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Covalent Attachment of Acetylene and Methylacetylene Functionality to Si(111) Surfaces: Scaffolds for Organic Surface Functionalization while Retaining Si−C Passivation of Si(111) Surface Sites

Hurley, Patrick T. and Nemanick, E. Joseph and Brunschwig, Bruce S. and Lewis, Nathan S. (2006) Covalent Attachment of Acetylene and Methylacetylene Functionality to Si(111) Surfaces: Scaffolds for Organic Surface Functionalization while Retaining Si−C Passivation of Si(111) Surface Sites. Journal of the American Chemical Society, 128 (31). pp. 9990-9991. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170424-100851525

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Abstract

Si(111) surfaces have been functionalized with Si−C⋮C−R species, where R = H or –CH_3, using a two-step reaction sequence involving chlorination of H−Si(111) followed by treatment with Na−C⋮C−H or CH_3−C⋮C−Na reagents. The resulting surfaces showed no detectable oxidation as evidenced by X-ray photoelectron spectroscopic (XPS) data in the Si 2p region, electrochemical measurements of Si−H oxidation, or infrared spectroscopy. The Si−C⋮C−R-terminated surfaces exhibited a characteristic C⋮C stretch in the infrared at 2179 cm^(-1), which was strongly polarized perpendicular to the Si(111) surface plane. XPS measurements in the C 1s region showed a low binding energy peak indicative of Si−C bonding, with a coverage that was, within experimental error, identical to that of the CH_3-terminated Si(111) surface, which has been shown to fully terminate the Si atop sites on an unreconstructed Si(111) surface. The Si−C⋮C−H-terminated surfaces were further functionalized by exposure to n-C_4H_9Li followed by exposure to para Br−C_6H_5−CF_3, allowing for introduction of para –C_6H_5CF_3 groups while maintaining the desirable chemical and electrical properties that accompany complete Si−C termination of the atop sites on the Si(111) surface.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja061969bDOIArticle
ORCID:
AuthorORCID
Nemanick, E. Joseph0000-0002-4650-6491
Brunschwig, Bruce S.0000-0002-6135-6727
Lewis, Nathan S.0000-0001-5245-0538
Additional Information:© 2006 American Chemical Society. Received March 31, 2006. Publication Date (Web): July 13, 2006. We acknowledge the Beckman Institute and NSF Grants CHE-0213589 and 0604894 for generous support.
Funders:
Funding AgencyGrant Number
Caltech Beckman InstituteUNSPECIFIED
NSFCHE-0213589
NSFCHE-0604894
Issue or Number:31
Record Number:CaltechAUTHORS:20170424-100851525
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170424-100851525
Official Citation:Covalent Attachment of Acetylene and Methylacetylene Functionality to Si(111) Surfaces: Scaffolds for Organic Surface Functionalization while Retaining Si−C Passivation of Si(111) Surface Sites Patrick T. Hurley, E. Joseph Nemanick, Bruce S. Brunschwig, and Nathan S. Lewis Journal of the American Chemical Society 2006 128 (31), 9990-9991 DOI: 10.1021/ja061969b
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76843
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:24 Apr 2017 17:22
Last Modified:29 Oct 2020 19:26

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