Synthesis of oligo(para-phenylenevinylene) methyl thiols for self-assembled monolayers on gold surfaces

All-trans oligo(para-phenylenevinylene) (OPV) methyl thiols of a two-ring phenylene-vinylene dimer and a three-ring trimer have been synthesized to prepare self-assembled monolayers (SMS) onto an Au(1 1 1) surface. The molecular level morphologies of the monolayers prepared on Au surfaces were probed by scanning tunneling microscopy (STM) or atomic force microscopy (AFM). The soluble dimer formed a highly ordered structure lying down on the Au surfaces. The molecules of trimer stand slantwise on the Au surfaces, but the structure of monolayers is less ordered. Another longer OPV methyl thioacetate, a slightly soluble four-ring tetramer, has also been synthesized. Although it was difficult for aggregative molecules of the longer OPV to self-assemble on Au, we could successfully insert the tetramer into tetradecane-1-thiol monolayers on Au surfaces by an exchange reaction. The mixture monolayer showed that the isolated tetramer was adsorbed almost vertically on the Au surfaces.