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. 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.