Enhanced Proclivity to Self-Aggregation of Phosphorus-Based Amphiphiles when Perfluoroalkylated : The (Perfluoroalkyl)Alkyl Dimorpholinophosphates

Dimorpholinophosphates 1, with a single perfluoroalkyl chain, self-aggregate when dispersed in water to give tubular structures which reversibly transform into giant vesicles when heated. Compounds 1 also allow the preparation of stable reverse water-in-fluorocarbon emulsions destined to pulmonary drug delivery. None of this could be achieved with non-fluorinated analogs.