Synthesis and chemiluminescent decomposition of spiro[1, 2-dioxetane-3,6'-benzo(c)chromene]s

Two spiro[1,2-dioxetane-3,6'-benzo(c)chromene]s bearing a t-butyldimethylsiloxy as a trigger at the 10'- or 2'-position were synthesized. On treatment with tetrabutylammonium fluoride in DMSO at 25 degrees C, the 10'-siloxyspiro[1,2-dioxetane-3, 6'-benzo(c)chromene] decomposed rapidly to afford a flash of blue light. The CIEEL decay of this spirochromenedioxetane was also induced by basic silica gel in hexane. By contrast, TBAF-induced decomposition of an analogous spiro[1,2-dioxetane-3, 6'-benzo(c)chromene] with a trigger at the 2'-position, resulted in emission of yellow light with very low efficiency.