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Reference type: Journal
Authors: Molinelli A, O'Mahony J, Nolan K, Smyth MR, Jakusch M, Mizaikoff B
Article Title: Analyzing the mechanisms of selectivity in biomimetic self-assemblies via IR and NMR spectroscopy of prepolymerization solutions and molecular dynamics simulations.
Publication date: 2005
Journal: Analytical Chemistry
Volume: 77
Issue: (16)
Page numbers: 5196-5204.
DOI: 10.1021/ac050525f

Abstract: Molecularly imprinted polymers (MIPs) for 2,4-dichloro-phenoxyacetic acid were synthesized via a noncovalent approach with 4-vinylpyridine as functional monomer and ethylene glycol dimethacrylate as cross-linker in a methanol/water mixture. Templated polymers synthesized in this self-assembly approach rely on complex formation between the target analyte and functional monomers in porogenic solution prior to radical polymerization. Consequently, the achievable selectivity is governed by the nature and stability of these complexes. The nature of noncovalent interactions responsible for complex formation during imprinting of the template 2,4-dichloro-phenoxyacetic acid (2,4-D) with the functional monomer 4-vinylpyridine has been investigated. Fourier transform infrared and H-1 NMR spectroscopies provide the fundamental analytical basis for rationalizing the mechanisms of recognition during the imprinting process probing the governing interactions for selective binding site formation at a molecular level. Molecular modeling studies in explicit solvent (chloroform and water) corroborate the importance of hydrogen bonding in aprotic solvents and of hydrophobic interactions in protic media in agreement with the experimental spectroscopic investigations of prepolymerization solutions. Furthermore, chromatographic studies of the synthesized MIPs provided insight on the importance of size, shape, and functionality during selective 2,4-D rebinding processes confirming the results obtained during the prepolymerization studies
Template and target information: 2,4-dichloro-phenoxyacetic acid, 2,4-D

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