Comparing the reactivity of alkynes and alkenes on silicon (100) surfaces

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dc.contributor.authorNg, Aen_AU
dc.contributor.authorCiampi, Sen_AU
dc.contributor.authorJames, Men_AU
dc.contributor.authorHarper, JBen_AU
dc.contributor.authorGooding, JJen_AU
dc.date.accessioned2010-01-21T05:16:58Zen_AU
dc.date.accessioned2010-04-30T05:05:18Zen_AU
dc.date.available2010-01-21T05:16:58Zen_AU
dc.date.available2010-04-30T05:05:18Zen_AU
dc.date.issued2009-12-15en_AU
dc.date.statistics2009-12-15en_AU
dc.description.abstractThe relative reactivities of alkynes to alkenes on hydrogen-terminated silicon (100) surfaces, under conditions where a monolayer will be produced via hydrosilylation, were measured using two different approaches. The first approach was to form monolayers from a series of solutions containing different mole fractions of an alkyne, with a trifluorothioacetate distal moiety and an alkene with a terminal carboxylic acid functional. X-ray photoelectron spectroscopic analysis of the resultant surfaces showed that the mole fraction of alkyne on the surface was larger than that in the respective alkyne/alkene mixture. By filling the XPS data, we estimated that the reactivity ratio of alkynec to alkene was approximately 1.7 +/- 0.2 when monolayers were formed at 120 degrees C. The second approach was using a molecule containing both an alkyne at one end and an alkene at the other, non-1-yne-8-ene, as the hydrosilylation reagent such that either end Could attach to the silicon surface. The relative orientation of this molecule, once reacted with it hydrogen-terminated Si(100) surface, was determined by coupling ail additional reagent to the distal end of the monolayer. The reagent used was azidoferrocene, which could attach onto free alkyne moieties on the surface only via the 1,3-Huisgen cycloaddition "click" reaction. Electrochemical analysis was then used to determine how many ferrocene moieties were attached to the SAM surface. In this way, it was shown that the alkyne end reacted preferentially with the silicon surface compared with the alkene end. The reactivity ratio of the alkyne end to the alkene end was increased front 2.0 +/- 0.2 to 9 +/- 1 when the temperature was decreased from 120 to 65 degrees C. © 2009, American Chemical Societyen_AU
dc.identifier.citationNg, A., Ciampi, S., James, M., Harper, J. B., & Gooding, J. J. (2009). Comparing the reactivity of alkynes and alkenes on silicon (100) surfaces. Langmuir, 25(24), 13934-13941. doi:10.1021/la901526een_AU
dc.identifier.govdoc1346en_AU
dc.identifier.issn0743-7463en_AU
dc.identifier.issue24en_AU
dc.identifier.journaltitleLangmuiren_AU
dc.identifier.pagination13934-13941en_AU
dc.identifier.urihttp://dx.doi.org/10.1021/la901526een_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/2732en_AU
dc.identifier.volume25en_AU
dc.language.isoenen_AU
dc.publisherAmerican Chemical Societyen_AU
dc.subjectAlkynesen_AU
dc.subjectAlkenesen_AU
dc.subjectReactivityen_AU
dc.subjectSiliconen_AU
dc.subjectSurfacesen_AU
dc.subjectHydrogenen_AU
dc.titleComparing the reactivity of alkynes and alkenes on silicon (100) surfacesen_AU
dc.typeJournal Articleen_AU
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