Advertisement

Microchimica Acta

, 186:145 | Cite as

Solid phase microextraction of polycyclic aromatic hydrocarbons by using an etched stainless-steel fiber coated with a covalent organic framework

  • Xiumin Yang
  • Junmin Wang
  • Wenjin Wang
  • Shuaihua Zhang
  • Chun Wang
  • Junhong Zhou
  • Zhi WangEmail author
Original Paper
  • 33 Downloads

Abstract

A new covalent organic framework (COF) was synthesized by the amide coupling between 1,3,5-tris(4-aminophenyl)benzene and trimesoyl chloride at room temperature. The COF was applied as a steel fiber coating for the solid phase microextraction of polycyclic aromatic hydrocarbons (PAHs) from water samples. The effect of extraction time, salt concentration, and extraction temperature on the efficiency of SPME was optimized by a Box-Behnken design. The PAHs were quantified by gas chromatography with mass spectrometric detection. Figures of merit include (a) a wide linear range (typically from 0.2 ng L−1 to 2 μg L−1), (b) low limits of detection (0.29 to 0.94 ng L−1 at S/N = 3), and (c) high enrichment factors (EFs; 819–2420). Density functional theory was employed to study the interaction between the COF cluster and the PAHs. The results demonstrated that the EFs increase with the enhancement of π stacking interaction. The repeatability (one fiber; n = 5) and reproducibility (fiber to fiber; n = 5), expressed as the relative standard deviations were in the range of 4.3%–8.4% and 8.5–11.0%, respectively. The recoveries of the PAHs from water samples spiked at levels of 20.0 and 100 ng L−1 ranged from 79.0% to 105.0%.

Graphical abstract

A covalent organic framework prepared from 1,3,5-tris(4-aminophenyl)benzene and trimesoyl chloride (TAPB-TMC-COF) was synthesized and employed as solid phase microextraction (SPME) fiber coating for the extraction of polycyclic aromatic hydrocarbons from water samples prior to gas chromatography (GC) - mass spectrometric (MS) detection.

Keywords

Density functional theory Gas chromatography Mass spectrometry Response surface methodology Real water samples 

Notes

Acknowledgements

The authors acknowledge the financial support from the National Natural Science Foundation of China (31571925 and 31671930) and the Natural Science Foundation of Hebei Province (B2016204146).

Compliance with ethical standards

The author(s) declare that they have no competing interests.

Supplementary material

604_2019_3258_MOESM1_ESM.docx (2.6 mb)
ESM 1 (DOCX 2.56 MB)

References

  1. 1.
    Piri-Moghadam H, Ahmadi F, Pawliszyn J (2016) A critical review of solid phase microextraction for analysis of water samples. TrAC Trends Anal Chem 85:133–143.  https://doi.org/10.1016/j.trac.2016.05.029 CrossRefGoogle Scholar
  2. 2.
    Varona M, Ding X, Clark KD, Anderson JL (2018) Solid-phase microextraction of DNA from mycobacteria in artificial sputum samples to enable visual detection using isothermal amplification. Anal Chem 90:6922–6928.  https://doi.org/10.1021/acs.analchem.8b01160 CrossRefPubMedGoogle Scholar
  3. 3.
    Xu C, Chen G, Xiong Z, Fan Y, Wang X, Liu Y (2016) Applications of solid-phase microextraction in food analysis. TrAC Trend Anal Chem 80:12–29.  https://doi.org/10.1016/j.trac.2016.02.022 CrossRefGoogle Scholar
  4. 4.
    Aziz-Zanjani MO, Mehdinia A (2014) A review on procedures for the preparation of coatings for solid phase microextraction. Microchim Acta 181:1169–1190.  https://doi.org/10.1007/s00604-014-1265-y CrossRefGoogle Scholar
  5. 5.
    Gutiérrez-Serpa A, Napolitano-Tabares PI, Pino V, Jiménez-Moreno F, Jiménez-Abizanda AI (2018) Silver nanoparticles supported onto a stainless steel wire for direct-immersion solid-phase microextraction of polycyclic aromatic hydrocarbons prior to their determination by gc-fid. Microchim Acta 185:341.  https://doi.org/10.1007/s00604-018-2880-9 CrossRefGoogle Scholar
  6. 6.
    Du J, Wang H, Zhang R, Wang X, Du X, Lu X (2018) Oriented zno nanoflakes on nickel-titanium alloy fibers for solid-phase microextraction of polychlorinated biphenyls and polycyclic aromatic hydrocarbons. Microchim Acta 185:441.  https://doi.org/10.1007/s00604-018-2971-7 CrossRefGoogle Scholar
  7. 7.
    Li J, Liu Y, Su H, Elaine Wong YL, Chen X, Dominic Chan TW, Chen Q (2017) In situ hydrothermal growth of a zirconium-based porphyrinic metal-organic framework on stainless steel fibers for solid-phase microextraction of nitrated polycyclic aromatic hydrocarbons. Microchim Acta 184:3809–3815.  https://doi.org/10.1007/s00604-017-2403-0 CrossRefGoogle Scholar
  8. 8.
    Zhang SH, Yang Q, Li Z, Wang WC, Wang C, Wang Z (2017) Covalent organic frameworks as a novel fiber coating for solid-phase microextraction of volatile benzene homologues. Anal Bioanal Chem 409:3429–3439.  https://doi.org/10.1007/s00216-017-0286-x CrossRefPubMedGoogle Scholar
  9. 9.
    Wang W, Li Z, Wang W, Zhang L, Zhang S, Wang C, Wang Z (2017) Microextraction of polycyclic aromatic hydrocarbons by using a stainless steel fiber coated with nanoparticles made from a porous aromatic framework. Microchim Acta 185:20–29.  https://doi.org/10.1007/s00604-017-2577-5 CrossRefGoogle Scholar
  10. 10.
    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 CrossRefPubMedGoogle Scholar
  11. 11.
    Côté AP, Benin AI, Ockwig NW, O'Keeffe M, Matzger AJ, Yaghi OM (2005) Porous, crystalline, covalent organic frameworks. Science 310:1166–1170.  https://doi.org/10.1126/science.1120411 CrossRefPubMedGoogle Scholar
  12. 12.
    Lin S, Diercks CS, Zhang Y-B, Kornienko N, Nichols EM, Zhao Y, Paris AR, Kim D, Yang P, Yaghi OM, Chang CJ (2015) Covalent organic frameworks comprising cobalt porphyrins for catalytic co2 reduction in water. Science 349:1208–1213.  https://doi.org/10.1126/science.aac8343 CrossRefPubMedGoogle Scholar
  13. 13.
    Lin C-Y, Zhang L, Zhao Z, Xia Z (2017) Design principles for covalent organic frameworks as efficient electrocatalysts in clean energy conversion and green oxidizer production. Adv Mater 29:1606635.  https://doi.org/10.1002/adma.201606635 CrossRefGoogle Scholar
  14. 14.
    Bai C, Li J, Liu S, Yang X, Yang X, Tian Y, Cao K, Huang Y, Ma L, Li S (2014) In situ preparation of nitrogen-rich and functional ultramicroporous carbonaceous cofs by “segregated” microwave irradiation. Micropor Mesopor Mat 197:148–155.  https://doi.org/10.1016/j.micromeso.2014.06.004 CrossRefGoogle Scholar
  15. 15.
    Reyes-Garcés N, Gionfriddo E, Gómez-Ríos GA, Alam MN, Boyacı E, Bojko B, Singh V, Grandy J, Pawliszyn J (2018) Advances in solid phase microextraction and perspective on future directions. Anal Chem 90:302–360.  https://doi.org/10.1021/acs.analchem.7b04502 CrossRefPubMedGoogle Scholar
  16. 16.
    Wu M, Chen G, Liu P, Zhou W, Jia Q (2016) Polydopamine-based immobilization of a hydrazone covalent organic framework for headspace solid-phase microextraction of pyrethroids in vegetables and fruits. J Chromatogr A 1456:34–41.  https://doi.org/10.1016/j.chroma.2016.05.100 CrossRefPubMedGoogle Scholar
  17. 17.
    Wu M, Chen G, Ma J, Liu P, Jia Q (2016) Fabrication of cross-linked hydrazone covalent organic frameworks by click chemistry and application to solid phase microextraction. Talanta 161:350–358.  https://doi.org/10.1016/j.talanta.2016.08.041 CrossRefPubMedGoogle Scholar
  18. 18.
    Kim KH, Jahan SA, Kabir E, Brown RJC (2013) A review of airborne polycyclic aromatic hydrocarbons (pahs) and their human health effects. Environ Int 60:71–80.  https://doi.org/10.1016/j.envint.2013.07.019 CrossRefPubMedGoogle Scholar
  19. 19.
    Eu' s drinking water standards. Council directive 98/83/EC of water intended for human consumption. Adopted by the council on 3 November. 1998 DOI: https://www.lenntech.com/who-eu-water-standards.htm
  20. 20.
    Djozan D, Assadi Y (1999) Monitoring of polycyclic aromatic hydrocarbons in water using headspace solid-phase microextraction and capillary gas chromatography. Microchem J 63:276–284.  https://doi.org/10.1006/mchj.1999.1791 CrossRefGoogle Scholar
  21. 21.
    Li J, Yang X, Bai C, Tian Y, Li B, Zhang S, Yang X, Ding S, Xia C, Tan X, Ma L, Li S (2015) A novel benzimidazole-functionalized 2-d cof material: synthesis and application as a selective solid-phase extractant for separation of uranium. J Colloid Interf Sci 437:211–218.  https://doi.org/10.1016/j.jcis.2014.09.046 CrossRefGoogle Scholar
  22. 22.
    Wang W, Wang W, Zhang S, Li Z, Wang C, Wang Z (2018) Hyper-crosslinked polymer nanoparticles as the solid-phase microextraction fiber coating for the extraction of organochlorines. J Chromatogr A 1556:47–54.  https://doi.org/10.1016/j.chroma.2018.05.001 CrossRefPubMedGoogle Scholar
  23. 23.
    Xia L, Liu Q (2016) Lithium doping on covalent organic framework-320 for enhancing hydrogen storage at ambient temperature. J Solid State Chem 244:1–5.  https://doi.org/10.1016/j.jssc.2016.09.007 CrossRefGoogle Scholar
  24. 24.
    Cui XY, Gu ZY, Jiang DQ, Li Y, Wang HF, Yan XP (2009) In situ hydrothermal growth of metal−organic framework 199 films on stainless steel fibers for solid-phase microextraction of gaseous benzene homologues. Anal Chem 81:9771–9777.  https://doi.org/10.1021/ac901663x CrossRefPubMedGoogle Scholar
  25. 25.
    Ou H, Zhang W, Yang X, Cheng Q, Liao G, Xia H, Wang D (2018) One-pot synthesis of g-c3n4-doped amine-rich porous organic polymer for chlorophenol removal. Environ Sci: Nano 5:169–182.  https://doi.org/10.1039/C7EN00787F CrossRefGoogle Scholar
  26. 26.
    Wei JS, Ding H, Wang YG, Xiong HM (2015) Hierarchical porous carbon materials with high capacitance derived from schiff-base networks. ACS Appl Mater Inter 7:5811–5819.  https://doi.org/10.1021/am508864c CrossRefGoogle Scholar
  27. 27.
    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 CrossRefGoogle Scholar
  28. 28.
    Zhang T, Gao C, Huang W, Chen Y, Wang Y, Wang J (2018) Covalent organic framework as a novel electrochemical platform for highly sensitive and stable detection of lead. Talanta 188:578–583.  https://doi.org/10.1016/j.talanta.2018.06.032 CrossRefPubMedGoogle Scholar
  29. 29.
    Roucoules V, Fail CA, Schofield WCE, Teare DOH, Badyal JPS (2005) Diels−alder chemistry on alkene functionalized films. Langmuir 21:1412–1415.  https://doi.org/10.1021/la0479657 CrossRefPubMedGoogle Scholar
  30. 30.
    Janiak C (2000) A critical account on π–π stacking in metal complexes with aromatic nitrogen-containing ligands. J Chem Soc Dalton Trans:3885–3896.  https://doi.org/10.1039/B003010O
  31. 31.
    Sinnokrot MO, Sherrill CD (2004) Substituent effects in π−π interactions: Sandwich and t-shaped configurations. J Am Chem Soc 126:7690–7697.  https://doi.org/10.1021/ja049434a CrossRefPubMedGoogle Scholar
  32. 32.
    Bagheri H, Soofi G, Javanmardi H, Karimi M (2018) A 3d nanoscale polyhedral oligomeric silsesquioxanes network for microextraction of polycyclic aromatic hydrocarbons. Microchim Acta 185:418.  https://doi.org/10.1007/s00604-018-2950-z CrossRefGoogle Scholar
  33. 33.
    Zhou Q, Lei M, Li J, Liu Y, Zhao K, Zhao D (2017) Magnetic solid phase extraction of n- and s-containing polycyclic aromatic hydrocarbons at ppb levels by using a zerovalent iron nanoscale material modified with a metal organic framework of type fe@mof-5, and their determination by hplc. Microchim Acta 184:1029–1036.  https://doi.org/10.1007/s00604-017-2094-6 CrossRefGoogle Scholar
  34. 34.
    Wang R, Chen Z (2017) A covalent organic framework-based magnetic sorbent for solid phase extraction of polycyclic aromatic hydrocarbons, and its hyphenation to hplc for quantitation. Microchim Acta 184:3867–3874.  https://doi.org/10.1007/s00604-017-2408-8 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  • Xiumin Yang
    • 1
  • Junmin Wang
    • 1
  • Wenjin Wang
    • 1
  • Shuaihua Zhang
    • 1
  • Chun Wang
    • 1
  • Junhong Zhou
    • 2
  • Zhi Wang
    • 1
    Email author
  1. 1.College of ScienceHebei Agricultural UniversityBaodingChina
  2. 2.Shanghai Institute of Organic ChemistryChinese Academy of ScienceShanghaiChina

Personalised recommendations