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231224s2012 xx |||||o 00| ||eng c |
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|a 10.1021/la203844v
|2 doi
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|a pubmed24n0710.xml
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|a (DE-627)NLM213023083
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|a (NLM)22081885
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|a eng
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1 |
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|a Zhang, Shuo
|e verfasserin
|4 aut
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|a Azide functional monolayers grafted to a germanium surface
|b model substrates for ATR-IR studies of interfacial click reactions
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|c 2012
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
|b c
|2 rdamedia
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|a ƒa Online-Ressource
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|2 rdacarrier
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|a Date Completed 25.04.2012
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|a Date Revised 10.01.2012
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|a published: Print-Electronic
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|a Citation Status PubMed-not-MEDLINE
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|a High-quality azide-functional substrates are prepared by a low temperature reaction of 11-bromoundecyltrichlorosilane with UV-ozone-treated germanium ATR-IR plates followed by nucleophilic substitution of the terminal bromine by addition of sodium azide. The resulting monolayer films are characterized by atomic force microscopy (AFM), contact angle analysis, X-ray photoelectron spectroscopy (XPS), attenuated total reflectance infrared spectroscopy (ATR-IR), and ellipsometry. XPS and ellipsometric thickness data correspond well to the results of molecular model calculations confirming the formation of a densely packed azide-functional monolayer. These azide-functional substrates enable interfacial "click" reactions with complementary alkyne-functional molecules to be studied in situ by ATR-IR. To illustrate their potential utility for kinetic studies we show that, in the presence of copper(I) catalyst, the azide-modified surfaces react rapidly and quantitatively with 5-chloro-pentyne to form triazoles via a 1,3-dipolar cycloaddition reaction. Time-resolved ATR-IR measurements indicate that the interfacial click reaction is initially first order in azide concentration as expected from the reaction mechanism, with a rate constant of 0.034 min(-1), and then transitions to apparent second order dependence, with a rate constant of 0.017 min(-1)/(chains/nm(2)), when the surface azide and triazole concentrations become similar, as predicted by Oyama et al. The reaction achieves an ultimate conversion of 50% consistent with the limit expected due to steric hindrance of the 5-chloro-pentyne reactant at the surface
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|a Journal Article
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|a Koberstein, Jeffrey T
|e verfasserin
|4 aut
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|i Enthalten in
|t Langmuir : the ACS journal of surfaces and colloids
|d 1992
|g 28(2012), 1 vom: 10. Jan., Seite 486-93
|w (DE-627)NLM098181009
|x 1520-5827
|7 nnns
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| 773 |
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|g volume:28
|g year:2012
|g number:1
|g day:10
|g month:01
|g pages:486-93
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|u http://dx.doi.org/10.1021/la203844v
|3 Volltext
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