In situ Raman monitoring triazole formation from self-assembled monolayers of 1,4-diethynylbenzene on Ag and Au surfaces via click cyclization

We prepared acetylenyl-terminated aromatic self-assembled monolayers (SAMs) of 1,4-diethynylbenzene on silver and gold. After the fabrication of pendent acetylenyl SAMs, the formation of triazoles was performed via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition click chemistry. A density functional theory (DFT) calculation of Raman frequencies showed good agreement with our experimental data to provide evidence of the formation of the triazole molecule. Our results indicated that click chemistry could be successfully applied to simple aromatic SAMs proximate (<1 nm) to roughened gold surfaces. The reaction process could be monitored in real time by measuring intensity changes of the V(C-C)free band in surface-enhanced Raman scattering (SERS) spectra. (c) 2007 Elsevier Inc. All rights reserved.