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231224s2014 xx |||||o 00| ||eng c |
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|a 10.1021/la403789a
|2 doi
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|a pubmed24n0778.xml
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|a (NLM)24328351
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|a DE-627
|b ger
|c DE-627
|e rakwb
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|a eng
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|a Liu, Wenjun
|e verfasserin
|4 aut
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|a Multifunctional silicon surfaces
|b reaction of dichlorocarbene generated from Seyferth reagent with hydrogen-terminated silicon (111) surfaces
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|c 2014
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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 22.08.2014
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|a Date Revised 16.11.2017
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a Insertion of dichlorocarbene (:CCl2), generated by decomposition of the Seyferth reagent PhHgCCl2Br, into the Si-H bond of a tertiary silane to form a Si-CCl2H group is an efficient homogeneous, molecular transformation. A heterogeneous version of this reaction, between PhHgCCl2Br and a silicon (111) surface terminated by tertiary Si-H bonds, was studied using a combination of surface-sensitive infrared and X-ray photoelectron spectroscopies. The insertion of dichlorocarbene into surface Si-H bonds parallels the corresponding reaction of silanes in solution, to produce surface-bound dichloromethyl groups (Si-CCl2H) covering ∼25% of the silicon surface sites. A significant fraction of the remaining Si-H bonds on the surface was converted to Si-Cl/Br groups during the same reaction, with PhHgCCl2Br serving as a halogen atom source. The presence of two distinct environments for the chlorine atoms (Si-CCl2H and Si-Cl) and one type of bromine atom (Si-Br) was confirmed by Cl 2p, Br 3d, and C 1s X-ray photoelectron spectroscopy. The formation of reactive, halogen-terminated atop silicon sites was also verified by reaction with sodium azide or the Grignard reagent (CH3MgBr), to produce Si-N3 or Si-Me functionalities, respectively. Thus, reaction of a hydrogen-terminated silicon (111) surface with PhHgCCl2Br provides a facile route to multifunctional surfaces possessing both stable silicon-carbon and labile silicon-halogen sites, in a single pot synthesis. The reactive silicon-halogen groups can be utilized for subsequent transformations and, potentially, the construction of more complex organic-silicon hybrid systems
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|a Journal Article
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|a Research Support, U.S. Gov't, Non-P.H.S.
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|a Hydrocarbons, Chlorinated
|2 NLM
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|a Indicators and Reagents
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|a Hydrogen
|2 NLM
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|a 7YNJ3PO35Z
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|a dichlorocarbene
|2 NLM
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|a E73HG1090V
|2 NLM
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|a Silicon
|2 NLM
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|a Z4152N8IUI
|2 NLM
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|a Sharp, Ian D
|e verfasserin
|4 aut
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|a Tilley, T Don
|e verfasserin
|4 aut
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| 773 |
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|i Enthalten in
|t Langmuir : the ACS journal of surfaces and colloids
|d 1992
|g 30(2014), 1 vom: 14. Jan., Seite 172-8
|w (DE-627)NLM098181009
|x 1520-5827
|7 nnns
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|g volume:30
|g year:2014
|g number:1
|g day:14
|g month:01
|g pages:172-8
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|u http://dx.doi.org/10.1021/la403789a
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