Solvent-promoted chemiluminescent decomposition of a bicyclic dioxetane bearing a 4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety |
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Authors: | Masakatsu Matsumoto Masatoshi Tanimura Taichi Akimoto Nobuko Watanabe Hisako K Ijuin |
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Institution: | Department of Chemistry, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, Japan |
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Abstract: | An aprotic polar solvent such as N-methylpyrrolidone (NMP) promoted the thermal decomposition of bicyclic dioxetane bearing a 4-(benzothiazol-2-yl)-3-hydroxyphenyl moiety 1 without the addition of any base. This solvent-promoted decomposition (SPD) gave light as effectively as the base-induced decomposition (BID) in an aprotic polar solvent. SPD caused intramolecular CT-induced chemiluminescence similar to BID, but, in contrast to BID, SPD proceeded through a pathway with a large negative entropy of activation. Dioxetane 1 was also shown to give light due to excited state intramolecular proton transfer (ESIPT) upon heating in p-xylene. |
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Keywords: | Dioxetane Chemiluminescence Solvent-promoted decomposition ESIPT |
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