Functionalization of acetylene-terminated monolayers on Si(100) surfaces: a click chemistry approach

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dc.contributor.authorCiampi, Sen_AU
dc.contributor.authorBocking, Ten_AU
dc.contributor.authorKilian, KAen_AU
dc.contributor.authorJames, Men_AU
dc.contributor.authorHarper, JBen_AU
dc.contributor.authorGooding, JJen_AU
dc.date.accessioned2008-04-07T03:56:06Zen_AU
dc.date.accessioned2010-04-30T05:02:38Zen_AU
dc.date.available2008-04-07T03:56:06Zen_AU
dc.date.available2010-04-30T05:02:38Zen_AU
dc.date.issued2007-08-28en_AU
dc.date.statistics2007-08en_AU
dc.description.abstractIn 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 Societyen_AU
dc.identifier.citationCiampi, 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/la701035gen_AU
dc.identifier.govdoc1165en_AU
dc.identifier.issn0743-7463en_AU
dc.identifier.issue18en_AU
dc.identifier.journaltitleLangmuiren_AU
dc.identifier.pagination9320-9329en_AU
dc.identifier.urihttp://dx.doi.org/10.1021/la701035gen_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/1037en_AU
dc.identifier.volume23en_AU
dc.language.isoenen_AU
dc.publisherAmerican Chemical Societyen_AU
dc.subjectX-ray photoelectron spectroscopyen_AU
dc.subjectCopperen_AU
dc.subjectAlkynesen_AU
dc.subjectAzidesen_AU
dc.subjectSiliconen_AU
dc.subjectAdsorptionen_AU
dc.subjectProteinsen_AU
dc.subjectElectrodesen_AU
dc.titleFunctionalization of acetylene-terminated monolayers on Si(100) surfaces: a click chemistry approachen_AU
dc.typeJournal Articleen_AU
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