Urea-Based Imprinted Polymer Hosts with Switchable Anion Preference
| Autor: | Gustaf D. Olsson, Sudhirkumar Shinde, Cem Esen, Anıl İncel, Javier Urraca, Ian A. Nicholls, Mona Mansour, Boerje Sellergren |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Fysikalisk kemi Trifluoromethyl Molecularly imprinted polymer Diad General Chemistry Polymer Sulfonic acid 010402 general chemistry 01 natural sciences Biochemistry Physical Chemistry Catalysis Article 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry Sulfonate Monomer chemistry Polymer chemistry Benzoic acid |
| Zdroj: | Shinde, S, Incel, A, Mansour, M, Olsson, G, Nicholls, I, Urraca, J & Sellergren, B 2020, ' Urea-Based Imprinted Polymer Hosts with Switchable Anion Preference ', Journal of the American Chemical Society (JACS), vol. 142, no. 26, pp. 11404-11416 . https://doi.org/10.1021/jacs.0c00707 Journal of the American Chemical Society |
| Popis: | The design of artificial oxyanion receptors with switchable ion preference is a challenging goal in host-guest chemistry. We here report on molecularly imprinted polymers (MIPs) with an external phospho-sulpho switch driven by small molecule modifiers. The polymers were prepared by hydrogen bond-mediated imprinting of the mono- or dianions of phenyl phosphonic acid (PPA), phenyl sulfonic acid (PSA), and benzoic acid (BA) using N-3,5-bis-(trifluoromethyl)-phenyl-Ń-4-vinylphenyl urea (1) as the functional host monomer. The interaction mode between the functional monomer and the monoanions was elucidated by 1H NMR titrations and 1H-1H NMR NOESY supported by molecular dynamic simulation, which confirmed the presence of high-order complexes. PPA imprinted polymers bound PPA with an equilibrium constant Keq = 1.8 × 105 M-1 in acetonitrile (0.1% 1,2,2,6,6-pentamethylpiperidine) and inorganic HPO42- and SO42- with Keq = 2.9 × 103 M-1 and 4.5 × 103 M-1, respectively, in aqueous buffer. Moreover, the chromatographic retentivity of phosphonate versus sulfonate was shown to be completely switched on this polymer when changing from a basic to an acidic modifier. Mechanistic insights into this system were obtained from kinetic investigations and DSC-, MALDI-TOF-MS-, 1H NMR-studies of linear polymers prepared in the presence of template. The results suggest the formation of template induced 1-1 diad repeats in the polymer main chain shedding unique light on the relative contributions of configurational and conformational imprinting. |
| Databáze: | OpenAIRE |
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