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Development of Site-Selective Direct Arylation Polycondensation

Research Project

Project/Area Number 25288052
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Polymer chemistry
Research InstitutionUniversity of Tsukuba

Principal Investigator

Kanbara Takaki  筑波大学, 数理物質系, 教授 (90204809)

Co-Investigator(Renkei-kenkyūsha) KUWABARA Junpei  筑波大学, 数理物質系, 講師 (70466655)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥18,460,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥4,260,000)
Fiscal Year 2015: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2014: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2013: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
Keywords高分子半導体 / 導電性高分子 / 直接的アリール化反応 / 結合位置 / 反応制御 / 配向基 / オルトメタル化反応
Outline of Final Research Achievements

Polycondensation via direct arylation of C-H bond in aromatic monomers afforded the corresponding conjugated polymers. However, the C-H functionalization sometimes occurs at undesired positions of the aromatic monomers, which affords the irregular structure in the polymer chains. To suppress the undesired side reactions, we focused on development of site-selective direct arylation polycondensation. The introduction of directing group into the aromatic monomer was effective for ortho-selective C-H bond functionalization and gave well-defined conjugated polymers. On the other hand, we examined the relationship between the reaction conditions and the nature of thiophene monomers; the optimal reaction conditions were applicable to site-selective direct arylation polycondensation and afforded well-defined conjugated polymers.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (48 results)

All 2016 2015 2014 2013

All Journal Article (13 results) (of which Peer Reviewed: 13 results,  Acknowledgement Compliant: 7 results,  Open Access: 2 results) Presentation (35 results) (of which Int'l Joint Research: 3 results,  Invited: 6 results)

  • [Journal Article] Synthesis of Conjugated Polymers Possessing Diketopyrrolopyrrole (DPP) Units Bearing Phenyl, Pyridyl, and Thiazolyl Groups by Direct Arylation Polycondensation: Effects of Aromatic Groups in DPP on Physical Properties2016

    • Author(s)
      Junpei Kuwabara, Naoto Takase, Takeshi Yasuda, Takaki Kanbara
    • Journal Title

      J. Polym. Sci. A Polym. Chem.

      Volume: 54 Issue: 15 Pages: 2337-2345

    • DOI

      10.1002/pola.28105

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Effects of the Terminal Structure, Purity, and Molecular Weight of an Amorphous Conjugated Polymer on Its Photovoltaic Characteristics2016

    • Author(s)
      Junpei Kuwabara, Takeshi Yasuda, Naoto Takase, and Takaki Kanbara
    • Journal Title

      ACS Appl. Mater. Interfaces

      Volume: 8 Issue: 3 Pages: 1752-1758

    • DOI

      10.1021/acsami.5b09482

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selectivity of Reaction Sites for Direct Arylation Polycondensation in Bithiophene Derivatives2015

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

      Mol. Cryst. Liq. Cryst.

      Volume: 622 Issue: 1 Pages: 14-18

    • DOI

      10.1080/15421406.2015.1096493

    • NAID

      120007130041

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Emission from Charge-Transfer States in Bulk Heterojunction Organic Photovoltaic Cells Based on Ethylenedioxythiophene-Fluorene Polymers2015

    • Author(s)
      Takeshi Yasuda, Junpei Kuwabara, Liyuan Han, and Takaki Kanbara
    • Journal Title

      Mol. Cryst. Liq. Cryst.

      Volume: 620 Issue: 1 Pages: 107-111

    • DOI

      10.1080/15421406.2015.1094887

    • NAID

      120007130043

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct Arylation Polycondensation of Thienothiophenes with Various Dibromoarylenes2015

    • Author(s)
      Tatsuya Kumada, Yuta Nohara, Junpei Kuwabara, and Takaki Kanbara
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 88 Issue: 11 Pages: 1530-1535

    • DOI

      10.1246/bcsj.20150235

    • NAID

      130005108570

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Improved power conversion efficiency of bulk-heterojunction organic photovoltaic cells using neat C70 as an effective acceptor for an amorphous π-conjugated polymer2015

    • Author(s)
      Takeshi Yasuda, Junpei Kuwabara, Liyuan Han, and Takaki Kanbara
    • Journal Title

      Org. Electron.

      Volume: 25 Pages: 99-104

    • DOI

      10.1016/j.orgel.2015.06.024

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The Effect of Solvent in Direct Arylation Polycondensation of Substituted Thiophenes2015

    • Author(s)
      Junpei Kuwabara, Kohtaro Yamazaki, Takuya Yamagata, Wataru, Tsuchida, and Takaki Kanbara
    • Journal Title

      Polym. Chem

      Volume: 6 Issue: 6 Pages: 891-895

    • DOI

      10.1039/c4py01387e

    • NAID

      120007130385

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Mechanistic Studies and Optimisation of a Pd-catalysed Direct Arylation Reaction Using Q1 Phosphine-free Systems2015

    • Author(s)
      Junpei Kuwabara, Masaru Sakai, Qiao Zhang and Takaki Kanbara
    • Journal Title

      Org. Chem. Front

      Volume: 2 Issue: 5 Pages: 520-525

    • DOI

      10.1039/c4qo00351a

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of Synthetic Method for π-Conjugated Polymers via Direct Arylation Polycondensation2014

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

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 72 Issue: 11 Pages: 1271-1278

    • DOI

      10.5059/yukigoseikyokaishi.72.1271

    • NAID

      130004749125

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Direct Arylation Polycondensation of Bithiazole Derivatives with Various Acceptors2014

    • Author(s)
      Masahiro Kuramochi, Junpei Kuwabara, Wei Lu, and Takaki Kanbara
    • Journal Title

      Macromolecules

      Volume: 42 Issue: 21 Pages: 7378-7385

    • DOI

      10.1021/ma5014397

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct Arylation Polycondensation: A Promising Method for the Synthesis of Highly Pure, High-Molecular-Weight Conjugated Polymers Needed for Improving the Performance of Organic Photovoltaics2014

    • Author(s)
      Junpei Kuwabara, Takeshi Yasuda, Seong Jib Choi, Wei Lu, Koutarou Yamazaki, Shigehiro Kagaya, Liyuan Han, and Takaki Kanbara
    • Journal Title

      Adv. Funct. Mater

      Volume: 24 Issue: 21 Pages: 3226-3233

    • DOI

      10.1002/adfm.201302851

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two-Step Direct Arylation for Synthesis of Naphthalenediimide-Based Conjugated Polymer2014

    • Author(s)
      Yuta Nohara, Junpei Kuwabara, Takeshi Yasuda, Liyuan Han, and Takaki Kanbara
    • Journal Title

      J. Polym. Sci.: Part A: Polym. Chem

      Volume: 52 Issue: 10 Pages: 1401-1407

    • DOI

      10.1002/pola.27140

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of π-Conjugated Polymer Consisting of Pyrrole and Fluorene Units by Ru-Catalyzed Site-Selective Direct Arylation Polycondensation2013

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

      Macromol. Rapid Commun

      Volume: 34 Issue: 14 Pages: 1151-1156

    • DOI

      10.1002/marc.201300303

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] Facile synthesis of fluorene-based conjugated polymers via direct arylation polycondensation2015

    • Author(s)
      Takaki Kanbara,Hitoshi Saito, Junpei Kuwabara
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      Mid-Pacific Center (Hilton Hawaiian Village),USA
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Effects of impurity in amorphous conjugated polymer for organic thin-film solar cells2015

    • Author(s)
      Junpei Kuwabara, Naoto Takase, Takeshi Yasuda, Takaki Kanbara
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      Hawaii Convention Center,USA
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新しい高分子半導体合成法の開発研究―有機デバイスの実用化に向けて―2015

    • Author(s)
      神原貴樹
    • Organizer
      第13回環境研究シンポジウム
    • Place of Presentation
      一橋大学一橋講堂(東京都千代田区)
    • Year and Date
      2015-11-10
    • Related Report
      2015 Annual Research Report
  • [Presentation] 直接的アリール化重縮合法における反応位置制御2015

    • Author(s)
      藤江陽平、桑原純平、神原貴樹
    • Organizer
      第30回高分子学会関東支部茨城地区若手の会
    • Place of Presentation
      つくばセミナーハウス(茨城県つくばみらい市)
    • Year and Date
      2015-10-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] ジクロロアリーレンを基質とした直接アリール化重縮合反応2015

    • Author(s)
      土田 渉、桑原 純平、神原 貴樹
    • Organizer
      第30回高分子学会関東支部茨城地区若手の会
    • Place of Presentation
      つくばセミナーハウス(茨城県つくばみらい市)
    • Year and Date
      2015-10-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] 脱カルボキシル化と直接的アリール化反応を用いた重縮合反応の開拓2015

    • Author(s)
      佐藤 剛大、氏家 義人、桑原 純平、神原貴樹
    • Organizer
      第30回高分子学会関東支部茨城地区若手の会
    • Place of Presentation
      つくばセミナーハウス(茨城県つくばみらい市)
    • Year and Date
      2015-10-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] Practical synthetic method of conjugated polymer materials for organic photovoltaics2015

    • Author(s)
      Junpei Kuwabara, Takaki Kanbara
    • Organizer
      TGSW2015
    • Place of Presentation
      EPOCAL TSUKUBA,Tsukuba,Ibaraki
    • Year and Date
      2015-09-30
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 共役高分子材料の純度や分子量が光電変換機能に及ぼす影響2015

    • Author(s)
      桑原 純平、高瀬 直人、安田 剛、神原 貴樹
    • Organizer
      第64回高分子討論会
    • Place of Presentation
      東北大学 川内キャンパス(宮城県仙台市)
    • Year and Date
      2015-09-17
    • Related Report
      2015 Annual Research Report
  • [Presentation] 脱カルボキシル化と直接的アリール化反応を用いた重縮合反応の開拓2015

    • Author(s)
      佐藤 剛大、氏家 義人、桑原 純平、神原貴樹
    • Organizer
      第64回高分子討論会
    • Place of Presentation
      東北大学 川内キャンパス(宮城県仙台市)
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] ジクロロアリーレンを基質とした直接アリール化重縮合反応2015

    • Author(s)
      土田 渉、桑原 純平、神原 貴樹
    • Organizer
      第64回高分子討論会
    • Place of Presentation
      東北大学 川内キャンパス(宮城県仙台市)
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] 直接的アリール化反応を利用した共役高分子の合成と機能2015

    • Author(s)
      神原 貴樹
    • Organizer
      ポリマーフロンティア21
    • Place of Presentation
      東工大蔵前会館ロイアルブルーホール(東京都目黒区)
    • Year and Date
      2015-06-12
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 直接アリール化反応によるベンゾジピロリドンユニットを有するポリマーの合成と物性評価2015

    • Author(s)
      王 志安、桑原 純平、安田 剛、神原 貴樹
    • Organizer
      第64回高分子学会年次大会
    • Place of Presentation
      札幌コンベンションセンター(北海道札幌市)
    • Year and Date
      2015-05-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] 直接的アリール化重縮合法におけるチオフェン環の電子密度の違いに基づく反応位置制御2015

    • Author(s)
      藤江 陽平、桑原 純平、神原 貴樹
    • Organizer
      第64回高分子学会年次大会
    • Place of Presentation
      札幌コンベンションセンター(北海道札幌市)
    • Year and Date
      2015-05-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis of Highly Pure, High-Molecular-Weight Conjugated Polymers by Direct Arylation Polycondensation for Improving the Performance of Organic Photovoltaics2014

    • Author(s)
      Junpei Kuwabara, Takeshi Yasuda, Seong Jib Choi, Wei Lu, Koutarou Yamazaki, Shigehiro Kagaya, Liyuan Han, Takaki Kanbara
    • Organizer
      The 10th SPSJ International Polymer Conference (IPC 2014)
    • Place of Presentation
      Tsukuba International CongressCenter (EPOCHAL TSUKUBA)(茨城県・つくば市)
    • Year and Date
      2014-12-04
    • Related Report
      2014 Annual Research Report
  • [Presentation] 直接的アリール化反応を利用した高分子半導体の合成2014

    • Author(s)
      神原貴樹
    • Organizer
      高分子学会関東支部第58回湘北地区懇話会講演会
    • Place of Presentation
      神奈川大学 横浜キャンパス(神奈川県・横浜市)
    • Year and Date
      2014-11-21
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 直接的アリール化重縮合におけるビチオフェン誘導体の反応位置選択性2014

    • Author(s)
      藤江陽平、桑原純平、神原貴樹
    • Organizer
      第29回高分子学会茨城地区若手の会
    • Place of Presentation
      つくばセミナーハウス(茨城県・つくばみらい市)
    • Year and Date
      2014-10-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] 高純度なπ共役高分子の合成と太陽電池特性の評価2014

    • Author(s)
      桑原 純平、野原 雄太、神原 貴樹
    • Organizer
      第63回高分子討論会
    • Place of Presentation
      長崎大学文教キャンパス(長崎県・長崎市)
    • Year and Date
      2014-09-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Direct Arylation Polycondensation of Bithiazole Derivative with Various Acceptors2014

    • Author(s)
      Masahiro Kuramochi, Junpei Kuwabara, Wei Lu, Takaki Kanbara
    • Organizer
      KJF-ICOMEP 2014
    • Place of Presentation
      International Congress Center (Epochal tsukuba)(茨城県・つくば市)
    • Year and Date
      2014-09-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] Selectivity of reaction sites for direct arylation polycondensation in bithiophene derivatives2014

    • Author(s)
      Yohei Fujie, Junpei Kuwabara, Takaki Kanbara
    • Organizer
      KJF-ICOMEP 2014
    • Place of Presentation
      Tsukuba International CongressCenter (EPOCHAL TSUKUBA)(茨城県・つくば市)
    • Year and Date
      2014-09-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] Mechanistic Study and Optimization of Pd-catalyzed DirectArylationReaction Using Phosphine-free System2014

    • Author(s)
      Junpei KUWABARA, Masaru SAKAI, Takuya YAMAGATA, Takaki KANBARA
    • Organizer
      26th ICOMC
    • Place of Presentation
      ロイトン札幌(北海道・札幌市)
    • Year and Date
      2014-07-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] 直接的アリール化重縮合におけるビチオフェンの反応位置選択性2014

    • Author(s)
      藤江陽平、倉持政宏、桑原純平、神原貴樹
    • Organizer
      第63回高分子学会年次大会
    • Place of Presentation
      名古屋国際会議場(愛知県・名古屋市)
    • Year and Date
      2014-05-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 直接アリール化重縮合における複素5員環化合物の反応性の評価2014

    • Author(s)
      志水大和、野原雄太、桑原純平、神原貴樹
    • Organizer
      第63回 高分子学会年次大会
    • Place of Presentation
      名古屋国際会議場(愛知県・名古屋市)
    • Year and Date
      2014-05-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] リン配位子を用いない直接アリール化反応に対する機構調査2014

    • Author(s)
      桑原純平・酒井優・神原貴樹
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Annual Research Report
  • [Presentation] Synthesis of Pyrrole-based π-Conjugated Polymer by Ru-catalyzed Site-selective Direct Arylation Polycondensation2013

    • Author(s)
      Wei Lu, Junpei Kuwabara, and Takaki Kanbara
    • Organizer
      The 15th Asian Chemical Congress
    • Place of Presentation
      Resorts World Sentosa Convention ,Singapore
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] EDOT の直接アリール化反応を用いて合成した共役高分子の特性評価2013

    • Author(s)
      桑原純平、野原雄太、山崎光太郎、崔星集、神原貴樹、安田剛、韓礼元
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都国際会館
    • Related Report
      2013 Annual Research Report
  • [Presentation] 直接的アリール化反応を利用したπ共役高分子の合成における脱離可能な配向基の導入効果2013

    • Author(s)
      盧葦、桑原純平、神原貴樹
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都国際会館
    • Related Report
      2013 Annual Research Report
  • [Presentation] 直接アリール化反応を用いたビチアゾールと種々のアクセプターの重縮合反応2013

    • Author(s)
      倉持政宏、盧葦、桑原純平、神原貴樹
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都国際会館
    • Related Report
      2013 Annual Research Report
  • [Presentation] 直接的アリール化反応を用いたチエノチオフェン骨格を有するD-A型ポリマーの合成2013

    • Author(s)
      熊田達也、野原雄太、桑原純平、神原貴樹
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都国際会館
    • Related Report
      2013 Annual Research Report
  • [Presentation] 直接アリール化重縮合による共役高分子材料の高純度化と高分子量化 -光電変換効率向上への寄与-2013

    • Author(s)
      桑原純平、崔星集、山崎光太郎、安田剛、韓礼元、加賀谷重浩、神原貴樹
    • Organizer
      第62回高分子討論会
    • Place of Presentation
      金沢大学角間キャンパス
    • Related Report
      2013 Annual Research Report
  • [Presentation] C-H結合の直接アリール化反応を利用した共役系高分子材料の効率的合成2013

    • Author(s)
      野原雄太、桑原純平、安田剛、韓礼元、神原貴樹
    • Organizer
      第62回高分子討論会
    • Place of Presentation
      金沢大学角間キャンパス
    • Related Report
      2013 Annual Research Report
  • [Presentation] 直接的アリール化重縮合法における結合位置制御を可能にする反応系の探索2013

    • Author(s)
      藤江陽平、倉持政宏、桑原純平、神原貴樹
    • Organizer
      第62回高分子討論会
    • Place of Presentation
      金沢大学角間キャンパス
    • Related Report
      2013 Annual Research Report
  • [Presentation] 直接的アリール化反応を利用した共役高分子の合成と機能2013

    • Author(s)
      神原貴樹
    • Organizer
      東京工業大学物質科学講演会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 直接的アリール化反応を利用した高分子半導体の合成2013

    • Author(s)
      神原貴樹
    • Organizer
      有機系太陽電池に関するワークショップ
    • Place of Presentation
      筑波大学筑波キャンパス
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 結合位置選択的な直接的アリール化反応によるπ共役高分子の合成2013

    • Author(s)
      氏家義人、盧葦、桑原純平、神原貴樹
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      タワーホール船堀(東京都)
    • Related Report
      2013 Annual Research Report
  • [Presentation] リン配位子を必要としないC-H直接官能基化反応の機構解明と最適条件の追及2013

    • Author(s)
      酒井優、桑原純平、神原貴樹
    • Organizer
      第3回CSJ化学フェスタ 2013
    • Place of Presentation
      タワーホール船堀(東京都)
    • Related Report
      2013 Annual Research Report

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Published: 2013-05-21   Modified: 2019-07-29  

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