Perfluoroalkylated amphiphiles with a morpholinophosphate or a dimorpholinophosphate polar head group

Some previously synthesized (perfluoroalkyl)alkyldimorpholinophosphates, C(n)F(2n+1)C(m)H(2m)OP(O)-[N(CH(2)CH(2))(2)O](2), were found remarkably to stabilize heat sterilizable water-in-fluorocarbon reverse emulsions and to have a strong proclivity to self-aggregate into microtubular assemblies when dispersed in water. This series has now been extended in order to allow structure-property relationships to be established and product optimization to be achieved. A new series of even more fluorophilic compounds consisting in bis[(perfluoroalkyl)alkyl]monomorpholinophosphates, (C(n)F(2n+1)C(m)H(2m)O)(2)P(O)N(CH(2)CH(2))(2)O, was also synthesized. Preliminary surfactant activity and biocompatibility data are presented and compared to data obtained with non-fluorinated analogues.