Synthesis, micellization behaviour and cytotoxic properties of imidazolium-based gemini surfactants

Abstract

A three-member series of imidazolium-based gemini surfactants, 1, 1′- (propane-1,3-diyl-2-ol) bis(3-alkyl-1H-imidazol-3-ium)bromide, [CnIm-3OH-ImCn]Br2, of variable hydrocarbon chain length and a hydroxyl group-containing spacer, was synthesized. Their structures were characterized by FT-IR, 1H NMR, 13C NMR and mass spectral techniques. The critical micelle concentration (cmc) of aqueous solutions of these surfactants was determined by conductivity and surface tension measurements. Owing to the lower cmc values of these imidazolium-based gemini surfactants they exhibit superior micellization behaviour than the ammonium as well as pyridinium gemini surfactants. The counterion binding constant and thermodynamic parameters were evaluated from conductivity data. The cytotoxic properties of these newly synthesized gemini surfactants were determined by their hemolytic assay (HC50 analysis). These surfactants were found to be less cytotoxic making them potentially applicable in industrial and biomedical fields, where safety and efficiency are closely related.