“Clickable” SBA-15 mesoporous materials: synthesis, characterization and their reaction with alkynes

Abstract

SBA-15 mesoporous silica has been functionalized with azidopropyl groups through both one-pot co-condensation and post-synthetic grafting. For both these methodologies, azidopropyltriethoxysilane was used to introduce the azidopropyl groups. The azidopropyl modified SBA-15 material synthesized by one-pot co-condensation had hexagonal crystallographic order, pore diameters up of 50 A, and the content of azidopropyl groups was found to be 1.3 mmol g À1 . The presence of the azidopropyl group was confirmed by multinuclear ( 13 C, 29 Si) solid state NMR and IR spectroscopy. Both these materials underwent very efficient Cu(I)-catalyzed azide alkyne ''click'' reaction (CuAAC) with a variety of alkynes. Nearly 85% of the azide present in the SBA-15 material was converted to the corresponding triazole when propargyl alcohol was used as the substrate. This methodology was also used to incorporate mannose into SBA-15. Incubation of this mannose labeled SBA-15 with fluorescein labeled Concanavalin-A led to the formation of a fluorescent silica-protein hybrid material. The ease of synthesis for the azide labeled SBA-15 material together with its ability to undergo very efficient chemoselective CuAAC in water would make it a very attractive platform for the development of covalently anchored catalysts, enzymes and sensors.

Photophysical studies of newly derivatized mono substituted phthalocyanines grafted onto silica nanoparticles via click chemistry

“…5(i) shows the SiAOASi peak at 1072 cm À1 , and the N 3 peak at 2101 cm À1 , the azide peak can be clearly observed as shown in the enlarged spectrum (see inset). Similar azide peaks have been observed in literature [11,25]. Fig.…”

“…The synthesis of silica nanoparticles functionalized with azide groups (SiNPs-N 3 ) has been reported in literature [24,25].…”

Synthesis and characterization of photoreactive silica nanoparticles for super-hydrophobic cotton fabrics application

“…3-Azido-propyltriethoxysilane was prepared according to the literature 27 with minor modifications. 3-Chloropropyltriethoxysilane (4.000 g, 16.6 mmol) was added to the solution of sodium azide (2.160 g, 33.2 mmol) and tetrabutylammonium bromide (1.288 g, 4.0 mmol) in dry acetonitrile (100 mL) in a nitrogen atmosphere.…”

High‐Density Glycosylation of Polymer Membrane Surfaces by Click Chemistry for Carbohydrate–Protein Recognition

“…[23] A non-specific interaction between Con A and a hydrophilic 1,2,3-triazole-functionalized surface has also been illustrated. [24] Therefore, in our case, the enhancement of fluorescent intensity on the membrane surface can be ascribed to the triazole moieties. Despite this, the fluorescent intensity is much lower than that of FL-Con A adsorption.…”