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Synthesis of novel redox systems having thiophenes highly integrated with quinone methides structure

Research Project

Project/Area Number 23550053
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionFukui University of Technology (2013)
Osaka University (2011-2012)

Principal Investigator

KURATA Hiroyuki  福井工業大学, 工学部, 教授 (40263199)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2013: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2011: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywordsキノメチド / チオフェン / フェノール / キノン / 酸化還元 / 立体障害 / ターチオフェン / ラジカル / 酸化反応 / オリゴチオフェン / 酸化還元系 / エレクトロクロミズム
Research Abstract

We have been interested in conjugated thiophene systems whose all hydrogen atoms are substituted by 2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dienone (quinone-methide) structure. We have prepared thiophene and bithiophene derivatives (we named them "tetraquinothiophene"(1) and "hexaquinobithiohene"(2), respectively). These attract attention in term of dynamic multi-stage redox system as well as cross conjugated system adopting sulfur atom. Compounds 1 and 2 were synthesized from bromothiophene derivatives via Suzuki-Miyaura coupling. The structure of 1 was determined by X-ray analysis. There were little torsion of pinch-bonds and central five membered ring formed twist boat like conformation. The electrochemical properties of 1 and 2 were examined by cyclic voltammetry and the first reduction waves of them were observed irreversibly. It indicates conformational changes occur with one-electron reduction about both 1 and 2.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (23 results)

All 2014 2013 2012 2011

All Journal Article (13 results) (of which Peer Reviewed: 13 results) Presentation (10 results)

  • [Journal Article] Bicyclo[6.3.0]undecapentaenyl Anion: The Next Higher Homolog of Indenyl Anion with Exceptionally Large Ion-Pairing Effects on its Tropicity2014

    • Author(s)
      Hiroaki Ozoe, Yasutaka Uno, Chitoshi Kitamura, Hiroyuki Kurata, Masaji Oda, John W. Jones, Jr., Lawrence T. Scott, Takeshi Kawase
    • Journal Title

      Chemistry-An Asian Journal

      Volume: 9 Issue: 3 Pages: 893-900

    • DOI

      10.1002/asia.201301307

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Nickel Complex of 4-Amino-3- pyridinethiolate2014

    • Author(s)
      Kouzou Matsumoto, Maho Nishizawa, Yasukazu Hirao, Hiroyuki Kurata, Takashi Kubo
    • Journal Title

      Heterocycles

      Volume: 87 Issue: 1 Pages: 175-178

    • DOI

      10.3987/com-13-s(s)2

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Investigating the edge state of graphene nanoribbons by a chemical approach: Synthesis and magnetic properties of zigzag-edged nanographene molecules2013

    • Author(s)
      Konishi, A.; Hirao, Y.; Kurata, H.; Kubo, T.
    • Journal Title

      Solid State Commun.

      Volume: 175-176 Pages: 62-70

    • DOI

      10.1016/j.ssc.2013.07.005

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile Synthesis and Lateral π-Expansion of Bisanthenes.2013

    • Author(s)
      Konishi, A.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Kubo, T.
    • Journal Title

      Chem. Lett.

      Volume: 42 Issue: 6 Pages: 592-594

    • DOI

      10.1246/cl.130153

    • NAID

      10031176018

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Quarteranthene : Elucidating the Characteristics of the Edge State of Graphene Nanoribbons at the Molecular Level2013

    • Author(s)
      Akihito Konishi
    • Journal Title

      Journal of American Chemical Society

      Volume: 135 Issue: 4 Pages: 1430-1437

    • DOI

      10.1021/ja309599m

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] 3,14-Bis(p-nitrophenyl)-77, 17-dipentyltetrabenzo [a,c,g,i] fluorene : A New Fluorophore Displaying Both Remarkable Solvatochromism and Crystalline-Induced Emission2013

    • Author(s)
      Ueda, U.; Tanigawa, Y.; Kitamura, C.; Ikeda, H.; Yoshimoto, Y.; Tanaka, M.; Mizuno K.; Kurata, H.; Kawase, T.
    • Journal Title

      Chem. Asian J.

      Volume: 8(印刷中) Issue: 2 Pages: 392-399

    • DOI

      10.1002/asia.201200976

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Aromaticity and π-bond covalency : prominent intermolecular covalent bonding interaction of a Kekulé hydrocarbon with very significant singlet biradical character2012

    • Author(s)
      Akihiro Shimizu, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo, Mikio Uruichi, Kyuya Yakushi
    • Journal Title

      Chemical Communications

      Volume: 48(45) Pages: 5629-5631

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Isolation And First X-Ray Structures of Nickel Complexes of 1, 2, 5-Thiadiazole-3, 4- Dithiolate (TDAS) in Protonated Forms2012

    • Author(s)
      Kouzou Matsumoto, Maho Nishizawa, Yasukazu Hirao, Hiroyuki Kurata, and Takashi Kubo
    • Journal Title

      Heterocycles

      Volume: 86(2) Pages: 2991-2996

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] 17,17-Dialkyltetrabenzo[a,c,g,i]fluorenes with Extremely High Solid-state Fluorescent Quantum Yields : Relationship between Crystal Structure and Fluorescent Properties2012

    • Author(s)
      北村千寿
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 6 Pages: 1688-1694

    • DOI

      10.1016/j.tet.2011.12.069

    • Related Report
      2013 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Aromaticity and π-bond covalency: prominent intermolecular covalent bonding interaction of a Kekule hydrocarbon with very significant singlet biradical character2012

    • Author(s)
      Shimizu, A.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Kubo, T.; Uruichi M.; Yakushi, K
    • Journal Title

      Chem. Commun

      Volume: 48 Issue: 45 Pages: 5629-5631

    • DOI

      10.1039/c2cc31955a

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Isolation And First X-Ray Structures of Nickel Complexes of 1,2,5-Thiadiazole-3,4-Dithiolate (TDAS) in Protonated Forms2012

    • Author(s)
      Kouzou Matsumoto, Maho Nishizawa, Yasukazu Hirao, Hiroyuki Kurata, and Takashi Kubo
    • Journal Title

      Heterocycles

      Volume: 86 Issue: 2 Pages: 991-996

    • DOI

      10.3987/com-12-s(n)107

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] "Marking" the Nitrogen Atoms of Phenyl-(2-pyridyl)-(3-pyridyl)-(4-pyridyl) methane. Synthesis and Absolute Configuration of the Corresponding Tris(pyridine N-oxide)2011

    • Author(s)
      Kouzou Matsumoto, Kaori Miki, Takuya Inagaki, Tatsuo Nehira, Gennaro Pescitelli, Yasukazu Hirao, Hiroyuki Kurata, Takeshi Kawase, Takashi Kubo
    • Journal Title

      Chirality

      Volume: 23 Pages: 543-548

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Triarylamines on [3]Radialene Scaffold : Novel [3]Radialene-based, Multi-step, Wide-range Redox Systems with Remarkably Low Oxidation Potentials2011

    • Author(s)
      松本幸三
    • Journal Title

      Chem.Lett.

      Volume: 40 Issue: 9 Pages: 1033-1035

    • DOI

      10.1246/cl.2011.1033

    • NAID

      10029522927

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] キノメチド置換オリゴチオフェンの酸化還元挙動2014

    • Author(s)
      鈴木 健志・蔵田 浩之・西内 智彦・平尾泰一・久保 孝史
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋(名古屋大学 東山キャンパス)
    • Related Report
      2013 Final Research Report
  • [Presentation] キノメチド置換オリゴチオフェンの酸化還元挙動2014

    • Author(s)
      鈴木 健志・蔵田 浩之・西内 智彦・平尾 泰一・久保 孝史
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Annual Research Report
  • [Presentation] キノメチド構造が高度に集積化されたオリゴチオフェン類の合成と性質2013

    • Author(s)
      鈴木 健志・蔵田 浩之・平尾 泰一・西内智彦・久保 孝史
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      東京(学習院大学目白キャンパス創立百周年記念会館)
    • Related Report
      2013 Final Research Report
  • [Presentation] キノメチド置換オリゴチオフェンの合成と物性2013

    • Author(s)
      鈴木 健志・蔵田 浩之・平尾 泰一・松本幸三・久保 孝史
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀(立命館大学 びわこ・くさつキャンパス)
    • Related Report
      2013 Final Research Report
  • [Presentation] キノメチド構造が高度に集積化されたオリゴチオフェン類の合成と性質2013

    • Author(s)
      鈴木健志・蔵田浩之・平尾泰一・西内智彦・久保孝史
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学目白キャンパス創立百周年記念会館
    • Related Report
      2013 Annual Research Report
  • [Presentation] キノメチド置換オリゴチオフェンの合成と物性2013

    • Author(s)
      鈴木健志・蔵田浩之・平尾泰一・久保孝史
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀(立命館大学びわこ・くさつキャンパス)
    • Related Report
      2012 Research-status Report
  • [Presentation] キノメチド構造が高度に集積化されたオリゴチオフェン類の合成と性質2012

    • Author(s)
      鈴木 健志・井上 泰平・蔵田 浩之・平尾泰一・松本 幸三・久保 孝史
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都(京都テルサ)
    • Related Report
      2013 Final Research Report
  • [Presentation] キノメチド構造が高度に集積化されたオリゴチオフェン類の合成と性質2012

    • Author(s)
      鈴木健志・井上泰平・蔵田浩之・平尾泰一・松本幸三・久保孝史
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都(京都テルサ)
    • Related Report
      2012 Research-status Report
  • [Presentation] キノメチド構造が高度に導入されたチオフェンおよびビチオフェンの合成と物性2011

    • Author(s)
      井上 泰平・蔵田 浩之・平尾 泰一・松本幸三・久保 孝史
    • Organizer
      第38回有機典型元素化学討論会
    • Place of Presentation
      金沢(石川県立音楽堂)
    • Related Report
      2013 Final Research Report
  • [Presentation] キノメチド構造が高度に導入されたチオフェンおよびビチオフェンの合成と物性2011

    • Author(s)
      井上泰平・蔵田浩之・平尾泰一・松本幸三・久保孝史
    • Organizer
      第38回有機典型元素化学討論会
    • Place of Presentation
      金沢(石川県立音楽堂)
    • Related Report
      2011 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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