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2012 Fiscal Year Final Research Report

Development of chemiluminescence probe using dioxetanes responsive to a conformational change

Research Project

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Project/Area Number 21550052
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

WATANABE Nobuko  神奈川大学, 理学部化学科, 助教 (40291744)

Co-Investigator(Kenkyū-buntansha) MATSUMOTO Masakatsu  神奈川大学, 理学部, 教授 (10260986)
Project Period (FY) 2009 – 2012
Keywords有機光化学 / 化学発光 / ジオキセタン / 発光プローブ
Research Abstract

An aryl-substituted dioxetane fused with N-acylpyrrolidine gave four conformational isomers due to rotation of an aryl ring around the bond joining it to a dioxetane ring and/or conformational isomerism of N-acyl group. These conformational isomers were found to become possible to be effectively isolated by design of the N-acyl group. The thus-isolated conformational isomers showed the unique chemiluminescence, the properties of which were significantly different from each other. A new dioxetane bearing a sterically congested bisnaphthol moiety was found to give chemiluminescence in the presence of a Mg alkoxide. Furthermore, the thermodynamic properties were clarified for chemiluminescent decomposition of benzothiazolylphenol-substituted dioxetanes.

  • Research Products

    (5 results)

All 2012 2011 2010

All Journal Article (3 results) (of which Peer Reviewed: 3 results) Presentation (2 results)

  • [Journal Article] N-Acylgroup-directed color modulation in the t-BuOK-mediated chemiluminescent decomposition of hydroxyaryl-substituted dioxetanes fused with a pyrrolidine ring2012

    • Author(s)
      N. Watanabe, K. Matsumoto, T. Tanaka, H. Suzuki, H. K. Ijuin, M. Matsumoto
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Pages: 5309-5313

    • DOI

      DOI:10.1016/j.tetlet.2012.07.086

    • Peer Reviewed
  • [Journal Article] Crucial dependence of chemiluminescence efficiency on the syn/anti conformation for intramolecular charge-transfer- induced decomposition of bicyclic dioxetanes bearing an oxidoaryl group2011

    • Author(s)
      M. Matsumoto, H. Suzuki, N. Watanabe, H. K. Ijuin, J. Tanaka, C. Tanaka
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 76 Pages: 5006-5017

    • DOI

      DOI:10.1021/jo2006945

    • Peer Reviewed
  • [Journal Article] Intramolecular charge-transfer-induced decomposition promotedby an aprotic polar solvent for bicyclic dioxetanes bearing4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety2011

    • Author(s)
      M. Tanimura, N. Watanabe, H. K. Ijuin, M. Matsumoto
    • Journal Title

      The Journal of Organic Chemistry.

      Volume: 76 Pages: 902-908

    • DOI

      DOI:10.1021/jo1021822

    • Peer Reviewed
  • [Presentation] (ベンゾチアゾール-2-イル)-3-ヒドロキシフェニルで置換された双環性ジオキセタンの発光分解2010

    • Author(s)
      谷村昌俊、渡辺信子、伊集院久子、松本正勝
    • Organizer
      2010年光化学討論会
    • Place of Presentation
      千葉大学西千葉キャンパス
    • Year and Date
      20100908-10
  • [Presentation] 立体的に込み合ったビナフチル置換ジオキセタンの合成と発光2010

    • Author(s)
      渡辺信子、川島英久、長谷川智司、松本正勝
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学本部キャンパス
    • Year and Date
      20100326-29

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Published: 2014-08-29  

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