On the effect of 1,4-diazabicyclo[2.2.2]octane on the singlet-oxygen dimol emission:: Chemical generation of (1O2)2 in peroxide reactions

The acetone-catalyzed decomposition of monoperoxysulfate ions, the molybdate ion-induced decay of hydrogen peroxide, and the reactions of N-chlorosuccinimide or N-bromosuccinimide with hydrogen peroxide and of dimethyldioxirane with tertiary amines as well as the thermal decomposition of 1,4-dimethylnaphthalene endoperoxide lead to the chemiluminescence of singlet-oxygen dimol species (O-1(2))(2) emitting at 634 and 703 nm. In contrast to the expected enhancement of (O-1(2))(2) chemiluminescence upon addition of 1,4-diazabicyclo[2.2.2]octane (DABCO) [Deneke, C.F.; Krinsky, N. I. J. Am. Chem. Soc. 1976, 98, 3041. Di Mascio, P.; Sies, H. J. Am. Chem. Soc. 1989, 111, 2909.], quenching has been observed. Our data show that enhancement of singlet-oxygen dimol chemiluminescence is not a general phenomenon and, consequently, DABCO is not a reliable chemiluminescent probe for the presence of (O-1(2))(2) in chemical and biochemical systems.