The synthesis of isomeric, functionalized 4-vinyl-1,2,3-triazole and 5-vinyl-1,2,3-triazole monomers is demonstrated using heterogeneous copper (copper-in-charcoal)-catalyzed azide-alkyne cycloaddition (CuAAC) or homogeneous ruthenium (Ru)-catalyzed azide-alkyne cycloadditions (RuAAC) "click" protocols. These reactions are regiospecific, exclusively forming 1,4- and 1, 5-disubstituted triazoles as determined by H-1 NMR, C-13 NMR, and X-ray crystallography analysis. Polymerizations were performed using living free radical procedures to yield materials with divergent properties. In the case of the 1,5-triazole materials, glass transition temperature were significantly higher that for the 1,4-derivatives while solubility was decreased.