SYNTHESIS AND VESICLE FORMATION OF CATIONIC SURFACTANTS BASED ON TRISUBSTITUTED PERFLUOROALKYLATED THIOUREA

New perfluoroalkyl double-chain surfactants were synthesized based on trisubstituted perfluoroalkylated thiourea. These amphiphiles have a modular structure consisting of hydrophobic tails, thiourea as connector, alkyl spacer, and ammonium head group. The modular organization allows an independent variation of the key features in the amphiphilic structure. The synthesis strategy was based on the condensation reaction of 2-(F-alkyl)ethyl isothiocyanates with 3-(dimethylamino)-N-(2-hydroxy-2-F-alkyl)ethyl)-alkylamines and subsequent quaternization by methyl iodide to produce the trisubstituted perfluoroalkylated thiourea. The two reaction steps proceed with high yields. The surface activity properties of the new amphiphiles were studied and the ability to self-assemble into bilayer vesicles was determined by freeze fracture electron microscopy and quasi-elastic light scattering.