• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Iron-catalyzed Activation of Unreactive Bonds for Organic Materials Synthesis

Research Project

Project/Area Number 19K15555
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionThe University of Tokyo

Principal Investigator

Shang Rui  東京大学, 大学院理学系研究科(理学部), 特任准教授 (50793212)

Project Period (FY) 2019-04-01 – 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 2020: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2019: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsiron-catalysis / C-H activation / polymerization / perovskite solar cells / tandem cyclization / non-fullerene acceptor / photodetector / iron-catalyzed / polycondensation / iron catalysis / C-O activation / C-C coupling / thiophene / annulation / narrow-band-gap / spiro-conjugated / C-H alkynylation / cyclization / phenylenevinylene / Iron Catalysis / pi-molecules / Materials
Outline of Research at the Start

The aim of the proposed research is to design and synthesize new classes of pi-conjugated optoelectronic materials through development of new reactions catalyzed by earth abundant and non- toxic catalysts represented by iron. The PI will focus on activation of unreactive bonds such as C-H and C-O bonds, as well as acetylenic bonds, in order to create new classes of pi-conjugated systems including angularly conjugated systems of semiconductive or conductive nature to be used for organic light emitting diodes (OLEDs) and perovskite solar cells (PVSC) applications.

Outline of Final Research Achievements

Through this research project, synthetic methods to access organic electronic materials using sustainable and economic iron based catalysts were developed. New organic optoelectronic materials for solar cells and light emitting diodes were developed.
Thiophene-based semiconductive polymers were produced by using iron-catalyzed thienyl C-H/C-H coupling using cheap reagents, offering a polymerization method of high sustainability and economic merits. New polymers made by iron-catalysis were found as highly efficient hole transporting to enable high performance perovskite solar cells. An iron-catalyzed one-pot tandem cyclization reaction was developed for synthesis of rigid carbon-bridged arylene-vinylene materials. Beside emissive materials, non-fullerene acceptor materials for near infrared photodetector was developed by using the new ladder molecule accessed by this iron-catalyzed tandem cyclization method.

Academic Significance and Societal Importance of the Research Achievements

鉄を触媒として有機電子材料を作ることのメリットは、現代の化学合成に求められる環境的、持続可能、経済的問題のために顕著です。 このプロジェクトの結果は、触媒作用として豊富な鉄塩を使用して新しい電子材料を合成する方法を提供し、有機金属化学と触媒作用の新しい知識を提供します。 新しく開発された鉄触媒を使用することによる材料アクセスは、太陽電池、光検出器、および発光のための効率的な材料として発見されました。 これらの鉄触媒プロセスは、持続不可能な資源への依存を回避し、有機電子材料の製造コストを削減するために、将来の産業用途に役立つ可能性があります。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (28 results)

All 2022 2021 2020 2019

All Journal Article (9 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 9 results,  Open Access: 5 results) Presentation (11 results) (of which Int'l Joint Research: 4 results,  Invited: 3 results) Book (1 results) Patent(Industrial Property Rights) (7 results)

  • [Journal Article] Triarylamine/Bithiophene Copolymer with Enhanced Quinoidal Character as Hole‐Transporting Material for Perovskite Solar Cells2022

    • Author(s)
      Lin Hao-Sheng、Doba Takahiro、Sato Wataru、Matsuo Yutaka、Shang Rui、Nakamura Eiichi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: - Issue: 27 Pages: 1-1

    • DOI

      10.1002/anie.202203949

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Iron-catalysed regioselective thienyl C-H/C-H coupling2021

    • Author(s)
      Doba Takahiro、Ilies Laurean、Sato Wataru、Shang Rui、Nakamura Eiichi
    • Journal Title

      Nature Catalysis

      Volume: 4 Issue: 7 Pages: 631-638

    • DOI

      10.1038/s41929-021-00653-7

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [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 2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] B<sub>2</sub>N<sub>2</sub>-Doped Dibenzo[<i>a,m</i>]Rubicene: Modular Synthesis, Properties, and Coordination-Induced Color Tunability2021

    • Author(s)
      Sakamaki Takumi、Nakamuro Takayuki、Yamashita Keitaro、Hirata Kunio、Shang Rui、Nakamura Eiichi
    • Journal Title

      Chemistry of Materials

      Volume: 33 Issue: 13 Pages: 5337-5344

    • DOI

      10.1021/acs.chemmater.1c01441

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Non-Aufbau Spiro-Conjugated Quinoidal & Aromatic Charged Radicals2021

    • Author(s)
      Medina Rivero Samara、Shang Rui、Hamada Hiroyoshi、Yan Qifan、Tsuji Hayato、Nakamura Eiichi*、Casado Juan*
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94 Issue: 3 Pages: 989-996

    • DOI

      10.1246/bcsj.20200385

    • NAID

      130008021802

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Axially Chiral Spiro-conjugated Carbon-bridged p-Phenylenevinylene Congeners: Synthetic Design and Materials Properties2020

    • Author(s)
      H. Hamada, Y. Itabashi, R. Shang, E. Nakamura
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 142 Issue: 4 Pages: 2059-2067

    • DOI

      10.1021/jacs.9b13019

    • Related Report
      2020 Research-status Report 2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Chromium(III)-Catalyzed C(sp2)-H Alkynylation, Allylation, and Naphthalenation of Secondary Amides with Trimethylaluminum as Base2020

    • Author(s)
      Chen Mengqing, Doba Takahiro, Sato Takenari, Razumkov Hlib, Ilies Laurean, Shang Rui, Nakamura Eiichi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 10 Pages: 4883-4891

    • DOI

      10.1021/jacs.0c00127

    • Related Report
      2020 Research-status Report 2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Spiro-conjugated Carbon/Heteroatom-bridged p-Phenylenevinylenes: Synthesis, Properties, and Microcrystal Electron Crystallographic Analysis of Racemic Solid Solutions2020

    • Author(s)
      H. Hamada, T. Nakamuro, K. Yamashita, H. Yanagisawa, O. Nureki, M. Kikkawa, K. Harano, R. Shang, E. Nakamura
    • Journal Title

      Bull. Chem. Soc. JP

      Volume: 93 Issue: 6 Pages: 776-782

    • DOI

      10.1246/bcsj.20200065

    • NAID

      130007856022

    • Related Report
      2020 Research-status Report 2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] B/N-Doped p-Arylenevinylene Chromophores: Synthesis, Properties, and Microcrystal Electron Crystallographic Study2020

    • Author(s)
      Hua Lu, Takayuki Nakamuro, Keitaro Yamashita, Haruaki Yanagisawa, Osamu Nureki, Masahide Kikkawa, Han Gao, Jiangwei Tian, Rui Shang, Eiichi Nakamura
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 44 Pages: 18990-18996

    • DOI

      10.1021/jacs.0c10337

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] Iron-catalysis for and photocatalysis inspired by development of organic electronic materials2022

    • Author(s)
      Rui Shang
    • Organizer
      Invited Talk for Riken CSRS Seminar
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Development of Iron-catalysis for Organic Electronic Materials2022

    • Author(s)
      Rui Shang and Eiichi Nakamura
    • Organizer
      ACS Spring 2022, Division of Organic Chemistry Virtual Symposia
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Iron-catalyzed Regioselective Thienyl C-H/C-H Coupling and Polycondensation for Organic Electronic Materials2021

    • Author(s)
      Rui Shang, Takahiro Doba, Eiichi Nakamura
    • Organizer
      ACS Publications Symposium: The Power of Chemical Transformations
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Iron-Catalysis: from Novel Reactions to Creating Material Functions2021

    • Author(s)
      Rui Shang
    • Organizer
      Invited Talk in Northeast Normal University
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Iron(III)- and chromium(III)-catalyzed deprotonative C-H activation2021

    • Author(s)
      Rui Shang and Eiichi Nakamura
    • Organizer
      International Chemical Congress of Pacific Basin Societies (Pacifichem 2021)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Takahiro DOBA, Laurean ILIES, Rui SHANG, Eiichi NAKAMURA2021

    • Author(s)
      Iron-Catalyzed Regioselective Thienyl C-H/C-H Coupling and Polycondensation
    • Organizer
      The 101th CSJ Annual Meeting
    • Related Report
      2020 Research-status Report
  • [Presentation] B2N2-Dibenzorubicene : Synthesis and Properties2021

    • Author(s)
      Takumi SAKAMAKI, Rui SHANG, Eiichi NAKAMURA
    • Organizer
      The 101th CSJ Annual Meeting
    • Related Report
      2020 Research-status Report
  • [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, Yuki ITABASHIi, Rui SHANG, Eiichi NAKAMURA
    • Organizer
      The 101th CSJ Annual Meeting
    • Related Report
      2020 Research-status Report
  • [Presentation] Polycarboxylates as synthetic tools for small and efficient perovskite quantum dots2021

    • Author(s)
      Olivier CHAVELIER, Takayuki NAKAMURO, Rui SHANG, Eiichi NAKAMURA
    • Organizer
      The 101th CSJ Annual Meeting
    • Related Report
      2020 Research-status Report
  • [Presentation] Iron-catalyzed Regioselective Thienyl C-H/C-H Coupling and Polycondensation for Organic Electronic Materials2021

    • Author(s)
      Takahiro DOBA, Rui SHANG, Eiichi NAKAMURA
    • Organizer
      ACS Publications Symposium: The Power of Chemical Transformations
    • Related Report
      2020 Research-status Report
  • [Presentation] Hybrid Materials in Perovskite Solar Cell Applications2019

    • Author(s)
      Rui Shang and Eiichi Nakamura
    • Organizer
      the 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Book] Chromium-catalyzed C-H Activation, Handbook of CH-Functionalization (CHF)2022

    • Author(s)
      Rui Shang
    • Total Pages
      1000
    • Publisher
      John Wiley & Sons
    • Related Report
      2021 Annual Research Report
  • [Patent(Industrial Property Rights)] 共役高分子の製造方法 共役高分子、該共役高分子を含有する有機半導体デバイス用インク及び有機半導体デバイス2022

    • Inventor(s)
      2022
    • Industrial Property Rights Holder
      2022
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2022-002916
    • Filing Date
      2022
    • Related Report
      2021 Annual Research Report
  • [Patent(Industrial Property Rights)] 光電変換素子及びその製造方法2021

    • Inventor(s)
      2021
    • Industrial Property Rights Holder
      2021
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2021-176630
    • Filing Date
      2021
    • Related Report
      2021 Annual Research Report
  • [Patent(Industrial Property Rights)] 新規鉄触媒を用いた共役高分子合成方法2020

    • Inventor(s)
      中村 栄一,SHANG Rui,佐藤 済, 道場 貴大
    • Industrial Property Rights Holder
      中村 栄一,SHANG Rui,佐藤 済, 道場 貴大
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Related Report
      2020 Research-status Report
  • [Patent(Industrial Property Rights)] 鉄触媒を用いた新規多環芳香族縮合環の化合物および製造方法2020

    • Inventor(s)
      中村 栄一,SHANG Rui,佐藤 済, 陳梦青
    • Industrial Property Rights Holder
      中村 栄一,SHANG Rui,佐藤 済, 陳梦青
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Related Report
      2020 Research-status Report
  • [Patent(Industrial Property Rights)] 量子ドット及びその作製方法2020

    • Inventor(s)
      中村 栄一, SHANG Rui et al
    • Industrial Property Rights Holder
      中村 栄一, SHANG Rui et al
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Related Report
      2020 Research-status Report
  • [Patent(Industrial Property Rights)] 光電変換素子及び太陽電池モジュール2019

    • Inventor(s)
      中村栄一,SHANG Rui, et al.
    • Industrial Property Rights Holder
      中村栄一,SHANG Rui, et al.
    • Industrial Property Rights Type
      特許
    • Patent Publication Number
      2019-046935
    • Filing Date
      2019
    • Related Report
      2020 Research-status Report
  • [Patent(Industrial Property Rights)] 光電変換素子及び太陽電池モジュール2019

    • Inventor(s)
      中村栄一, Shang Rui, 周 忠敏, 武井 出
    • Industrial Property Rights Holder
      中村栄一, Shang Rui, 周 忠敏, 武井 出
    • Industrial Property Rights Type
      特許
    • Patent Publication Number
      2020-013898
    • Filing Date
      2019
    • Related Report
      2019 Research-status Report

URL: 

Published: 2019-04-18   Modified: 2023-03-23  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi