Preparation and Characterization of Glycerol-Based Cleavable Surfactantsand Derived Vesicles

Article abstract of DOI:10.1021/ja00190a038

Four cleavable double-chain surfactants were synthesized: <(2,2-diheptadecyl-1,3-dioxolan-4-yl)methyl>trimethylammonium methanesulfonate 1a, the analogous bromide 1b, <(2,2-diheptadecyl-1,3-dioxolan-4-yl)methyl>dimethyl(3-sulfopropyl)ammonium hydroxide inner salt 1c, and sodium 3-<(2,2-diheptadecyl-1,3-dioxolan-4-yl)methoxy>-1-propanesulfonate 1d.Vesicles of 1a, 1b, and 1d prepared by sonication were characterized by 1H NMR line width narrowing, dynamic laser light scattering, differential scanning calorimetry, and dye entrapment and leakage studies.In vesicular form, the hydrolytic lability of 1d was greater than that of 1a/1b, due to a combination of electrostatic effects resulting from the different subtituents on the dioxolane ring.Neutral organic compounds can be readily isolated from vesicular solutions of 1d after its hydrolysis.Thus 1d is appropriate for the applicaton of vesicular media to preparative chemistry.