Development of chemiluminescence probe using dioxetanes responsive to a conformational change

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An aryl-substituted dioxetane fused with N-acylpyrrolidine gave four conformational isomers due to rotation of an aryl ring around the bond joining it to a dioxetane ring and/or conformational isomerism of N-acyl group. These conformational isomers were found to become possible to be effectively isolated by design of the N-acyl group. The thus-isolated conformational isomers showed the unique chemiluminescence, the properties of which were significantly different from each other. A new dioxetane bearing a sterically congested bisnaphthol moiety was found to give chemiluminescence in the presence of a Mg alkoxide. Furthermore, the thermodynamic properties were clarified for chemiluminescent decomposition of benzothiazolylphenol-substituted dioxetanes.