Abstract
Dummy molecularly imprinted mesoporous silicates (MIMS-2) were made by co-condensation of tetraethyl orthosilicate (TEOS) with precursors of bi-functional mimic of 2-naphthol, 2,7-dihydroxynaphthalene, around triblock copolymer surfactant Pluronic (P123) micelles. The bi-functional template was linked to two functional monomers through thermally cleavable covalent bonds to generate imprint precursor. This provides the possibility of incorporating the target into the cross-linked mesoporous silicate matrix in the non-ionic surfactant templated sol-gel process. P123 was eluted by ethanol extraction and template molecules were removed by refluxing the materials in a mixture of dimethyl sulfoxide (DMSO) and water. MIMS-1 was prepared similarly except that 2-naphthol was used as template instead of 2,7-dihydroxynaphthalene. Solid phase extraction studies showed that MIMS-2 exhibited good retention and selectivity for 2-naphthol among its structural analogues. The mono-functional molecule 2-naphthol was unable to be incorporated into the silica matrix of mesoporous material by the identical method, and the resulting material MIMS-1 exhibits poor selectivity to the template analogues.
Graphical Abstract
References
[1] Katz A., Davis M.E., Molecular imprinting of bulk, microporous silica, Nature, 2000, 403, 286-289 10.1038/35002032Search in Google Scholar PubMed
[2] Gao D.M., Zhang Z.P., Wu M.H., Xie C.G., Guan G.J., Wang D.P., A Surface Functional Monomer-Directing Strategy for HighlyDense Imprinting of TNT at Surface of Silica Nanoparticles, J. Am. Chem. Soc., 2007, 129, 7859-7866 10.1021/ja070975kSearch in Google Scholar PubMed
[3] Trotta F., Drioli E., Baggiani C., Lacopo D., Molecular imprinted polymeric membrane for naringin recognition, J. Membr. Sci., 2002, 201, 77-84 10.1016/S0376-7388(01)00705-0Search in Google Scholar
[4] Kobayashi T., Reddy P.S., Ohta M., Abe M., Fujii N., Molecularly Imprinted Polysulfone Membranes Having Acceptor Sites for Donor Dibenzofuran as Novel Membrane Adsorbents: Charge Transfer Interaction as Recognition Origin, Chem. Mater., 2002, 14, 2499-2505 10.1021/cm0109692Search in Google Scholar
[5] Terry T.J., Stack T.D.P., Covalent Heterogenization of a Discrete Mn(II) Bis-Phen Complex by a Metal-Template/Metal-Exchange Method: An Epoxidation Catalyst with Enhanced Reactivity, J. Am. Chem. Soc., 2008, 130, 4945-4953 10.1021/ja0742030Search in Google Scholar PubMed PubMed Central
[6] Dai S., Hierarchically Imprinted Sorbents, Chem. Eur. J., 2001, 7, 763-768 10.1002/1521-3765(20010216)7:4<763::AID-CHEM763>3.0.CO;2-6Search in Google Scholar
[7] Paik P., Gedanken A., Mastai Y., Chiral separation abilities: Aspartic acid block copolymer-imprinted mesoporous silica, Micropor. Mesopor. Mater., 2010, 129, 82-89 10.1016/j.micromeso.2009.09.001Search in Google Scholar
[8] Johnson B.J., Melde B.J., Charles P.T., Cardona D.C., Dinderman M.A., Malanoski A.P., et al., Imprinted Nanoporous Organosilicas for Selective Adsorption of Nitroenergetic Targets, Langmuir., 2008, 24, 9024-9029 10.1021/la800615ySearch in Google Scholar
[9] Wang Y.Q., Yang Y.Y., Xu L., Zhang J., Bisphenol A sensing based on surface molecularly imprinted, ordered mesoporous silica, Electrochimica Acta., 2011, 56, 2105-2109 10.1016/j.electacta.2010.11.077Search in Google Scholar
[10] Mehdinia A., Ahmadifar M., Aziz-Zanjani M.O., Jabbari A., Hashtroudi M.S., Selective adsorption of 2,4-dinitrophenol on molecularly imprinted nanocomposites of mesoporous silica SBA-15/polyaniline, Analyst., 2012, 137, 4368-4374 10.1039/c2an16244jSearch in Google Scholar
[11] Jung B.M., Kim M.S., Kim W.J., Chang J.Y., Molecularly imprinted mesoporous silica particles showing a rapid kinetic binding, Chem. Commun., 2010, 46, 3699-3701 10.1039/c003173aSearch in Google Scholar PubMed
[12] Lofgreen J.E., Moudrakovski I.L., Ozin G.A., Molecularly Imprinted Mesoporous Organosilica, ACS Nano., 2011, 5, 2277- 2287 10.1021/nn1035697Search in Google Scholar PubMed
[13] Roch F., Alexander M., Biodegradation of hydrophobic compounds in the presence of surfactants, Environ. Toxicol. Chem., 1995, 14, 115-1158 10.1002/etc.5620140705Search in Google Scholar
[14] Li X., Liu D., Wang Z., Highly selective recognition of naphthol isomers based on the fluorescence dye-incorporated SH-- cyclodextrin functionalized gold nanoparticles, Biosen. Bioelectron., 2011, 26, 2329-2333 10.1016/j.bios.2010.10.005Search in Google Scholar PubMed
[15] Guo L.Q., Zeng Y.B., Guan A.H., Chen G.N., Preparation and characterization of molecularly imprinted silica particles for selective adsorption of naphthalene, Reactive & Function Polymers., 2011, 71, 1172-1176 10.1016/j.reactfunctpolym.2011.08.005Search in Google Scholar
[16] Mehdi A., Reye C., Brandes S., Guilard R., Corriu R.J.P., Synthesis of large ordered mesoporous silicas containing aminoprpyl groups, New Journal of Chemistry, 2005, 25, 965-968 10.1039/b502848pSearch in Google Scholar
[17] Maria Chong A.S., Zhao X.S., Functionalization of SBA-15 with APTES and Characterization of Functionalized Materials, J. Phys. Chem. B., 2003, 107, 12650-12657 10.1021/jp035877+Search in Google Scholar
[18] Sing K.S., EVERETT W.D.H., HAUL R.A.W., MOSCOU L.,PIEROTTI R.A., ROUQUEROL J., et al., REPORTING PHYSISORPTION DATA FOR GAS/SOLID SYSTEMS with Special Reference to the Determination of Surface Area and Porosity, Pure & Appl. Chem., 1985, 57, 603-619 10.1351/pac198557040603Search in Google Scholar
[19] Wei Q., Nie Z.R., Hao L.Y., Liu L., Chen Z.X., Zou J.X., Effect of synthesis conditions on the mesoscopical order of mesoporous silica SBA-15 functionalized by amino groups, J. Sol-gel Sci. Techn., 2006, 39, 103-109 10.1007/s10971-006-9171-3Search in Google Scholar
[20] Sanz R., Calleja G., Arencibia A., Sanz-Perez E.S., Amino functionalized mesostructured SBA-15 silica for CO2 capture: Exploring the relation between the adsorption capacity and the distribution of amino groups by TEM, Micropor. Mesopor. Mater., 2012, 158, 309-317 10.1016/j.micromeso.2012.03.053Search in Google Scholar
[21] Thomas A., Polarz S., Antonietti M., Influence of Spatial Restrictions on Equilibrium Reactions: A Case Study about the Excimer Formation of Pyrene, J. Phys. Chem. B., 2003, 107, 5081- 5087 10.1021/jp026587gSearch in Google Scholar
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