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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
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.
References
Amiel C, Galant C, Auvray L (2004) Ternary complexes involving a β-cyclodextrin polymer, a cationic surfactant and an anionic polymer. Progr Colloid Polym Sci 126:44–46. https://doi.org/10.1007/b93967
Anderson JL, Clark KD (2018) Ionic liquids as tunable materials in (bio)analytical chemistry. Anal Bioanal Chem 410:4565–4566. https://doi.org/10.1007/s00216-018-1125-4
Antoniuk I, Amiel C (2016) Cyclodextrin-mediated hierarchical self-assembly and its potential in drug delivery applications. J Pharm Sci 1-19. 105:2570–2588. https://doi.org/10.1016/j.xphs.2016.05.010
Badruddoza AZ, Bhattarai B, Suri RPS (2017) Environmentally friendly β-cyclodextrin-ionic liquid polyurethane-modified magnetic sorbent for the removal of PFOA, PFOS, and Cr(VI) from water. ACS Sustain Chem Eng 5:9223–9232. https://doi.org/10.1021/acssuschemeng.7b02186
Bakheet AAA, Liu J, Zhu X (2016) New magnetic solid phase extractor based on ionic liquid modified β-cyclodextrin polymer/Fe3O4 nanocomposites for selective separation and determination of Linuron. J Anal Sc Techn 7:1–10. https://doi.org/10.1186/s40543-016-0082-9
Bakheet AAA, Zhu XS (2017) Determination of rhodamine B in food samples by Fe3O4@ionic liquids-β-cyclodextrin cross linked polymer solid phase extraction coupled with fluorescence spectrophotometry. J Fluoresc 27:1087–1094. https://doi.org/10.1007/s10895-017-2042-1
Bally G, Mesnage V, Deloffre J, Clarisse O, Lafite R, Dupont J-P (2004) Chemical characterization of porewaters in an intertidal mudflat of the Seine estuary: relationship with erosion–deposition cycles. Mar Pollut Bull 49:163–173. https://doi.org/10.1016/j.marpolbul.2004.02.005
Bally G, Mesnage V, Verney R, Clarisse O, Dupont J-P, Ouddanne B, Lafite R (2005) Exchange and release processes dialysis porewater sampler: a strategy for time equilibration optimization. In: Seranno, L., Golterman, H.L. (Eds.), Phosphates in Sediments, Proceedings of the 4th International Symposium. Backhuys, The Netherlands, 9–20.
Barhoumi Z, Saini M, Amdouni N, Pal A (2016) Interaction between amphiphilic ionic liquid 1-butyl-3-methylimidazolium octyl sulfate and anionic polymer of sodium polystyrene sulfonate in aqueous medium. Chem Phys Lett 661:173–178. https://doi.org/10.1016/j.cplett.2016.08.016
Brinkman A, Van Raasphorst W, Lijklema L (1982) In situ sampling of interstitial water from lake sediments. Hydrobiologia 92:659–663. https://doi.org/10.1007/BF00000065
Bufflap SE, Allen HE (1995) Sediment pore water collection methods for trace metal analysis: a review. Water Res 29:165–177. https://doi.org/10.1016/0043-1354(94)E0105-F
Cyclolab (2021) Compounds 8 and 10 are also commercially available: https://cyclolab.hu/products/cationic_cyclodextrins-c18
D’Souza VT (1998) Cyclodextrins. Chem Rev 98:1741–2076. https://doi.org/10.1021/cr980027p
Eftink MR, Harrison JC (1981) Calorimetric studies of p-nitrophenol binding to α- and β-cyclodextrin. Bioorg Chem 10:388–398. https://doi.org/10.1016/0045-2068(81)90051-1
Favrelle A, Gouhier G, Guillen F, Martin C, Mofaddel N, Mundy K, Pitre S, Wagner B (2015) Structure−binding effects: comparative binding of 2-anilino-6-naphthalenesulfonate by a series of alkyl- and hydroxyalkyl-substituted β-cyclodextrins. J Phys Chem B 119:12921–12930. https://doi.org/10.1021/acs.jpcb.5b07157
Galant C, Amiel C (2004) Tailorable polyelectrolyte complexes using cyclodextrin polymers. J Phys Chem B 108:19218–19227. https://doi.org/10.1021/jp047494x
Gao Q, Liu W, Zhu X (2020) Glycine ionic liquid functionalized β-cyclodextrin polymer high-performance liquid chromatography for the separation/analysis of pyrethroids. J Liquid Chromat Related Tech 43:809–818. https://doi.org/10.1080/10826076.2020.1816550
Gelb RI, Raso S, Alper JS (1995) Complexation reactions of β-cyclodextrin, per-(2,3,6-O-methyl) cycloheptaamylose and γ-cyclodextrin with phenolphthalein, adamantane carboxylate and adamantane acetate. Supramol Chem 4:279–285. https://doi.org/10.1080/10610279508028937
Hallett JP, Welton T (2011) Room-temperature ionic liquids: solvents for synthesis and catalysis. Chem Rev 111:3508–3576. https://doi.org/10.1021/cr1003248
Hayes R, Warr GG, Atkin R (2015) Structure and nanostructure in ionic liquids. Chem Rev 115:6357–6426. https://doi.org/10.1021/cr500411q
Jiao Y, Chou T, Akcora P (2015) Design of ion-containing polymer-grafted nanoparticles for conductive membranes. Macromol 48:4910–4917. https://doi.org/10.1021/acs.macromol.5b00758
Jicsinszky L, Caporaso M, Tuza K, Martina K, Gaudino EC, Cravotto G (2016) Nucleophilic substitutions of 6I-O-monotosyl-β-cyclodextrin in a planetary ball mill. ACS Sustain Chem Eng 4:919–929. https://doi.org/10.1021/acssuschemeng.5b01006
Khalafi L, Rafiee M (2013) Cyclodextrin based spectral changes. Intech chapter 19:472–493. https://doi.org/10.5772/52824
Kissoudi M, Samanidou V (2018) Recent advances in applications of ionic liquids in miniaturized microextraction techniques. Molecules 23:1437–1449. https://doi.org/10.3390/molecules23061437
Koel M (2016) Analytical application of ionic liquids. World Scientific:1–438. https://doi.org/10.1142/q0021
Li J, Wang X, Duan H, Wang Y, Bu Y, Luo C (2016) Based on magnetic graphene oxide highly sensitive and selective imprinted sensor for determination of sunset yellow. Talanta 147:169–176. https://doi.org/10.1016/j.talanta.2015.09.056
Mahlambi MM, Malefeste TJ, Mamba BB, Krause RW (2010) β-Cyclodextrin-ionic liquid polyurethanes for the removal of organic pollutants and heavy metals from water: synthesis and characterization. J Polym Res 17:589–600. https://doi.org/10.1002/jctb.1681
Mahlambi MM, Malefeste TJ, Mamba BB, Krause RW (2011) Ionic liquids: applications and perspectives. InTech, Chapter 7. https://doi.org/10.5772/1782
Mesnage V, Ogier S, Bally G, Disnar J-R, Lottier N, Dedieu K, Rabouille C, Copard Y (2007) Nutrient dynamics at the sediment–water interface in a Mediterranean lagoon (Thau, France): influence of biodeposition by shellfish farming activities. Mar Environ Res 63:257–277. https://doi.org/10.1016/j.marenvres.2006.10.001
Mesnage V, Lecoq N, Sakho I, Vennin A (2013) Modelling nutrients fluxes at the sediment-water interface in two contrasted climate estuaries: Seine estuary (France) and Somone (Senegal). Compte-Rendu Géosciences 345:439–445. https://doi.org/10.1016/j.crte.2013.11.003
Mincheva Z, Bonnette F, Lavastre O (2007) Ionic liquid supports stable under conditions of peptide couplings, deprotections and traceless Suzuki reactions. Collect Czechoslov Chem Commun 72:417–434. https://doi.org/10.1135/cccc20070417
Mofaddel N, Fourmentin S, Guillen F, Landy D, Gouhier G (2016) Ionic liquids and cyclodextrin inclusion complexes: limitation of the affinity capillary electrophoresis technique. Anal Bioanal Chem 408:8211–8220. https://doi.org/10.1007/s00216-016-9931-z
Mohamad S, Chandrasekaram K, Rasdi FLM, Manan NSA, Raoov M, Sidek N, Fathullah SF (2015) Supramolecular interaction of 2,4-dichlorophenol and β-cyclodextrin functionalized ionic liquid and its preliminary study in sensor application. J Mol Liq 212:850–856. https://doi.org/10.1016/j.molliq.2015.10.044
Moutard S, Perly B, Godé P, Demailly G, Djedaïni-Pilard F (2002) Novel glucolipids based on cyclodextrins. J Inclusion Phen Macrocyc Chem 44:317–322. https://doi.org/10.1023/A:1023014718447
Nielsen TT, Wintgens V, Amiel C, Wimmer R, Larsen KL (2010) Facile synthesis of β-cyclodextrin-dextran polymers by “click” chemistry. Biomacromolecules 11:1710–1715. https://doi.org/10.1021/bm9013233
Pandey S (2006) Analytical applications of room-temperature ionic liquids: a review of recent efforts. Anal Chim Acta 556:38–45. https://doi.org/10.1016/j.aca.2005.06.038
Qin X, Zhu X (2017) Ionic liquid-β-cyclodextrin polymer for the separation/analysis of iornoxicam. Supramol Chem 29:205–214. https://doi.org/10.1080/10610278.2016.1202411
Quin X, Chen S, Gu W, Zhu X (2016) Speciation analysis of Mn(II)/Mn(IV) using Fe3O4@ionic liquid-β-cyclodextrin polymer magnetic solid phase extraction coupled with ICP-OES. Talanta 161:325–332. https://doi.org/10.1016/j.talanta.2016.08.062
Rahim NY, Tay KS, Mohamad S (2016a) β-Cyclodextrin functionalized ionic liquid as chiral stationary phase of high performance liquid chromatography for enantioseparation of β-blockers. J Incl Phenom Macrocycl Chem 85:303–315. https://doi.org/10.1007/s10847-016-0629-9
Rahim NY, Tay KS, Mohamad S (2016b) Chromatographic and spectroscopic studies on β-cyclodextrin functionalized ionic liquid as chiral stationary phase: enantioseparation of flavonoids. Chromatographia 79:1445–1455. https://doi.org/10.1177/0263617416686798
Raoov M, Mohamad S, Abas MR (2013) Removal of 2,4-dichlorophenol using cyclodextrin-ionic liquid polymer as a macroporous material: characterization, adsorption isotherm, kinetic study, thermodynamics. J Hazardous Mat 263:501–516. https://doi.org/10.1016/j.jhazmat.2013.10.003
Raoov M, Mohamad S, Abas MR (2014a) Synthesis and characterization of β-cyclodextrin functionalized ionic liquid polymer as a macroporous material for the removal of phenols and As(V). Int J Mol Sci 15:100–119. https://doi.org/10.3390/ijms15010100
Raoov M, Mohamed S, Abas MR, Surikumaran H (2014b) New macroporous β-cyclodextrin functionalized ionic liquid polymer as an adsorbent for solid phase extraction with phenols. Talanta 130:155–163. https://doi.org/10.1016/j.talanta.2014.06.067
Rasdi FLM, Mohamad S, Manan NSA, Nodeh HR (2016) Electrochemical determination of 2,4-dichlorophenol at β-cyclodextrin functionalized ionic liquid modified chemical sensor: voltammetric and amperometric studies. RSC Adv 6:100186–100194. https://doi.org/10.1039/c6ra19816c
Rogalski M, Modaressi A, Magri P, Mutelet F, Grydziuszko A, Wlazło M, Domańska U (2013) Cloud point extraction of parabens using non-ionic surfactant with cyclodextrin functionalized ionic liquid as a modifier. Int J Mol Sci 14:16638–16655. https://doi.org/10.3390/ijms141224531
Sinniah S, Mohamad S, Manan NSA (2015) Magnetite nanoparticles coated with β-cyclodextrin functionalized-ionic liquid: synthesis and its preliminary investigation as a new sensing material. App Surface Sci 357:543–550. https://doi.org/10.1016/j.apsusc.2015.09.078
Taguchi K (1986) Transient binding mode of phenolphthalein-β-cyclodextrin complex: an example of induced geometrical distortion. J Am Chem Soc 108:2705–2709. https://doi.org/10.1021/ja00270a032
Tang W, Ng SC (2008) Facile synthesis of mono-6-amino-6-deoxy-α-,β,-γ-cyclodextrin hydrochlorides for molecular recognition, chiral separation and drug delivery. Nat Protoc 3:691–697. https://doi.org/10.1038/nprot.2008.37
Wagner B, Fitzpatrick SJ (2000) A Comparison of the host–guest inclusion complexes of 1,8-ANS and 2,6-ANS in parent and modified cyclodextrins. J Incl Phenom Macrocycl Chem 38:467–478. https://doi.org/10.1023/A:1008198825835
Wang HM, Song LX (2007) A good linear relationship between the logarithms of formation constants and the stabilization energies of α- and β-cyclodextrin complexes of several phenol and benzoic derivatives. Chem Lett 36:596–597. https://doi.org/10.1246/cl.2007.596
Wu X, Yang M, Zeng H, Xi X, Zhang S, Lu R, Gao H, Zhou W (2016) Effervescence-assisted dispersive solid-phase extraction using ionic-liquid-modified magnetic β-cyclodextrin/attapulgite coupled with high-performance liquid chromatography for fungicide detection in honey and juice. J Sep Sci 39:4422–4428. https://doi.org/10.1002/jssc.201600596
Yang M, Xi X, Wu X, Lu R, Zhou W, Zhang S, Gao H (2015) Vortex-assisted magnetic β-cyclodextrin/attapulgite-linked ionic liquid dispersive liquid–liquid microextraction coupled with high-performance liquid chromatography for the fast determination of four fungicides in water samples. J Chromatogr A 1381:37–47. https://doi.org/10.1016/j.chroma.2015.01.016
Yusoff MM, Raoov M, Yahaya N, Salleh NM (2017) An ionic liquid loaded magnetically confined polymeric mesoporous adsorbent for extraction of parabens from environmental and cosmetic samples. RSC Adv 7:35832–35844. https://doi.org/10.1039/C7RA06682A
Zgani I, Idriss H, Barbot C, Djedaini-Pilard F, Petit S, Hubert-Roux M, Estour F, Gouhier G (2016) Positive variation of the MRI signal via intramolecular inclusion complexation of a C-2 functionalized β-cyclodextrin. Org Biomol Chem 15:564–569. https://doi.org/10.1039/C6OB02583H
Zhang LX, Liu T, Luo AQ (2011) Application of quaternary aminated β-cyclodextrin ionic liquid stationary phase in capillary gas chromatography. Adv Mater Res 317-319:1936–1939. https://doi.org/10.4028/www.scientific.net/AMR.317-319.1936
Zhao F, Xiao F, Zeng B (2010) Electrodeposition of PtCo alloy nanoparticles on inclusion complex film of functionalized cyclodextrin-ionic liquid and their application in glucose sensing. Electrochem Commun 12:168–171. https://doi.org/10.1016/j.elecom.2009.11.016
Zhou C, Deng J, Shi G, Zhou T (2017) β-cyclodextrin-ionic liquid polymer based dynamically coating for simultaneous determination of tetracyclines by capillary electrophoresis. Electrophoresis 38:1060–1067. https://doi.org/10.1002/elps.201600229
Zhou N, Zhu XS (2014) Ionic liquids functionalized β-cyclodextrin polymer for separation/analysis of magnolol. J Pharm Anal 4:242–249. https://doi.org/10.1016/j.jpha.2013.12.005
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.
Author information
Authors and Affiliations
Contributions
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.
Corresponding author
Ethics declarations
Ethics approval
The authors confirm that the manuscript has been read and approved by all authors and not under consideration for publication elsewhere.
Consent to participate
The authors have been personally and actively involved in substantive work leading to the manuscript and will hold themselves jointly and individually responsible for its content.
Consent for publication
The authors consent to publish this research.
Competing interests
The authors declare no competing interests.
Additional information
Responsible Editor: Santiago V. Luis
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11356-021-16374-0