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Published July 26, 2006 | Accepted Version
Journal Article Open

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-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.

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).

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Accepted Version - nihms-61215.pdf


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