Synthesis and RAFT polymerization of a novel vinyl monomer containing both triarylimidazole and triazole moieties

Abstract

A novel monomer consisting of a 4-vinyl-1,2,3-triazole unit directly linked to a triphenylimidazole unit, 1-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl)-4-vinyl-1H-1,2,3-triazole (DVT), has been successfully synthesized using click chemistry followed by elimination reaction. Subsequently, poly(DVT) was prepared by the reversible addition-fragmentation chain transfer (RAFT) polymerization of DVT in dimethyl sulfoxide using S-dodecyl-S′-(α,α′-dimethyl-α″-acetic acid)-trithiocarbonate (DMP) as the RAFT agent and 2,2′-azobis(isobutyronitrile) (AIBN) as the initiator. Kinetic studies demonstrated that the polymerization process of DVT followed pseudo-first-order kinetics with respect to the monomer concentrations. The molecular weight of the resulting polymer increased linearly with monomer conversion, while a low polydispersity was maintained throughout. In addition, the poly(DVT) showed the characteristic of temperature-dependent absorbance in the near-ultraviolet (UV) spectral region, of which a linear dependence of UV absorbance on temperature was confirmed for the polymer both in solution and in solid states.