Silicon and silicon oxide surface modification using thiamine-catalyzed benzoin condensations

Abstract

The benzoin condensation that involves the umpolung coupling of two aldehyde groups has been applied to the formation of functionalized silicon and silicon oxide surfaces using thiamine and other N-heterocyclic carbene (NHC) catalysis in water. This bioorthogonal conjugation of an aldehyde to a modified silicon or silicon oxide surface has been monitored and characterized using X-ray photoelectron spectroscopy and IR spectroscopy. NHC catalysis was found to be efficient in water mediating full conversion of the aldehyde functionalized silicon oxide surfaces at the interface.