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Development of donor-acceptor-type highly-polarized pi-conjugated molecules and their application to organic transistors

Research Project

Project/Area Number 16K05744
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Functional solid state chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

Ueda Akira  東京大学, 物性研究所, 助教 (20589585)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords有機半導体 / ドナーアクセプター / 化学修飾 / テトラチアフルバレン / o-ベンゾキノン / ドナー・アクセプター / 分極 / ベンゾキノン / ドナーアクセプター分子 / 置換基効果 / 有機トランジスタ / テトラチアフルバレン誘導体 / 分子性固体 / 半導体物性 / 結晶成長 / 電子・電気材料 / 合成化学
Outline of Final Research Achievements

A series of highly-polarized pi-conjugated molecules with o-benzoquinone-tetrathiafulvalene fused structure was successfully synthesized and characterized. The synthetic yield and solubility were greatly improved by introducing alkylthio groups into the tetrathiafulvalene moiety. All the derivatives show highly amphoteric redox properties, small HOMO-LUMO gap, large intramolecular polarization, and effective intermolecular pi-pi interactions. In addition, the intermolecular interactions between the pi-stacks are increased with increasing the alkyl chain length. The field-effect transistors using single crystals of these compounds were fabricated; however, significant transistor properties have not been observed yet.

Academic Significance and Societal Importance of the Research Achievements

特異な分子構造・電子構造を有するπ共役系有機分子の設計・合成は、基礎化学的な観点はもとより、近年では機能性物質・電子材料開発の観点からも重要な課題として盛んに研究が進められている。本研究では、本研究代表者が独自に開発した新しいπ共役系分子であるo-ベンゾキノン-テトラチアフルバレン誘導体の効果的な合成法を見いだし、これらの構造と性質を分子レベルで詳細に明らかにすることに成功した。これらの結果から、この新分子群は有機半導体材料の新たな候補物質であることが示唆され、その第一歩として有機トランジスタの作製と評価を試みた。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (41 results)

All 2019 2018 2017 2016 Other

All Journal Article (14 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 13 results,  Open Access: 4 results,  Acknowledgement Compliant: 1 results) Presentation (21 results) (of which Int'l Joint Research: 9 results,  Invited: 8 results) Remarks (6 results)

  • [Journal Article] Di- and tetramethoxy benzothienobenzothiophenes: substitution position effects on the intermolecular interactions, crystal packing and transistor properties2019

    • Author(s)
      Toshiki Higashino, Akira Ueda and Hatsumi Mori
    • Journal Title

      New Journal of Chemistry

      Volume: 43 Issue: 2 Pages: 884-892

    • DOI

      10.1039/c8nj04251a

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Charge Order and Poor Glass-forming Ability of an Anisotropic Triangular-lattice System, θ-(BEDT-TTF)2TlCo(SCN)4, Investigated by NMR2019

    • Author(s)
      K. Miyagawa, T. Sato, H. Hashimoto, M. Kodama, K. Ohnoh, A. Ueda, H. Mori, and K. Kanoda
    • Journal Title

      Jouranal of Physical Society of Japan

      Volume: 88 Issue: 3 Pages: 034705-034705

    • DOI

      10.7566/jpsj.88.034705

    • NAID

      210000135132

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hysteretic Current-Voltage Characteristics in the Deuterium-Dynamics- Triggered Charge-Ordered Phase of κ-D3(Cat-EDT-TTF)22019

    • Author(s)
      A. Ueda, K. Kishimoto, Y. Sunairi, J. Yoshida, H. Yamakawa, T. Miyamoto, T. Terashige, H. Okamoto and H. Mori
    • Journal Title

      J. Phys. Soc. Jpn.

      Volume: 88 Issue: 3 Pages: 034710-034710

    • DOI

      10.7566/jpsj.88.034710

    • NAID

      210000135137

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] New pai-extended catecholato complexes of Pt(II) and Pd(II) containing a benzothienobenzothiophene (BTBT) moiety: synthesis, electrochemical behavior and charge transfer properties2019

    • Author(s)
      K. Tahara, Y. Ashihara, T. Higashino, Y. Ozawa, T. Kadoya, K. Sugimoto, A. Ueda, H. Mori and M. Abe
    • Journal Title

      Dalton Transactions

      Volume: 印刷中 Issue: 21 Pages: 7367-7377

    • DOI

      10.1039/c8dt05057k

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Strange metal from a frustration-driven charge order instability2019

    • Author(s)
      T. Sato, K. Kitai, K. Miyagawa, M. Tamura, A. Ueda, H. Mori and K. Kanoda
    • Journal Title

      Nature Materials

      Volume: 18 Issue: 3 Pages: 229-233

    • DOI

      10.1038/s41563-019-0284-9

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] π電子とプロトンの連動による新しい量子液体状態 ―絶対零度まで揺らぎ続ける電気・磁気双極子―2019

    • Author(s)
      下澤雅明、上田 顕、橋本顕一郎、中 惇
    • Journal Title

      固体物理

      Volume: 1 Pages: 43-54

    • NAID

      40021787191

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 水素ダイナミクスを有する有機伝導体の開発2018

    • Author(s)
      上田 顕
    • Journal Title

      化学工業

      Volume: 7 Pages: 36-42

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Strong Hydrogen Bonds at the Interface between Proton-Donating and -Accepting Self-Assembled Monolayers on Au(111)2018

    • Author(s)
      Kato Hiroyuki S.、Yoshimoto Shinya、Ueda Akira、Yamamoto Susumu、Kanematsu Yusuke、Tachikawa Masanori、Mori Hatsumi、Yoshinobu Jun、Matsuda Iwao
    • Journal Title

      Langmuir

      Volume: 34 Issue: 5 Pages: 2189-2197

    • DOI

      10.1021/acs.langmuir.7b03451

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] A phenol-fused tetrathiafulvalene: modulation of hydrogen-bond patterns and electrical conductivity in the charge-transfer salt2018

    • Author(s)
      Ueda Akira、Mori Hatsumi
    • Journal Title

      Materials Chemistry Frontiers

      Volume: 2 Issue: 3 Pages: 566-572

    • DOI

      10.1039/c7qm00574a

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Development of Novel Functional Organic Crystals by Utilizing Proton- and π-Electron-Donating/Accepting Abilities2017

    • Author(s)
      Ueda Akira
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 90 Issue: 11 Pages: 1181-1188

    • DOI

      10.1246/bcsj.20170239

    • NAID

      130006201452

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of Novel Functional Molecular Crystals by Utilizing Dynamic Hydrogen Bonds2017

    • Author(s)
      Ueda Akira、Yoshida Junya、Takahashi Kazuyuki、Mori Hatsumi
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 75 Issue: 10 Pages: 1045-1054

    • DOI

      10.5059/yukigoseikyokaishi.75.1045

    • NAID

      130006156692

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Crystallization and vitrification of electrons in a glass-forming charge liquid2017

    • Author(s)
      Sasaki S.、Hashimoto K.、Kobayashi R.、Itoh K.、Iguchi S.、Nishio Y.、Ikemoto Y.、Moriwaki T.、Yoneyama N.、Watanabe M.、Ueda A.、Mori H.、Kobayashi K.、Kumai R.、Murakami Y.、M?ller J.、Sasaki T.
    • Journal Title

      Science

      Volume: 357 Issue: 6358 Pages: 1381-1385

    • DOI

      10.1126/science.aal3120

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Quantum-disordered state of magnetic and electric dipoles in an organic Mott system2017

    • Author(s)
      Shimozawa M.、Hashimoto K.、Ueda A.、Suzuki Y.、Sugii K.、Yamada S.、Imai Y.、Kobayashi R.、Itoh K.、Iguchi S.、Naka M.、Ishihara S.、Mori H.、Sasaki T.、Yamashita M.
    • Journal Title

      Nature Communications

      Volume: 8 Issue: 1 Pages: 1-6

    • DOI

      10.1038/s41467-017-01849-x

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Improved stability of a metallic state in benzothienobenzothiophene-based molecular conductors: An effective increase of dimensionality with hydrogen bonds2017

    • Author(s)
      T. Higashino, A. Ueda, J. Yoshida, H. Mori
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 24 Pages: 3426-3429

    • DOI

      10.1039/c7cc00784a

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] カテコール縮環型金属ジチオレン錯体の構造と物性に対する中心金属置換効果2019

    • Author(s)
      横森 創・上田 顕・森 初果
    • Organizer
      日本化学会第99春季年会2019
    • Related Report
      2018 Annual Research Report
  • [Presentation] ジメトキシベンゼンが縮環した中性の金属ジチオレン錯体の合成、構造、性質ならびに電界効果トランジスタ特性2019

    • Author(s)
      高橋 優介・横森 創・上田 顕・榎本 真哉・森 初果
    • Organizer
      日本化学会第99春季年会2019
    • Related Report
      2018 Annual Research Report
  • [Presentation] Exploration of Molecular Conductors with Hydrogen-Bond Dynamics2018

    • Author(s)
      Akira Ueda
    • Organizer
      The International Conference on Science and Technology of Synthetic Metals 2018 (ICSM 2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of a New Type of Molecular Conductors with Dynamic Hydrogen Bonds2018

    • Author(s)
      Akira Ueda
    • Organizer
      8th TOYOTA RIKEN International Workshop on Organic Semiconductors, Conductors, and Electronics
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of hydrogen-bonded molecular conductors based on catechol-fused TTF system2018

    • Author(s)
      Akira Ueda, Hatsumi Mori
    • Organizer
      43rd International Conference on Coordination Chemistry (ICCC2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Syntheses, Structures, and Properties of Novel Metal-Dithiolene Complexes with Hydrogen-Bonds2018

    • Author(s)
      So Yokomori, Akira Ueda, Reiji Kumai, Youichi Murakami, and Hatsumi Mori
    • Organizer
      The International Conference on Science and Technology of Synthetic Metals 2018 (ICSM 2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Syntheses, Structures and Physical Properties of Novel Metal-dithiolene Complexes with Hydrogen bonds2018

    • Author(s)
      So Yokomori, Akira Ueda, Reiji Kumai, Youichi Murakami, and Hatsumi Mori
    • Organizer
      8th TOYOTA RIKEN International Workshop on Organic Semiconductors, Conductors, and Electronics
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 動的水素結合を有する新しい有機伝導体の開発2018

    • Author(s)
      上田 顕
    • Organizer
      錯体化学若手の会・関東支部 前期勉強会2018
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 水素結合を活用した新しいπ電子系機能物質の開発2018

    • Author(s)
      上田 顕
    • Organizer
      日本化学会研究会「低次元系光機能材料研究会」第7回研究講演会 ~二次元構造を有するπ電子系の光・電子機能~
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 水素ダイナミクスを有する新しい有機伝導体の合成と構造、物性2018

    • Author(s)
      上田 顕
    • Organizer
      第15回 水素量子アトミクス研究会/第1回ハイドロジェノミクス研究会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 新規カテコール縮環型金属ジチオレン錯体の合成と水素結合型フレームワーク構造2018

    • Author(s)
      横森 創、上田 顕、熊井玲児、村上洋一、森 初果
    • Organizer
      錯体化学会 第68回討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 半導体-絶縁体転移を示す新規カテコール-TTF系水素結合型電荷移動塩の合成と構造、物性2018

    • Author(s)
      上田 顕、熊井玲児、村上洋一、森 初果
    • Organizer
      第12回分子科学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] カテコール縮環型金属ジチオレン錯体:水素結合による多様な集積構造と中心金属置換効果2018

    • Author(s)
      横森 創、上田 顕、熊井玲児、村上洋一、森 初果
    • Organizer
      第12回分子科学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] エチレンジオキシ基を有するカテコール縮環型TTF誘導体を用いた水素結合型の新規電荷移動塩の合成と構造、物性2018

    • Author(s)
      池田 潤、上田 顕、横森 創、吉田順哉、森 初果
    • Organizer
      第12回分子科学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] フェノールを縮環させたTTF誘導体の合成とその電荷移動塩の構造・物性2018

    • Author(s)
      上田 顕、森 初果
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] TTF-o-ベンゾキノン骨格を有する新規ドナー・アクセプター型有機分子の合成と置換基効果の調査2018

    • Author(s)
      寺岡なつみ、上田 顕、横森 創、榎本真哉、森 初果
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] プロトン・π電子授受能を活用した新規機能性有機結晶の開発2017

    • Author(s)
      上田 顕
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学 日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Development of a New Class of Molecular Conductors with Hydrogen-bond Dynamics2017

    • Author(s)
      A. Ueda
    • Organizer
      INTERNATIONAL SYMPOSIUM ON PURE & APPLIED CHEMISTRY (ISPAC) 2017
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of a New Class of Molecular Conductors with Hydrogen-Bond Dynamics: Chemical Modification of Catechol-Fused TTF System2017

    • Author(s)
      A. Ueda, H. Mori
    • Organizer
      The 12th International Symposium on Crystalline Organic Metals, Superconductors and Magnets (ISCOM2017)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Methoxy-substituted BTBT derivatives: Synthesis and substitution position effect on the solid-state structures and transistor properties2017

    • Author(s)
      T. Higashino, A. Ueda, H. Mori
    • Organizer
      The 12th International Symposium on Crystalline Organic Metals, Superconductors and Magnets (ISCOM2017)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Symmetric and Asymmetric Methoxy-substitution on BTBT: Steric and Hydrogen-bonding Interactions2016

    • Author(s)
      T. Higashino, A. Ueda, H. Mori
    • Organizer
      The International Conference on Science and Technology of Synthetic Metals in 2016 (ICSM2016)
    • Place of Presentation
      Guangzhou, China
    • Year and Date
      2016-06-26
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Remarks] Researcher ID

    • URL

      https://publons.com/researcher/1185987/akira-ueda/

    • Related Report
      2018 Annual Research Report
  • [Remarks] Google Scholar Citations

    • URL

      http://scholar.google.com/citations?user=WUuqJhMAAAAJ&hl=en

    • Related Report
      2018 Annual Research Report
  • [Remarks] ORCID

    • URL

      https://orcid.org/0000-0002-9600-5409

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
  • [Remarks] Researcher ID

    • URL

      http://www.researcherid.com/rid/A-2624-2012

    • Related Report
      2017 Research-status Report 2016 Research-status Report
  • [Remarks] 東京大学物性研究所 森研究室website

    • URL

      http://hmori.issp.u-tokyo.ac.jp/

    • Related Report
      2017 Research-status Report
  • [Remarks] 東京大学物性研究所 森研究室website

    • URL

      http://hmori.issp.u-tokyo.ac.jp/

    • Related Report
      2016 Research-status Report

URL: 

Published: 2016-04-21   Modified: 2020-03-30  

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