Notable Difference between Tetrabutylammonium Fluoride and Organic Superbases as Triggers for The Chemiluminescent Decomposition of Bicyclic Dioxetanes Bearing A 4-(N-Phenylbenzimidazol-2-Yl)-3-Hydroxyphenyl Moiety

Chemiluminescent decomposition of bicyclic dioxetanes 3a-3c bearing a 4-(N-phenylbenzimidazol-2-yl)-3-hydroxyphenyl moiety was effectively induced by organic superbases, BTPP [(tert-butylimino)tris(pyrrolidino)phosphorene], TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene), MTBD (7-methyl-1,5,7-tri azabicyclo [4.4.0] dec-5-ene), DBU (1,8-diazabicyclo-[5.4.0]-undec-7-ene), and TMG (tetramethylguanidine), as well as TBAF in acetonitrile. Dioxetane 3c bearing a 3,5-dihydroxyphenyl moiety showed diverse chemiluminescence profiles depending on the base used. BTPP caused chemiluminescent decomposition due to the di-oxido anion of dioxetane, while DBU and TMG induced chemiluminescence from the mono-oxido anion of dioxetane. On the other hand, TBAF caused effective chemiluminescence due to the mono-oxido anion, though it acted as a stronger base than BTPP with regard to the rate of decomposition of 3c.