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Development of narrow energy gap thienoisoindigo-based polymer with the aim of producing photothermoelectric energy conversion activity

Research Project

Project/Area Number 17K05830
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Functional solid state chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Ashizawa Minoru  東京工業大学, 物質理工学院, 助教 (80391845)

Co-Investigator(Kenkyū-buntansha) 松本 英俊  東京工業大学, 物質理工学院, 准教授 (40345393)
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: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords有機半導体 / 電子輸送性ポリマー / 近赤外光 / 電界効果トランジスタ / 光熱電変換素子 / チエノイソインジゴ / キノイド構造 / 電気伝導度 / 光熱変換 / キノキサリンイミド / 光熱電変換 / 近赤外光吸収 / キャリア輸送特性 / 機能性有機半導体 / 有機合成 / 近赤外光熱電変換素子 / 有機導体
Outline of Final Research Achievements

As a versatile electron-accepting units, diazaisoindigo and thiadiazole-fused quinoxalineimide molecules have been developed. Thiadiazole-fused quinoxalineimide molecules exhibited air stable n-channel field-effect transistor performance attributed to low-lying LUMO level.
We have developed novel hole-transporting thienoisoindigo polymer and electron-transporting thiadiazole-fused quinoxalineimide bearing very low energy gap. The photothermoelectric conversion device utilizing these polymers displayed efficient energy conversion from near infrared light (NIR) of 1700 nm to respective p- and n-channel thermoelectric power.

Academic Significance and Societal Importance of the Research Achievements

近赤外から赤外領域にわたる光は、高い生体透過性と人体の組織に対して害が少ない特徴を持つ。しかしこの領域の光を吸収するためには、非常に狭いエネルギーギャップを実現する必要があり、一般的にこの特性を持つポリマーの合成は困難であった。本研究課題はこの課題をクリアし、且つ領域の光エネルギーを熱エネルギーを介して電気エネルギーとして取り出すことに成功した。また国際共同研究を行い、人体への高い透過性を利用して腫瘍に対してこの領域の光を照射することで正確に腫瘍の位置をマッピングすることに成功したことはこれまでの電子材料としてのポリマーに新機能を付与した点で社会的な意義がある。

Report

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

    (31 results)

All 2020 2019 2018 2017 Other

All Int'l Joint Research (2 results) Journal Article (6 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 6 results,  Open Access: 2 results,  Acknowledgement Compliant: 1 results) Presentation (23 results) (of which Int'l Joint Research: 8 results,  Invited: 1 results)

  • [Int'l Joint Research] Purdue Univ.(米国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] Boston Univ./Purdue Univ.(米国)

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Functionalized NIR-II Semiconducting Polymer Nanoparticles for Single-cell to Whole-Organ Imaging of PSMA-Positive Prostate Cancer2020

    • Author(s)
      Jiayingzi Wu, Hyeon Jeong Lee, Liyan You, Xuyi Luo, Tsukasa Hasegawa, Kai-Chih Huang, Peng Lin, Timothy Ratliff, Minoru Ashizawa, Jianguo Mei,* and Ji-Xin Cheng*
    • Journal Title

      Small

      Volume: 2020 Issue: 19

    • DOI

      10.1002/smll.202001215

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] n-Type Organic Field-Effect Transistors Based on Bisthienoisatin Derivatives2019

    • Author(s)
      Dongho Yoo,,* Xuyi Luo, Tsukasa Hasegawa, Minoru Ashizawa,* Tadashi Kawamoto, Hiroyasu Masunaga, Noboru Ohta, Hidetoshi Matsumoto, Jianguo Mei, and Takehiko Mori*
    • Journal Title

      ACS Appl. Electron. Mater.

      Volume: 1 Issue: 5 Pages: 764-771

    • DOI

      10.1021/acsaelm.9b00105

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Fluorination and chlorination effects on quinoxalineimides as an electron-deficient building block for n-channel organic semiconductors2019

    • Author(s)
      Tsukasa Hasegawa, Minoru Ashizawa, Susumu Kawauchi, Hiroyasu Masunaga, Noboru Ohta, and Hidetoshi Matsumoto
    • Journal Title

      RSC Advances

      Volume: 9 Issue: 19 Pages: 10807-10813

    • DOI

      10.1039/c9ra02413a

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] p- and n-Channel photothermoelectric conversion based on ultralong near-infrared wavelengths absorbing polymers2019

    • Author(s)
      Tsukasa Hasegawa, Minoru Ashizawa, Yoshihiro Hayashi, Susumu Kawauchi, Hiroyasu Masunaga, Takaaki Hikima, Takaaki Manaka, and Hidetoshi Matsumoto
    • Journal Title

      ACS Applied Polymer Materials

      Volume: 1 Issue: 3 Pages: 542-551

    • DOI

      10.1021/acsapm.8b00234

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Thiadiazole-fused quinoxalineimide as an electron-deficient building block for n-type organic semiconductors2017

    • Author(s)
      Tsukasa Hasegawa, Minoru Ashizawa, Koutarou Aoyagi, Hiroyasu Masunaga, Takaaki Hikima, and Hidetoshi Matsumoto
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 12 Pages: 3275-3278

    • DOI

      10.1021/acs.orglett.7b01424

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] N-unsubstituted thienoisoindigos: preparation, molecular packing and ambipolar organic field-effect transistors2017

    • Author(s)
      Dongho Yoo, Tsukasa Hasegawa, Minoru Ashizawa, Tadashi Kawamoto, Hiroyasu Masunaga, Takaaki Hikima, Hidetoshi Matsumoto, and Takehiko Mori
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 5 Issue: 10 Pages: 2509-2512

    • DOI

      10.1039/c7tc00327g

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] キノイド構造を有するビスチエノイサチン誘導体の合成と有機電界効果トランジスタへの応用2020

    • Author(s)
      小原章宏, 長谷川司, 芦沢実, 増永啓康, 太田昇, 松本英俊
    • Organizer
      日本化学会第100春季年会, 東京理大学野田キャンパス, 令和2年3月22-25日
    • Related Report
      2019 Annual Research Report
  • [Presentation] キノイド構造を有するビスチエノイサチン誘導体の合成と物性2019

    • Author(s)
      小原章宏, 長谷川司, 芦沢実, 松本英俊
    • Organizer
      第66回応用物理学会春季学術講演会
    • Related Report
      2018 Research-status Report
  • [Presentation] Organic field-effect transistors based on bisthienoisatin analogs2018

    • Author(s)
      D. Yoo, T. Hasegawa, M. Ashizawa, T. Kawamoto, H. Matsumoto, T. Mori
    • Organizer
      The 8th TOYOTA RIKEN International Workshop on Organic Semiconductors, Conductors, and Electronics
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of ultra-low energy-gap conjugated polymers for photo-thermo-electric conversion2018

    • Author(s)
      H. Matsumoto, M. Ashizawa, T. Hasegawa
    • Organizer
      Collaborative Workshop on Organic Electronics and Molecular Photophysics/Photochemistry between Imperial College London and Tokyo Institute of Technology
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Organic field-effect transistors based on α-substituted thienoisoindigo derivatives2018

    • Author(s)
      D. Yoo, T. Hasegawa, M. Ashizawa, T. Kawamoto, H. Matsumoto, T. Mori
    • Organizer
      The international conference on science and technology of synthetic metals 2018 (ICSM 2018)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] フッ素置換したキノキサリンイミド誘導体の合成と物性2018

    • Author(s)
      長谷川司, 芦沢実, 川内進, 松本英俊
    • Organizer
      平成30年度繊維学会秋季研究発表会
    • Related Report
      2018 Research-status Report
  • [Presentation] フッ素置換したキノキサリンイミド誘導体の合成とキャリア輸送特性2018

    • Author(s)
      長谷川司, 芦沢実, 川内進, 松本英俊
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] キノイド構造を有するベンゾジピロリドン誘導体の物性と電界効果トランジスタ特性2018

    • Author(s)
      小原章宏, 長谷川司, 芦沢実, 松本英俊
    • Organizer
      小原章宏, 長谷川司, 芦沢実, 松本英俊
    • Related Report
      2018 Research-status Report
  • [Presentation] ビスイサチン類縁体を用いた有機電界効果トランジスタ2018

    • Author(s)
      劉東昊,長谷川司,芦沢実,川本正,松本英俊,森健彦
    • Organizer
      第12回分子科学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] キノイド構造を有するジピロロピラジンジオン誘導体の合成と物性2018

    • Author(s)
      小原章宏, 長谷川司, 芦沢実, 松本英俊
    • Organizer
      平成30年度繊維学会年次大会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis and properties of quinoxalineimide-based electron-deficient building block for n-type organic semiconductors2018

    • Author(s)
      M. Ashizawa, T. Hasegawa, K. Aoyagi, H. Masunaga, T. Hikima, S. Kawauchi, H. Matsumoto
    • Organizer
      2018 MRS Spring Meeting & Exhibit
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Towards the development of supramolecular fiber with ferroelectricity2018

    • Author(s)
      M. Kunishima, M. Ashizawa, D. Miyajima, F. Araoka, H. Matsumoto
    • Organizer
      CEMS International Symposium on Supramolecular Chemistry & Functional Materials 2018
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Disorderly-assembled graphene nanoribbon electrodes for high-performance supercapacitors2017

    • Author(s)
      Y. Saito, M. Ashizawa, H. Matsumoto
    • Organizer
      2017 E-MRS Fall Meeting and Exhibit
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] NIR-photo-thermo-electric conversion thin-film devices based on ultra-low energy-gap conjugated polymers2017

    • Author(s)
      T. Hasegawa, M. Ashizawa, T. Manaka, S. Kawauchi, H. Matsumoto
    • Organizer
      2017 E-MRS Fall Meeting and Exhibit
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] N-Unsubstituted thienoisoindigo derivatives: preparation, molecular packing, and ambipolar organic field-effect transistors2017

    • Author(s)
      D. Yoo, T. Hasegawa, M. Ashizawa, T. Kawamoto, H. Masunaga, T. Hikima, H. Matsumoto, T. Mori
    • Organizer
      The 8th International Conference on Flexible on Printed Electronics 2017 (ICFPE 2017)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 電界紡糸イオン交換ナノファイバーを複合化した高分子電解質膜の構造と物性2017

    • Author(s)
      清野史康, 鴻巣裕一, 芦沢実, 比嘉充, 松本英俊
    • Organizer
      繊維学会関東支部平成29年度研究交流会
    • Related Report
      2017 Research-status Report
  • [Presentation] 電界紡糸法を用いたカラムナー液晶ファイバーの作製と評価2017

    • Author(s)
      國嶋密道, 芦沢実, 松本英俊, 宮島大吾, 荒岡史人
    • Organizer
      平成29年度 繊維学会秋季研究発表会
    • Related Report
      2017 Research-status Report
  • [Presentation] チエノイソインジゴのα位置換体を用いた有機電界効果トランジスタ2017

    • Author(s)
      劉東昊,長谷川司,芦沢実,川本正,松本英俊,森健彦
    • Organizer
      第11回分子科学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 狭エネルギーギャップポリマーの開発と光熱電変換特性:分子設計からのアプローチ2017

    • Author(s)
      芦沢実, 長谷川司, 間中孝彰, 川内進, 松本英俊
    • Organizer
      第14回日本熱電学会学術講演会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] 二酸化マンガンナノワイヤ・カーボンナノファイバー複合電極の作製と電気化学キャパシタへの応用2017

    • Author(s)
      齋藤慶考,芦沢実,松本英俊
    • Organizer
      ナノファイバー学会第8回年次大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 電界紡糸法を用いたカラムナー液晶ファイバーの作製と評価2017

    • Author(s)
      國嶋密道,芦沢実,松本英俊, 宮島大吾,荒岡史人
    • Organizer
      ナノファイバー学会第8回年次大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 電界紡糸イオン交換ナノファイバーを複合化した高分子電解質膜の構造と物性2017

    • Author(s)
      清野史康, 鴻巣裕一, 芦沢実, 松本英俊, 比嘉充
    • Organizer
      ナノファイバー学会第8回年次大会
    • Related Report
      2017 Research-status Report
  • [Presentation] フォノン輸送制御を目的とした有機無機ハイブリッド薄膜の作製2017

    • Author(s)
      田邊祐馬, 室屋好希, ジャンサ フィルマン, 松本英俊, 芦沢実, 森川淳子, 野崎智洋
    • Organizer
      第54回日本伝熱シンポジウム
    • Related Report
      2017 Research-status Report

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

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