pH-Responsive Surface Activity and Solubilization with Novel Pyrrolidone-Based Gemini Surfactants

A new series of pH-responsive Gemini surfactants with 2-pyrrolidone head groups, N,N′-dialkyl-N,N′-di­(ethyl-2-pyrrolidone)­ethylenediamine (Di-CnP, where n = 6, 8 10, 12), were synthesized and characterized by 1H NMR, 13C NMR, ESI-MS, and elemental analysis. The surface activity and micellization behavior at acidic, neutral, and basic conditions were characterized by equilibrium surface tension and fluorescence techniques. It was found that the surface activity of Di-CnP depends on the pH of aqueous solutions due to the protonation state of surfactant molecules when pH was varied. The new compounds have lower cmc and γcmc in comparison with that of m-2-m type conventional cationic Gemini surfactants and gluconamide-type nonionic Gemini surfactants. Fluorescence data confirm that micelles are formed when the concentration is above the cmc. Since micellization is of fundamental importance in surfactant applications such as solubilization, microemulsion, and related technologies, the significant difference in cmc at different pH of this new Gemini surfactant is employed to solubilize cyclohexane. The preliminary result indeed shows that the solubilization capacity of Di-CnP can be tuned by pH.