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Development of Molecularly Imprinted Polymer in Porous Film Format for Binding of Phenol and Alkylphenols from Water

Department of Chemistry, Memorial University of Newfoundland, St. John's, NL A1B 3X7, Canada
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Int. J. Mol. Sci. 2014, 15(1), 1338-1357; https://doi.org/10.3390/ijms15011338
Received: 16 November 2013 / Revised: 4 January 2014 / Accepted: 9 January 2014 / Published: 20 January 2014
(This article belongs to the Section Molecular Recognition)
Molecularly imprinted polymers (MIPs) were fabricated on glass slides with a “sandwich” technique giving ~20 µm thick films. Methanol/water as a solvent, and polyethyleneglycol and polyvinylacetate as solvent modifiers, were used to give a porous morphology, which was studied with scanning electron microscopy and gravimetric analysis. Various MIPs were synthesized through non-covalent imprinting with phenol as the template; itaconic acid, 4-vinylpyridine, and styrene as monomers; ethylene glycol dimethacrylate, triethylene glycol dimethacrylate, and pentaerythritol triacrylate (PETA) as cross-linkers. Binding and imprinting properties of the MIPs were evaluated based on phenol adsorption isotherms. Since phenol has only one weakly acidic hydroxyl group and lacks unique structural characteristics necessary for binding specificity, the preparation of selective MIPs was challenging. The recognition of phenol via hydrogen bonding is suppressed in water, while hydrophobic interactions, though promoted, are not specific enough for highly-selective phenol recognition. Nevertheless, the styrene-PETA MIP gave modest imprinting effects, which were higher at lower concentrations (Imprinting Factor (IF) = 1.16 at 0.5 mg·L−1). The isotherm was of a Freundlich type over 0.1–40 mg·L−1 and there was broad cross-reactivity towards other structurally similar phenols. This shows that phenol MIPs or simple adsorbents can be developed based on styrene for hydrophobic binding, and PETA to form a tighter, hydrophilic network. View Full-Text
Keywords: thin film fabrication; “sandwich” technique; MIP porosity; monomer-template interactions; hydrophobic interactions; styrene; pentaerythritol triacrylate (PETA); methanol/water; phenol adsorption isotherms; imprinting effect thin film fabrication; “sandwich” technique; MIP porosity; monomer-template interactions; hydrophobic interactions; styrene; pentaerythritol triacrylate (PETA); methanol/water; phenol adsorption isotherms; imprinting effect
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Gryshchenko, A.O.; Bottaro, C.S. Development of Molecularly Imprinted Polymer in Porous Film Format for Binding of Phenol and Alkylphenols from Water. Int. J. Mol. Sci. 2014, 15, 1338-1357.

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