title: Aqueous solution properties of disulfide linked gemini and cleaved monomeric thiol surfactants.
abstract: Monomeric thiol surfactants, [C(n)H(2n+1)N(CH(3))(2)CH(2)CH(2)SH]Br, were produced by the cleavage of gemini surfactant containing a disulfide bond in the spacer chain, [C(n)H(2n+1)N(CH(3))(2)CH(2)CH(2)SSCH(2)CH(2)N(CH(3))(2)C(n)H(2n+1)]2Br. The disulfide bond was completely reduced by the addition of four times moles of dithiothreitol in water at room temperature. The critical micelle concentrations of monomeric surfactants were significantly increased in comparison with original gemini surfactants. The monomeric thiol surfactants were stable in the presence of dithiothreitol, whereas they returned gradually to their original gemini surfactants within several days due to air oxidation in water without dithiothreitol. The micelle formation induced by the disulfide linkage formation was suggested by the fluorescence intensity ratio of pyrene. The time course of decrease in thiol concentration associated with the recovery of gemini surfactants was confirmed by the absorption spectra utilizing the reactions with 4,4'-dithiopyridine.
authors.affiliation: Division of Material Sciences, Graduate School of Natural Science & Technology, Kanazawa University, JAPAN. asakawa@t.kanazawa-u.ac.jp
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Asakawa
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Shimizu
authors.forename: Tadahiro
authors.initials: T
authors.lastname: Ozawa
authors.forename: Akio
authors.initials: A
authors.lastname: Ohta
authors.forename: Shigeyoshi
authors.initials: S
authors.lastname: Miyagishi
mesh_terms: D004220:Disulfides / Q000737:chemistry*; D008823:Micelles; D011725:Pyridines / Q000737:chemistry; D012996:Solutions; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D004220:Disulfides; D008823:Micelles; D011725:Pyridines; D012996:Solutions; D013438:Sulfhydryl Compounds; D013501:Surface-Active Agents; D014867:Water; C007542:4,4'-dipyridyl disulfide