Functionalization of SBA-15 Mesoporous Materials using “Thiol–Ene Click” Michael Addition Reaction

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.

Guanine/Ionic Liquid Derived Ordered Mesoporous Carbon Decorated with AuNPs as Efficient NADH Biosensor and Suitable Platform for Enzymes Immobilization and Biofuel Cell Design

“…It affects the interaction between enzyme and support, the configuration of immobilized enzyme, the diffusion rate of substrate, and the accessibility of active site which determines the eventual catalytic activity, stability, and reusability of the immobilized enzyme . Chemical properties of the internal surface of mesoporous materials can be tuned facility by functionalization with various organic groups offering a great opportunity to impart desired microenvironment properties to the immobilized enzymes . These properties of the mesoporous materials (high electrocatalytic activity and suitable host for enzymes) make them as an efficient electrochemical support for cofactor‐dependent dehydrogenase enzymes, whose activity requires the presence of an electron‐carrying cofactor (e. g., β‐nicotinamide adenine dinucleotide (NAD + )) in the Rossmann fold of the protein.…”

Modular Thiol–Ene Chemistry Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls

“…The resulting material showed high catalytic activity and easy reusability in dioxirane‐mediated epoxidation reactions of alkenes. More recently, thiol–ene click reactions have also been used to access surface‐functionalized SBA‐15 or MCM‐41 silica mesophases 43. 44…”

“…More recently, thiol-ene click reactions have also been used to access surface-functionalized SBA-15 or MCM-41 silica mesophases. [43,44] Following our multiple research activities in the field of the synthesis of surface-functionalized mesoporous silicas, [45][46][47] we focused herein on postsynthetic modification of functionalized silica. This manuscript reports on the synthesis of silica precursor monoliths with double bonds or thiol groups and their functionalization by thiol-ene reaction with complementary thiols and olefins, respectively.…”

Sustaining guest molecules on bio-surfaces by grafting the surfaces with cyclodextrins

“…The reaction can proceed under a mild base (Kumari, Malvi, Ganai, Pillai, & Sen Gupta, 2011;Wong et al, 2010) or nucleophilic catalyst (Chan, Hoyle, & Lowe, 2009) or even in the absence of catalyst in strongly polar solvents, such as water (Kakwere & Perrier, 2009). That M-␤-CD is a good choice for biological functionalization is because a number of biomaterials contain proteins with cysteine residues (thiol source), thus fitting well with our platform.…”