Synthesis and self-assembling behavior of F-amphiphilic functionalized amines

A simple route to fluoroalkylated functionalized secondary amines is proposed by the treatment of 2-perfluoroalkylprop-2-enoic acids with various primary amines. Two of these compounds were obtained from oxyethylenic diamine and present an amphiphilic structure.These compounds exhibit an excellent surface activity since they are lowering the surface tension to 18–20 mN/m and this, at very low concentrations (around 10−5 M). DLS measurements and TEM studies show an original behavior of the monocatenar fluorinated surfactants 5n and 5o, which are able to spontaneously self-assembles into vesicles, and therefore it makes them suitable candidates as carriers in drug or gene delivery systems.

A very simple and efficient access to novel fluorinated/hydrogenated secondary amines, starting from commercially available fluorinated acids and a variety of primary hydrogenated amines, is described. By combining a rigid fluorinated hydrophobic tag and a flexible ethylenoxide moiety, one can design original monocatenar lipids, which are able to spontaneously form vesicles in water.Figure optionsDownload as PowerPoint slideHighlights
► An efficient pathway to novel fluorinated secondary amines from fluorinated acids is described.
► A primary amine substitutes the vinylic F by Michael addition and elimination of fluoride.
► Aminoethoxilated monocatenar F-surfactants are spontaneously self-assembling into vesicles.