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Development of high-performance pi-conjugated polymers using cis-trans photoisomerization as a key step

Research Project

Project/Area Number 17K05883
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Polymer chemistry
Research InstitutionKyoto University

Principal Investigator

Wakioka Masayuki  京都大学, 化学研究所, 助教 (50598844)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsπ共役系高分子 / シス・トランス異性化 / 有機電子デバイス / シス-トランス異性化 / 有機電界効果トランジスタ / 直接的アリール化重合 / 高分子合成 / 触媒化学 / 半導体物性
Outline of Final Research Achievements

trans-Polythienylenevinylenes (PTVs), which is known as an excellent polymer semiconductor, occasionally show poor solubility due to its high crystallinity, making it difficult to prepare the polymers with high molecular weight and to form homogeneous thin films. In this study, we investigated cis-trans isomerization as a solution to the solubility problem. As a result, we have found that cis-PTVs with high solubility undergo one-way isomerization in the thin film under heating conditions, and the corresponding trans-PTVs are formed. Furthermore, using this isomerization method, we have succeeded in clarifying the characteristics of trans-PTV that could not be synthesized due to the solubility problem.

Academic Significance and Societal Importance of the Research Achievements

これまで,優れた高分子半導体として知られるtrans-ポリチエニレンビニレン(PTV)の研究において,取り扱うことのできる骨格は,溶解性の問題により制限されていた.一方我々は,cis-PTVがtrans-PTVの優れた前駆体であることを見出した.すなわち,溶解性の高いシス体が前駆体として用い,その薄膜を加熱することで異性化が進行し,対応するトランス体の薄膜を調製できることを見出した.本研究で確立されたtrans-PTV薄膜の調製法は,溶解性の問題に対する有効な解決策であり,次世代有機電子デバイスの開発研究の突破口となることが期待される.

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (21 results)

All 2020 2019 2018 2017

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Open Access: 1 results) Presentation (17 results) (of which Int'l Joint Research: 1 results,  Invited: 8 results)

  • [Journal Article] Mixed-Ligand Approach to Palladium-Catalyzed Direct Arylation Polymerization: Synthesis of Donor?Acceptor Polymers Containing Unsubstituted Bithiophene Units2020

    • Author(s)
      Wakioka Masayuki、Morita Hazuki、Ichihara Nobuko、Saito Masahiko、Osaka Itaru、Ozawa Fumiyuki
    • Journal Title

      Macromolecules

      Volume: 53 Issue: 1 Pages: 158-164

    • DOI

      10.1021/acs.macromol.9b02298

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Efficient Catalysts for Direct Arylation Polymerization (DArP)2018

    • Author(s)
      Wakioka Masayuki、Ozawa Fumiyuki
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 7 Issue: 7 Pages: 1206-1216

    • DOI

      10.1002/ajoc.201800227

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a 1,2-Dithienylethene-Containing Donor-Acceptor Polymer via Palladium-Catalyzed Direct Arylation Polymerization (DArP)2018

    • Author(s)
      Masayuki Wakioka, Natsumi Yamashita, Hiroki Mori, Yasushi Nishihara, Fumiyuki Ozawa
    • Journal Title

      Molecules

      Volume: 23 Issue: 4 Pages: 981-981

    • DOI

      10.3390/molecules23040981

    • NAID

      120006510297

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of Palladium-Catalyzed Direct Arylation Polymerization (DArP)2017

    • Author(s)
      脇岡正幸, 小澤文幸
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 75 Issue: 8 Pages: 810-820

    • DOI

      10.5059/yukigoseikyokaishi.75.810

    • NAID

      130005966748

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 高選択的直接的アリール化重合によるチオフェン置換ジケトピロロピロールとジチエニルエテンの交互共重合体の合成2019

    • Author(s)
      脇岡正幸・石塚里沙・小澤文幸
    • Organizer
      第68回高分子討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] パラジウム触媒直接的アリール化重合:π共役系高分子の簡便かつ高精度な合成法2019

    • Author(s)
      脇岡正幸
    • Organizer
      有機化学研究会(白鷺セミナー) 第85回講演会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 二次元拡張型π共役系高分子の合成とその配向性2019

    • Author(s)
      脇岡正幸
    • Organizer
      第4回MAIRS ワークショップ:薄膜・分子吸着の構造にどこまで迫れるか
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] パラジウム触媒直接的アリール化重合:π共役系高分子の新規簡便合成法2018

    • Author(s)
      脇岡正幸
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] Highly Selective Direct Arylation Polymerization Catalysts for the Synthesis of π-Conjugated Polymers with Least Defect Formation2018

    • Author(s)
      Masayuki Wakioka, Fumiyuki Ozawa
    • Organizer
      The 28th International Conference on Organometallic Chemistry
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 高選択的直接的アリール化重合により合成された1,2-ジチエニルエテン含有DAポリマーの構造とFET特性2018

    • Author(s)
      脇岡正幸・山下菜摘・森 裕樹・西原康師・小澤文幸
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] π共役ポリマーの精密合成のための高性能直接的アリール化重合触媒2018

    • Author(s)
      脇岡正幸・山下菜摘・森田葉月・市原暢子・小澤文幸
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 直接的アリール化重合による1,2-ジチエニルエテン含有DAポリマーの合成2018

    • Author(s)
      脇岡正幸・山下菜摘・森田葉月・市原暢子・小澤文幸
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Highly Efficient Palladium Catalysts for Precise Synthesis of Donor-Acceptor Conjugated Polymers via Direct Arylation Polymerization (DArP)2018

    • Author(s)
      Masayuki Wakioka, Natsumi Yamashita, Naohiro Torii, Hazuki Morita, Nobuko Ichihara, Fumiyuki Ozawa
    • Organizer
      The 12th SPSJ International Polymer Conference (IPC2018)
    • Related Report
      2018 Research-status Report
  • [Presentation] 1,2-ジチエニルエテン含有 DA ポリマーの構造制御合成と異性化挙動2018

    • Author(s)
      脇岡正幸
    • Organizer
      第3回pMAIRS ワークショップ:分子配向解析の波及効果
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] 直接的アリール化重合による1,2-ジチエニルエテン含有DAポリマーの構造制御合成とその光異性化挙動2018

    • Author(s)
      山下菜摘・脇岡正幸・森 裕樹・西原康師・小澤文幸
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 高性能直接的アリール化重合触媒の開発2018

    • Author(s)
      脇岡正幸
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] パラジウム触媒直接的アリール化重合:π共役系高分子の簡便かつ高精度な合成法2018

    • Author(s)
      脇岡正幸
    • Organizer
      平成29年度第2回有機金属若手研究者の会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] 直接的アリール化重合:π共役系高分子の新簡便合成法2017

    • Author(s)
      脇岡正幸
    • Organizer
      第4回次世代の有機化学・広島シンポジウム
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] パラジウム触媒によるビチオフェン類の高選択的直接的アリール化重合2017

    • Author(s)
      脇岡正幸・森田葉月・山下菜摘・市原暢子・小澤文幸
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 高選択的パラジウム触媒によるジチエニルエテンの直接的アリール化重合2017

    • Author(s)
      山下菜摘・脇岡正幸・森 裕樹・西原康師・小澤文幸
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Mixed-Ligand Palladium Catalysts for Highly Selective Direct Arylation Polymerization2017

    • Author(s)
      Masayuki Wakioka, Fumiyuki Ozawa
    • Organizer
      International Symposium on Pure & Applied Chemistry 2017 (ISPAC 2017)
    • Related Report
      2017 Research-status Report
    • Invited

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Published: 2017-04-28   Modified: 2021-02-19  

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