Synthesis and characterization of pyrrole and thiophene functional polystyrenes via "click chemistry"

Novel side-chain pyrrole or thiophene functional polystyrenes (PS-Py and PS-Th) were synthesized by using "click chemistry'' strategy. First, approximately 40% of chloro groups of poly(styrene-co-chloromethylstyrene) P(S-co-CMS), prepared by nitroxide mediated radical polymerization (NMRP), were converted to azido groups by using NaN(3) in N,N-dimethylformamide. Propargyl pyrrole was prepared by etherification of 4-(1H-pyrrol-1-yl) phenol prepared by Clauson-Kaas reaction using propargylbromide. Propargyl thiophene was synthesized by heterogeneous esterification reaction between 3-thiophenecarboxylic acid and propargylbromide. Finally, azido-functionalized polystyrene was coupled to these propargyl functional heterocyclics with high efficiency by click chemistry. The intermediates at various stages and final polymers were characterized by spectral analysis and cyclic voltammetry.