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Fabrication of carbonyl-functional hypercrosslinked polymers as solid-phase extraction sorbent for enrichment of chlorophenols from water, honey and beverage samples

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Abstract

Three carbonyl-functional novel hypercrosslinked polymers (HCP-TPS, HCP-TPA, and HCP-TPP) were successfully fabricated through an one-step Friedel–Crafts acylation reaction by copolymerizing paraphthaloyl chloride with triphenylsilane, triphenylamine, and triphenylphosphine, respectively. The resultant HCPs contained plenty of carbonyl-functional groups. Among the series of such HCPs, HCP-TPS displayed the best adsorption capability to chlorophenols (CPs), and thus it was employed as solid-phase extraction (SPE) adsorbent for enrichment of chlorophenols from water, honey, and white peach beverage prior to determination by high-performance liquid chromatography. Under the optimal conditions, the detection limits of the method (S/N = 3) were 0.15–0.3 ng mL−1 for tap water and leak water, 2.5–6.0 ng g−1 for honey sample and 0.4–0.6 ng mL−1 for white peach beverage sample. The recoveries of CPs in the spiked water, honey samples, and white peach beverage were in the range of 89.0–108.4%, 81.4–118.2%, and 85.0–113.5%, respectively. This work provides a new strategy for constructing functionalized HCPs as efficient SPE adsorbents.

Graphical abstract

In this work, three novel hypercrosslinked polymers (HCPs) were synthesized by the Friedel–Crafts alkylation reaction (paraphthaloyl chloride as the alkylating agent, triphenylsilane, triphenylamine, and triphenylphosphine as the aromatic units). Then, HCP-TPS was applied to soild-phase extraction sorbent for enrichment CPs from water, honey, and white peach beverage samples.

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References

  1. Zhou T, Wang Y, Li T, Li H, Yang C, Sun D, Che G (2021) Fabricating magnetic hydrophilic molecularly imprinted resin with enhanced adsorption and recognition performance for targeted detecting chlorophenols in environmental water. Chem Eng J 420:129904. https://doi.org/10.1016/j.cej.2021.129904

    Article  CAS  Google Scholar 

  2. Wang Q, Yao L, Hao L, Li Y, Wang C, Wu Q, Wang Z (2019) Ferrocene-based nanoporous organic polymer as solid-phase extraction sorbent for the extraction of chlorophenols from tap water, tea drink and peach juice samples. Food Chem 297:124962. https://doi.org/10.1016/j.foodchem.2019.124962

    Article  CAS  PubMed  Google Scholar 

  3. Enyoh CE, Isiuku BO (2021) Competitive biosorption and phytotoxicity of chlorophenols in aqueous solution to Canna indica L. Curr Res in Green and Sustain Chem 4:100094. https://doi.org/10.1016/j.crgsc.2021.100094

    Article  Google Scholar 

  4. Wu T, Zang X, Wang M, Chang Q, Wang C, Wu Q, Wang Z (2018) Covalent organic framework as fiber coating for solid-phase microextraction of chlorophenols followed by quantification with gas chromatography-mass spectrometry. J Agric Food Chem 66:11158–11165. https://doi.org/10.1021/acs.jafc.8b01643

    Article  CAS  PubMed  Google Scholar 

  5. Wang Y, Ma R, Xiao R, Hao L, Wu Q, Wang C, Wang Z (2018) A hyper-cross linked polymer as an adsorbent for the extraction of chlorophenols. Microchim Acta 185:108. https://doi.org/10.1007/s00604-017-2649-6

    Article  CAS  Google Scholar 

  6. Liu W, Wang J, Liu J, Hou F, Wu Q, Wang C, Wang Z (2020) Preparation of phenylboronic acid based hypercrosslinked polymers for effective adsorption of chlorophenols. J Chromatogr A 1628:461470. https://doi.org/10.1016/j.chroma.2020.461470

    Article  CAS  PubMed  Google Scholar 

  7. Wang C, Ma R, Wu Q, Sun M, Wang Z (2014) Magnetic porous carbon as an adsorbent for the enrichment of chlorophenols from water and peach juice samples. J Chromatogr A 1361:60–66. https://doi.org/10.1016/j.chroma.2014.08.002

    Article  CAS  PubMed  Google Scholar 

  8. Mercedes VN, María RP, Luis PB, Manuel FT, Callejón M, Miguel BL (2012) Application of three phase hollow fiber based liquid phase microextraction (HF-LPME) for the simultaneous HPLC determination of phenol substituting compounds (alkyl-, chloro- and nitrophenols). Talanta 99:55–61. 10.1016j.talanta.2012.05.020

  9. Feng J, Loussala HM, Han S, Ji X, Li C, Sun M (2020) Recent advances of ionic liquids in sample preparation. Trends Anal Chem 125:115833. https://doi.org/10.1016/j.trac.2020.115833

    Article  CAS  Google Scholar 

  10. Feng J, Feng J, Ji X, Li C, Han S, Sun H, Sun M (2021) Recent advances of covalent organic frameworks for solid-phase microextraction. Trends Anal Chem 137:116208. https://doi.org/10.1016/j.trac.2021.116208

    Article  CAS  Google Scholar 

  11. Feng J, Wang X, Han S, Ji X, Li C, Luo C, Sun M (2019) An ionic-liquid-modified melamine-formaldehyde aerogel for in-tube solid-phase microextraction of estrogens followed by high performance liquid chromatography with diode array detection. Microchim Acta 186:769. https://doi.org/10.1007/s00604-019-3909-4

    Article  CAS  Google Scholar 

  12. Meng WK, Liu L, Wang X, Zhao RS, Wang ML, Lin JM (2018) Polyphenylene core-conjugated microporous polymer coating for highly sensitive solid-phase microextraction of polar phenol compounds in water samples. Anal Chim Acta 1015:27–34. https://doi.org/10.1016/j.aca.2018.02.035

    Article  CAS  PubMed  Google Scholar 

  13. Zhang Y, Jin X, Ma X, Wang Y (2021) Chiral porous organic frameworks and their application in enantioseparation. Anal Methods 13:8–33. https://doi.org/10.1039/d0ay01831g

    Article  CAS  PubMed  Google Scholar 

  14. Zhang S, Yang Q, Wang C, Luo X, Kim J, Wang Z, Yamauchi Y (2018) Porous organic frameworks: advanced materials in analytical chemistry. Adv Sci 5:1801116. https://doi.org/10.1002/advs.201801116

    Article  CAS  Google Scholar 

  15. Wang Q, Li G, Wang C, Wu Q, Wang Z (2020) Layered porous organic frameworks as a novel adsorbent for the solid phase extraction of chlorophenols prior to their determination by HPLC-DAD. Microchim Acta 187:211. https://doi.org/10.1007/s00604-020-4195-x

    Article  CAS  Google Scholar 

  16. Wang W, Wang J, Zhang S, Cui P, Wang C, Wang Z (2016) A novel Schiff base network-1 nanocomposite coated fiber for solid-phase microextraction of phenols from honey samples. Talanta 161:22–30. https://doi.org/10.1016/j.talanta.2016.08.009

    Article  CAS  PubMed  Google Scholar 

  17. Liu X, Wang C, Wu Q, Wang Z (2015) Metal-organic framework-templated synthesis of magnetic nanoporous carbon as an efficient absorbent for enrichment of phenylurea herbicides. Anal Chim Acta 870:67–74. https://doi.org/10.1016/j.aca.2015.02.036

    Article  CAS  PubMed  Google Scholar 

  18. Wood CD, Tan B, Trewin A, Su F, Rosseinsky MJ, Bradshaw D, Cooper AI (2008) Microporous organic polymers for methane storage. Adv Mater 20:1916–1921. https://doi.org/10.1002/adma.200702397

    Article  CAS  Google Scholar 

  19. Tan L, Tan B (2017) Hypercrosslinked porous polymer materials: design, synthesis, and applications. Chem Soc Rev 46:3322–3356. https://doi.org/10.1039/c6cs00851h

    Article  CAS  PubMed  Google Scholar 

  20. Bratkowska D, Fontanals N, Borrull F, Cormack PA, Sherrington DC, Marce RM (2010) Hydrophilic hypercrosslinked polymeric sorbents for the solid-phase extraction of polar contaminants from water. J Chromatogr A 1217:3238–3243. https://doi.org/10.1016/j.chroma.2009.08.091

    Article  CAS  PubMed  Google Scholar 

  21. Wu J, Ma R, Hao L, Wang C, Wu Q, Wang Z (2017) Triphenylamine-based hypercrosslinked organic polymer as adsorbent for the extraction of phenylurea herbicides. J Chromatogr A 1520:48–57. https://doi.org/10.1016/j.chroma.2017.09.012

    Article  CAS  PubMed  Google Scholar 

  22. Wang Q, Wang C, Wu Q, Wang Z (2019) Preparation of a magnetic nanoporous polymer for the fast and efficient extraction of 5-nitroimidazoles in milk. J Agric Food Chem 67:11527–11535. https://doi.org/10.1021/acs.jafc.9b03127

    Article  CAS  PubMed  Google Scholar 

  23. Wang Q, Wang C, Wang J, Liu W, Hao L, Zhou J, Wu Q (2020) Sensitive determination of phenylurea herbicides in soybean milk and tomato samples by a novel hypercrosslinked polymer based solid-phase extraction coupled with high performance liquid chromatography. Food Chem 317:126410. https://doi.org/10.1016/j.foodchem.2020.126410

    Article  CAS  PubMed  Google Scholar 

  24. Puthiaraj P, Lee YR, Ahn WS (2017) Microporous amine-functionalized aromatic polymers and their carbonized products for CO2 adsorption. Chem Eng J 319:65–74. https://doi.org/10.1016/j.cej.2017.03.001

    Article  CAS  Google Scholar 

  25. Puthiaraj P, Yu K, Baeck SH, Ahn WS (2020) Cascade knoevenagel condensation-chemoselective transfer hydrogenation catalyzed by Pd nanoparticles stabilized on amine-functionalized aromatic porous polymer. Catal Today 352:298–307. https://doi.org/10.1016/j.cattod.2019.09.004

    Article  Google Scholar 

  26. Xiong S, Fu X, Xiang L, Yu G, Guan J, Wang Z, Pan C (2014) Liquid acid-catalysed fabrication of nanoporous 1,3,5-triazine frameworks with efficient and selective CO2 uptake. Polym Chem 5:1–8. https://doi.org/10.1039/c3py01471a

    Article  CAS  Google Scholar 

  27. Hao L, Liu W, Wang C, Wu Q, Wang Z (2019) Novel porous Fe3O4@C nanocomposite from magnetic metal-phenolic networks for the extraction of chlorophenols from environmental samples. Talanta 194:673–679. https://doi.org/10.1016/j.talanta.2018.10.096

    Article  CAS  PubMed  Google Scholar 

  28. Law KY (2014) Definitions for hydrophilicity, hydrophobicity, and superhydrophobicity: getting the basics right. J Phys Chem Lett 5:686–688. https://doi.org/10.1021/jz402762h

    Article  CAS  PubMed  Google Scholar 

  29. Guo Y, Wang J, Hao L, Wu Q, Wang C, Wang Z (2021) Triazine-triphenylphosphine based porous organic polymer as sorbent for solid phase extraction of nitroimidazoles from honey and water. J Chromatogr A 1649:462238. https://doi.org/10.1016/j.chroma.2021.462238

    Article  CAS  PubMed  Google Scholar 

  30. Guo Y, Ma R, Liu W, Hao L, Wu Q, Wang Z (2020) Facile synthesis of conjugated microporous polymer with spherical structure for solid phase extraction of phenyl urea herbicides. J Chromatogr A 1622:461131. https://doi.org/10.1016/j.chroma.2020.461131

    Article  CAS  PubMed  Google Scholar 

  31. Xu M, Luo X, Zhang G, Zhao B, Li S, Xiao Z, Wu Q, Wang Z, Wang C (2021) Construction of imine-linked covalent organic framework as advanced adsorbent for the sensitive determination of chlorophenols. J Chromatogr A 1658:462610. https://doi.org/10.1016/j.chroma.2021.462610

    Article  CAS  PubMed  Google Scholar 

  32. Wang X, Wang H, Huang P, Ma X, Lu X, Du C (2016) Preparation of 3D mesoporous polymer in situ polymerization solid phase microextraction fiber and its application to the determination of seven chlorophenols. J Chromatogr A 1479:40–47. https://doi.org/10.1016/j.chroma.2016.12.010

    Article  CAS  PubMed  Google Scholar 

  33. Luo Y, Zhu G, Li X, Yuan B, Feng Y (2013) Facile fabrication of reduced graphene oxide-encapsulated silica: a sorbent for solid-phase extraction. J Chromatogr A 1299:10–17. https://doi.org/10.1016/j.chroma.2013.05.036

    Article  CAS  PubMed  Google Scholar 

  34. Padilla JA, Bolanos P, González R, Bonilla N, Martínez JL, Frenich A (2011) Simultaneous analysis of chlorophenols, alkylphenols, nitrophenols and cresols in wastewater effluents, using solid phase extraction and further determination by gas chromatography–tandem mass spectrometry. Talanta 85:2397–2404. https://doi.org/10.1016/j.talanta.2011.07.081

    Article  CAS  Google Scholar 

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Funding

Financial supports from the National Natural Science Foundation of China (32072295, 31671930, 31571925, 31471643), the Natural Science Foundation of Hebei Province (B2020204001, C2020204020, C2020204136, B2021204006, B2017204025, C2018204076), the Scientific and Technological Research Foundation of the Department of Education of Hebei Province (ZD2021060, ZD2020196, ZD2016085, QN2019034), and the Food Processing Discipline Group of Hebei Agricultural University (No. 2020–10).

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Authors and Affiliations

  1. College of Science, Hebei Agricultural University, Baoding, 071001, Hebei, China

    Yuting Zhang, Weihua Liu, Min Li, Sichang Jiang, Lin Hao, Zhi Wang, Qiuhua Wu & Chun Wang

  2. Department of Basic Course Teaching, Hebei Agricultural University, Huanghua, 061100, China

    Guijiang Zhang

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  1. Yuting Zhang
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Correspondence to Chun Wang.

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Zhang, Y., Zhang, G., Liu, W. et al. Fabrication of carbonyl-functional hypercrosslinked polymers as solid-phase extraction sorbent for enrichment of chlorophenols from water, honey and beverage samples. Microchim Acta 189, 21 (2022). https://doi.org/10.1007/s00604-021-05123-2

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