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Int. J. Mol. Sci. 2015, 16(2), 3656-3676; doi:10.3390/ijms16023656

Exploiting β-Cyclodextrin in Molecular Imprinting for Achieving Recognition of Benzylparaben in Aqueous Media

1
Department of Chemistry, Faculty of Science, University of Malaya, Lembah Pantai 50603, Kuala Lumpur, Malaysia
2
Department of Science and Mathematics, Faculty of Science, Technology and Human Development, University of Tun Hussein Onn Malaysia, Parit Raja 86400, Johor, Malaysia
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: John George Hardy
Received: 29 December 2014 / Revised: 8 January 2015 / Accepted: 19 January 2015 / Published: 6 February 2015
(This article belongs to the Special Issue Supramolecular Interactions)
View Full-Text   |   Download PDF [3536 KB, uploaded 6 February 2015]   |  

Abstract

The molecularly imprinted polymer (MIP) based on methacrylic acid functionalized β-cyclodextrin (MAA-β-CD) monomer was synthesized for the purpose of selective recognition of benzylparaben (BzP). The MAA-β-CD monomer was produced by bridging a methacrylic acid (MAA) and β-cyclodextrin (β-CD) using toluene-2,4-diisocyanate (TDI) by reacting the –OH group of MAA and one of the primary –OH groups of β-CD. This monomer comprised of triple interactions that included an inclusion complex, π–π interaction, and hydrogen bonding. To demonstrate β-CD performance in MIPs, two MIPs were prepared; molecularly imprinted polymer-methacrylic acid functionalized β-cyclodextrin, MIP(MAA-β-CD), and molecularly imprinted polymer-methacrylic acid, MIP(MAA); both prepared by a reversible addition fragmentation chain transfer polymerization (RAFT) in the bulk polymerization process. Both MIPs were characterized using the Fourier Transform Infrared Spectroscopy (FTIR), Field Emission Scanning Electron Microscopy (FESEM), and Brunauer-Emmett-Teller (BET). The presence of β-CD not only influenced the morphological structure, it also affected the specific surface area, average pore diameter, and total pore volume of the MIP. The rebinding of the imprinting effect was evaluated in binding experiments, which proved that the β-CD contributed significantly to the enhancement of the recognition affinity and selective adsorption of the MIP. View Full-Text
Keywords: molecularly imprinted polymer; methacrylic acid functionalized β-cyclodextrin; benzylparaben molecularly imprinted polymer; methacrylic acid functionalized β-cyclodextrin; benzylparaben
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Asman, S.; Mohamad, S.; Sarih, N.M. Exploiting β-Cyclodextrin in Molecular Imprinting for Achieving Recognition of Benzylparaben in Aqueous Media. Int. J. Mol. Sci. 2015, 16, 3656-3676.

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