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Redox-based switching of electronic conductivity on oligothiophene-gold nanoparticles system

Research Project

Project/Area Number 17K05977
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic and hybrid materials
Research InstitutionTokyo Metropolitan University

Principal Investigator

Nishinaga Tohru  首都大学東京, 理学研究科, 准教授 (30281108)

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: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords金微粒子 / オリゴチオフェン / ラジカルカチオン / 導電性 / 自己組織化
Outline of Final Research Achievements

Co-oligomer E2P2 composed of two 3,4-ethylenedioxythiophene(EDOT:E) units, which is the monomer of representative conducting polymer PEDOT, and two 3,4-propylenedioxythiophene (ProDOT:P) units, was newly synthesized. One-electron oxidized radical cationic species of E2P2 end-capped with methylthio groups was highly stabilized, and the radical cation was found to have the ability of face-to-face interaction, namely, pi-dimerization. Furthermore, gold-nanoparticles partially protected by the thiolate of E2P2 together with dodecylamine (AuNPs-E2P2) was successfully synthesized. The electronic conductivity of a film prepared from the partially oxidized AuNPs-E2P2 with some radical cationic units was shown to be ca. 200 times higher than that of a film prepared from neutral AuNPs-E2P2.

Academic Significance and Societal Importance of the Research Achievements

代表的な導電性高分子の部分構造とその類縁体を組み合わせたオリゴマー分子を用い、一電子酸化させることにより、分子間の相互作用が促進される系を新たに設計・合成した。さらに、そのような系を保護基に用いた金微粒子の合成にも成功し、その金微粒子の分散液から作成したフィルムの導電性が、酸化還元状態の変化に応じてスイッチングさせうることを示すことに成功した。これにより、酸化還元状態に基づく新たなスイッチング素子が溶液から作成できる可能性を示すことができた

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 Journal Article (11 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 11 results) Presentation (17 results) (of which Int'l Joint Research: 1 results) Book (1 results) Remarks (2 results)

  • [Journal Article] Antiaromaticity and Reactivity of Planar Cyclooctatetraene and its Application to Organic Semiconductor2020

    • Author(s)
      西長 亨
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 78 Issue: 2 Pages: 140-147

    • DOI

      10.5059/yukigoseikyokaishi.78.140

    • NAID

      130007795911

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2020-02-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation, Spectroscopic Characterization and Theoretical Study of a Three-Dimensional Conjugated 70 π-Electron Thiophene 6-Mer Radical Cation π-Dimer2020

    • Author(s)
      T. Fujiwara, A. Muranaka, T. Nishinaga, S. Aoyagi, N. Kobayashi, M. Uchiyama, H. Otani, M. Iyoda
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 142 Issue: 13 Pages: 5933-5937

    • DOI

      10.1021/jacs.9b13573

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of a Tricyclic Hexaketone Monohydrate with Hexabutyl Side Chain2019

    • Author(s)
      M. Ishita, M. Ohkoshi, Y. Kuwatani, H. Otani, T. Nishinaga, M. Iyoda
    • Journal Title

      Heterocycles

      Volume: 99 Issue: 2 Pages: 1145-1153

    • DOI

      10.3987/com-18-s(f)85

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Oxidation of a Dithieno[3,4‐ b :3′,4′‐ d ]thiophene Cyclic Dimer Containing a Planar Cyclooctatetraene Ring: Retention of High Antiaromaticity During Reactions2019

    • Author(s)
      Hamaoka Hinako、Shiroma Shun、Aburaya Kazuaki、Hasegawa Masashi、Nishinaga Tohru
    • Journal Title

      ChemPlusChem

      Volume: 印刷中 Issue: 6 Pages: 704-711

    • DOI

      10.1002/cplu.201900064

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Computational and experimental study on the index of antiaromaticity for 4n π-systems (n>2)2019

    • Author(s)
      Tohru Nishinaga, Hinako Hamaoka
    • Journal Title

      Chem. Commun.

      Volume: 55 Issue: 10 Pages: 1514-1517

    • DOI

      10.1039/c8cc09448a

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Antiaromaticity of Planar Bisdehydro[12]- and Tetrakisdehydro[16]-annulenes fused with Dithieno[3,4-b:3’,4’-d]thiophenes2018

    • Author(s)
      Tohru Nishinaga, Shun Shiroma, Masashi Hasegawa
    • Journal Title

      Org. Lett.

      Volume: 20 Issue: 11 Pages: 3426-3429

    • DOI

      10.1021/acs.orglett.8b01405

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chemical Stability of the 5-Mesityl-5′′-(nitronyl nitroxide)-2,2′:5′,2′′-ter(3,4-ethylenedioxythiophene) Radical Cation2018

    • Author(s)
      Tahara Takuma、Suzuki Shuichi、Kozaki Masatoshi、Nishinaga Tohru、Okada Keiji
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 91 Issue: 8 Pages: 1193-1195

    • DOI

      10.1246/bcsj.20180078

    • NAID

      130007433399

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Radical Cation π-Dimers of Conjugated Oligomers as Molecular Wires: An Analysis Based on Nitronyl Nitroxide Spin Labels2018

    • Author(s)
      Nishinaga Tohru、Kanzaki Yuki、Shiomi Daisuke、Matsuda Kenji、Suzuki Shuichi、Okada Keiji
    • Journal Title

      Chemistry - A European Journal

      Volume: 24 Issue: 45 Pages: 11717-11728

    • DOI

      10.1002/chem.201801712

    • NAID

      120006716400

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019731

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] π-Dimerization Ability of Conjugated Oligomer Dication Diradicaloids Composed of Dithienylpyrrole and Benzodithiophene Units2018

    • Author(s)
      Takahiro Akahane, Masayoshi Takase, Yasuhiro Mazaki, Tohru Nishinaga
    • Journal Title

      Heteroatom Chem.

      Volume: 29 Issue: 5-6

    • DOI

      10.1002/hc.21452

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Saturn-like Complex Composed of Macrocyclic Oligothiophene and [60]fullerene: Structure, Stability, and Photophysical Properties in Solution and the Solid State2018

    • Author(s)
      Hideyuki Shimizu, Kyu Hyung Park, Hiroyuki Otani, Shinobu Aoyagi, Tohru Nishinaga, Yoshio Aso, Dongho Kim, Masahiko Iyoda
    • Journal Title

      Chem. Eur. J.

      Volume: 24 Issue: 15 Pages: 3793-3801

    • DOI

      10.1002/chem.201705565

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Stable Radical Cations and Their π-Dimers Prepared from Ethylene- and Propylene-3,4-dioxythiophene Co-oligomers: Combined Experimental and Theoretical Investigations2017

    • Author(s)
      Nishinaga Tohru、Sotome Yusuke
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 14 Pages: 7245-7253

    • DOI

      10.1021/acs.joc.7b00816

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 3,4-ジオキシチオフェン混合オリゴマーで保護された金微粒子の合成と性質2020

    • Author(s)
      松尾 一輝・野村 琴広・西長 亨
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Relative Hardness as a New Experimentally Accessible Antiaromaticity Index2019

    • Author(s)
      Tohru Nishinaga
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds
    • Related Report
      2019 Annual Research Report
  • [Presentation] Oxidation Reactions of Dithienotiophene Cyclic Dimer Including an Antiaromatic Ring2019

    • Author(s)
      Hinako Hamaoka, Shun Shiroma, Kotohiro Nomura, Tohru Nishinaga
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds
    • Related Report
      2019 Annual Research Report
  • [Presentation] 3,4-ジオキシチオフェン混合オリゴマーで保護された金微粒子の合成と性質2019

    • Author(s)
      松尾一輝・野村琴広・西長亨
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 大環状π拡張チオフェン 6 量体の酸化種の示す特異な 光学および電子物性2019

    • Author(s)
      藤原稔大・村中厚哉・西長 亨・青柳忍・大谷裕之・小林長 夫・伊與田正彦
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 3,4-ジオキシチオフェン混合オリゴマーのジカチオンジラジカルのπダイマー形成2019

    • Author(s)
      西長 亨
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 大環状チオフェン6量体πダイマーの作る3次元共役70π電子系の構造と物性2019

    • Author(s)
      藤原稔大・村中厚哉・西長亨・青柳忍・大谷裕之・小林長夫・伊與田正彦
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 反芳香環を内包するジチエノチオフェン環状2量体の酸化反応2019

    • Author(s)
      濱岡日向子, 城間 駿, 野村琴広, 西長 亨
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Control of radical cation π-dimer formation of 3,4-dioxythiophen co-oligomers2018

    • Author(s)
      Y. Sotome, K. Nomura, T. Nishinaga
    • Organizer
      28th International Symposium on the Organic Chemistry of Sulfur
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] ジチエノチオフェンの縮環で平面化させた反芳香族性[4n]アヌレン類の反応2018

    • Author(s)
      濱岡日向子, 城間 駿, 野村琴広, 西長 亨
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] [4n]アヌレン類の反芳香族性とHOMO-LUMO ギャップとの関連2018

    • Author(s)
      西長 亨
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ジチエノチオフェンの縮環で平面化させた[4n]アヌレン類の反芳香族性と反応性2018

    • Author(s)
      西長 亨, 城間 駿, 濱岡日向子, 野村琴広
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ジチエノチオフェンが縮環した平面デヒドロ[12]および[16]アヌレンの合成と性質2018

    • Author(s)
      城間 駿, 野村琴広, 西長 亨
    • Organizer
      日本化学会第98年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 分子ワイヤーとしての共役オリゴマーラジカルカチオンπダイマー:ニトロニルニトロキシドスピンラベルによる解析2017

    • Author(s)
      西長 亨・神崎祐貴・塩見大輔・鈴木修一・岡田惠次
    • Organizer
      第41回有機電子移動化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 分子ワイヤーとしての共役オリゴマーラジカルカチオンπダイマー:ニトロニルニトロキシドスピンラベルによる解析2017

    • Author(s)
      西長 亨・神崎祐貴・塩見大輔・松田建児・鈴木修一・岡田惠次
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 3,4-ジオキシチオフェン混合オリゴマーのラジカルカチオンπ-ダイマーの形成制御2017

    • Author(s)
      五月女 祐亮、野村 琴広、西長 亨
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 中央に嵩高い置換基をもつπ共役オリゴマーのジカチオン種のジラジカル性とπダイマー2017

    • Author(s)
      西長 亨, 赤羽根敬弘, 高瀬雅祥, 野村琴広, 真崎康博
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Research-status Report
  • [Book] マテリアルサイエンス有機化学―基礎と機能材料への展開―第2版2018

    • Author(s)
      伊与田正彦、横山 泰、西長 亨
    • Total Pages
      180
    • Publisher
      東京化学同人
    • ISBN
      9784807909346
    • Related Report
      2018 Research-status Report
  • [Remarks] http://tmu-orgchem-lab.com/

    • Related Report
      2018 Research-status Report
  • [Remarks] 首都大学東京

    • URL

      http://tmu-orgchem-lab.com/

    • Related Report
      2017 Research-status Report

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

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