Synthesis And Photophysical Properties Of Triarylimidazole Substituted Vinyl Polymer

Triarylimidazoles and their derivatives have attracted considerable attention inrecent years because of their unique properties and applications in diverse fields. Thechemical flexibility of this class of compounds allows the preparation of a largevariety of related structures and, consequently, the tailoring of the chemiluminescent,photochromic, redox, and biological properties. Current efforts have been devoted topreparing triarylimidazole monomers based on acrylates and styrenic derivatives.Polymeric triarylimidazoles are composed of triarylimidazole groups bound topolymer, which offer the advantage of allowing a range of chemo-physical properties.But these monomers often lack desired properties such as chemical stability foracrylates or structural diversity for styrenic monomers.Because of the benign reaction conditions, functional group tolerance and broadapplicability, the Cu(Ⅰ)-catalyzed cycloaddition of azides and alkynes reaction hasbeen developed as a powerful tool in the synthesis of triazole-based vinylic monomerwhich combines the features such as aromaticity, polarity and structural diversity.We herein report the synthesis of1-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl)-4-vinyl-1H-1,2,3-triazole (DPVT), a novel monomer based on triarylimidazole andtriazole. The monomer was carefully purified, and characterized by1H NMR,13CNMR, MALDI-TOF-MS and FT-IR spectroscopic methods. The reversible addition-fragmentation chain transfer (RAFT) polymerization of DPVT was performed indimethyl sulfoxide (DMSO) using S-dodecyl-S’-(α,α’-dimethyl-α’’-acetic acid)-trithiocarbonate (DMP) as the chain transfer agent. The obtained polymers werecharacterized by gel permeation chromatography (GPC).The effect of temperature on ultraviolet spectra of the polymer was studied. Theresults demonstrate that the absorbances of DPVT and its polymer vary linearly withtemperature between30oC and90oC. A similar sensitivity to temperature changeswas showed by both the absorbances of polymer solution and film.