014年

Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3 査読

李靖, 奥田靖浩, 趙家冀, 森聖治, 西原康師

Org. Lett. 16 ( 19 ) 5220 - 5223 2014年

Phenanthro[1,2-b:8,7-b']dithiophene: A new picene-type molecule for rransistor applications 査読

西原康師, 木下恵, 兵頭恵太, 奥田靖浩, 江口律子, 後藤秀徳, 浜尾志乃, 高林康裕, 久保園芳博

RSC Advances 3 ( 42 ) 19341 - 19347 2014年

Synthesis, structure, and isomerization of alkoxycarbonyl(chloro)(cyano)rhodium(III) complexes, mer- RhCl(CO2R)(CN)(PMe3)3 (R = Me, Et, nPr, iPr, nBu, and Bn) through C–C bond cleavage of cyanoformates 査読

奥田靖浩, 岡本尊, 山本有沙, 李靖, 中島清彦, 西原康師

Chem. Lett. 43 ( 4 ) 417 - 419 2014年

Experimental and Theoretical Studies on the Platinum-Mediated Selective C(sp)-Si Bond Cleavage of Alkynylsilanes 査読

奥田靖浩, 石黒雄也, 森聖治, 中島清彦, 西原康師

Organometallics 33 ( 7 ) 1878 - 1889 2014年

Palladium-Catalyzed Annulation of o-lodobiphenyls with o-Bromobenzyl Alcohols: Synthesis of Functionalized Triphenylenes via C-C and C-H Bond Cleavages 査読

Masayuki Iwasaki, Shohel Lino, Yasushi Nishihara

ORGANIC LETTERS 15 ( 20 ) 5326 - 5329 2013年10月

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

Treatment of o-iodobiphenyls with abromobenzyl alcohols in the presence of cesium carbonate under palladium catalysis affords a series of highly substituted triphenylenes. The reaction involves two C-C bond formations and C-C and C-H bond cleavages. A combination of palladium and an electron-deficient phosphine ligand proves to be effective for both decarbonylative cross-coupling and intramolecular cyclization.

DOI： 10.1021/oI4025869

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Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Silylborylation of an Alkynylboronate/Chemoselective Cross-Coupling Sequences 査読

Jiao Jiao, Kiyohiko Nakajima, Yasushi Nishihara

ORGANIC LETTERS 15 ( 13 ) 3294 - 3297 2013年7月

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 highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-B-pin undergoes a Pd(OAc)(2)/(t)OctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (2)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.

DOI： 10.1021/ol401333j

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Synthesis of cyclic 1-alkenylboronates via Zr-mediated double functionalization of alkynylboronates and sequential Ru-catalyzed ring-closing olefin metathesis 査読

Yasushi Nishihara, Masato Suetsugu, Daisuke Saito, Megumi Kinoshita, Masayuki Iwasaki

Organic Letters 15 ( 10 ) 2418 - 2421 2013年5月

記述言語：英語掲載種別：研究論文（学術雑誌）

Synthesis of novel cyclic 1-alkenylboronates is accomplished through the zirconium-mediated regio- and stereoselective double functionalization of 1-alkynylboronates and the subsequent ruthenium-catalyzed ring-closing metathesis (RCM). The obtained substituted cyclic 1-alkenylboronates are transformed into o-terphenyl and triphenylene derivatives. © 2013 American Chemical Society.

DOI： 10.1021/ol400896u

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Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: efficient synthetic methods for diaryl ketones and chalcones at room temperature 査読

Daisuke Ogawa, Keita Hyodo, Masato Suetsugu, Jing Li, Yoshiaki Inoue, Mamoru Fujisawa, Masayuki Iwasaki, Kentaro Takagi, Yasushi Nishihara

TETRAHEDRON 69 ( 12 ) 2565 - 2571 2013年3月

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

Palladium-catalyzed cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides in the presence of copper(I) thiophene-2-carboxylate (CuTC) as an activator in diethyl ether at room temperature under strictly non-basic conditions affords the diaryl ketones or chalcones in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible. (C) 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2013.01.058

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Palladium-free synthesis of unsymmetrical diarylethynes by cross-coupling reaction of alkynylboronates with aryl iodides catalyzed by CuCl 査読

Daisuke Ogawa, Jing Li, Masato Suetsugu, Jiao Jiao, Masayuki Iwasaki, Yasushi Nishihara

TETRAHEDRON LETTERS 54 ( 6 ) 518 - 521 2013年2月

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

A series of unsymmetrical diarylethynes have been synthesized by the copper-catalyzed cross-coupling reaction of alkynylboronates with aryl iodides in high to excellent yields under palladium-free conditions. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible with this reaction. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2012.11.069

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Synthesis of substituted [6]phenacenes through Suzuki–Miyaura coupling of polyhalobenzene with alkenylboronates and sequential intramolecular cyclization via C–H bond activation 査読

常寧輝, 森裕樹, 陳璽朝, 奥田靖浩, 岡本尊, 西原康師

Chem. Lett. 42 ( 10 ) 1257 - 1259 2013年

Synthesis of Substituted Picenes through Pd-Catalyzed Cross-Coupling Reaction/Annulation Sequences and Their Physicochemical Properties 査読

常寧輝, 陳璽朝, 野々部瑛, 奥田靖浩, 森裕樹, 中島清彦, 西原康師

Org. Lett. 15 ( 14 ) 3558 - 3561 2013年

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