Kinetics of 1,3-dipolar cycloaddition on the surfaces of Au nanoparticles

Triazole formation via 1,3-dipolar cycloaddition, or “click” chemistry, is a powerful synthetic method for incorporating chemical functionality onto the surfaces of Au nanoparticles. To investigate the factors that govern azide/alkyne reactivity at particle surfaces, we measured the general kinetic trends for the uncatalyzed reaction using FTIR spectroscopy. This study examines the roles of ligand length, electronic substitution of the alkyne species, and solvent on the reaction under pseudo-first-order conditions. The conversion of azide to triazole is found to depend more strongly on the relative surface coverage of azide terminated alkanethiol than on the ligand length and solvent.

Graphical abstractThe general kinetic trends for the uncatalyzed triazole formation on Au nanoparticle surfaces were measured using FTIR spectroscopy. This study examines the roles of ligand length, electronic substitution of the alkyne species, and solvent on the reaction under pseudo-first-order conditions. The conversion of azide to triazole is found to depend more strongly on the relative surface coverage of azide terminated alkanethiol than on the ligand length and solvent.Figure optionsDownload full-size imageDownload as PowerPoint slide