Chemiexcitation efficiency for the charge-transfer-induced chemiluminescent decomposition of 3-hydroxyphenyl-substituted dioxetanes in an aqueous system

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• 作者：Nobuko Watanabe ; Azusa Oguri ; Miho Horikoshi ; Hikaru Takatsuka ; Hisako K. Ijuin ; Masakatsu Matsumoto
• 关键词：Chemiluminescence ; Dioxetane ; Chemiexcitation efficiency ; Aqueous system
• 刊名：Tetrahedron Letters
• 出版年：26 February, 2014
• 年：2014
• 卷：55
• 期：9
• 页码：1644-1647
• 全文大小：1231 K

文摘

The decomposition of 3-oxyphenyl-3-methoxy-4-(2鈥?spiroadamantane)-1,2-dioxetane (A) and 5-tert-butyl-4,4-dimethyl-1-(3-oxyphenyl)bicyclo[3.2.0]heptane (B) in NaOH/H₂O gives light in poor yield, which is several orders of magnitude lower than that in aprotic solvents. To understand the poor chemiluminescence efficiency in NaOH/H₂O, we investigated the behaviors of the authentic emitters, methyl 3-oxidobenzoate (C) and 2,2,4,4-tetramethyl-3-oxopentyl 3-oxidobenzoate (D). We found that D was weakly fluorescent though hydrolyzed in NaOH/H₂O, and estimated that the singlet-chemiexcitation efficiency 桅_S was 6.1 脳 10^鈭? for the decomposition of B in NaOH/H₂O. On the other hand, 桅_S for A could not be estimated, since C was hydrolyzed too rapidly to observe its fluorescence.