Crystalline-state chemiluminescence reactions of two-fluorophore-linked adamantylideneadamantane 1,2-dioxetane isomers accompanied by solid-to-solid phase transitions

Structural isomers (cis-syn, cis-anti and trans isomers) of adamantylideneadamantane 1,2-dioxetane having two fluorophore side chains were prepared and their chemiluminescence (CL) properties in the crystalline state were investigated. The real-time monitoring of CL reactions of the isomers in the crystalline state showed contrasting isomeric differences in the reactivities and led to the finding that the crystalline-state CL reactions of cis-syn and cis-anti isomers proceeded accompanied by characteristic solid-to-solid phase transitions.