Development of ambipolar organic semiconductor using properties of antiaromatic ring

• Project/Area Number: 24655036
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Tokyo Metropolitan University
• Principal Investigator: NISHINAGA Tohru 首都大学東京, 理工学研究科, 准教授 (30281108)
• Project Period (FY): 2012-04-01 – 2014-03-31
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 反芳香族性 / 有機半導体 / トランジスタ / 電界効果トランジスタ / 両極性半導体 / シクロオクタテトラエン / 低バンドギャップ

Research Abstract

It is difficult to realize an ambipolar organic semiconductor with high and balanced mobility and only a few example of such semiconductors have been reported. In this work, unlike the conventional donor-acceptor structure, we succeeded in the development of a novel ambipolar semiconductor based on cyclic tetrathiophene having narrow HOMO-LUMO gap derived from antiaromatic planar COT ring.

Research Products

• [Journal Article] Multifunctional π-Expanded Macrocyclic Oligothiophene 6-Mers and Related Macrocyclic Oligomers (2014)
  • Author(s): Iyoda, M.; Tanaka, K.; Shimizu, H.; Hasegawa, M.; Nishinaga, T.; Nishiuchi, T.; Kunugi, Y.; Ishida, T.; Otani, H.; Sato, H.; Inukai, K.; Tahara, K.; Tobe, Y.
  • Journal Title: J. Am. Chem. Soc. Volume: 136 Issue: 6 Pages: 2389-2396
  • DOI: 10.1021/ja4101744
  • Peer Reviewed
• [Journal Article] Effect of Substituents on the Structure, Stability, and pi-Dimerization of Dithienylpyrrole Radical Cations (2013)
  • Author(s): T. Nishinaga, T. Kageyama, M. Koizumi, K. Ando, M. Takase, M. Iyoda
  • Journal Title: J. Org. Chem. Volume: 78 Issue: 18 Pages: 9205-9213
  • DOI: 10.1021/jo401453s
  • Peer Reviewed
• [Journal Article] Dithieno[3,4-b:3’,4’-d]thiophene-Annelated Antiaromatic Planar Cyclooctatetraene with Olefinic Protons (2013)
  • Author(s): K. Aita, T. Ohmae, M. Takase, K. Nomura, H. Kimura, T. Nishinaga
  • Journal Title: Org. Lett. Volume: 15 Issue: 14 Pages: 3522-3525
  • DOI: 10.1021/ol401125f
  • Peer Reviewed
• [Journal Article] Donor-Acceptor Segregated Paracyclophanes Composed of Naphthobipyrrole and Stacked Fluoroarenes (2013)
  • Author(s): Masayoshi Takase, Ayumi Inabe, Yuki Sugawara, Wataru Fujita, Tohru Nishinaga, Kotohiro Nomura
  • Journal Title: Org. Lett. Volume: 15 Issue: 13 Pages: 3202-3205
  • DOI: 10.1021/ol400882q
  • Peer Reviewed
• [Journal Article] Pyrrole-Fused Azacoronene Family: The Influence of Replacement with Dialkoxybenzenes on the Optical and Electronic Properties in Neutral and Oxidized States (2013)
  • Author(s): M. Takase, T. Narita, W. Fujita, M. S. Asano, T. Nishinaga, H. Benten, K. Yoza, K. Müllen
  • Journal Title: J. Am. Chem. Soc Volume: 135 Issue: 21 Pages: 8031-8040
  • DOI: 10.1021/ja402371f
  • Peer Reviewed
• [Journal Article] Antiaromatic planar cyclooctatetraene: a strategy for ambipolar semiconductors in field effect transistors (2013)
  • Author(s): T. Nishinaga, T. Ohmae, K. Aita, M. Takase, M. Iyoda, T. Arai, Y. Kunugi
  • Journal Title: Chem. Commun. Volume: 49 Issue: 47 Pages: 5354-5356
  • DOI: 10.1039/c3cc41764f
  • Peer Reviewed
• [Journal Article] Steric Control in the pi-Dimerization of Oligothiophene Radical Cations Annelated with Bicyclo[2.2.2]octene Units (2013)
  • Author(s): M. Tateno, M. Takase, M. Iyoda, K. Komatsu, T. Nishinaga
  • Journal Title: Chem. Eur. J. Volume: 19 Issue: 17 Pages: 5457-5467
  • DOI: 10.1002/chem.201204332
  • Peer Reviewed
• [Journal Article] Solvent-induced Crystalline State Emission and Multichromism of Bent pi-Surface System Composed of Dibenzocyclooctatetraene Units (2013)
  • Author(s): T. Nishiuchi, K. Tanaka, Y. Kuwatani, J. Sung, T. Nishinaga, D. Kim, M. Iyoda
  • Journal Title: Chem. Eur. J. Volume: 19 Issue: 13 Pages: 4110-4116
  • DOI: 10.1002/chem.201203952
  • Peer Reviewed
• [Journal Article] Self-Assembly, Chromic Properties, and Nanostructure Formation of Tetrathiafulvalene-Fused Dodecadehydro[18]annulenes (2012)
  • Author(s): H. Enozawa
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 85 Issue: 10 Pages: 1120-1137
  • DOI: 10.1246/bcsj.20120135
  • NAID: 10031120562
  • ISSN: 0009-2673, 1348-0634
  • Peer Reviewed
• [Journal Article] Syntheses, Molecular Structures, and Antiviral Activities of 1-and2-(20-deoxy-D-ribofuranosyl)cyclohepta[d][1,2,3]triazol-6(1H)-ones and 1-(20-deoxy-D-ribofuranosyl)cyclohepta[b]pyrrol-8(1H)-one (2012)
  • Author(s): Tomoo Nakazawa, Takeshi Ohmae, Masahiro Fujimuro, Masahiko Ito, Tohru Nishinaga, Masahiko Iyoda
  • Journal Title: Tetrahedron Volume: 68 Issue: 27-28 Pages: 5368-5374
  • DOI: 10.1016/j.tet.2012.04.109
  • Peer Reviewed
• [Presentation] 反芳香族COT環を持つ環状テトラチオフェンのオリゴマー化 (2014)
  • Author(s): 中所亮輔, 相田一成, 高瀬雅祥, 野村琴広, 西長亨
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋
  • Year and Date: 2014-03-27
• [Presentation] 非局在型ビラジカル構造を有するピロール縮環アザコロネンの合成と物性 (2014)
  • Author(s): 高瀬雅祥, 成田智幸, 藤田渉, 西長亨, 野村琴広
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋
  • Year and Date: 2014-03-27
• [Presentation] πダイマーを利用したチオフェンピロール混合オリゴマーの酸化種における集積体の構築 (2014)
  • Author(s): 影山拓哉, 高瀬雅祥, 野村琴広, 西長亨
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋
  • Year and Date: 2014-03-27
• [Presentation] 反芳香族COT環を持つ環状テトラチオフェンのオリゴマー化 (2014)
  • Author(s): 中所亮輔, 相田一成, 高瀬雅祥, 野村琴広, 西長 亨
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋大学
• [Presentation] 新奇オリゴチオフェン類の設計・合成と機能化 (2013)
  • Author(s): 西長亨
  • Organizer: 第7回有機π電子系シンポジウム
  • Place of Presentation: 高崎
  • Year and Date: 2013-12-14
  • Invited
• [Presentation] チオフェンピロール混合オリゴマーのπダイマー形成制御 (2013)
  • Author(s): 影山拓哉, 高瀬雅祥, 野村琴広, 西長亨
  • Organizer: 第40回有機典型元素化学討論会
  • Place of Presentation: 東大阪
  • Year and Date: 2013-12-06
• [Presentation] スタックしたフルオロアレーンを持つドナー・アクセプター分離型オリゴマーの合成 (2013)
  • Author(s): 菅原由紀, 高瀬雅祥, 西長亨, 野村琴広
  • Organizer: 第40回有機典型元素化学討論会
  • Place of Presentation: 東大阪
  • Year and Date: 2013-12-06
• [Presentation] Self-Association and its Steric Control of Cationic Oligothiophenes (2013)
  • Author(s): Tohru Nishinaga
  • Organizer: 2013 ACS National Meeting
  • Place of Presentation: インディアナポリス(米国)
  • Year and Date: 2013-09-10
  • Invited
• [Presentation] ジチエニルピロール誘導体における一電子酸化種の安定性と自己会合挙動 (2013)
  • Author(s): 影山拓哉, 高瀬雅祥, 野村琴広, 西長亨
  • Organizer: 第24回基礎有機化学討論会
  • Place of Presentation: 東京
  • Year and Date: 2013-09-06
• [Presentation] スタックしたフルオロアレーン部位を有するドナー・アクセプター分離型π共役オリゴマーの合成と物性 (2013)
  • Author(s): 菅原由紀, 高瀬雅祥, 西長亨, 野村琴広
  • Organizer: 第24回基礎有機化学討論会
  • Place of Presentation: 東京
  • Year and Date: 2013-09-06
• [Presentation] ピロールを用いた芳香族求核置換反応を鍵とする機能性分子の合成と物性 (2013)
  • Author(s): 高瀬雅祥, 吉田尚史, 成田智幸, 西長亨, 伊與田正彦
  • Organizer: 第24回基礎有機化学討論会
  • Place of Presentation: 東京
  • Year and Date: 2013-09-05
• [Presentation] Dithieno[3,4-b : 3',4'-d]thiophene-ann elated antiaromatic planar cyclooctatetraene with olefinic protons (2013)
  • Author(s): Tohru Nishinaga, Kazunari Aita, Takeshi Ohmae, Masayoshi Takase, Kotohiro Nomura, Hideaki Kimura
  • Organizer: 15th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: 台北(台湾)
  • Year and Date: 2013-08-01
• [Presentation] Conjugated oligomer with donor-acceptor segregation composed of naphthobipyrrole and stacked fluoroarenes (2013)
  • Author(s): Yuki Sugawara, Ayumi Inabe, Masayoshi Takase, Tohru Nishinaga, Kotohiro Nomura
  • Organizer: 15th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: 台北(台湾)
  • Year and Date: 2013-08-01
• [Presentation] Effect of substituents on the structure, stability, andπ-dimerization of dithienylpyrrole radical cations (2013)
  • Author(s): Takuya Kageyama, Masahide Koizumi, Masayoshi Takase, Kotohiro Nomura, Tohru Nishinaga
  • Organizer: 15th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: 台北(台湾)
  • Year and Date: 2013-07-30
• [Presentation] Pyrrole-fused azacoronenes : synthesis and optical and electronic properties in neutral and oxidized states (2013)
  • Author(s): Masayoshi Takase, Tomoyuki Narita, Tohru Nishinaga, Klaus Müllen
  • Organizer: 15th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: 台北(台湾)
  • Year and Date: 2013-07-30
• [Presentation] Self-Association and its Steric Control of Cationic Oligothiophenes (2013)
  • Author(s): Tohru Nishinaga
  • Organizer: 2013 Physical Organic Chemistry Gordon Research Conference
  • Place of Presentation: プリマス(米国)
  • Year and Date: 2013-06-25
  • Invited
• [Presentation] チオフェンピロール混合オリゴマーのラジカルカチオン種のπダイマー形成 (2013)
  • Author(s): 影山拓哉, 小泉匡秀, 高瀬雅祥, 野村琴広, 西長亨
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津
  • Year and Date: 2013-03-22
• [Presentation] Self-Association and its Steric Control of Cationic Oligothiophenes (2013)
  • Author(s): Tohru Nishinaga
  • Organizer: 2013 Physical Organic Chemistry Gordon Research Conference
  • Place of Presentation: Plymouth, NH
  • Invited
• [Presentation] Self-Association and its Steric Control of Cationic Oligothiophenes (2013)
  • Author(s): Tohru Nishinaga
  • Organizer: 2013 ACS National Meeting
  • Place of Presentation: Indianapolice, IN
  • Invited
• [Presentation] 新奇オリゴチオフェン類の設計・合成と機能化 (2013)
  • Author(s): 西長 亨
  • Organizer: 第７回有機π電子系シンポジウム
  • Place of Presentation: 高崎
  • Invited
• [Presentation] Dithieno[3,4-b:3’,4’-d]thiophene-annelated antiaromatic planar cyclooctatetraene with olefinic protons (2013)
  • Author(s): T. Nishinaga, K. Aita, T. Ohmae, M. Takase, K. Nomura, H. Kimura
  • Organizer: 15th International Symposium on Novel Aromatic Compounds
  • Place of Presentation: Taipei
• [Presentation] ジチエノチオフェンが縮環した平面シクロオクタテトラエン誘導体の合成と物性 (2013)
  • Author(s): 相田一成, 大前武士, 高瀬雅祥, 野村琴広, 西長 亨
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 草津
• [Presentation] Self-Association and its Steric Control of Cationic Oligothiophenes toward Constraction of Conducting Supramolecular Wires (2012)
  • Author(s): Tohru Nishinaga
  • Organizer: International Conference on Emerging Advanced Nanomaterials
  • Place of Presentation: ブリスベン(豪国)
  • Year and Date: 2012-10-21
  • Invited
• [Presentation] オリゴチオフェンラジカルカチオンのπダイマー形成に関する実験・理論的研究 (2012)
  • Author(s): 舘野将輝, 高瀬雅祥, 小松鉱一, 伊与田正彦, 西長亨
  • Organizer: 第23回基礎有機討論会
  • Place of Presentation: 京都
  • Year and Date: 2012-09-19
• [Presentation] アリール縮環チオフェンピロール混合オリゴマーのジカチオン種のビラジカル性 (2012)
  • Author(s): 影山拓哉, 采女俊介, 高瀬雅祥, 野村琴広, 西長亨
  • Organizer: 第23回基礎有機討論会
  • Place of Presentation: 京都
  • Year and Date: 2012-09-19
• [Presentation] Properties of SAMs and Gold-nanoparticle of Oligothiophenes Annelated with Bicyclo[2.2.2]octen Units (2012)
  • Author(s): Masaki Tateno, Masayoshi Takase, Kotohiro Nomura, Tohru Nishinaga
  • Organizer: The 6th International Conference on Gold Science
  • Place of Presentation: 東京
  • Year and Date: 2012-09-05
• [Presentation] Effect of benzo-annelation on the biradical character of thiophene-pyrrole oligomer dication (2012)
  • Author(s): Takuya. Kageyama, Syunsuke Uneme, Masayoshi Takase, Kotohiro Nomura, Tohru Nishinaga
  • Organizer: 10th International Conference on Heteroatom Chemistry
  • Place of Presentation: 京都
  • Year and Date: 2012-05-20
• [Presentation] Self-Association and its Steric Control of Cationic Oligothiophenes (2012)
  • Author(s): Tohru Nishinaga
  • Organizer: The 21st IUPAC International Conference on Physical Organic Chemistry
  • Place of Presentation: ダラム(英国)
• [Presentation] Self-Association and its Steric Control of Cationic Oligothiophenes (2012)
  • Author(s): Tohru Nishinaga
  • Organizer: The 21st IUPAC International Conference on Physical Organic Chemistry
  • Place of Presentation: ダラム（英国）
• [Presentation] Self-Association and its Steric Control of Cationic Oligothiophenes toward Constraction of Conducting Supramolecular Wires (2012)
  • Author(s): Tohru Nishinaga
  • Organizer: International Conference on Emerging Advanced Nanomaterials
  • Place of Presentation: ブリスベン（豪国）
  • Invited
• [Presentation] 平面シクロオクタテトラエン誘導体の反芳香族性と有機FET特性 (2012)
  • Author(s): 相田一成，大前武士，高瀬雅祥，野村琴広，西長 亨，功刀義人
  • Organizer: 第39回有機典型元素化学討論会
  • Place of Presentation: 盛岡
• [Book] 基礎から学ぶ有機化学 (2013)
  • Author(s): 伊與田正彦、佐藤総一、西長亨、三島正規
  • Total Pages: 182
  • Publisher: 朝倉書店
• [Remarks] 首都大学東京 有機化学研究室
  • URL: http://www.comp.tmu.ac.jp/tmuorg/
• [Remarks] 首都大学東京 有機化学研究室
  • URL: http://www.comp.tmu.ac.jp/tmuorg/