SYNTHESIS OF TRIAZOLE-CONTAINING CONJUGATED POLYMER THROUGH CLICK POLYMERIZATION

Abstract

Novel triazole-containing conjugated polymers from monofunctional and bifunctional monomers were synthesized via copper-catalyzed azide-alkyne cycloaddition (CuAAC) Click polymerizations. The two diazide precursors: 1,4-diazidobenzene (4) and 2,7-diazidofluorene (6) were synthesized from their corresponding diamino and dinitro derivatives in 68 and 76% yields, respectively. The bifunctional monomer 5-azido-2-ethynylpyridine (11) was obtained in five steps from 2-chloro-5-nitropyridine with an overall yield of 11%. Polymer P1, P2 or P3 were prepared from Click polymerizations of 1,4-diethynylbenzene with either compound 3, 5 or 4,4’-diazido-2,2’-stilbenedisulfonate in 91%, quantitative, or 44% yields, respectively. The bifunctional monomer 5-azido-2-ethynylpyridine (12) was also used to synthesize polymer P4 in 67% yield via similar processes.