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Development of new triggering system in solid state for unprecedented topochemiluminescence with high efficiency

Research Project

Project/Area Number 25410056
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionKanagawa University

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) MATSUMOTO Masakatsu  神奈川大学, 付置研究所, プロジェクト研究員 (10260986)
Co-Investigator(Renkei-kenkyūsha) IJUIN Hisako  神奈川大学, 付置研究所, プロジェクト研究員 (60398948)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords化学固体発光 / ジオキセタン型発光基質 / トポロジー
Outline of Final Research Achievements

A 3-hydroxyphenyl-substituted dioxetane fused with a tetrahydrofuran ring thermally decomposes (TD) in apolar solution to give a 3-oxopropyl 3-hydroxybenzoate with the emission [Lmax = 405 nm] due to excited ketone moiety. The dioxetane gave also the keto ester by TD in crystal (TDcryst), though the light emitted was due to excited oxidobenzoate [Lmax = 464 nm] formed by CTID (CT-induced decomposition) mechanism. The unique chemiluminescent TDcryst of the dioxetane was presumably the result of hydrogen bonding (HB) formed in the crystal between a phenolic proton of a dioxetane molecule and a peroxide oxygen of another dioxetane. On the other hand, a 4-benzazolyl-3-hydroxyphenyl substituted dioxetanes underwent TDcryst to effectively give light. Furthermore, photolysis of a crystalline dioxetane bearing a 4-benzimidazolyl-3-hydroxyphenyl group at -78o gave the corresponding keto ester, the stereochemistry of which was apparently different from that of authentic one.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (6 results)

All 2016 2015 2014 2013 Other

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

  • [Journal Article] Hydrogen bonding network-assisted chemiluminescent thermal decomposition of 3-hydroxyphenyl-substituted dioxetanes in crystal2016

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

      Tetrahedron Lett.

      Volume: 57

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of bicyclic dioxetanes bearing a hydroxyphenanthrene or hydroxy[4]helicene moiety and their base-induced chemiluminescent decomposition2015

    • Author(s)
      Yohei Koyama, Nobuko Watanabe, Hisako K. Ijuin, and Masakatsu Matsumoto
    • Journal Title

      HETEROCYCLES

      Volume: 90 Issue: 1 Pages: 462-481

    • DOI

      10.3987/com-14-s(k)43

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chemiexcitation efficiency for the charge-transfer-induced chemiluminescent decomposition of 3-hydroxyphenyl-substituted dioxetanes in an aqueous system2014

    • Author(s)
      N. Watanabe, A. Oguri, M. Horikoshi, H. Takatsuka, H. K. Ijuin, M. Matsumoto
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Issue: 9 Pages: 1644-1647

    • DOI

      10.1016/j.tetlet.2014.01.089

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] コハクオナジマイマイのライフサイクルにおける黄色蛍光物質の変遷2014

    • Author(s)
      伊集院久子、渡邉信子、浅見崇比呂、松本正勝
    • Organizer
      生物発光化学発光研究会第31回学術講演会
    • Place of Presentation
      信州大学繊維学部講堂(長野県上田市)
    • Year and Date
      2014-11-01
    • Related Report
      2014 Research-status Report
  • [Presentation] ω-位を官能基化したリンカーで修飾されたジオキセタン型化学発光化合物2013

    • Author(s)
      入江花風、渡邉信子、伊集院久子、山口和夫、松本正勝
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      愛媛大学
    • Related Report
      2013 Research-status Report
  • [Presentation] コハクオナジマイマイおよびその近縁種の黄色蛍光物質

    • Author(s)
      伊集院久子、重田沙季江、品田麻美、中島愛乃、渡邉信子、浅見嵩比呂、松本正勝
    • Organizer
      生物発光化学発光研究会 第30回学術講演会
    • Place of Presentation
      東京工業大学
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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