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

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2006-07, Vol.128 (29), p.9518-9525
Main Authors: Rohde, Rosemary D, Agnew, Heather D, Yeo, Woon-Seok, Bailey, Ryan C, Heath, James R
Format: Article
Language:English
Subjects:
Chemistry
Crystallization
Electrochemistry
Exact sciences and technology
General and physical chemistry
Kinetics and mechanism of reactions
Molecular Structure
Oxidation-Reduction
Semiconductors
Silicon - chemistry
Surface Properties
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja062012b