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2021 Fiscal Year Annual Research Report

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

Research Project

Project/Area Number 21J22172
Allocation TypeSingle-year Grants
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) 2021-04-28 – 2024-03-31
KeywordsIron / optoelectronic
Outline of Annual Research Achievements

An entirely flat, strained, and chemically stable 1,4-dihydropentalene framework represents the core structure of oligophenylenevinylene system first developed by the applicant's lab (Prof. Eiichi Nakamura lab) for optoelectronic materials research. Since the previously reported synthesis is too complicated to be used for any applications, the applicant has developed a method to construct the strained skeleton in a single step using earth-abundant iron as a catalyst in combination with magnesium. The synthesis provides an expeditious access to a series of fused thiophene-containing molecules having a high HOMO level and narrow HOMO-LUMO band gap which act as an effective donor moiety in the molecules developed for utilization of light above 1000nm in near-infrared photodetector device.

Current Status of Research Progress
Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

The applicant’s research is conducted smoothly exactly as planned.

Strategy for Future Research Activity

During previous year’s study, the applicant has established a method to construct strained and chemically stable 1,4-dihydropentalene skeleton using iron catalysis in a tandem manner delivering a tremendous class of analogues named as CPVs and CTV. Therefore, in the coming one year, further functionalization based on these core structures would be investigated. Furthermore, the applicant is also interested in studying multiple-cyclization in one-pot synthesis to extend the length of oligo-phenylenevinylene system.

  • Research Products

    (8 results)

All 2022 2021

All Journal Article (1 results) Presentation (7 results) (of which Int'l Joint Research: 3 results)

  • [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 Pages: 6823~6828

    • DOI

      10.1021/jacs.1c03394

  • [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
    • 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
  • [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)
    • 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
    • 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
  • [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
  • [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

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Published: 2022-12-28   Modified: 2023-08-01  

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