Stable Dioxetane Precursors as Selective Trap-and-Trigger Chemiluminescent Probes for Singlet Oxygen

A set of highly selective chemiluminescent probes has been developed for the detection and quantitation of singlet oxygen ( 1 O 2 ), a reactive oxygen species that is known to transform organic pollutants in the aquatic environment and elicits cytotoxic effects in biological systems. In this study, a trap-and-trigger detection method is employed, based on the reaction of 1 O 2 with a spiroadamantyl-substituted vinyl ether probe to form the corresponding thermally stable dioxetane, which undergoes chemiluminescent decomposition upon addition of a chemical trigger. The detection method is highly selective for 1 O 2 relative to superoxide anion and hydrogen peroxide. The sensitivity of this method allows for the accurate measurement of environmentally relevant (picomolar) steady-state 1 O 2 concentrations in relatively short exposure times. The detection method was used to detect and quantify 1 O 2 production in the reaction of dibenzoyl peroxide with superoxide anion.