A facile route for the chemical functionalisation of polydivinylbenzenes and the application of amphoteric polydivinylbenzene microspheres to the simultaneous solid-phase extraction of acidic and basic drugs from water samples

Francesc Borrull, Peter A.G. Cormack*, Alan Corrigan, Calum Craig, Núria Fontanals, Rosa Maria Marcé, Alberto Moral, Greg Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

Mixed-mode ion-exchange sorbents with amphoteric character are intriguing materials because not only can anions and cations be extracted from liquid samples using one single sorbent rather than two (anion extraction under one set of conditions, cation extraction under a second set of conditions), but it may be feasible to establish extraction conditions where anionic and cationic analytes can be extracted simultaneously. In the present study, an unusual but versatile synthetic route was used to install amphoteric character into polydivinylbenzene microspheres produced through precipitation polymerisation. The key synthetic step used for the chemical functionalisation of the polydivinylbenzenes exploited Diels–Alder cycloaddition chemistry to target the pendent styryl groups that are present in polydivinylbenzenes. With maleic anhydride as a dienophile, Diels–Alder cycloaddition yielded polydivinylbenzenes decorated with anhydride moieties. Whilst such materials are interesting in their own right as reactive resins, ring-opening of the polymer-bound anhydride units with ethylenediamine yielded an amphoteric material with both weak anion-exchange (WAX) and weak cation-exchange (WCX) character. This polymer was evaluated as a pH-tuneable sorbent for the solid-phase extraction (SPE) of acidic and basic pharmaceuticals from water samples. Following optimisation of the analytical method including the SPE, the method was subjected to validation and then applied to the extraction and determination of acidic and basic pharmaceuticals present at low concentrations in river water, effluent wastewater and influent wastewater samples. Simultaneous extraction and determination of acidic and basic compounds was found to be achievable, with method quantification limits down to 1 ng L−1.
Original languageEnglish
Pages (from-to)751-761
Number of pages11
JournalPolymer Chemistry
Volume16
Issue number6
Early online date28 Dec 2024
DOIs
Publication statusPublished - 14 Feb 2025

Funding

AC would like to thank the University of Strathclyde and the Engineering and Physical Sciences Research Council (EPSRC) for his Student Excellence Award funded through the Strathclyde Research Studentship Scheme. AM would like to thank Universitat Rovira i Virgili (URV) for his PhD grant (2020PMF-PIPF-33). This research was also part of projects PID2020-114587GB-I00 and PID2023-148939NB-I00 funded by MCIN/AEI/10.13039/501100011033.

Keywords

  • sorbents
  • amphoteric
  • polydivinylbenzene
  • polymers

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