《Click Chemistry in Mesoporous Materials Functionalization of Porous Silicon Rugate Filters》.pdf

5888 Langmuir 2008, 24, 5888-5892 Click Chemistry in Mesoporous Materials: Functionalization of Porous Silicon Rugate Filters Simone Ciampi, Till Böcking, Kristopher A. Kilian, Jason B. Harper, and J. Justin Gooding* School of Chemistry, The UniVersity of New South Wales, Sydney, NSW, 2052 Australia Recei Ved February 9, 2008. ReVised Manuscript ReceiVed February 28, 2008 In this paper we report the use of the optical properties of porous silicon photonic crystals, combined with the chemical versatility of acetylene-terminated SAMs, to demonstrate the applicability of “click” chemistry to mesoporous materials. Cu(I)-catalyzed alkyne-azide cycloaddition reactions were employed to modify the internal pore surfaces through a two-step hydrosilylation/cycloaddition procedure. A positive outcome of this catalytic process, here performed in a spatially confined environment, was only observed in the presence of a ligand-stabilized Cu(I) species. Detailed characterization using Fourier transform infrared spectroscopy and optical reflectivity measurements demonstrated that the surface acetylenes had reacted in moderate to high yield to afford surfaces exposing chemical functionalities of interest. The porous silicon photonic crystals modified by the two-step strategy, and exposing oligoether moieties, displayed improved resistance toward the nonspecific adsorption of proteins as determined with fluorescently labeled bovine serum albumin. These results demonstrate that “click” immobilization offers a versatile, experimentally simple,