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A Non-Oxidative Approach toward Chemically and Electrochemically Functionalizing Si(111)

Rohde, Rosemary D. and Agnew, Heather D. and Yeo, Woon-Seok and Bailey, Ryan C. and Heath, James R. (2006) A Non-Oxidative Approach toward Chemically and Electrochemically Functionalizing Si(111). Journal of the American Chemical Society, 128 (29). pp. 9518-9525. ISSN 0002-7863. PMCID PMC3695602. https://resolver.caltech.edu/CaltechAUTHORS:20170509-155331656

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Abstract

A general method for the non-oxidative functionalization of single-crystal silicon(111) surfaces is described. The silicon surface is fully acetylenylated using two-step chlorination/alkylation chemistry. A benzoquinone-masked primary amine is attached to this surface via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition (“click” chemistry). The benzoquinone is electrochemically reduced, resulting in quantitative cleavage of the molecule and exposing the amine terminus. Molecules presenting a carboxylic acid have been immobilized to the exposed amine sites. X-ray photoelectron spectroscopy (XPS), Fourier transform infrared spectroscopy (FTIR), cyclic voltammetry (CV), and contact angle goniometry were utilized to characterize and quantitate each step in the functionalization process. This work represents a strategy for providing a general platform that can incorporate organic and biological molecules on Si(111) with minimal oxidation of the silicon surface.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ja062012bDOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3695602PubMed CentralArticle
ORCID:
AuthorORCID
Heath, James R.0000-0001-5356-4385
Additional Information:© 2006 American Chemical Society. Received March 23, 2006. Publication Date (Web): July 1, 2006. R.D.R. thanks the Hispanic Scholarship Fund and the Bill and Melinda Gates Foundation. H.D.A. is supported by the National Science Foundation Graduate Research Fellowship. We acknowledge support from the National Cancer Institute, the Institute for Collaborative Biotechnologies funded by the Army Research Office, and a subcontract from the MITRE Corporation for support of this research. The XPS measurements were carried out at the Molecular Materials Research Center of the Beckman Institute at Caltech. We thank Professor Nate Lewis, Dr. Pat Hurley, and Dr. Joe Nemanick for kind advice and help regarding the acetylenylation of Si(111).
Funders:
Funding AgencyGrant Number
Hispanic Scholarship FundUNSPECIFIED
Bill and Melinda Gates FoundationUNSPECIFIED
NSF Graduate Research FellowshipUNSPECIFIED
National Cancer InstituteUNSPECIFIED
Army Research Office (ARO)UNSPECIFIED
MITRE CorporationUNSPECIFIED
NIHUNSPECIFIED
Issue or Number:29
PubMed Central ID:PMC3695602
Record Number:CaltechAUTHORS:20170509-155331656
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170509-155331656
Official Citation:A Non-Oxidative Approach toward Chemically and Electrochemically Functionalizing Si(111) Rosemary D. Rohde, Heather D. Agnew, Woon-Seok Yeo, Ryan C. Bailey, and James R. Heath Journal of the American Chemical Society 2006 128 (29), 9518-9525 DOI: 10.1021/ja062012b
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77315
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:16 May 2017 21:59
Last Modified:23 Dec 2019 16:57

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