ホタルの生物発光とそれらに関連する化学発光の機構解明

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  • 2006ネンド カナガワ ダイガク ソウゴウ リガク ケンキュウジョ ジョセイ キョウドウ ケンキュウ ホタル ノ セイブツ ハッコウ ト ソレラ ニ カンレンスル カガク ハッコウ ノ キコウ カイメイ
  • Mechanistic Study on Bioluminescence of Fireflies and Related Chemiluminescence

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A dioxetane bearing a phenoxide anion decomposes with the accompanying emission of light, effectively by the intramolecular charge-transfer-induced chemiluminescence (CTICL) mechanism, by which the bioluminescence of fireflies has been believed to take place through an intermediary dioxetanone. In the course of our investigation of highly effective dioxetane-based chemilumine scent substrates, bicyclic dioxetanes bearing a 3-hydroxyphenyl moiety substituted with a 5-aryl, such as naphthalen-1-yl, carbazol-9-yl, indol-1-yl, and benzotriazol-1-yl, were synthesized. Base-induced decomposition of these dioxetanes displayed intense light, the maximum wavelength of which changed depending on the crown ether complex used as a base. As a further development, we realized four optically isomeric bicyclic dioxetanes bearing a 2-hydroxy-1, 1'-binaphthy1-4-y1 moiety. These isomeric dioxetanes were decomposed with the accompanying emission of light on treatment with three base systems. The chemiluminescence efficiencies of all isomers were practically the same for tetrabutylammonium fluoride (TBAF) in the DMSO system, whereas they split into two diastereomer-groups for 18-crown-6 ether complex of t-BuOK in the benzene-THF system. For the base system using t-BuOK complex of optically active crown ether, the chemiluminescence efficiencies split further into four. The shape of the chemiluminescence spectrum, maximum wavelength, and rate of decomposition were also different between each of the four stereoisomers.

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