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Development of reactions for bottom-up synthesis of BN-embedded carbon nanotube

Research Project

Project/Area Number 19K22191
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 33:Organic chemistry and related fields
Research InstitutionKwansei Gakuin University

Principal Investigator

Hatakeyama Takuji  関西学院大学, 理工学部, 教授 (90432319)

Project Period (FY) 2019-06-28 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2020: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2019: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Keywordsナノ材料 / 有機導体 / 有機化学 / カーボンナノチューブ
Outline of Research at the Start

本研究では,タンデムボラFriedel-Crafts反応を鍵反応として用いることで,含BNカーボンナノチューブの部分構造である含BNバッキーボウルおよび含BNシクラセンを合成する。更に,これら含BN湾曲π共役分子をテンプレート分子として用いることで,化学気相成長法による含BNカーボンナノチューブの精密合成を目指す。

Outline of Final Research Achievements

Recently, we have succeeded in the short-step synthesis of BN-embedded tetrabenzocorannulene using the tandem bora-Friedel-Crafts reaction. Firstly, we have developed a one-shot borylation reaction that enables the facile boron substitution into various aromatic hydrocarbons. The regioselectivity is controlled kinetically: the borylation takes place at the least sterically hindered carbon where the HOMO is located. Secondly, based on this methodology, we have successfully synthesized various extended π-conjugated molecules, which are substructures of BN-containing carbon nanotubes.

Academic Significance and Societal Importance of the Research Achievements

本研究で合成した様々な含BN拡張π共役分子は,優れた発光特性や導電性といった機能を有しており,有機エレクトロニクス分野の発展に寄与するものと考えられる。また研究を通じて確立したone-shotホウ素化反応を応用し,含BNバッキーボウルや含BNカーボンナノベルトを合成することが可能であり,これらをテンプレート分子として用いた含BNカーボンナノチューブのボトムアップ合成への展開が期待できる。

Report

(3 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • Research Products

    (33 results)

All 2021 2020 2019 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 2 results) Presentation (23 results) (of which Int'l Joint Research: 5 results,  Invited: 11 results) Remarks (1 results)

  • [Journal Article] Development of One-Shot/One-Pot Borylation Reactions toward Organoboron-Based Materials2021

    • Author(s)
      Oda Susumu、Hatakeyama Takuji
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94 Issue: 3 Pages: 950-960

    • DOI

      10.1246/bcsj.20200372

    • NAID

      130008021806

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Syntheses and Physical Properties of Cationic BN‐Embedded Polycyclic Aromatic Hydrocarbons2021

    • Author(s)
      Gotoh Hajime、Nakatsuka Soichiro、Tanaka Hiroki、Yasuda Nobuhiro、Haketa Yohei、Maeda Hiromitsu、Hatakeyama Takuji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: - Issue: 23 Pages: 12835-12840

    • DOI

      10.1002/anie.202103488

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Carbazole‐Based DABNA Analogues as Highly Efficient Thermally Activated Delayed Fluorescence Materials for Narrowband Organic Light‐Emitting Diodes2020

    • Author(s)
      Oda Susumu、Kumano Wataru、Hama Toshiki、Kawasumi Ryosuke、Yoshiura Kazuki、Hatakeyama Takuji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 6 Pages: 2882-2886

    • DOI

      10.1002/anie.202012891

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solution‐Processable Pure Green Thermally Activated Delayed Fluorescence Emitter Based on the Multiple Resonance Effect2020

    • Author(s)
      Ikeda Naoya、Oda Susumu、Matsumoto Ryuji、Yoshioka Mayu、Fukushima Daisuke、Yoshiura Kazuki、Yasuda Nobuhiro、Hatakeyama Takuji
    • Journal Title

      Advanced Materials

      Volume: 32 Issue: 40 Pages: 2004072-2004072

    • DOI

      10.1002/adma.202004072

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solvent‐Vapor‐Induced Reversible Single‐Crystal‐to‐Single‐Crystal Transformation of a Triphosphaazatriangulene‐Based Metal-Organic Framework2020

    • Author(s)
      Nakatsuka Soichiro、Watanabe Yusuke、Kamakura Yoshinobu、Horike Satoshi、Tanaka Daisuke、Hatakeyama Takuji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 59 Issue: 4 Pages: 1435-1439

    • DOI

      10.1002/anie.201912195

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Multiple Electrophilic C-H Borylation of Arenes Using Boron Triiodide2020

    • Author(s)
      Oda Susumu、Ueura Kenta、Kawakami Bungo、Hatakeyama Takuji
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 2 Pages: 700-704

    • DOI

      10.1021/acs.orglett.9b04483

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] The Role of Reverse Intersystem Crossing Using a TADF‐Type Acceptor Molecule on the Device Stability of Exciplex‐Based Organic Light‐Emitting Diodes2020

    • Author(s)
      Thanh Ba Nguyen, Hajime Nakanotani, Takuji Hatakeyama, Chihaya Adachi
    • Journal Title

      Advanced Materials

      Volume: 32 Issue: 9 Pages: 1906614-1906614

    • DOI

      10.1002/adma.201906614

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Narrowband deep-blue organic light-emitting diode featuring an organoboron-based emitter2019

    • Author(s)
      Kondo Yasuhiro、Yoshiura Kazuki、Kitera Sayuri、Nishi Hiroki、Oda Susumu、Gotoh Hajime、Sasada Yasuyuki、Yanai Motoki、Hatakeyama Takuji
    • Journal Title

      Nature Photonics

      Volume: 13 Issue: 10 Pages: 678-682

    • DOI

      10.1038/s41566-019-0476-5

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Multiple Resonance Effect-Induced Sky-Blue Thermally Activated Delayed Fluorescence with a Narrow Emission Band2019

    • Author(s)
      Oda Susumu、Kawakami Bungo、Kawasumi Ryosuke、Okita Ryota、Hatakeyama Takuji
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 23 Pages: 9311-9314

    • DOI

      10.1021/acs.orglett.9b03342

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Presentation] One-Shot多重ホウ素化による含BNノナセン類縁体の合成2021

    • Author(s)
      新谷 俊樹・小田 晋・畠山 琢次
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ハロホウ素化反応を利用した含BNコランニュレンの合成2021

    • Author(s)
      岡田 直也・大矢 遥花・後藤 玄・中塚 宗一郎・畠山 琢次
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ハロホウ素化反応を利用した含BNコランニュレンの合成2020

    • Author(s)
      岡田直也・大矢遥花・後藤玄・中塚宗一郎・畠山琢次
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 脱芳香族化を伴うホウ素化反応による含BNヘキサベンゾコロネンの合成2020

    • Author(s)
      山本 健寛・阿部 紘明・後藤 玄・中塚 宗一郎・小田 晋・畠山 琢次
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 多重共鳴効果を鍵とした次世代の高色純度発光材料の開発2020

    • Author(s)
      畠山琢次
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] Multiple Resonance Effect-Based Narrowband TADF Emitters2020

    • Author(s)
      Takuji Hatakeyama
    • Organizer
      The 27th International Display Workshops (IDW’20)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 多重共鳴効果を利用した超高色純度熱活性化遅延蛍光材料の開発2020

    • Author(s)
      畠山琢次
    • Organizer
      日本学術振興会光電相互変換第125委員会セミナー
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] タンデムヘテロFriedel-Crafts反応が拓く新材料化学2020

    • Author(s)
      畠山琢次
    • Organizer
      明治大学理工学部講演会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 含BPNコランニュレン誘導体の合成2020

    • Author(s)
      大矢 遥花,中塚 宗一郎,畠山 琢次
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] シアノ基を有するDABNA誘導体の合成と物性2020

    • Author(s)
      杉谷 拓己,田中 裕之,田端 敬太,畠山 琢次
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 脱芳香族化を伴うホウ素化反応による含BNヘキサベンゾコロネンの合成2020

    • Author(s)
      山本 健寛,阿部 紘明,後藤 玄,中塚 宗一郎,小田 晋,畠山 琢次
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 高色純度青色蛍光を示す含BNO多環芳香族化合物の合成と応用2020

    • Author(s)
      上田 悠太,小田 晋,畠山 琢次
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 超高色純度青色熱活性化遅延蛍光材料の開発2020

    • Author(s)
      畠山琢次
    • Organizer
      第379回蛍光体同学会講演会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] タンデムボラFriedel-Crafts反応が拓く新材料化学2019

    • Author(s)
      畠山琢次
    • Organizer
      大阪府立大学白鷺セミナー
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] タンデムボラFriedel-Crafts反応を鍵とした有機エレクトロニクス材料の開発2019

    • Author(s)
      畠山琢次
    • Organizer
      富士フイルム有機合成化学研究所講演会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Development of DABNA and beyond2019

    • Author(s)
      Takuji Hatakeyama
    • Organizer
      Samsung Display講演会
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 高色純度青色熱活性化遅延蛍光材料の開発2019

    • Author(s)
      畠山琢次
    • Organizer
      第68回高分子討論会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] タンデムボラFriedel-Crafts反応を鍵とした有機エレクトロニクス材料の開発2019

    • Author(s)
      畠山琢次
    • Organizer
      第116回有機合成シンポジウム
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] 超高色純度熱活性化遅延蛍光材料の開発2019

    • Author(s)
      畠山琢次
    • Organizer
      第5回統合物質創製化学研究機構シンポジウム
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Synthesis and Physical Properties of Triangulenes Containing Group 14 Elements at the Center2019

    • Author(s)
      Hajime Gotoh, Soichiro Nakatsuka, Takuji Hatakeyama
    • Organizer
      International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin and Lead
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Physical Properties of Antimony-Centered Triangulene2019

    • Author(s)
      Hajime Gotoh, Soichiro Nakatsuka, Keisuke Kinoshita, Nobuhiro Yasuda, Takuji Hatakeyama
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Physical Properties of Tetracoordinate Boron-Fused Double Helicenes2019

    • Author(s)
      Susumu Oda, Takeshi Shimizu, Takazumi Katayama, Hirofumi Yoshikawa, Takuji Hatakeyama
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 含ピリジン大環状化合物を用いたヘテロトリアンギュレンの合成2019

    • Author(s)
      後藤 玄,畠山 琢次
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Research-status Report
  • [Remarks] 研究室ホームページ

    • URL

      http://sci-tech.ksc.kwansei.ac.jp/~hatakeyama/index.html

    • Related Report
      2020 Annual Research Report 2019 Research-status Report

URL: 

Published: 2019-07-04   Modified: 2024-12-25  

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