Synthesis, characterization and polymerization of a novel acrylate monomer containing both 4H-pyran-4-one and 1,2,3-triazole moiety and evaluation of their antibacterial activity

A novel acrylate monomer containing 4H-pyran-4-one and 1,2,3-triazole ring, {1-[4-(4-oxo-6-phenyl-4H-pyran-2-yl)benzyl]-1,2,3-triazol-4-yl}methyl acrylate was synthesized by the reaction of 2-{4-[(4-(hydroxymethyl)-1,2,3-triazol-1-yl)methyl]phenyl}-6-phenyl-4H-pyran-4-one with acryloyl chloride in the presence of triethylamine. The structure of the acrylate monomer was established on the basis of FT-IR, 1H NMR, 13C NMR, MS and elemental analysis. This monomer was polymerized using 2,2´-azobisisobutyronitrile (AIBN) as the initiator in N,N-dimethylformamide solution. Thermal stability of the polymer was investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The synthesized compounds were evaluated for their antibacterial activity against Gram-positive and Gram-negative bacteria using the disk diffusion method. The results of antibacterial assay indicated that these compounds exhibited moderate bactericidal activity.

Keywords:

4H-Pyran-4-one , triazole , acrylate monomer , antibacterial activity , free radical polymerization , thermal properties