Design and Synthesis of Dioxetane-Based Chemiluminescent Substrates with High Efficiency in Aqueous System(By a grant Research Institute for Integrated Science, Kanagawa University)
The chemiluminescent efficiency of hydroxyphenyl-substituted dioxetanes is well known to decrease significantly in an aqueous medium, though more than bioluminescence in an aprotic medium. We investigated here the effect of hydrogen bonding on singlet-chemiexcitation and fluorescence efficiency of the emitter produced for charge-transfer-induced chemiluminescence by the use of dioxetanes bearing a 3-hydroxyphenyl moiety substituted with a proton-donating group at the 4-position as a model substrate. Based on this investigation, four bicyclic dioxetanes bearing a 4-(benzoazol-2-yl)-3-hydroxyphenyl moiety were designed and synthesized. The thus-realized dioxetanes exhibited chemiluminescence with markedly high efficiency in aqueous medium as well as in aprotic medium
