Spontaneous assembly of silylethane-thiol derivatives on Au(111): A chemically robust thiol protecting group as the precursor for the direct formation of aromatic gold thiolate monolayers

Abstract

Self-assembled monolayers (SAMs) on gold were obtained by the direct absorption of a fully conjugated phenylenethienylene derivative (4) presenting robust silylethane-thiol protecting groups as anchoring agents. The thiol deprotection and SAM formation have been evidenced by quartz crystal microbalance (QCM) measurements and X-ray photoelectron spectroscopy (XPS), and have been compared to the SAM obtained from its thioacetate analog (5). The chemically robust silylethane-thiol protecting group appeared as a surprisingly effective anchoring agent for the preparation of aromatic SAMs on Au(111), suitable for subsequent post-functionalization.