| Abstract: | Viologens that bore a terminal vinyl group were synthesized by four sequences of reactions: (1) N-vinylbenzyl-N′-n-propyl-4,4′-bipyridinium bromide chloride (V) was synthesized by the reaction of 4-(4′-pyrodyl)-N-n-propyl pyridinium bromide (III) with vinylbenzyl chloride; (2) N-β-acrylamidoethyl-N′-n-propyl-4,4′-bipyridinium dibromide (IX) was synthesized by the Menschutkin reaction of III with 2-aminoethyl bromide hydrobromide and subsequent reaction with acryloyl chloride; (3) N-β-methacryloyloxyethyl-N′-n-propyl-4,4′-bipyridinium dibromide and its analogs (XI) were synthesized by the reactions of III with the corresponding acyloxyalkyl bromides; and (4) N-vinyloxycarbonylmethyl-N′-n-propyl-4,4′-bipyridinium bromide chloride (XIII) was synthesized by the reaction of III with vinyl chloroacetate. With the exception of monomer XIII in which hydrolysis in large extent was observed during attempted polymerization, the synthesized monomers polymerized smoothly in aqueous solutions by a conventional radical procedure. Comparisons of the absorption peaks of the radical cations produced by reductions in aqueous solutions with those produced in films by ultraviolet (UV) irradiation indicate that the radical cations of polymers are associated intramolecularly in aqueous solutions. |
