Relationship between structure and photoinitiating abilities of selected bromide salts of 2-oxo-2,3-dihydro-1H-imidazo[1,2-a]pyridine (IMP): influence of the solvent and the substitution in benzaldehyde on the course of its reaction with IMP

Abstract

2-Oxo-2,3-dihydro-1H-imidazo[1,2-a]pyridinium bromide and its C3-substituted derivatives have been synthesized and structurally characterized by X-ray crystallography and quantum chemical calculations. Their potential as photoinitiators for free-radical polymerization has been investigated experimentally and compared with theoretical results. It has been established that the course of the reaction that introduces the substituted benzylidene group to the imidazole ring is different in the protic and dipolar aprotic solvents, and also depends on the character of the substituent, as the energy change in the reaction favours either R 1 R 2C=CHR 3 or R 1 R 2CH—CH(OCH3)R 3 formation.