Application of clickable nanoporous silica surface for immobilization of ionic liquids
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Ghodsi Mohammadi Ziarani Department of Chemistry, Faculty of Science, Alzahra University, Tehran, Iran (Received 13 June 2011; accepted 14 October 2011)
A clickable surface was prepared using nanoporous SBA-15 support. Methylimidazolium, an ionic liquid, was immobilized on this surface through the click reaction. Detailed characterization using nitrogen adsorption, elemental analysis, x-ray diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy, and thermogravimetric analysis showed that the ionic system was fixed inside the channels and the ordered porous structure remained stationary. Influence of this material on photoluminescence emission of 5-amino-4-hydroxy-7sulfonaphthalene-2-sulfonate anion (H-acid) in aqueous solutions was evaluated. This click reaction product can be used effectively for H-acid removal from wastewater. I. INTRODUCTION
Over the decade since the inception of click chemistry, this series of reactions has grown substantially. Cu(I)catalyzed 1,3-dipolar cycloaddition between an organic azide and a terminal alkyne is the most important reaction in this family because of its simplicity, reliability, and stereospecificity.1 Surface scientists have recognized the click reaction as a powerful tool for binding the linkages onto a surface. Clickable materials, species with click reaction capability, should contain the azide or alkyne groups. In this way, clickable polymers have been prepared using an acetylene-containing monomer.2 The click reaction was also used for the modification of block copolymers3 and cylindrical brush polymers.4 In addition, click reaction is suitable for the functionalization of metal nanoparticles,5 silicon wafer,6 silicon rugate filters,7 and porous silica surfaces.8,9 Recently, some significant researches on clickable mesoporous silica have been reported in the literatures. For example, grafting of monosaccharides on the surface of ordered mesoporous silica,10 immobilization of pincer catalysts on high pore volume, low surface area silica materials,11 and bi-functionalization of porous silicon rugate filters for biosensing applications.12 Clickable mesoporous silica is a suitable target for functionalization by biomolecules such as enzymes because of its very high grafting yield.8 Currently, immobilization of ionic liquids onto the organic and inorganic supports such as polymers, carbon nanotubes, silica, and alumina has attracted attention for different applications in catalysis,13–17 extraction,18,19 and
also in solar cells.20 Alkyl imidazolium cation is a common commercially available ionic liquid. Modification of TiO2 nanoparticles,21 nanocomposites,20 and MCM-4122 using this cation has also been reported. Among functionalization methods, ionic liquids have not been immobilized on the silica surface via click reaction. The importance of click chemistry in supported materials is not only because of anchoring an arbitrary species onto the surface but also because of the triazole ring formed during this reaction which often improves properties such
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