Synthesis of Novel Alkyl- and Aryl Sulfides and Thiols as Precursors for Self-Assembled Monolayers on Gold

A series of 4-alkyl-1-bromosulfanylbenzenes having S-methyl 2, S-t-butyl 3, S-trityl 4, S-benzyl 5, and S-silylethoxymethyl 6 substituents were prepared and evaluated for their ability to form a monolayer consisting of anS-aryl adsorbate on Au (111) surface. The monolayer was formed via the selective hydrolytic removal of an alkyl group protecting the sulfur functionality upon adsorbtion onto the gold surface. Thiols having variable carbon chain length and a peripheral thiophene moiety 9, 10, 17, 18 and 23-26 were also prepared.