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Development of base-metal-catalyzed reactions applicable for new design of organic semiconductor materials

Research Project

Project/Area Number 22KJ0667
Project/Area Number (Other) 21J22172 (2021-2022)
Research Category

Grant-in-Aid for JSPS Fellows

Allocation TypeMulti-year Fund (2023)
Single-year Grants (2021-2022)
Section国内
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionThe University of Tokyo

Principal Investigator

陳 夢青  東京大学, 理学系研究科, 特別研究員(DC1)

Project Period (FY) 2023-03-08 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 2023: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2022: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2021: ¥800,000 (Direct Cost: ¥800,000)
Keywordsiron / oligophenylenevinylenes / tetra-annulation / spiro / Iron / optoelectronic
Outline of Research at the Start

I developed environmentally benign organic synthesis using iron catalysis constructing strained complicated π-conjugated framework which provides expeditious access to a series of fused thiophene-containing molecules with high HOMO level and narrow HOMO-LUMO gap useful for narrow band gap materials.

Outline of Annual Research Achievements

Despite the great potential of organic electronic materials in revolutionizing electronics compared to traditional silicon-based counterparts, large-scale production still faces several challenges. One significant challenge is precisely controlling synthesis demands over molecular structure and properties. Constructing oligophenylenevinylene structures, pioneered by the Nakamura lab, which features a flat-strained-chemically stable framework conducive to optoelectronic applications, heavily relies on harsh conditions. In this research, by leveraging the reactivity of organoiron species to lower the activation energy of key synthetic transformations, such as 5-endo-dig cyclization, we managed to construct highly strained oligophenylenevinylenes and protocol chemical-electronic application.

Report

(3 results)
  • 2023 Annual Research Report
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • Research Products

    (14 results)

All 2024 2023 2022 2021

All Journal Article (2 results) (of which Peer Reviewed: 1 results) Presentation (12 results) (of which Int'l Joint Research: 5 results)

  • [Journal Article] Iron-Catalyzed 5-Endo-Dig Synthetic Approach to Indenes and Its Bidirectional Extension to Narrow Bandgap π-Systems2024

    • Author(s)
      Chen Mengqing、Itabashi Yuki、Fukuma Shota、Shang Rui、Nakamura Eiichi
    • Journal Title

      ACS Catalysis

      Volume: 14 Issue: 3 Pages: 1375-1383

    • DOI

      10.1021/acscatal.3c04961

    • Related Report
      2023 Annual Research Report
  • [Journal Article] Iron-Catalyzed Tandem Cyclization of Diarylacetylene to a Strained 1,4-Dihydropentalene Framework for Narrow-Band-Gap Materials2021

    • Author(s)
      Chen Mengqing、Sato Wataru、Shang Rui、Nakamura Eiichi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 18 Pages: 6823-6828

    • DOI

      10.1021/jacs.1c03394

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Presentation] Iron-Catalyzed C-O Activation/Tandem Tetra-Annulation for the Synthesis of Carbon-bridged Oligo-(p-arylenevinylene)s2023

    • Author(s)
      Chen, M.; Shang, R.; Nakamura, E.
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Base-Metal Catalysis for the Synthetic Design of New Semiconductor Materials2023

    • Author(s)
      Chen, M.; Shang, R.; Nakamura, E.
    • Organizer
      14th HOPE Meeting with Nobel Laureates
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Iron-Catalyzed Tandem Cyclization of Diarylacetylene to a Strained 1,4-Dihydropentalene Framework for Narrow-Band-Gap Materials2022

    • Author(s)
      Chen, M.; Sato, W.; Shang, R.; Nakamura, E.
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Iron-Catalyzed C-O Activation/Tandem Tetra-Annulation for the Synthesis of Carbon-bridged Oligo-(p-arylenevinylene)s.2022

    • Author(s)
      Chen, M.; Sato, W.; Shang, R.; Nakamura, E.
    • Organizer
      日本化学会第12回CSJ化学フェスタ
    • Related Report
      2022 Annual Research Report
  • [Presentation] Iron-Catalyzed Tandem Cyclization of Diarylacetylene to a Strained 1,4-Dihydropentalene Framework for Narrow-Band-Gap Materials2022

    • Author(s)
      Chen, M.; Sato, W.; Shang, R.; Nakamura, E.
    • Organizer
      11th SINGAPORE INTERNATIONAL CHEMISTRY CONFERENCE
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Iron-Catalyzed Tandem Cyclization of Diarylacetylene to a Strained 1,4-Dihydropentalene Framework for Narrow-Band-Gap Materials2022

    • Author(s)
      Mengqing Chen, Wataru Sato, Rui Shang, Eiichi Nakamura
    • Organizer
      ACS SPRING 2022
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Iron-Catalyzed Tandem Cyclization of Diarylacetylene to a Strained 1,4-Dihydropentalene Framework for Organic Electronic Materials2022

    • Author(s)
      Mengqing Chen, Rui Shang, Eiichi Nakamura
    • Organizer
      日本化学会第102回春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Chromium(III)-Catalyzed C(sp2)-H Alkynylation, Allylation, and Naphthalenation of Secondary Amides with Trimethylaluminum as Base2021

    • Author(s)
      Mengqing Chen, Takahiro Doba, Takenari Sato, Hlib Razumkov, Laurean Ilies, Rui Shang, Eiichi Nakamura
    • Organizer
      ACS Pubilication Symposium (The Power of Chemical Transformations)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Chromium(III)-Catalyzed C(sp2)-H Alkynylation, Allylation, and Naphthalenation of Secondary Amides with Trimethylaluminum as Base2021

    • Author(s)
      Mengqing Chen, Takahiro Doba, Takenari Sato, Hlib Razumkov, Laurean Ilies, Rui Shang, Eiichi Nakamura
    • Organizer
      PACIFICHEM 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Accessing 1H-Indenyl and Dihydro-s-Indacenyl Magnesium Reagents via Iron-catalyzed C-O Activation/Acetylenic Cyclization with Magnesium Powder2021

    • Author(s)
      Mengqing Chen, Rui Shang, Eiichi Nakamura
    • Organizer
      日本化学会第101回春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Iron-Catalyzed Tandem Cyclization of Diarylacetylene to a Strained 1,4-Dihydropentalene Framework for Narrow-Band-Gap Materials2021

    • Author(s)
      Mengqing Chen, Wataru Sato, Rui Shang, Eiichi Nakamura
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Iron-Catalyzed Tandem Cyclization of Diarylacetylene to a Strained 1,4-Dihydropentalene Framework for Narrow-Band-Gap Materials2021

    • Author(s)
      Mengqing Chen, Wataru Sato, Rui Shang, Eiichi Nakamura
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2021 Annual Research Report

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Published: 2021-05-27   Modified: 2024-12-25  

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