Efficient Preparation of Novel Phenolic Surfactants for Self-Assembled Monolayers

Abstract

Novel molecules have been synthesized that combine the phenolic nature of tannins and self-assembling properties of surfactants. These single-chain (C12) surfactants with potential biocompatibility have been synthesized with an ω-thiol or disulfide functionality, both commonly used anchors in self-assembly onto gold surfaces, using a modular route. Protecting groups for the phenol and thiol moieties played a key role for overcoming the challenges often associated with the purification of surfactants. The tasks of unmasking the thiol moiety and simultaneously deprotecting the acetyl protecting groups of the phenols were accomplished using sodium thiomethoxide. This modular route can be extended to synthesize other surfactants with the potential ability to form robust layers with biocompatible properties. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]