Synthesis, emulsification and self-assembly properties of sugar-containing semifluorinated amphiphiles
Andrew V Razgulin1, Sandro Mecozzi2
1Department of Chemistry, University of Wisconsin, 777 Highland Avenue, Madison, WI 53705, USA.
Abstract:
Surfactants with two and three monosaccharide-based heads and a perfluoroalkyl tail have been synthesized. Perfluoroalkyl C3-symmetric triol and C2-symmetric diol were conveniently prepared via Cu-catalyzed azide-alkyne cycloaddition between a fluorous alkyne and tertiary and secondary azides, respectively. Glycosylation of the perfluoroalkyl diol and triol led to orthoester-type structures, which were evaluated for their capacity to stabilize aqueous emulsions of highly fluorinated anesthetics. The self-assembly properties of the tri-sugar amphiphile were examined by transmission electron microscopy.
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