title: Functionalization of acetylene-terminated monolayers on Si(100) surfaces: a click chemistry approach.
abstract: In this article, we report the functionalization of alkyne-terminated alkyl monolayers on Si(100) using "click" chemistry, specifically, the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of azides with surface-bound alkynes. Covalently immobilized, structurally well-defined acetylene-terminated organic monolayers were prepared from a commercially available terminal diyne species using a one-step hydrosilylation procedure. Subsequent derivatization of the alkyne-terminated monolayers in aqueous environments with representative azide species via a selective, reliable, robust cycloaddition process afforded disubstituted surface-bound [1,2,3]-triazole species. Neither activation procedures nor protection/deprotection steps were required, as is the case with more established grafting approaches for silicon surfaces. Detailed characterization using X-ray photoelectron spectroscopy and X-ray reflectometry demonstrated that the surface acetylenes had reacted in moderate to high yield to give surfaces exposing alkyl chains, oligoether anti-fouling moieties, and functionalized aromatic structures. These results demonstrate that click immobilization offers a versatile, experimentally simple, chemically unambiguous modular approach to producing modified silicon surfaces with organic functionality for applications as diverse as biosensors and molecular electronics.
authors.affiliation: School of Chemistry, The University of New South Wales, Sydney, NSW, Australia.
authors.forename: Simone
authors.initials: S
authors.lastname: Ciampi
authors.forename: Till
authors.initials: T
authors.lastname: Böcking
authors.forename: Kristopher A
authors.initials: KA
authors.lastname: Kilian
authors.forename: Michael
authors.initials: M
authors.lastname: James
authors.forename: Jason B
authors.initials: JB
authors.lastname: Harper
authors.forename: J Justin
authors.initials: JJ
authors.lastname: Gooding