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Synthesis and Properties of Novel Non-planar Extended Quinonoid Molecules Having o-Quinonoid Structure

Research Project

Project/Area Number 16550036
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, Graduate School of Science, Assistant Professor, 大学院・理学研究科, 助手 (40263199)

Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2005: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2004: ¥3,000,000 (Direct Cost: ¥3,000,000)
Keywordsquinone / non-planar / spiro-compound / photo-responce / Suzuki-Miyaura coupling / thiophene / redox behavior / diradical / チオインジゴ / フェノキシラジカル / 光スイッチング / ESR
Research Abstract

Our research results are summarized as follows.
1.Synthesis and properties of the extended pyracyloquinone derivative
The extended-quinone derivativeof cyclopenta[fg]acenaphthylene-1, 2-dione (pyracyloquinone) was first synthesized and characterized. The molecular structure determined by X-ray analysis and redox behavior reflect the antiaromatic characted of the pyracylene moiety.
2.Synthesis and properties of novel redox system having dithieno snnelsted bis(spirodienone) skeleton
In the course of the synthetic study on thioindigo-extended quinones, we prepared bis(benzo[b]thiophene)-annelated dispiro[5.4.5.0]hexadeca-1,4,7,9,12,15-hexaene-3,14-dione, a new skeleton molecule. This compound showed a ring-opening trasformation by two-electron reduction, and a photo-responsive property detected by ESR spectroscopy. Furthermore, a novel quaterquinone derivative based on dithieno-annelated dispiro[5.4.5.0]hexadeca-1,4,7,9,12,15-hexaene-3,14-dione was synthesized, which is a dark-green crystalline substance with metallic luster, shows a srtong absorption at 675nm. The temperature dependency of the redox process was elucidated by cyclic voltammetry.
3.Synthesis of dithieno annelated o-terphenoquinone derivatives
Novel o-terphenoquinone derivatives having benzo[2,1-b : 3,4-b']dithiophene and benzo[1,2-b : 4,3-b']dithiophene skeletons were synthesized from the correspondig bisphenols, prepared by McMurry coupling of the diketone derivatives. These quinones exist as the equiblibium mixture of the quinone-form and the diradical-form. Further oxidation of them afforded another speaces having deep-red and deep-blue color respectively. Detailed study of these compouds are in progress.

Report

(3 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • Research Products

    (6 results)

All 2006 2005

All Journal Article (6 results)

  • [Journal Article] 7,7-dipyridyl-2,6-di-tert-butyl-p-quinone methides : Synthesis, complexation with silver(I) ion, and oxidation to their pyridine N-oxide.2006

    • Author(s)
      Kouzou Matsumoto
    • Journal Title

      Chemistry Letters 35,1

      Pages: 74-75

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis, Structure and Properties of a Cyclopent[fg]acenaphthylene-l,2-bis(p-quinone methide)s Derivative. An Extended Pyracyloquinone2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Letters 34,12

      Pages: 1660-1661

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis, Structure and Properties of a Cyclopent[fg]acenaphthylene-1,2-bis(p-quinone methide)s Derivative. An Extended Pyracyloquinone2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Letters 34(12)

      Pages: 1660-1661

    • NAID

      10016892060

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis, Structure and Properties of a Cyclopent[fg]acenaphthylene-1,2-bis(p-quinone methide)s Derivative. An Extended Pyracyloquinone2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Letters 34,12

      Pages: 1660-1661

    • NAID

      10016892060

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of tetrakis(2-furyl)methane2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Letters 34,7

      Pages: 910-911

    • NAID

      10016468417

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Stilbene-extended trithienylmethanophanes : A novel C3-symmetric cage molecule capable of accommodating an organic molecule as well as three silver(I) ions2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Letters 34,4

      Pages: 484-485

    • Related Report
      2005 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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