Synthesis of 3-alkoxymethyl-4-aryl-3-tert-butyl-4-methoxy-1,2-dioxetanes as a chemiluminescent substrate with short half-life emission

Article abstract of DOI:10.1016/0040-4039(96)01282-8

Treatment of 3-alkoxymethyl-3-tert-butyl-4-(3-tert-butyldimethylsiloxy)phenyl-4-met hoxy-1,2-dioxetanes (2) with TBAF in DMSO gives intensive blue light emission (λmax=463 nm, Φ(CL)>0.1) with short half-life (t(1/2)<1 sec), whereas the methylene analogues (6) cause chemiluminescence with far longer half-life. A dioxetane (1) bearing a phosphoryloxyphenyl is cleaved enzymatically by alkaline phosphatase to generate light with high intensity.