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Development of Direct Borylation of pi-Conjugated Polymers

Research Project

Project/Area Number 17K19164
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Research Field Polymer, Organic materials, 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) 2017-06-30 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2018: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2017: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Keywords高分子合成 / 有機導体 / 有機化学 / 電子・電気材料
Outline of Final Research Achievements

By screening the borylating agents, additives, solvents, and reaction conditions in the tandem bora Friedel-Crafts reaction, we have developed regioselective and efficient multiple C-H borylation reactions. It allowed us to introduce up to 4 boron atoms to triarylamines in a highly selective manner. In addition, the precise synthesis of graphene nanoribbons with boron and nitrogen has been achieved by surface-assisted polymerization reaction on a gold substrate using dihydrodibenzo[b,e][1,4]azaborine with a 10-haloanthracene substituent as a precursor.

Academic Significance and Societal Importance of the Research Achievements

本研究で合成された含BN拡張π共役分子は,一重項励起エネルギーと三重項励起エネルギーの差が小さく,色純度の高い青色蛍光を示すことから,熱活性化遅延蛍光材料として有用である。また,含BNグラフェンナノリボンは基板上で完全な平面構造をとっており,新たな導電材料,半導体材料としての応用が期待できる。加えて,本研究を通じて確立したホウ素化反応は汎用性に優れており,様々な含ホウ素機能性π共役ポリマーの開発の促進が期待できる。

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (18 results)

All 2019 2018 2017

All Journal Article (6 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 6 results,  Open Access: 1 results) Presentation (12 results) (of which Int'l Joint Research: 2 results,  Invited: 6 results)

  • [Journal Article] Tetracoordinate Boron-Fused Double [5]Helicenes as Cathode Active Materials for Lithium Batteries2019

    • Author(s)
      Oda Susumu、Shimizu Takeshi、Katayama Takazumi、Yoshikawa Hirofumi、Hatakeyama Takuji
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 6 Pages: 1770-1773

    • DOI

      10.1021/acs.orglett.9b00337

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Multiple hetero-atom substitution to Graphene Nanoribbon2018

    • Author(s)
      S. Kawai, S. Nakatsuka, T. Hatakeyama, R. Pawlak, T, Meier, J. Tracey, E. Meyer, and A. S. Foster
    • Journal Title

      Science Advances

      Volume: 4 Issue: 4

    • DOI

      10.1126/sciadv.aar7181

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] π-Stacked Polymer Consisting of a Pseudo-meta-[2.2]Paracyclophane Skeleton2018

    • Author(s)
      Maeda, H.; Kameda, M.; Hatakeyama, T.; Morisaki, Y.
    • Journal Title

      Polymers

      Volume: 10 Issue: 10 Pages: 1140-1140

    • DOI

      10.3390/polym10101140

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Four-Step Synthesis of B2N2-Embedded Corannulene2018

    • Author(s)
      Nakatsuka Soichiro、Yasuda Nobuhiro、Hatakeyama Takuji
    • Journal Title

      Journal of the American Chemical Society

      Volume: 140 Issue: 42 Pages: 13562-13565

    • DOI

      10.1021/jacs.8b08197

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 5,9-Dioxa-13b-Oxophosphanaphtho[3,2,1-de]anthracenes Prepared by Tandem Phospha-Friedel?Crafts Reaction as Hole-/Exciton-Blocking Materials for OLEDs2017

    • Author(s)
      Nakatsuka Soichiro、Gotoh Hajime、Kageyama Akiko、Sasada Yasuyuki、Ikuta Toshiaki、Hatakeyama Takuji
    • Journal Title

      Organometallics

      Volume: 36 Issue: 14 Pages: 2622-2631

    • DOI

      10.1021/acs.organomet.7b00242

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-Shot Multiple Borylation toward BN-Doped Nanographenes2017

    • Author(s)
      Matsui Kohei、Oda Susumu、Yoshiura Kazuki、Nakajima Kiichi、Yasuda Nobuhiro、Hatakeyama Takuji
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 140 Issue: 4 Pages: 1195-1198

    • DOI

      10.1021/jacs.7b10578

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 高色純度緑色熱活性化遅延蛍光を示す含BNO多環芳香族化合物の合成2019

    • Author(s)
      池田 尚矢,吉浦 一基,小田 晋,畠山 琢次
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 高色純度青色発光を示す含BNO多環芳香族化合物の合成2019

    • Author(s)
      上田 悠太,小森 崇央,吉浦 一基,小田 晋,畠山 琢次
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] One-Shot多重ホウ素化反応による含BNヘリセンの合成2019

    • Author(s)
      川上 文吾,中塚 宗一郎,小田 晋,畠山 琢次
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis and Physical Properties of Tetracoordinate Boron-Fused Double Helicenes2019

    • Author(s)
      Susumu Oda, Takeshi Shimizu, Takazumi Katayama, Hirofumi Yoshikawa, Takuji Hatakeyama
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 多重共鳴効果を利用した高色純度熱活性化遅延蛍光材料の開発2018

    • Author(s)
      畠山琢次
    • Organizer
      2018年度有機エレクトロニクスシンポジウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] タンデムボラFriedel-Crafts反応が拓く新材料化学2018

    • Author(s)
      畠山琢次
    • Organizer
      第53回有機反応若手の会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Development of Ultrapure Blue TADF Materials by Multiple Resonance Effect2018

    • Author(s)
      Takuji Hatakeyama
    • Organizer
      19th International Workshop on Inorganic and Organic Electroluminescence (EL2018) & 2018 International Conference on the Science and Technology of Emitting Displays and Lighting
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of BN-embedded Corannulene via Electrophilic C-H Borylation2018

    • Author(s)
      中塚宗一郎・畠山琢次
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Development of Optoelectronic Materials through Borylation Reactions2018

    • Author(s)
      Takuji Hatakeyama
    • Organizer
      10th China-Japan Joint Symposium on Functional Supramolecular Architectures
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 芳香族化合物の多重C-Hホウ素化反応の開発2017

    • Author(s)
      小田晋・植浦健太・松井晃平・吉浦一基・畠山琢次
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Research-status Report
  • [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2017

    • Author(s)
      畠山琢次
    • Organizer
      九州大学先導物質化学研究所講演会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] タンデムヘテロFriedel-Crafts反応を基盤とした新材料化学2017

    • Author(s)
      畠山琢次
    • Organizer
      ITbM/IGER Organic Chemistry Workshop 2017
    • Related Report
      2017 Research-status Report
    • Invited

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Published: 2017-07-21   Modified: 2022-12-28  

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