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Title: Functionalization of acetylene-terminated monolayers on Si(100) surfaces: a click chemistry approach
Authors: Ciampi, S
Bocking, T
Kilian, KA
James, M
Harper, JB
Gooding, JJ
Keywords: X-ray photoelectron spectroscopy
Issue Date: 28-Aug-2007
Publisher: American Chemical Society
Citation: Ciampi, S., Bocking, T., Kilian, K. A., James, M., Harper, J. B., & Gooding, J. J. (2007). Functionalization of acetylene-terminated monolayers on Si(100) surfaces: a click chemistry approach. Langmuir, 23(18), 9320-9329. doi:10.1021/la701035g
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. © 2007, American Chemical Society
Gov't Doc #: 1165
ISSN: 0743-7463
Appears in Collections:Journal Articles

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