• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Synthesis and Response toward External Stimulli of Bithiophene Derivatives Bridged by Spirodienone Structure

Research Project

Project/Area Number 20550039
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

KURATA Hiroyuki  Osaka University, 理学研究科, 講師 (40263199)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2010: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2009: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsチオフェン / 分子スイッチング / 酸化還元系 / メカノクロミズム / スピロ構造 / アモルファス / ビラジカル / 粉末X線回折 / ジスピロ構造 / 合成化学 / 分子機械 / 分子スイッチ / サイクリックボルタンメトリー
Research Abstract

Bithiophene derivtives bridged with a bis (spirodienone) unit were synthesized and characterized. Palladium-catalyzed cross-coupling reactions with bromides afforded a variety of pi-extended derivatives. In these compounds, bond breaking and formation under redox conditions were observed by cyclic voltammetry (CV). Especially, 2,2'-bridged-3,3'-bithiophene derivatives showed significant temperature- and scan rate-dependence on CV. These phenomena indicate the existence of the equilibrium between dispiro-compounds and open-ring biradicals. Furthermore, mechanochromism, N,N-dialkylaminophenyl-substituted 2,2'-bridged-3,3'-bithiophene derivatives showed mechanochromism. During grinding the crystals, the color was changed from yellow to reddish orange, and by exposure to organic solvents, the reddish-orange color was immediately turned back to yellow.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (45 results)

All 2010 2009 2008 Other

All Journal Article (30 results) (of which Peer Reviewed: 30 results) Presentation (14 results) Remarks (1 results)

  • [Journal Article] An effective Synthesis of N,N-Dimethyl- amides from Carboxylic Acids and a New Route from N,N-Dimethylamides to 1,2- Diaryl-1,2-diketones.2010

    • Author(s)
      T.Kumagai, T.Anki, T.Ebi, A.Konishi, K.Matsumoto, H.Kurata, T.Kubo, K.Katsumoto, C.Kitamura T.Kawase
    • Journal Title

      Tetrahedron 66(46)

      Pages: 8968-8973

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Dinaphthopentalenes : Pentalene Derivatives for Organic Thin-Film Transistors.2010

    • Author(s)
      T.Kawase, T.Fujiwara, C.Kitamura, A.Konishi, Y.Hirao, K.Matsumoto, H.Kurata, T.Kubo, S.Shinamura, H.Mori, E.Miyazaki, K.Takimiya
    • Journal Title

      Angewandte Chemie International Edition 49(42)

      Pages: 7728-7732

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Alternating Covalent Bonding Inter- actions in a One-Dimensional Chain of a Phenalenyl- Based Singlet Biradical Molecule Having Kekule Structures.2010

    • Author(s)
      A.Shimizu, T.Kubo, M.Uruichi, K.Yakushi, M.Nakano, D.Shiomi, K.Sato, T.Takui, Y.Hirao, K.Matsumoto, H.Kurata, Y.Morita, K.Nakasuji
    • Journal Title

      Journal of the American Chemical Society 132(41)

      Pages: 14421-14428

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Teranthene : A Singlet Biradical Polycyclic Aromatic Hydrocarbon Having Kekule Structures.2010

    • Author(s)
      A.Konishi, Y.Hirao, M.Nakano, A.Shimizu, E.Botek, B.Champagne, D.Shiomi, K.Sato, T.Takui, K.Matsumoto, H.Kurata, T.Kubo
    • Journal Title

      Journal of the American Chemical Society 132(32)

      Pages: 11021-11023

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Hydrogen-Bonded Quartz-type Network of Diprotonated Tetrakis(4-pyridyl)- methane Dications.2010

    • Author(s)
      K.Matsumoto, D.Inokuchi, Y.Hirao, H.Kurata, T.Kubo
    • Journal Title

      Crystal Growth & Design 10(7)

      Pages: 2854-2856

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Identification of a Trimethylenemethane Derivative π-Extended with Three Pyridinyl Radicals.2010

    • Author(s)
      K.Matsumoto, D.Inokuchi, Y.Hirao, H.Kurata, K.Sato, T.Takui, T.Kubo
    • Journal Title

      Organic Letters 12(4)

      Pages: 836-839

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Pentaleno[1,2-c:4,5-c']dithiophene Derivatives : First Synthesis, Properties, and a Molecular Structure.2010

    • Author(s)
      A.Konishi, T.Fujiwara, N.Ogawa, Y.Hirao, K.Matsumoto, H.Kurata, T.Kubo, C.Kitamura, T.Kawase
    • Journal Title

      Chemistry Letters 39(3)

      Pages: 300-301

    • NAID

      10027178748

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] An effective synthesis of N,N-dimethylamides from carboxylic acids and a new route from N,N-dimethylamides to 1,2-diaryl-1,2-diketones2010

    • Author(s)
      Takashi Kumagai, Hiroyuki Kurata
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 8968-8973

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dinaphthopentalenes : Pentalene Derivatives for Organic Thin-Film Transistors2010

    • Author(s)
      Takeshi Kawase, Hiroyuki Kurata
    • Journal Title

      Angewandte Chemie, International Edition

      Volume: 49 Pages: 7728-7732

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Alternating Covalent Bonding Interactions in a One-Dimensional Chain of a Phenalenyl-Based Singlet Biradical Molecule Having Kekule Structures2010

    • Author(s)
      Akihiro Shimizu, Hiroyuki Kurata
    • Journal Title

      Journal of the American Chemical Society

      Volume: 132 Pages: 14421-14428

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Teranthene : A Singlet Biradical Polycyclic Aromatic Hydrocarbon Having Kekule Structures2010

    • Author(s)
      Akihito Konishi, Hiroyuki Kurata
    • Journal Title

      Journal of the American Chemical Society

      Volume: 132 Pages: 11021-11023

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hydrogen-Bonded Quartz-type Network of Diprotonated Tetrakis(4-pyridyl)methane Dications2010

    • Author(s)
      Kouzou Matsumoto, Hiroyuki Kurata
    • Journal Title

      Crystal Growth & Design

      Volume: 10 Pages: 2854-2856

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Identification of a Trimethylenemethane Derivative π-Extended with Three Pyridinyl Radicals2010

    • Author(s)
      Kouzou Matsumoto, Hiroyuki Kurata
    • Journal Title

      Organic Letters

      Volume: 12 Pages: 836-839

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pentaleno[1,2-c : 4,5-c']dithiophene Derivatives : First Synthesis, Properties, and a Molecular Structure2010

    • Author(s)
      Akihito Konishi
    • Journal Title

      Chemistry Letters 39

      Pages: 300-301

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Resonance Balance Shift in π-π One-Dimensional Chain of Delocalized Singlet Biradical.2009

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

      Angewandte Chemie, International Edition 48(30)

      Pages: 5482-5486

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Shape-Persistent, Double-Helically Twisted Macrocycles with Two Quaterphenyl Moieties : Synthesis, Structure and Physicochemical Properties for a Chiral Sensor.2009

    • Author(s)
      T.Kawase, Y.Daifuku, Y.Hirao, K.Matsumoto, H.Kurata, T.Kubo
    • Journal Title

      Comptes Rendus Chimie 12(3-4)

      Pages: 403-411

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] An Extremely Simple Dibenzopentalene Synthesis from 2-Bromo-1-ethynyl- benzenes Using Nickel(0) Complexes : Construction of Its Derivatives with Various Functionalities.2009

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

      Chemistry- A European Journal 15(11)

      Pages: 2653-2661

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Resonance Balance Shift in π-π One-Dimensional Chain of Delocalized Singlet Biradical2009

    • Author(s)
      Akihiro Shimizu
    • Journal Title

      Angewandte Chemie, International Edition 48

      Pages: 5482-5486

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Shape-Persistent, Double-Helically Twisted Macrocycles with Two Quaterphenyl Moieties : Synthesis, Structure and Physicochemical Properties for a Chiral Sensor2009

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Comptes Rendus Chimie 12

      Pages: 403-411

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Shape-Persistent, Double-Helically Twisted Macrocycles with TwoQuaterphenyl Moieties : Synthesis, Structure and PhysicochemicalProperties for a Chiral Sensor2009

    • Author(s)
      川瀬 毅
    • Journal Title

      Comptes Rendus Chimie 12

      Pages: 403-411

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An Extremely Simple Dibenzopentalene Synthesis from2-Bromo-1-ethynylbenzenes Using Nickel(O)Complexes : Construction ofIts Derivatives with Various Functionalities2009

    • Author(s)
      川瀬 毅
    • Journal Title

      Chemistry-A European Journal 15

      Pages: 2653-2661

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Tetrakis(2-thienyl)methane Derivative : A Possible Precursor for Cryptochiral Tetraalkylmethanes.2008

    • Author(s)
      K.Matsumoto, K.Miki, H.Kurata, N.Rikitake, T.Nehira, T.Inagaki, G.Pescitelli, Y.Hirao, T.Kawase, M.Oda, T.Kubo
    • Journal Title

      Chemistry Letters 37(12)

      Pages: 1236-1237

    • NAID

      10024397925

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Tetrahedral Oligothiophenes ; Synthesis, X-ray Analysis, and Optoelectronic Properties of Highly Symmetrical, 3D-Branched Oligothiophenes.2008

    • Author(s)
      K.Matsumoto, T.Tanaka, S.Kugo, T.Inagaki, Y.Hirao, H.Kurata, T.Kawase, T.Kubo
    • Journal Title

      Chemistry- An Asian Journal 3(12)

      Pages: 2024-2032

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] The First Synthesis of 2,2':5',2"- Terthiazole.2008

    • Author(s)
      H.Kurata, H.Takakuwa, K.Matsumoto, T.Kawase, M.Oda
    • Journal Title

      Synlett 18

      Pages: 2882-2884

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Functionalization of 3,3-Bis(spirodienone)-Bridged 2,2-Bithiophene : A New Building Block for Redox-Active Molecular Switching Materials.2008

    • Author(s)
      H.Kurata, S.Kim, T.Fujimoto, K.Matsumoto, T.Kawase, T.Kubo
    • Journal Title

      Organic Letters 10(17)

      Pages: 3837-3840

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] 8,14,30,36-Tetramethoxy[2.0.2.0](1,6) naphthalenophane-1,19-diyne : A Double-Helically Twisted Cyclophane by Diastereoselective Dimerization.2008

    • Author(s)
      T.Kawase, T.Nakamura, K.Utsumi, K.Matsumoto, H.Kurata, M.Oda
    • Journal Title

      Chemistry- An Asian Journal 3(3)

      Pages: 573-577

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Tetrakis(2-thienyl)methane Derivative : A Possible Precursor forCryptochiral Tetraalkylmethanes2008

    • Author(s)
      松本幸三
    • Journal Title

      Chemistry Letters 37

      Pages: 1236-1237

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tetrahedral oligothiophenes ; synthesis, X-ray analysis, and optoelectronicproperties of highly symmetrical. 3D-branched oligothiopheaes2008

    • Author(s)
      松本幸三
    • Journal Title

      Chemistry-An Asian Journal 3

      Pages: 2024-2032

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The First Synthesis of 2, 2' : 5', 2"-Terthiazole2008

    • Author(s)
      蔵田浩之
    • Journal Title

      Synlett

      Pages: 2882-2884

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Functionalization of 3, 3-Bis(spirodienone)-Bridged2, 2-Bithiophene : A New Building Block for Redox-Active MolecularSwitching Materials2008

    • Author(s)
      蔵田浩之
    • Journal Title

      Organic Letters 10

      Pages: 3837-3840

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis and Properties of 2,2'-Bis(spirodienone)-Bridged-3,3'-Bithiophene Derivatives-An Unusual Redox Behavior Coused by Ring-Opening2010

    • Author(s)
      蔵田浩之
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii (USA)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] Mechanochromism of 2, 2'-Bis(spirodienone)-Bridged-3, 3'-Bithiophene Derivatives2010

    • Author(s)
      蔵田浩之
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii (USA)
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] 2,2'-ビス(スピロジエノン)-3,3'-ビチオフェン誘導体のメカノクロミズム2010

    • Author(s)
      蔵田浩之
    • Organizer
      第21回基礎有機化学討論会
    • Place of Presentation
      名古屋大学(名古屋市)
    • Year and Date
      2010-09-10
    • Related Report
      2010 Annual Research Report
  • [Presentation] ビラジカル性を有する拡張キノン系分子の合成と性質2010

    • Author(s)
      蔵田浩之
    • Organizer
      シンポジウム「電子状態理論の新機軸」
    • Place of Presentation
      岡崎コンファレンスセンター(岡崎市)
    • Year and Date
      2010-08-10
    • Related Report
      2010 Annual Research Report
  • [Presentation] 2, 2'-ビス (スピロジエノン) 架橋-3, 3'-ビチオフェン誘導体のメカノクロミズム2010

    • Author(s)
      蔵田浩之
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪 (近畿大学)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis and Properties of 2,2'-Bis(spirodienone)-Bridged-3,3'- Bithiophene Derivatives -An Unusual Redox Behavior Coused by Ring- Opening.2010

    • Author(s)
      蔵田浩之, 藤本貴久, 阿辻裕美子, 平尾泰一, 松本幸三, 久保孝史
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Related Report
      2010 Final Research Report
  • [Presentation] Mechanochromism of 2,2'-Bis(spiro- dienone)-Bridged-3,3'-Bithiophene Derivatives.2010

    • Author(s)
      蔵田浩之, 阿辻裕美子, 平尾泰一, 松本幸三, 網本貴一, 久保孝史
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Related Report
      2010 Final Research Report
  • [Presentation] 2,2'-ビス(スピロジエノン)-3,3'-ビチオフェン誘導体のメカノクロミズム2010

    • Author(s)
      蔵田浩之・阿辻裕美子・平尾泰一・松本幸三・網本貴一・久保孝史
    • Organizer
      第21回基礎有機化学討論会
    • Place of Presentation
      名古屋(名古屋大学)
    • Related Report
      2010 Final Research Report
  • [Presentation] ビラジカル性を有する拡張キノン系分子の合成と性質2010

    • Author(s)
      蔵田浩之・阿辻裕美子・小西彬仁・平尾泰一・松本幸三・久保孝史
    • Organizer
      シンポジウム「電子状態理論の新機軸」
    • Place of Presentation
      岡崎(岡崎コンファレンスセンター)
    • Related Report
      2010 Final Research Report
  • [Presentation] 2,2'-ビス(スピロジエノン)架橋-3,3'-ビチオフェン誘導体のメカノクロミズム2010

    • Author(s)
      阿辻裕美子・蔵田浩之・藤本貴久・平尾泰一・松本幸三・網本貴一・久保孝史
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪(近畿大学)
    • Related Report
      2010 Final Research Report
  • [Presentation] ビス(スピロジエノン)架橋ビチオフェン類の合成と特異な酸化還元挙動2008

    • Author(s)
      藤本貴久・蔵田浩之・平尾泰一・松本幸三・久保孝史
    • Organizer
      第35回有機典型元素化学討論会
    • Place of Presentation
      八王子(首都大東京)
    • Related Report
      2010 Final Research Report
  • [Presentation] ビス(スピロジエノン)構造で架橋されたビチオフェン誘導体の合成・構造・反応性2008

    • Author(s)
      蔵田浩之・藤本貴久・金 翔・平尾泰一・松本幸三・川瀬毅・久保孝史
    • Organizer
      第19回基礎有機化学討論会
    • Place of Presentation
      吹田(大阪大学)
    • Related Report
      2010 Final Research Report 2008 Annual Research Report
  • [Presentation] ビス(スピロジェノン)架橋ビチオフェン類の合成と特異な酸化還元挙動2008

    • Author(s)
      藤本貴久
    • Organizer
      第35回有機典型元素化学討論会
    • Place of Presentation
      八王子(首都大東京)
    • Related Report
      2008 Annual Research Report
  • [Presentation] 2, 2'-ビス(スピロジェノン)架橋3, 3'-ビチオフェン類の合成とその特異な酸化還元挙動2008

    • Author(s)
      藤本貴久
    • Organizer
      第19回基礎有機化学討論会
    • Place of Presentation
      吹田(大阪大学)
    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.chem.sci.osaka-u.ac.jp/lab/kubo/Start.html

    • Related Report
      2010 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi