Abstract
We developed a new hybrid material resulting from an innovative supramolecular tripartite association between an ionic liquid covalently immobilized on primary β-cyclodextrins rim and an anionic water-soluble polymer. Two hydrophilic ternary complexes based on native and permethylated β-cyclodextrins substituted with an ionic liquid and immobilized on poly(styrene sulfonate) (CD-IL+PSS− and CD(OMe)IL+PSS−) were obtained by simple dialysis with a cyclodextrin maximal grafting rate of 25% and 20% on the polymer, respectively. These polyelectrolytes are based on electrostatic interactions between the opposite charges of the imidazolium cation of the ionic liquid and the poly(styrene sulfonate) anion. The inclusion properties of the free cavities of the cyclodextrins and the synergic effect of the polymeric matrix were studied with three reference guests such as phenolphthalein, p-nitrophenol, and 2-anilinonaphthalene-6-sulfonic acid using UV-visible, fluorescent, and NMR spectroscopies. The support has been applied successfully in dialysis device to extract and concentrated aromatic model molecule. This simple and flexible synthetic strategy opens the way to new hybrid materials useful for fast and low-cost ecofriendly extraction techniques relevant for green analytical chemistry.
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Data availability
All data generated or analyzed during this study are included in this published article. Supplementary materials are represented by the dagger symbol in the text. The materials, method, synthesis, and characterization details of products 2, 3, 4, 7, 9, 11, 12, and 13 are available online. Graphs of p-nitrophenol inclusion study (absorbance and job plot, stability constants table) and NOESY NMR of inclusion complex of 13:2,6-ANS obtained with the dialyzer were also reported.
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Acknowledgements
We thank Christophe Rihouey from PBS laboratory for the chromatography analysis. We are also grateful for the company Cyclolab, https://cyclolab.hu/, for its contribution by sending β-CD-NH2 10.
Funding
This work was supported by “le Conseil Régional de Haute-Normandie” and “l'Institut Normand de Chimie Moléculaire, Macromoléculaire et Médicinale” INC3M, FR 3038 CNRS (A. F.-H.). We are grateful to Erasmus Mundus program Battuta for the fellowship (A. B.), the CNRS/CNRST international program (A. B.), and the MRT for their financial supports (B. S. S. B). This work has been partially supported by University of Rouen Normandy, INSA Rouen Normandy, the Centre National de la Recherche Scientifique (CNRS), European Regional Development Fund (ERDF), Labex SynOrg (ANR-11-LABX-0029), Carnot Institute I2C, the graduate school for research XL-Chem (ANR-18-EURE-0020 XL CHEM), and by Région Normandie. We also received financial support from the European Union for the purchase of equipment.
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Conceptualization, G.G. and D.L.; Methodology, G.G, D.L., C.K-D., F.G., V.M. and M.L.; Validation, G.G, D.L., C.K-D., F.G., V.M.; Formal Analysis, A.B., S.B., A.F-H., F.G., B.S.S.B. and C.K-D.; Investigation, A.B., S.B., A.F.-H., F.G., B.S.S.B. and C.K-D.; Writing-Original draft preparation G.G.; Writing-review and editing, G.G., D.L, M.L. F.G, V.M. and C.K.-D. Supervision, G.G, D.L., C.K-D., F.G. and M.L.; Project administration, Funding acquisition, G.G., M.L. and D.L.
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Bouyahya, ., Sembo-Backonly, BS., Favrelle-Huret, A. et al. New ternary water-soluble support from self-assembly of β-cyclodextrin-ionic liquid and an anionic polymer for a dialysis device. Environ Sci Pollut Res 29, 271–283 (2022). https://doi.org/10.1007/s11356-021-16374-0
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DOI: https://doi.org/10.1007/s11356-021-16374-0