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Efficient synthetic methodology for accelerating development of conjugated polymer materials

Research Project

Project/Area Number 17K05973
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic and hybrid materials
Research InstitutionUniversity of Tsukuba

Principal Investigator

Kuwabara Junpei  筑波大学, 数理物質系, 准教授 (70466655)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2019: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords高分子半導体 / 有機EL / 有機薄膜太陽電池 / 直接アリール化反応 / 共役高分子 / 直接アリール化重縮合 / 重縮合 / 有機電子デバイス / 有機半導体
Outline of Final Research Achievements

This research aimed development of an efficient synthetic strategy for conjugated polymer materials, which serve as key materials of organic devices. C-H direct arylation reaction is a key reaction for shortcut of synthetic steps. Two steps can be omitted by using direct arylation in both monomer and polymer synthesis. Optimization of reaction conditions enables to afford high-quality materials in terms of molecular weight, structural accuracy, and purity, which are essential points for application in organic devices. The obtained polymers serve as active materials in organic light emitting diode and organic photovoltaics.

Academic Significance and Societal Importance of the Research Achievements

共役高分子材料は、高分子半導体として様々な有機電子デバイスへの応用が期待されている。求められる性能を満たすために構造が複雑化しており、長い合成工程を必要としていた。これに対し本研究では、簡便に高い品質の共役高分子材料を提供できる方法論の一つを確立した。これによって、研究段階においては構造のスクリーニングを迅速に行うことを可能にし、実用化の段階においては低コスト製造が実現できる。

Report

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

    (35 results)

All 2020 2019 2018 2017

All Journal Article (12 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 11 results,  Open Access: 1 results) Presentation (22 results) (of which Int'l Joint Research: 1 results,  Invited: 3 results) Book (1 results)

  • [Journal Article] Synthesis of an Air-Stable Pd(0) Catalyst Bearing Donor and Acceptor Phosphine Ligands2020

    • Author(s)
      Ryota Sato, Takaki Kanbara, and Junpei Kuwabara
    • Journal Title

      Organometallics

      Volume: 39 Issue: 2 Pages: 235-238

    • DOI

      10.1021/acs.organomet.9b00646

    • NAID

      120007132679

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mechanistic Study of Pd/Ag-Dual Catalyzed Cross Dehydrogenative Coupling of Perfluoroarenes with Thiophenes2020

    • Author(s)
      Yuto Shimoyama, Junpei Kuwabara, Takaki Kanbara
    • Journal Title

      ACS Catal.

      Volume: 10 Issue: 5 Pages: 3390-3397

    • DOI

      10.1021/acscatal.9b05326

    • NAID

      120007127594

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Conjugated Polymers via Direct C_H/C_Cl Coupling Reactions Using a Pd/Cu Binary Catalytic System2019

    • Author(s)
      Junpei Kuwabara, Wataru Tsuchida, Shuyang Guo, Ziwei Hu, Takeshi Yasuda, and Takaki Kanbara
    • Journal Title

      Polym. Chem.

      Volume: 10 Issue: 18 Pages: 2298-2304

    • DOI

      10.1039/c9py00232d

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Conjugated Polymer Consisting of Three-Component Aromatic Units via Two-Step Cross-Dehydrogenative-Coupling Reactions2019

    • Author(s)
      Chie Tanaka, Junpei Kuwabara, Takeshi Yasuda, Takaki Kanbara
    • Journal Title

      Synth. Met.

      Volume: 254 Pages: 180-183

    • DOI

      10.1016/j.synthmet.2019.06.014

    • NAID

      120007127858

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effect of Purification Solvent on Polymer Impurities and Device Performance2019

    • Author(s)
      Shunsuke Kodama, Junpei Kuwabara, Xin Jiang, Iori Fukushima, and Takaki Kanbara
    • Journal Title

      ACS Appl. Polym. Mater.

      Volume: 1 Issue: 8 Pages: 2083-2088

    • DOI

      10.1021/acsapm.9b00385

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Facile Synthesis of Thienopyrroledione-Based π-Conjugated Polymers via Direct Arylation Polycondensation under Aerobic Conditions2018

    • Author(s)
      Akito Ichige, Hitoshi Saito, Junpei Kuwabara, Takeshi Yasuda, Jun-Chul Choi, and Takaki Kanbara
    • Journal Title

      Macromolecules

      Volume: 51 Issue: 17 Pages: 6782-6788

    • DOI

      10.1021/acs.macromol.8b01289

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Polyfluoro Arylene‐Based Poly(arylenevinylene)s via Pd‐Catalyzed Dehydrogenative Direct Alkenylation2018

    • Author(s)
      Hitoshi Saito, Junpei Kuwabara, Takeshi Yasuda, and Takaki Kanbara
    • Journal Title

      Macromol. Rapid Commun.

      Volume: 39 Issue: 18 Pages: 1800414-1800414

    • DOI

      10.1002/marc.201800414

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Facile Synthesis of π-Conjugated Polymers via Direct Arylation Polycondensation2018

    • Author(s)
      Junpei Kuwabara, Takaki Kanbara
    • Journal Title

      Bull. Chem. Soc. Jpn.,

      Volume: 92 Issue: 1 Pages: 152-161

    • DOI

      10.1246/bcsj.20180249

    • NAID

      130007578609

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Direct arylation polycondensation for synthesis of optoelectronic materials2018

    • Author(s)
      Junpei Kuwabara
    • Journal Title

      Polym. J.

      Volume: 50 Issue: 12 Pages: 1099-1106

    • DOI

      10.1038/s41428-018-0101-3

    • NAID

      120007133442

    • Related Report
      2018 Research-status Report
  • [Journal Article] Synthesis of bithiazole-based semiconducting polymers via Cu-catalysed aerobic oxidative coupling2018

    • Author(s)
      Alanna Faradhiyani, Qiao Zhang, Keisuke Maruyama, Junpei Kuwabara, Takeshi Yasuda, and Takaki Kanbara
    • Journal Title

      Mater. Chem. Front.

      Volume: 2 Issue: 7 Pages: 1306-1309

    • DOI

      10.1039/c7qm00584a

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Conjugated Polymers Containing Octafluorobiphenylene Unit via Pd-Catalyzed Cross-Dehydrogenative-Coupling Reaction2017

    • Author(s)
      Aoki Hideaki、Saito Hitoshi、Shimoyama Yuto、Kuwabara Junpei、Yasuda Takeshi、Kanbara Takaki
    • Journal Title

      ACS Macro Lett.

      Volume: 7 Issue: 1 Pages: 90-94

    • DOI

      10.1021/acsmacrolett.7b00887

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Facile one-pot access to π-conjugated polymers via sequential bromination/direct arylation polycondensation2017

    • Author(s)
      Hitoshi Saito, Jieran Chen, Junpei Kuwabara, Takeshi Yasuda and Takaki Kanbara
    • Journal Title

      Polym. Chem.

      Volume: 8 Issue: 19 Pages: 3006-3012

    • DOI

      10.1039/c7py00332c

    • NAID

      120007129028

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] フルオレン誘導体をユニットとするポリアジンの合成2020

    • Author(s)
      村上 寛樹、桑原 純平、神原 貴樹
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Pd/Cu触媒を利用したジクロロアリーレンの直接アリール化重縮合2019

    • Author(s)
      郭 舒揚、土田 渉、桑原 純平、安田 剛、神原 貴樹
    • Organizer
      第68回高分子学会年次大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 大気中での直接的アリール化重縮合による簡便な共役高分子の合成2019

    • Author(s)
      陳 熹、市毛 明斗、桑原 純平、神原 貴樹
    • Organizer
      第68回高分子学会年次大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 脱水素型クロスカップリング反応に基づく三成分系共役高分子の合成と物性評価2019

    • Author(s)
      田中 智恵、桑原 純平、安田 剛、神原 貴樹
    • Organizer
      第68回高分子学会年次大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 空気に安定なPd(0)触媒前駆体の開発と触媒機能評価2019

    • Author(s)
      佐藤 亮太、桑原 純平、神原 貴樹
    • Organizer
      第8回JACI/GSCシンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] 異種のリン配位子を有する空気に安定なPd(0)錯体の様々なクロスカップリング反応への適応2019

    • Author(s)
      佐藤 亮太、桑原 純平、神原 貴樹
    • Organizer
      第9回CSJ科学フェスタ
    • Related Report
      2019 Annual Research Report
  • [Presentation] 直接アリール化重縮合を用いた含ビチアゾール共役高分子の合成と特性評価2018

    • Author(s)
      桑原 純平
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] ベンゾジチオフェン-4,8-ジオンの直接アリール化重縮合によるドナーアクセプターポリマーの合成2018

    • Author(s)
      江 シン、桑原 純平、神原 貴樹
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      2018 Research-status Report
  • [Presentation] Direct Arylation Polycondensation:Facile Synthesis Ofconjugated Polymers for OPV Application2018

    • Author(s)
      Junpei Kuwabara, Takeshi Yasuda, Takaki Kanbara
    • Organizer
      icsm2018
    • Related Report
      2018 Research-status Report
  • [Presentation] 直接アリール化重縮合を利用した高純度な共役高分子の合成と光電変換特性2018

    • Author(s)
      桑原 純平、浅井 遥香、丸本 一弘、安田 剛、神原 貴樹
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 銅触媒を用いたベンゾビスチアゾール誘導体の酸素酸化重合2018

    • Author(s)
      丸山啓輔、桑原純平、神原貴樹
    • Organizer
      第8回CSJ化学フェスタ2018
    • Related Report
      2018 Research-status Report
  • [Presentation] 脱水縮合によるアジン結合形成を利用したπ共役高分子の合成2018

    • Author(s)
      鈴木佳太、桑原純平、神原貴樹
    • Organizer
      第8回CSJ化学フェスタ2018
    • Related Report
      2018 Research-status Report
  • [Presentation] Direct Arylation Polycondensation: Facile Synthetic Approach for π-Conjugated Polymers2018

    • Author(s)
      Junpei Kuwabara, Takaki Kanbara
    • Organizer
      π-System Figuration European-Japanese Workshop 2018
    • Related Report
      2018 Research-status Report
  • [Presentation] ベンゾジチオフェン-4,8-ジオンの直接アリール化重縮合によるOPV 材料の合成と評価2018

    • Author(s)
      江 シン、桑原 純平、安田 剛、神原 貴樹
    • Organizer
      第27回ポリマー材料フォーラム
    • Related Report
      2018 Research-status Report
  • [Presentation] アジン結合を有するπ共役高分子の合成法の最適化と半導体材料への応用2018

    • Author(s)
      鈴木佳太・桑原純平・神原貴樹
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Pd/Cu二元系触媒を用いたクロロチオフェン類をモノマーとする 直接アリール化重縮合2017

    • Author(s)
      桑原 純平、土田 渉、神原 貴樹
    • Organizer
      第66回高分子学会年次大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 連続的な臭素化-直接的アリール化重合により合成した高分子半導体のデバイス機能評価2017

    • Author(s)
      齋藤 仁志、陳 捷然、桑原 純平、 安田 剛、神原 貴樹
    • Organizer
      第66回高分子学会年次大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 直接アリール化重縮合による共役高分子材料の新規環境調和型合成2017

    • Author(s)
      桑原純平
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] Synthesis of dye-containing polymers using polycondensation via aerobic oxidative coupling reaction2017

    • Author(s)
      Alanna Faradhiyani, Junpei Kuwabara, Takaki Kanbara
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Direct Arylation Polycondensation: Facile Synthetic Approach to Organic Photovoltaic Materials2017

    • Author(s)
      Junpei Kuwabara
    • Organizer
      2017 GLOBAL RESEARCH EFFORTS ON ENERGY AND NANOMATERIALS
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 脱水素型クロスカップリング反応による共役系高分子の合成2017

    • Author(s)
      青木 英晃、齋藤 仁志、桑原 純平、神原 貴樹
    • Organizer
      第66回高分子学会年次大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 水分・酸素に対して安定な直接的アリール化重縮合の開発2017

    • Author(s)
      市毛 明斗、齋藤 仁志、桑原 純平、神原 貴樹
    • Organizer
      第66回高分子学会年次大会
    • Related Report
      2017 Research-status Report
  • [Book] 直接的芳香族カップリング反応の設計と応用(分担,第18章 直接アリール化重合による高分子半導体の合成 200-212頁)2019

    • Author(s)
      桑原 純平,神原 貴樹
    • Total Pages
      212
    • Publisher
      シーエムシー出版
    • ISBN
      9784781314211
    • Related Report
      2019 Annual Research Report

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

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