Synthesis of New Potential Hydrophobic Agents Composed of Three-Module Type Molecules

A new synthetic route was developed to three-module type potential hydrophobic agents, with the molecule consisting of an N-[3-(triethoxysilyl)propyl]amide anchor part (I), a connecting unit formed upon 1,3-propansultone ring cleavage (II), and a polyfluoroheptyloxy functional hydrophobic spacer (III). Proceeding from commercially available polyfluorinated heptanols 1a and 1b and 1,3-propanesultone 3, potassium sulfonates 4a and 4b were prepared. The reaction of 4a and 4b with phosphorus oxychloride resulted in the first synthesis of fluorine-containing sulfonyl chlorides 5a and 5b, which were reacted with 3-aminopropyltriethoxysilane 6 to give the target N-[3-(triethoxysilyl)propyl]-3-(polyfluoroheptyloxy)propane-1-sulfonamides 7a and 7b. The structures of the compounds were proved by NMR spectroscopy, mass spectrometry, and elemental analysis. The studies of their hydrophobizing properties are in progress.