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The influence of a methyl substituent on molecularly imprinted polymer morphology and recognition - Acrylic acid versus methacrylic acid
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC. Linnaeus Univ, Bioorgan & Biophys Chem Lab, Ctr Biomat Chem, Dept Chem & Biomed Sci, SE-39182 Kalmar, Sweden..
Linnaeus Univ, Bioorgan & Biophys Chem Lab, Ctr Biomat Chem, Dept Chem & Biomed Sci, SE-39182 Kalmar, Sweden..
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. Linnaeus Univ, Bioorgan & Biophys Chem Lab, Ctr Biomat Chem, Dept Chem & Biomed Sci, SE-39182 Kalmar, Sweden..ORCID iD: 0000-0002-0407-6542
2017 (English)In: European Polymer Journal, ISSN 0014-3057, E-ISSN 1873-1945, Vol. 92, 137-149 p.Article in journal (Refereed) Published
Abstract [en]

In this report, we have investigated factors contributing to the morphology and template recognition of bupivacaine-imprinted copolymers of methacrylic acid (MAA) and ethyleneglycol dimethacrylate (EGDMA). To this end, MAA, the most commonly used functional monomer in non-covalent molecular imprinting protocols, was compared and contrasted with the closely related acrylic acid (AA) in terms of polymer morphologies, recognition characteristics, and molecular level events in the corresponding pre-polymerization mixtures. Two series of analogous bupivacaine-imprinted EGDMA-copolymers containing increasing fractions of either AA or MAA were studied through all-component MD simulations in the pre-polymerization phase, equilibrium binding experiments on corresponding synthesized polymers and morphology characterization by N-2-sorption measurements. A higher degree of hydrogen bonding frequency between respective functional monomer and bupivacaine was recorded for the mixtures containing AA compared to those containing MAA. In contrast, results from binding experiments demonstrated higher binding capacities for the polymers prepared with MAA than for those prepared with AA, which is explained by differences in polymer morphology. The surface areas and pore volumes of the AA-polymers were higher than for the MAA-polymers and the overall pore structure in the AA-polymers was ink-bottle shaped while the pores in the MAA-polymers were slit-shaped. We suggest that the methyl substituent of MAA contributes to differences in the reaction kinetics for AA and MAA during polymerization and resulted in different morphologies, in particular pore shape, which affected mass-transfer and consequently the binding qualities of the materials.

Place, publisher, year, edition, pages
PERGAMON-ELSEVIER SCIENCE LTD , 2017. Vol. 92, 137-149 p.
Keyword [en]
Molecularly imprinted polymer, Molecular dynamics, Molecular recognition, Morphology, Methacrylic acid, Acrylic acid
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-328971DOI: 10.1016/j.eurpolymj.2017.04.043ISI: 000404315600013OAI: oai:DiVA.org:uu-328971DiVA: diva2:1140631
Funder
Swedish Research Council, 2014-4573EU, FP7, Seventh Framework Programme, 602699
Available from: 2017-09-12 Created: 2017-09-12 Last updated: 2017-09-12Bibliographically approved

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Nicholls, Ian

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