LAUSR

In this study polyhedral oligomeric silsesquioxane (POSS) with multifunctional sulfonamide groups were synthesized via click reaction (copper catalyzed Huisgen 1,3-dipolar cycloaddition reaction) between octakis(3-azidopropyl)octasilsesquioxane (POSS-(N3)8) and propargylated sulfonamides. Propargyl containing sulfonamides were synthesized by direct propargylation of sulfonamids (sulfadiazine, sulfadimidine and sulfaquinoxaline) with propargyl bromide in dimethyl formamide. Propargylated sulfonamides were analyzed by IR, 1H NMR, 13C NMR and MS analyses. Polyhedral oligomeric silsesquioxane with multifunctional sulfonamide groups were analyzed by different methods such as IR, TGA, SEM and NMR methods which have confirmed that POSS were functionalized with sulfonamide groups. This method provides a simple and efficient route to functionalize a wide range of new structures on the surface of silsesquioxanes. The antibacterial activities of synthesized sulfonamide functionalized polyhedral oligomeric silsesquioxanes were tested against Staphylococcus aureus as gram positive bacteria and Escherichia coli as gram negative bacteria. Antimicrobial activities of synthesized compounds 5(a–c) in comparison with their relative sulfonamides, were markedly reduced by particles mass increasing and solubility decreasing.Graphical Abstract