Synthesis and characterization of tri-block fluorinated-n-alkanes

A series of triblock semifluorinated n-alkanes of general formula F(CF2)n(CH2)m(CF2)nF (n = 6, 8 and m = 4, 6, 8) have been synthesized and characterized. The synthesis of triblock compounds was performed in two different ways according to the length of the hydrogenated moiety. Coupling of two molecules of β-(perfluoro-n-alkyl)ethyl iodides leads to the triblock materials F(CF2)6(CH2)4(CF2)6F and F(CF2)8(CH2)4(CF2)8F. The synthesis of compounds with larger hydrogenated part is accomplished in two steps by the addition of perfluoro-n-alkyl iodide F(CF2)nI to 1,5-hexadiene and 1,7-octadiene, respectively to give the diiodo-adducts which are subsequently deiodinated to the final triblock products F(CF2)6(CH2)6(CF2)6F, F(CF2)6(CH2)8(CF2)6F, F(CF2)8(CH2)6(CF2)8F and F(CF2)8(CH2)8(CF2)8F. The obtained triblock semifluorinated n-alkanes are characterized by low surface free energies with good lubricant properties usable as additives in ski-wax formulations.

Triblock semifluorinated n-alkanes are obtained, for instance, by double addition of perfluoroalkyl iodides F(CF2)nI to a linear diene to give the corresponding diiodo adducts and subsequent deiodination under reductive conditions.Figure optionsDownload as PowerPoint slide