Tandem "click" reactions at acetylene-terminated Si(100) monolayers
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We demonstrate a simple method for coupling alkynes to alkynes. The method involves tandem azide-alkyne cycloaddition reactions ("click" chemistry) for the immobilization of 1-alkyne species onto an alkyne modified surface in a one-pot procedure. In the case presented, these reactions take place on a nonoxidized Si(100) surface although the approach is general for linking alkynes to alkynes. The applicability of the method in the preparation of electrically well-behaved functionalized surfaces is demonstrated by coupling an alkyne-tagged ferrocene species onto alkyne-terminated Si(100) surfaces. The utility of the approach in biotechnology is shown by constructing a DNA sensing interface by derivatization of the acetylenyl surface with commercially available alkyne-tagged oligonucleotides. Cyclic voltametry, electrochemical impedance spectroscopy, X-ray photoelectron spectroscopy, and X-ray reflectometry are used to characterize the coupling reactions and performance of the final modified surfaces. These data show that this synthetic protocol gives chemically well-defined, electronically well-behaved, and robust (bio)functionalized monolayers on silicon semiconducting surfaces. © 2011 American Chemical Society.
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Ng, A.; Ciampi, Simone; James, M.; Harper, J.; Gooding, J. (2009)The relative reactivities of alkynes to alkenes on hydrogen-terminated silicon (100) surfaces, under conditions where a monolayer will be produced via hydrosilylation, were measured using two different approaches. The ...
James, M.; Ciampi, Simone; Darwish, T.; Hanley, T.; Sylvester, S.; Gooding, J. (2011)We have examined the nanoscale adsorption of molecular water under ambient conditions onto a series of well-characterized functionalized surfaces produced by Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC or "click") ...
Silicon (100) electrodes resistant to oxidation in aqueous solutions: An unexpected benefit of surface acetylene moietiesCiampi, Simone; Eggers, P.; Le Saux, G.; James, M.; Harper, J.; Gooding, J. (2009)Here we report on the functionalization of alkyne-terminated alkyl monolayers on highly doped Si(100) using "click" reactions to immobilize ferrocene derivatives. The reaction of hydrogen-terminated silicon surfaces with ...