Synthesis and properties of functionalized oligo(arylene) molecular wires with thiolated termini: competing thiol-Au and nitro-Au assembly

The synthesis by Suzuki cross-coupling methodology of oligo(arylene) molecular wires with protected thiolates at both termini and a central electron-acceptor unit (3,5-dinitrofluorenone) or an electron-donor unit [9-(1,3-dithiol-2-ylidene)fluorene] in the backbone is described. The studies have shown that thiolated molecules that possess strongly electron-withdrawing core units containing nitro groups are not suitable for controlled assembly in junctions.