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Photoredox catalyzed reactions using thermally activated delayed fluorescent molecules

Research Project

Project/Area Number 20K15291
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionKwansei Gakuin University

Principal Investigator

Oda Susumu  関西学院大学, 理学部, 助教 (00789901)

Project Period (FY) 2020-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2021: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2020: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords光レドックス触媒 / 有機ホウ素 / 熱活性化遅延蛍光 / 光触媒 / 脱ハロゲン化 / カルバゾール / 熱活性化遅延蛍光分子 / 有機ホウ素化合物
Outline of Research at the Start

近年,光レドックス触媒は,難易度の高い新たな分子変換を生み出す強力なツールとなっている.熱活性化遅延蛍光(TADF)分子は金属を用いずに効率的に光エネルギーを利用できる魅力的な分子であるにも関わらず,光レドックス触媒としての応用は未だ発展途上である.本研究では,新たに有機ホウ素由来のTADF分子を合成し,これを用いて光レドックス触媒反応の開発を行う.これらの分子は,高い還元力を有することから,今まで未開拓であった電位窓での独自の反応への応用が期待される.また,TADF特性と触媒活性の相関を明らかにし,高活性なTADF触媒の分子設計の指針を見出す.

Outline of Final Research Achievements

Organoboron thermally activated delayed fluorescence molecules (DABNA) were employed as photoredox catalysts. A series of DABNA analogs were synthesized by regioselective one-shot borylation, which were then applied to photoredox catalyzed dehalogenation of aryl halides. Under the radiation of blue LED, the dechlorination of aryl chloride proceeded in moderate yield. Furthermore, by using DOBNA bearing oxygen atoms in place of nitrogen atoms, the reductive cyclization of nitroaromatic compounds was achieved to afford carbazole in good yields at room temperature.

Academic Significance and Societal Importance of the Research Achievements

近年,光レドックス触媒は,難易度の高い新たな分子変換を生み出す強力なツールとなっている。熱活性化遅延蛍光(TADF)分子は金属を用いずに効率的に光を利用できるにも関わらず,光レドックス触媒としての応用は未だ発展途上である。本研究では,研究代表者が所属する研究室で開発した有機ホウ素由来のTADF分子(DABNA)を用いることで,脱ハロゲン化および還元的環化反応に成功しており,光レドックス触媒への応用の可能性を見出した。

Report

(3 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • Research Products

    (6 results)

All 2022 2021 2020

All Journal Article (4 results) (of which Peer Reviewed: 3 results,  Open Access: 1 results) Presentation (2 results)

  • [Journal Article] Hypsochromic Shift of Multiple‐Resonance‐Induced Thermally Activated Delayed Fluorescence by Oxygen Atom Incorporation2021

    • Author(s)
      Tanaka Hiroyuki、Oda Susumu、Ricci Gaetano、Gotoh Hajime、Tabata Keita、Kawasumi Ryosuke、Beljonne David、Olivier Yoann、Hatakeyama Takuji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 33 Pages: 17910-17914

    • DOI

      10.1002/anie.202105032

    • Related Report
      2021 Annual Research Report
  • [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
      2021 Annual Research Report 2020 Research-status Report
    • Peer Reviewed / Open Access
  • [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 Research-status Report
    • Peer Reviewed
  • [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 Research-status Report
    • Peer Reviewed
  • [Presentation] 有機ホウ素光触媒によるCadogan環化反応の開発2022

    • Author(s)
      岡田 正樹,小田 晋,畠山 琢次
    • Organizer
      日本化学会第101春季年会(2021)
    • Related Report
      2021 Annual Research Report
  • [Presentation] Carbazole-Based DABNA Analogs as Highly Efficient Thermally Activated Delayed Fluorescence Materials for Narrowband Organic Light-Emitting Diodes2020

    • Author(s)
      小田 晋・熊野 航・濵 俊輝・川角 亮介・ 吉浦 一基・畠山 琢次
    • Organizer
      基礎有機化学会 若手オンラインシンポジウム
    • Related Report
      2020 Research-status Report

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Published: 2020-04-28   Modified: 2023-01-30  

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