A systematic computational analysis of the ability of aromatic carbon-bound fluorine to participate in hydrogen bonding and electrostatic interactions has been completed. The interaction energies between the most common fluoroaromatics used in medicinal chemistry and both water, the prototypical hydrogen bond donor, and several cations have been calculated at different levels of theory (HF, MP2, DFT). Our results show that aromatic fluorine can participate in significant hydrogen bonds and can also interact with charged molecules.

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.