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Design and Synthesis of Highly Efficient Chemiluminescent Substrates

Research Project

Project/Area Number 09640650
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

MATSUMOTO Masakatsu  Kanagawa University, Faculty of Science, Professor, 理学部, 教授 (10260986)

Co-Investigator(Kenkyū-buntansha) WATANABE Nobuko  Kanagawa University, Faculty of Science, Assistant professor, 理学部, 助手 (40291744)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1998: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1997: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsChemiluminescence / 1,2-Dioxetane / Thermal stability / Trigger / Charge transfer / 赤色発光
Research Abstract

1. Design of Thermally Stable Dioxetanes : Bicyclic dioxetanes, 5-Alkyl-1-aryl-4,4-dimethyl-2-oxabicyclo[3.2.O]heptanes were synthesized. Among them, dioxetanes bearing a 5-tert-butyl were found to possess marked thermal stability. Even dioxetanes fused with six-membered ring, which have been reported to be in general far less stable than their five-membered ring analogs, were found to become very stable thermally by means of 3,3-steric interaction.
2. Design of New Triggering System : By deprotonation or deprotection (triggering), a dioxetane bearing a phenolic group produce an unstable dioxetane bearing an oxyphenyl anion, which decomposes rapidly to emit light by intramolecular charge transfer mechanism where an oxyphenyl anion acts as an electron donor. An anion of m-aminophenyl group acts also as an aromatic electron donor other than phenolic moiety to induce decomposition of a dioxetane to emit flash red light.
3. Design of Fluorophore : Six dioxetanes bearing a 2-naphthyl with a tert-butyldimethylsiloxy at the various position were synthesized and their fluoride-induced chemiluminescent decomposition was examined. Naphthyl-substituted dioxetanes having a trigger (siloxy) at the 5-, 7-, or 8-position emitted red light, while their analogs with a trigger at the 3- or 6-position afforded flash blue light. Dioxetanes bearing a benzofuran, benzothiophene, or benzothiazole were also synthesized.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] M.Matsumoto, N.Watanabe,: "Synthesis of 5-alkyl-1-aryl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptanes as a chemiluminescent substrate with remarkable thermal stability" Tetrahedron Lett.38. 2863-2866 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, N.Watanabe,: "Chemiluminescence of spiro[1, 2-dioxetane-3, 1'-dihydroisobenzofuran]s, spiro[1, 2-dioxetane-3, 1'-isochroman]s and a spiro[1, 2-dioxetane-3, 1'-(2-" Tetrahedron Lett.38. 5825-5828 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto and M.Azami: "F-induced decomposition of 3-[(teret-butyldimethylsiloxy)phenoxy]-3-phenyl-1, 2-dioxetanes without C-C bond cleavage of hte dioxetane ring." Tetrahedron Lett.38. 8947-8〓0 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, N.Watanabe,: "Base-induced cyclization of 7-aryl-2, 2, 4, 4-tetramethyl-6-oxaheptan-3-ones : intramolecular nucleophilic addition of an anion of the benzyl ether to the" J.Chem.Soc.Chem.Commun.2395-2396 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, H.Murakami, and N.Watanabe.: "Thermal decomposition of 1-(aminophenyl)-5-tert-butyl-4, 4-dimethyl-2, 6, 7-trioxabicyclo[3.2.0]heptanes, unusual O-O bond cleavage competing with" J.Chem.Soc.Chem.Commun.2319-2320 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Watanabe, M.Matsumoto,: "Synthesis of 3-alkoxy-3-aryl-4, 4-diisopropyl-1, 2-dioxetanes and their base-induced chemiluminescence" Tetrahedron. 4287-4298 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Watanabe, H.Suganuma, H.Kobayashi, H.Mutoh, Y.Katao, and M.Matsumoto: "Synthesis of 3-alkoxy-3-aryl-4,4, disopropy-1,2-dioxetanes and their base-induced chemiluminescence" Tetrahedron. 55. 4287-4298 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto: "Control of mode selectivity in singlet oxygenation of olefins" Photochemistry. 28. 31-38 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, H.Murakami, and N.Watanabe: "Thermal decomposition of 1-(aminophenyl)-5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo [3.2.0] heptanes, unusual O-O bond cleavage competing with normal fragmentation of 1,2-dioxetanes." J.Chem.Soc.Chem.Commun.2319-2320 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, and N.Watanabe, A.Ishikawa, and H.Murakami: "Base-induced cyclization of 7-aryl-2,2,4,4-tetramethyl-6-oxaheptan-3-ones : intramolecular nuclephilic addition of an anion of the benzyl ether to the carbonyl moiety." J.Chem.Soc.Chem.Commun.2395-2396 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, and M.Azami: "F-induced decomposition of 3-[(teret-butyldimethylsiloxy)-phenoxy]-3-phenyl-1,2-dioxetanes without C-C bond cleavage of hte dioxetane ring." Tetrahedron Lett.38. 8947-8950 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, N.Watanabe, T.Shiono, and H.Suganuma: "Chemiluminescence of spiro [1,2-dioxetane-3,1'-dihydroiso-benzofuran]s, spiro [1,2-dioxetane-3,1'-isochroman]s and a spiro [1,2-dioxetane-3,1'-(2-benzoxepane)]." Tetrahedron Lett.38. 5825-5828 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, N.Watanabe, N.C.Kasuga, and F.Hamada: "Synthesis of 5-alkyl-1-aryl-4,4-dimethyl-2,6,7-trioxabicyclo-[3.2.0] heptanes as a chemiluminescent substrate with remarkable thermal stability" Tetrahedron Lett.38. 2863-2866 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Matsumoto, N.Watanabe, H.Kobayashi, and M.Azami: "Synthesis and chemiluminescence of 3,3-diisopropyl-4-methoxy-4-(2-naphthyl)-1,2, -dioxetanes" Tetrahedron Lett.38. 411-414 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] N.Watanabe,H.Suganuma,H.Kobayashi,H.Mutoh,Y.Katao,M.Matsumoto: "Synthesis of 3-Alkoxy-3-aryl-4,4-diisopropyl-1,2-dioxetanes and their Base-Induced Chemiluminescence" Tetrahedron. (印刷中). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Matsumoto: "Control of Mode Selectivity in Singlet Oxygenation of Olefins" Photochemistry. 28. 31-38 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Matsumoto,H.Murakami,N.Watanabe: "Thermal Decomposition of 1-(Aminophenyl)-5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo-[3.2.0]heptanes;unusual O-O bond cleavage competing with normal fragmentation of" J.Chem.Soc.Chem.Commun.2319-2320 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Matsumoto, N.Watanabe, A.Ishikawa, H.Murakami: "Base-Induced Cyclization of 7-Aryl-2,2,4,4-tetramethyl-6-oxaheptan-3-ones:Intramolecular Nucleophilic Addition of an Anion of the Benzyl Ether to the Carbonyl Moiety…" J.Chem.Soc.,Chem.Commun.1997. 2395-2396 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Matsumoto, M.Azami: "F--Induced Decomposition of 3-[(tert-Butyldimethylsiloxy)phenoxy]-3-phenyl-1,2-dioxetanes without C-C Bond Cleavage of the Dioxetane Ring" Tetrahedron Lett.38. 8947-8950 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Matsumoto, N.Watanabe, T.Shiono, H.Suganuma: "Chemiluminescence of Spiro[1,2-dioxetane-3,1'-dihydroisobenzofuran]s,Spiro[1,2-dioxetane-3,1'-isochroman]s and a Spiro[1,2-dioxetane-3,1'-(2-benzoxepane)]" Tetrahedron Lett.38. 5825-5828 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Matsumoto, N.Watanabe, N.C.Kasuga, F.Hamada: "Synthesis of 5-Alkyl-1-aryl-4,4,-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptanes as a Chemiluminescent Substrate with Remarkable Thermal Stability" Tetrahedron Lett.38. 2863-2866 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Matsumoto, N.Watanabe, H.Kobayashi, M.Azami: "Synthesis and Chemiluminescence of 3,3-Diisopropyl-4-methoxy-4-(2-naphthyl)-1,2-dioxetanes" Tetrahedron Lett.38. 411-414 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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