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

Synthesis of pi-Conjugated Polymers via Regioselective Direct Arylation Polycondensation using Heterogeneous Catalyst

Research Project

Project/Area Number 15K17872
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Polymer chemistry
Research Institution防衛大学校(総合教育学群、人文社会科学群、応用科学群、電気情報学群及びシステム工学群)

Principal Investigator

Hayashi Shotaro  防衛大学校(総合教育学群、人文社会科学群、応用科学群、電気情報学群及びシステム工学群), 応用科学群, 講師 (00532954)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords直接的アリール化 / 共役系高分子 / 不均一系触媒 / パラジウム / π共役系高分子 / 不均一系 / 不均一系パラジウム触媒 / 不均一系パラジウム / 直接的アリール化重縮合
Outline of Final Research Achievements

Synthesis of fluorescent and/or semiconducting polymers (π-conjugated polymers) has attracted much attention with the development of palladium-catalyzed cross-coupling reactions. Conventional cross-coupling reactions such as Stille-type (Ar-SnR3 + Br-Ar) and Suzuki-Miyaura (Ar-BR3 + Br-Ar) for carbon-carbon bond formation have contributed to efficient synthetic pathways to π-conjugated polymers.Recently, direct arylation reaction (Ar-H + Br-Ar) has been developed to replace the common pathway of π-conjugated polymer synthesis because the reaction uses easily accessible to the monomers proceeds with high atom efficiency without generation of organometallic byproducts that occur with conventional pathways. Direct arylation polycondensation using solid-supported palladium catalysts results in highly regioselective polythiophenes. Moreover, various π-conjugated polymer structures such as linear, bent, branched, and network were also synthesized via direct arylation of unique monomers.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (27 results)

All 2018 2017 2016 2015 Other

All Journal Article (19 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 19 results,  Acknowledgement Compliant: 10 results,  Open Access: 2 results) Presentation (7 results) (of which Int'l Joint Research: 1 results,  Invited: 7 results) Remarks (1 results)

  • [Journal Article] Direct arylation polycondensation of β-unprotected chalcogen heteroles under phosphine-free conditions2017

    • Author(s)
      Shotaro Hayashi, Yoshihisa Kojima, Toshio Koizumi
    • Journal Title

      Polymer

      Volume: 113 Pages: 214-220

    • DOI

      10.1016/j.polymer.2017.02.067

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium on Carbon (Pd/C)-Catalyzed Direct C-H Arylation Polycondensation of 3,4-Ethylenedioxythiophene with Various Dibromoarenes2017

    • Author(s)
      Yoshihisa Kojima, Shotaro Hayashi, Toshio Koizumi
    • Journal Title

      Journal of Polymer Science: Part A: Polymer Chemistry

      Volume: 55 Issue: 7 Pages: 1183-1188

    • DOI

      10.1002/pola.28475

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Effects of Molecular Weight on the Optical and Electrochemical Properties of EDOT-based π-Conjugated Polymers2017

    • Author(s)
      S. Hayashi, S. Yamamoto, T. Koizumi
    • Journal Title

      Scientific Reports

      Volume: 7 Issue: 1 Pages: 1027-1027

    • DOI

      10.1038/s41598-017-01132-5

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of π-Conjugated Network Polymers Based on Fluoroarene and Fluorescent Units via Direct Arylation Polycondensation and Their Porosity and Fluorescent Properties2017

    • Author(s)
      Shotaro Hayashi, Yuki Togawa, Shin-Ichi Yamamoto, Toshio Koizumi, Koji Nishi, Atsushi Asano
    • Journal Title

      Journal of Polymer Science: Part A: Polymer Chemistry

      Volume: 55 Issue: 23 Pages: 3862-3867

    • DOI

      10.1002/pola.28770

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Arylation for the Control of π-Conjugated Polymer Structure2017

    • Author(s)
      林 正太郎
    • Journal Title

      KOBUNSHI RONBUNSHU

      Volume: 74 Issue: 5 Pages: 375-395

    • DOI

      10.1295/koron.2017-0022

    • NAID

      130006096670

    • ISSN
      0386-2186, 1881-5685
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Elastic Bending Flexibility of Fluorescent Organic Single Crystal: New Aspects of Commonly Used Building Block “4,7-Dibromo-2,1,3-benzothiadiazole”2017

    • Author(s)
      S. Hayashi, T. Koizumi, K. Kamiya
    • Journal Title

      Crystal Growth & Design

      Volume: 17 Issue: 12 Pages: 6158-6162

    • DOI

      10.1021/acs.cgd.7b00992

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorescent Organic Single Crystals with Elastic Bending Flexibility: 1,4-Bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene Derivatives2017

    • Author(s)
      S. Hayashi, A. Asano, N. Kamiya, Y. Yokomori, T. Maeda, T. Koizumi
    • Journal Title

      Scientific Reports

      Volume: 7 Issue: 1 Pages: 9543-9543

    • DOI

      10.1038/s41598-017-09848-0

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] From Propargylic Biscarbonate to Diaryl[n]dendralenes2017

    • Author(s)
      Shotaro Hayashi, Masakatsu Kasuya, Junsuke Machida, and Toshio Koizumi
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 25 Pages: 2429-2432

    • DOI

      10.1016/j.tetlet.2017.05.016

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a Bithiophene-Isoindigo-Based &pi;-Conjugated Polymer <i>via</i> Direct Arylation Polycondensation Using Palladium Immobilized on Thiol-modified Silica Gel (PITS)2017

    • Author(s)
      林 正太郎,小泉 俊雄
    • Journal Title

      KOBUNSHI RONBUNSHU

      Volume: 74 Issue: 6 Pages: 584-587

    • DOI

      10.1295/koron.2017-0029

    • NAID

      130006218873

    • ISSN
      0386-2186, 1881-5685
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Study on Direct Arylation Polycondensation of 3,4-Ethylenedioxythiophene with Dibromocarbazole2017

    • Author(s)
      林 正太郎,清水 弘樹,小島 督央,山本 進一,小泉 俊雄
    • Journal Title

      KOBUNSHI RONBUNSHU

      Volume: 74 Issue: 6 Pages: 588-593

    • DOI

      10.1295/koron.2017-0037

    • NAID

      130006218929

    • ISSN
      0386-2186, 1881-5685
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Network Polymers Containing Triazine <i>via</i> Direct Arylation of Fluoroarenes and Their Properties2017

    • Author(s)
      林 正太郎、外川 雪、浅野 敦志、西 宏二、山本 進一、小泉 俊雄
    • Journal Title

      KOBUNSHI RONBUNSHU

      Volume: 74 Issue: 6 Pages: 453-459

    • DOI

      10.1295/koron.2017-0030

    • NAID

      130006218863

    • ISSN
      0386-2186, 1881-5685
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Cyclic Compound based on Xanthene-linked π-Stacked Dimer via Direct Arylation2016

    • Author(s)
      Shotaro Hayashi, Shin-ichi Yamamoto, and Toshio Koizumi
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 2 Pages: 200-203

    • DOI

      10.1246/cl.160930

    • NAID

      130005317058

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of π-conjugated porous polymers via direct arylation of fluoroarenes with three-arm triazine2016

    • Author(s)
      Shotaro Hayashi, Yuki Togawa, Jun Ashida, Koji Nishi, Atsushi Asano, Toshio Koizumi
    • Journal Title

      Polymer

      Volume: 90 Pages: 187-192

    • DOI

      10.1016/j.polymer.2015.11.056

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Small Band Gap Poly[Bis-EDOT-Isoindigo] via Direct Arylation and Oxidative Electropolymerization, and Its Optoelectronic Properties2016

    • Author(s)
      Shotaro Hayashi and Toshio Koizumi
    • Journal Title

      Electrochemistry

      Volume: 84 Issue: 8 Pages: 570-573

    • DOI

      10.5796/electrochemistry.84.570

    • NAID

      130005253803

    • ISSN
      1344-3542, 2186-2451
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-immobilized on thiol-modified silica gel: an effective catalyst for direct arylation approach2016

    • Author(s)
      Shotaro Hayashi, Atsushi Takigami, and Toshio Koizumi
    • Journal Title

      ChemPlusChem

      Volume: 7 Issue: 9 Pages: 930-934

    • DOI

      10.1002/cplu.201600188

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct arylation of fluoroarenes toward linear, bent-shaped and branched π-conjugated polymers: polycondensation post-polymerization approaches2016

    • Author(s)
      Shotaro Hayashi, Yuki Togawa, Yoshihisa Kojima and Toshio Koizumi
    • Journal Title

      Polymer Chemistry

      Volume: 7 Issue: 36 Pages: 5671-5686

    • DOI

      10.1039/c6py01237j

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Elastic Organic Crystals of a Fluorescent π-Conjugated Molecule2016

    • Author(s)
      Shotaro Hayashi and Toshio Koizumi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55 Issue: 8 Pages: 2701-2704

    • DOI

      10.1002/anie.201509319

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Chloride-promoted Pd-catalyzed direct C-H arylation for highly efficient phosphine-free synthesis of π-conjugated polymers2015

    • Author(s)
      Shotaro Hayashi and Toshio Koizumi
    • Journal Title

      Polymer Chemistry

      Volume: 6 Issue: 28 Pages: 5036-5039

    • DOI

      10.1039/c5py00871a

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Direct Arylation Polycondensation of 1,2,4,5-Tetrafluorobenzene Using Palladium on Carbon2015

    • Author(s)
      小島 督央, 外川 雪, 林 正太郎,小泉 俊雄
    • Journal Title

      KOBUNSHI RONBUNSHU

      Volume: 72 Issue: 8 Pages: 524-527

    • DOI

      10.1295/koron.2015-0022

    • NAID

      130005094701

    • ISSN
      0386-2186, 1881-5685
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 柔軟で稠密なπ造形システム~Elastic Organic Crystals of π-Conjugated Molecules~2018

    • Author(s)
      S. Hayashi
    • Organizer
      物質科学セミナー@筑波大学
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Elastic Organic Crystal based on Fluorescent Molecule2018

    • Author(s)
      S. Hayashi
    • Organizer
      International Congress on Pure & Applied Chemistry (ICPAC) 2018
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 弾性有機単結晶:稠密で柔軟な新素材の開発2017

    • Author(s)
      S. Hayashi
    • Organizer
      第21回アンビエント技術研究会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 弾性柔軟性を示す有機単結晶の開発とその特異な物性2016

    • Author(s)
      林 正太郎
    • Organizer
      第155回東海高分子研究会講演会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2016-04-23
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 直接的アリール化反応によるπ共役系高分子の合成2015

    • Author(s)
      林 正太郎
    • Organizer
      第12回触媒相模セミナー
    • Place of Presentation
      相模中央研究所
    • Year and Date
      2015-11-12
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 直接的アリール化重縮合によるπ共役系高分子の合成2015

    • Author(s)
      林 正太郎
    • Organizer
      グリーンマテリアル加工研究所
    • Place of Presentation
      グリーンマテリアル加工研究所
    • Year and Date
      2015-09-18
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 含フッ素π共役系オリゴマー/ポリマーの組織化による新規ソフトマテリアルの創製2015

    • Author(s)
      林 正太郎
    • Organizer
      第64回高分子討論会
    • Place of Presentation
      東北大学
    • Year and Date
      2015-09-15
    • Related Report
      2015 Research-status Report
    • Invited
  • [Remarks] HP: shayashi

    • URL

      http://s1016forest.wixsite.com/labo

    • Related Report
      2017 Annual Research Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi