Preparation of a new class of cleavable surfactants based on the silicon-carbon bond

Abstract

The ability of silicon to direct electrophiles to the ipso-position is used in developing a new class of cleavable amphiphiles containing an acid labile siliconcarbon (aromatic) bond. The synthesis of these amphiphiles is carried out in four steps to yield the positively charged surfactants 4, in 37–50% overall yield. The amphiphiles are soluble in a variety of solvents as disparate as benzene and water. They are indefinitely stable in the air, in all of the solvents used in this study, and in aqueous solution over a range of pH values from 3–14. Around a pH of 1, the surfactant molecules are cleaved in less than 5 min, resulting in aqueous and organic soluble moieties that are easily recovered. The cleavage is independent of the kind of acid used.