CHEMILUMINESCENCE OF 9,10-ANTHRASEMIQUINONE RADICAL-ANION UPON AUTOOXIDATION OF DIPHENYLMETHANE IN THE PRESENCE OF 9,10-DIBROMOANTHRACENE IN ALKALINE-MEDIUM

The autooxidation reaction of Ph(2)CH(2) in dimethylsulfoxide in the p resence of tert-BuOK is accompanied by chemiluminescence emitted by tr iplet benzophenone. Addition of 9,10-dibromoanthracene activator to th is system leads to the appearance of the band with lambda(max) = 580 n m in addition to the 9,10-dibromoanthracene emission (430 nm) in the c hemiluminescence spectrum. It was shown by ESR and fluorescence spectr oscopy that one of the final products of this reaction is the 9,10-ant hrasemiquinone radical anion. The similarity of absorption, ESR, and f luorescence spectra of the reaction mixture to those of the radical an ion suggests that this compound is responsible for the long-wavelength band of the chemiluminescence spectrum. A possible route is considere d for the generation of the 9, 10-anthrasemiquinone radical anion upon degradation of the dioxetane cycle formed during the nucleophilic sub stitution of a diphenylmethylperoxy anion for bromine in the 9,10-dibr omoanthracene molecule.