Synthesis of phospholipids containing perfluorooctyl group and their interfacial properties

Highly fluorinated single-chained and/or double-chained phospholipids containing the perfluorooctyl group as the terminal segment of hydrophobic chains and a phosphocholine moiety as the hydrophilic headgroup were synthesized in order to investigate the effect of fluorinated segments on the stability of phospholipid monolayers formed at the air–water interface. Judging from the equilibrium spreading pressures (πes) of their monolayers at the air–water interface, all of the fluorinated phospholipids formed more stable monolayers than the corresponding non-fluorinated counterparts. In addition, the fluorinated double-chained phosphatidylcholine containing C–C triple bond (monoyne group) formed stable and fluid vesicle membranes in water, although the single-chained phospholipids did not form vesicle membranes but micellar solutions under the present conditions.

Graphical abstractIntroduction of the perfluorooctyl moiety into the alkyn compound under the mild condition was successful by using Na2S2O4 as a free radical initiator to yield the flexible hydrophobic components of fluorinated phosphatidylcholine. The fluorinated phosphatidylcholine formed stable and fluid vesicle membrane in water at ambient temperature. Figure optionsDownload full-size imageDownload as PowerPoint slide