Synthesis and characterization of poly(N-vinyl-1,2,3-triazole)s derived from monomers obtained by highly efficient Wolff's cyclocondensation

Abstract

Four N-vinyl-1,2,3-triazole monomers were prepared in high yields from 2-aminoethanol and α-diazo-β-oxoamides via modified Wolff's cyclocondensation reactions. Then a series of poly(N-vinyl-1,2,3-triazole)s were synthesized through conventional free radical polymerization of these monomers. The chemical structures of these monomers and polymers were confirmed by proton and carbon nuclear magnetic resonance (¹H and ¹³C NMR). The properties of poly(N-vinyl-1,2,3-triazole)s were systematically characterized by a variety of analytical techniques including thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), gel permeation chromatography (GPC), and solubility testing. The results indicated that these polymers exhibited higher glass transition temperatures (196–212 °C) than most of the commodity vinyl polymers such as polystyrene (100 °C) and poly(methyl methacrylate) (110 °C). Moreover, these polymers can be further functionalized through hydrolysis of amide groups. These results revealed that this methodology has great potential for constructing 1,2,3-triazole-containing monomers and polymers.