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231223s2010 xx |||||o 00| ||eng c |
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|a 10.1021/la100858q
|2 doi
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|a pubmed24n0661.xml
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|a DE-627
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|a eng
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|a Scheres, Luc
|e verfasserin
|4 aut
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|a Self-assembly of organic monolayers onto hydrogen-terminated silicon
|b 1-alkynes are better than 1-alkenes
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|c 2010
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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
|b cr
|2 rdacarrier
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|a Date Completed 30.09.2010
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|a Date Revised 23.12.2020
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|a published: Print
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|a Citation Status PubMed-not-MEDLINE
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|a Recently, a new method for the preparation of high-quality organic monolayers with 1-alkynes at room temperature in the dark (i.e., without any external activation) was reported. To pinpoint the precise origin of this self-assembly process and to compare the reactivity of 1-alkenes and 1-alkynes toward hydrogen-terminated Si(111) [H-Si(111)], we followed the gradual formation of both monolayers at room temperature by static water contact angle measurements. Subsequently, attenuated total reflection infrared spectroscopy (ATR-IR) and X-ray photoelectron spectroscopy (XPS) were used to obtain detailed information about the structure and quality of the resulting monolayers. Our data clearly demonstrate that 1-alkynes are considerably more reactive toward H-Si(111) than 1-alkenes. 1-Alkynes are able to self-assemble into densely packed hydrophobic monolayers without any external activation (i.e., at room temperature under ambient light and even in the dark) whereas for 1-alkenes under the same conditions hardly any reactivity toward H-Si(111) was observed. The self-assembly of 1-alkynes on H-Si(111) at room temperature is explained by three factors: the higher nucleophilicity of 1-alkynes, which results in a facile attack at the electron-hole pairs at the H-Si surface and easy Si-C bond formation, the stabilization of the beta radical by delocalization over the double bond, and the lower-energy barrier encountered for H abstractions
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|a Journal Article
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|a Giesbers, Marcel
|e verfasserin
|4 aut
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|a Zuilhof, Han
|e verfasserin
|4 aut
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|i Enthalten in
|t Langmuir : the ACS journal of surfaces and colloids
|d 1992
|g 26(2010), 13 vom: 06. Juli, Seite 10924-9
|w (DE-627)NLM098181009
|x 1520-5827
|7 nnns
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|g volume:26
|g year:2010
|g number:13
|g day:06
|g month:07
|g pages:10924-9
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|u http://dx.doi.org/10.1021/la100858q
|3 Volltext
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