Synthesis, emulsification and self-assembly properties of sugar-containing semifluorinated amphiphiles.

Surfactants with two and three monosaccharide-based heads and a perfluoroalkyl tail have been synthesized. Perfluoroalkyl C 3 -symmetric triol and C 2 -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. [ABSTRACT FROM AUTHOR]