Chemiluminescence in anisotropic microenvironment: splitting of chemiluminescence efficiency for charge-transfer-induced decomposition of optically active bicyclic dioxetanes bearing a 2-hydroxy-1,1′-binaphthyl-4-yl moiety under chiral recognition

Four optical isomers of dioxetane 2 bearing a 2-hydroxy-1,1′-binaphthyl-4-yl moiety decomposed with 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 DMSO system, whereas they split into two diastereomer-groups for 18-crown-6 ether complex of t-BuOK in benzene–THF system. For the base system using t-BuOK complex of optically active crown ether, (Ra,Ra)-7 or (Sa,Sa)-7, the chemiluminescence efficiencies split further into four. The shape of chemiluminescence spectrum, maximum wavelength, and the rate of decomposition were also different between each of the four stereoisomers.