title: pH-responsive surface activity and solubilization with novel pyrrolidone-based Gemini surfactants.
abstract: A new series of pH-responsive Gemini surfactants with 2-pyrrolidone head groups, N,N'-dialkyl-N,N'-di(ethyl-2-pyrrolidone)ethylenediamine (Di-C(n)P, where n = 6, 8 10, 12), were synthesized and characterized by (1)H NMR, (13)C 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-C(n)P 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 γ(cmc) 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-C(n)P can be tuned by pH.
authors.affiliation: College of Chemistry and Molecules Sciences, Wuhan University, Wuhan, P. R. China 430072.
authors.forename: Zan
authors.initials: Z
authors.lastname: Jiang
authors.forename: Xuefeng
authors.initials: X
authors.lastname: Li
authors.forename: Guangfu
authors.initials: G
authors.lastname: Yang
authors.forename: Li
authors.initials: L
authors.lastname: Cheng
authors.forename: Bo
authors.initials: B
authors.lastname: Cai
authors.forename: Yi
authors.initials: Y
authors.lastname: Yang
authors.forename: Jinfeng
authors.initials: J
authors.lastname: Dong
mesh_terms: D000327:Adsorption; D000388:Air; D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D011760:Pyrrolidinones / Q000737:chemistry*; D012995:Solubility; D013499:Surface Properties; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: C411462:1,25-dihydroxy-21-(3-hydroxy-3-methylbutyl)vitamin D(3); D011760:Pyrrolidinones; D013501:Surface-Active Agents; D014867:Water; D002117:Calcitriol