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Structural isomers (cis-syn, cis-anti and trans isomers) of an adamantylideneadamantane 1,2-dioxetane having two fluorophore side chains were prepared and investigated their chemiluminescence (CL) properties in the crystalline state. Real-time monitoring...

Crystalline-state chemiluminescence of 1,2-dioxetane isomers showed contrastive luminescence and reaction properties depending on the crystal-structural characteristics.

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Adamantylideneadamantane 1,2-dioxetane (Adox), one of the most stable 1,2-dioxetanes, was used to investigate the kinetic properties of its chemiluminescent thermolytic reaction in the crystalline state by monitoring chemiluminescence (CL) in real time. Soon after heating of single crystals at 140 °C, it was found that the thermolytic reactions of Adox in the crystals proceeded with zero-order kinetics for several minutes. During the period showing the zero-order kinetics, CL intensities were dependent on the volumes of crystals, and the inside crystals were maintained in a thermal steady state with a constant thermal diffusivity. After this period, the heated crystals of Adox started to break showing different kinetics. This study indicates that a crystalline-state CL reaction is useful to track its progress in real time for analyzing the kinetics.