Functionalization of SBA-15 Mesoporous Materials using “Thiol–Ene Click” Michael Addition Reaction
Citations Over TimeTop 12% of 2011 papers
Abstract
Methacrylate-labeled SBA-15 has been successfully synthesized from calcined SBA-15 and commercially available 3-trichlorosilyl propylmethacrylate. This material undergoes efficient thiol–ene “click reaction” with a variety of both thiol and disulfide-containing substrates in aqueous and organic media. The products were thoroughly characterized by a variety of analytical techniques including multinuclear (13C, 29Si) solid-state NMR, TG-DTA, and nitrogen adsorption desorption studies. Disulfide-containing substrates in which the TCEP-mediated reduction of the disulfide bond and its subsequent addition to the methacrylate group anchored in SBA-15 in one-pot were used to synthesize a silica–protein hybrid material composed of biotin-labeled SBA-15 and streptavidin. Electrochemically active material was synthesized from the reaction of ferrocene-containing thiol and the methacrylate-labeled SBA-15. The ease of synthesis for the methacrylate-labeled SBA-15 material together with its ability to undergo efficient chemoselective thiol–ene reaction would make it a very attractive platform for the development of covalently anchored enzymes and sensors.
Related Papers
- → Synthetic studies on arene-olefin cycloadditions-VIII. Total syntheses of (±)-silphiperfol-6-ene, (±)-7 α H-silphiperfol-5-ene and (±)-7 β H-silphiperfol-5-ene(1985)46 cited
- → Product yields in the reactions of ozone with Z-but-2-ene, E-but-2-ene and 2-methylbut-2-ene(1999)31 cited
- → Gas-phase rate coefficients for the reactions of nitrate radicals with (Z)-pent-2-ene, (E)-pent-2-ene, (Z)-hex-2-ene, (E)-hex-2-ene, (Z)-hex-3-ene, (E)-hex-3-ene and (E)-3-methylpent-2-ene at room temperature(2005)17 cited
- → Thermal conductivities of hex-1-ene, hept-1-ene, oct-1-ene, and dec-1-ene at 302?374 K(1988)
- → Stereoselective Polymerization of Higher Alk-1-enes: Isotactic Poly(hex-1-ene) and Poly(oct-1-ene); Syndiotactic Poly(hex-1-ene) and Poly(oct-1-ene)(2011)