Synthesis of pi-conjugated cmopounds based on heteroaromatics such as carbazole and their application to host molecules

• Project/Area Number: 15K05415
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Gunma University
• Principal Investigator: Nakamura Yosuke 群馬大学, 大学院理工学府, 教授 (60261864)
• Co-Investigator(Kenkyū-buntansha): 加藤 真一郎 滋賀県立大学, 工学部, 准教授 (70586792)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
• Keywords: ヘテロ環 / カルバゾール / シクロファン / ホスト / 大環状化合物 / 錯形成 / 光物性 / ドナー / フェノチアジン / π共役

Outline of Final Research Achievements

Acyclic host compounds (molecular receptors) possessing ethynylcarbazole moieties at 1,8-positions of carbazole were systematically synthesized, and the complexation behavior with some acceptors was investigated. Conjugated macrocycles composed of carbazole and triazole or triazolium moieties were successfully synthesized by click reactions, and their self-association and complexation with anions such as iodide ion were clarified. Cyclophanes bearing carbazole or dibenzofuran bridged by disiloxane or disilane linkages were synthesized, and their structure-property relationship was disclosed.

Research Products

• [Journal Article] Trithiazolyl-1,3,5-triazines bearing decyloxybenzene moieties: synthesis, photophysical and electrochemical properties, as well as self-assembly behavior (2018)
  • Author(s): S.-i. Kato, S. Jin, T. Kimura, N. Yoshikawa, D. Nara, K. Imamura, Y. Shiota, K. Yoshizawa, R. Katoono, T. Yamanobe, H. Uehara, Y. Nakamura
  • Journal Title: Organic & Biomolecular Chemistry Volume: 16 Issue: 19 Pages: 3584-3595
  • DOI: 10.1039/c8ob00471d
  • Peer Reviewed
• [Journal Article] Tetraalkoxyphenanthrene-Fused Hexadecadehydro[20]- and Tetracosadehydro[30]annulenes: Syntheses, Characterizations, Electronic Properties, and Self-Assembly (2017)
  • Author(s): Nobutaka Takahashi, Shin-ichiro Kato, Minoru Yamaji, Masahiko Ueno, Ryunosuke Iwabuchi, Yui Shimizu, Masashi Nitani, Yutaka Ie, Yoshio Aso, Takeshi Yamanobe, Hiroki Uehara, Yosuke Nakamura
  • Journal Title: J. Org. Chem. Volume: 82 Issue: 17 Pages: 8882-8896
  • DOI: 10.1021/acs.joc.7b01165
  • Peer Reviewed
• [Journal Article] Blue Fluorescence from BF2 Complexes of N,O-Benzamide Ligands: Synthesis, Structure, and Photophysical Properties (2017)
  • Author(s): M. Yamaji, S.-i. Kato, K. Tomonari, M. Mamiya, K. Goto, H. Okamoto, Y. Nakamura, F. Tani
  • Journal Title: Inorganic Chemistry Volume: 56 Issue: 20 Pages: 12514-12519
  • DOI: 10.1021/acs.inorgchem.7b02013
  • Peer Reviewed
• [Journal Article] Tetraalkoxyphenanthrene-Fused Thiadiazoloquinoxalines: Synthesis, Electronic, Optical, and Electrochemical Properties, and Self-Assembly (2016)
  • Author(s): Shin-ichiro Kato, Keitaro Watanabe, Misaki Tamura, Masahiko Ueno, Masashi Nitani, Yutaka Ie, Yoshio Aso, Takeshi Yamanobe, Hiroki Uehara, and Yosuke Nakamura
  • Journal Title: J. Org. Chem. Volume: 82 Issue: 6 Pages: 3132-3143
  • DOI: 10.1021/acs.joc.7b00084
  • Peer Reviewed
• [Journal Article] Synthesis, Self-association, and Anion Recognition of Conjugated Macrocycles Composed of Carbazole and Triazolium Moieties (2016)
  • Author(s): S. Jin, S.-i. Kato, Y. Nakamura
  • Journal Title: Chemistry Letters Volume: 45 Issue: 8 Pages: 869-871
  • DOI: 10.1246/cl.160400
  • NAID: 130005254537
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Benzo- and Naphthopentalenes: Syntheses, Structures, and Properties (2016)
  • Author(s): S.-i. Kato, S. Kuwako, N. Takahashi, T. Kijima, Y. Nakamura
  • Journal Title: The Journal of Organic Chemistry Volume: 81 Issue: 17 Pages: 7700-7710
  • DOI: 10.1021/acs.joc.6b01409
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Push-pull fluorenones and benzazulenequinones: unprecedented regioselective [4 + 2] and [2 + 2] cycloadditions of benzopentalenequinone derivative and alkynes bearing an aniline moiety (2016)
  • Author(s): S. Kato, T. Kijima, Y. Shiota, T. Yoshihara, S. Tobita, K. Yoshizawa, and Y. Nakamura
  • Journal Title: Tetrahedron Lett. Volume: 57 Issue: 41 Pages: 4604-4607
  • DOI: 10.1016/j.tetlet.2016.09.002
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Synthesis and Electronic, Optical, and Electrochemical Properties of a Series of Tetracyanobutadiene-Substituted Carbazoles (2016)
  • Author(s): S.-i. Kato, H. Noguchi, S. Jin, Y. Nakamura
  • Journal Title: Asian Journal of Organic Chemistry Volume: 5 Issue: 2 Pages: 246-256
  • DOI: 10.1002/ajoc.201500431
  • Peer Reviewed
• [Journal Article] A Series of π-Extended Thiadiazoles Fused with Electron-Donating Heteroaromatic Moieties: Syntheses, Properties, and Polymorphic Crystals (2015)
  • Author(s): S.-i. Kato, T. Furuya, M. Nitani, N. Hasebe, Y. Ie, Y. Aso, T. Yoshihara, S. Tobita, Y. Nakamura
  • Journal Title: Chemistry A European Journal Volume: 21 Issue: 7 Pages: 3115-3125
  • DOI: 10.1002/chem.201405478
  • Peer Reviewed
• [Journal Article] A Series of Carbazole-Pyrimidine Conjugates: Syntheses and Electronic, Photophysical, and Electrochemical Properties (2015)
  • Author(s): S.-i. Kato, Y. Yamada, H. Hiyoshi, K. Umezu, Y. Nakamura
  • Journal Title: The Journal of Organic Chemistry Volume: 80 Issue: 18 Pages: 9076-9090
  • DOI: 10.1021/acs.joc.5b01409
  • Peer Reviewed
• [Presentation] フェノチアジンの1,9位にエチニレンを介して種々の芳香環を導入した共役系化合物の合成と物性 (2018)
  • Author(s): 関 克也，山本浩司，中村洋介
  • Organizer: 日本化学会第98春季年会
• [Presentation] ピリミジンとフェノチアジンが交互に連結した非環状および環状化合物の合成と物性 (2018)
  • Author(s): 大嶋祐貴，加藤真一郎，山本浩司，中村洋介
  • Organizer: 日本化学会第98春季年会
• [Presentation] ジベンゾチオフェンとトリアゾールからなる大環状共役系化合物の合成、自己会合、およびアニオン認識 (2017)
  • Author(s): 神聖史，加藤真一郎，中村洋介
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2017-03-16
• [Presentation] ケイ素を含む架橋鎖でジベンゾフランを連結したシクロファンの合成と物性 (2017)
  • Author(s): 磯野裕汰，加藤真一郎，中村洋介
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2017-03-16
• [Presentation] カルバゾールが置換したピリミジン誘導体とその白金錯体の合成と物性 (2017)
  • Author(s): 吉川直樹，加藤真一郎，中村洋介
  • Organizer: 第28回基礎有機化学討論会
• [Presentation] フェノチアジンを種々の架橋鎖で連結したシクロファンの合成と物性 (2017)
  • Author(s): 矢川未悠，山本浩司，中村洋介
  • Organizer: 第11回有機π電子系シンポジウム
• [Presentation] カルバゾールとトリアゾリウムからなる大環状共役系化合物の合成、自己会合、およびアニオン認識 (2016)
  • Author(s): 神聖史，加藤真一郎，中村洋介
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学京田辺キャンパス（京田辺）
  • Year and Date: 2016-03-24
• [Presentation] ジベンゾフランをジシロキサンまたはジシランで架橋したシクロファン類の合成と物性 (2016)
  • Author(s): 磯野裕汰，加藤真一郎，中村洋介
  • Organizer: 日本化学会第96春季年会
  • Place of Presentation: 同志社大学京田辺キャンパス（京田辺）
  • Year and Date: 2016-03-24
• [Presentation] カルバゾールとトリアゾールまたはトリアゾリウムからなる大環状共役系化合物の合成と物性 (2015)
  • Author(s): 神聖史，加藤真一郎，中村洋介
  • Organizer: 第26回基礎有機化学討論会
  • Place of Presentation: 愛媛大学（松山）
  • Year and Date: 2015-09-24
• [Presentation] カルバゾールまたはフルオレンとトリアゾールからなる大環状共役系化合物の合成、自己会合、およびアニオン認識 (2015)
  • Author(s): 神聖史，加藤真一郎，中村洋介
  • Organizer: 第13回ホスト・ゲスト化学シンポジウム
  • Place of Presentation: 東北大学川内キャンパス（仙台）
  • Year and Date: 2015-06-06