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Microchimica Acta

, 186:4 | Cite as

A triazine based organic framework with micropores and mesopores for use in headspace solid phase microextraction of phthalate esters

  • Huihua Guo
  • Gang Chen
  • Jiutong Ma
  • Qiong Jia
Original Paper
  • 52 Downloads

Abstract

A dual-pore covalent organic framework (COF) that contains micropores and mesopores was prepared from 2,4,6-triphenoxy-1,3,5-triazine (TPT). A building block is used in which double linking sites were introduced at each branch of a C3-symmetric skeleton. The COF is shown to be a viable coating for fibers for solid-phase microextraction of phthalic acid esters (PAEs). Its high specific surface, high hydrophobicity, and wide pore size distribution of a TPT-COF coated fiber result in extraordinarily powerful extraction of PAEs. The enrichment factor is up to 7790 under optimum conditions. The method has detection limits that range between 5 and 95 ng L−1. The inter-batch relative standard deviations are between 3.1 and 10.9%, and those for intra-batch assays are from 0.8 to 4.7%. The TPT-COF coated fibers were applied to the extraction of PAEs from (spiked) juice samples, and satisfactory recoveries were achieved.

Graphical abstract

TPT-COF coated SPME fiber was prepared for the preconcentration of phthalate esters coupled with GC-FID.

Keywords

Covalent organic framework Multiple-linking-site SPME Gas chromatography 

Notes

Acknowledgements

The project was supported by Open Project of State Key Laboratory of Supramolecular Structure and Materials, Jilin University, China (sklssm201815).

Compliance with ethical standards

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

Supplementary material

604_2018_3060_MOESM1_ESM.docx (860 kb)
ESM 1 (DOCX 859 kb)

References

  1. 1.
    Al-Saleh I, Elkhatib R (2016) Screening of phthalate esters in 47 branded perfumes. Environ Sci Pollut Res Int 23:455–468CrossRefPubMedGoogle Scholar
  2. 2.
    Barp L, Purcaro G, Franchina F, Zoccali M, Sciarrone D, Tranchida P, Mondello L (2015) Determination of phthalate esters in vegetable oils using direct immersion solid-phase microextraction and fast gas chromatography coupled with triple quadrupole mass spectrometry. Anal Chim Acta 887:237–244CrossRefPubMedGoogle Scholar
  3. 3.
    Amiri A, Ghaemi F (2017) Microextraction in packed syringe by using a three-dimensional carbon nanotube/carbon nanofiber–graphene nanostructure coupled to dispersive liquid-liquid microextraction for the determination of phthalate esters in water samples. Microchim Acta 184:3851–3858CrossRefGoogle Scholar
  4. 4.
    Jiao C, Ma R, Li M, Hao L, Wang C, Wu Q, Wang Z (2017) Magnetic cobalt-nitrogen-doped carbon microspheres for the preconcentration of phthalate esters from beverage and milk samples. Microchim Acta 184:2551–2559CrossRefGoogle Scholar
  5. 5.
    Yamini Y, Faraji M, Adeli M (2015) Magnetic silica nanomaterials for solid-phase extraction combined with dispersive liquid-liquid microextraction of ultra-trace quantities of plasticizers. Microchim Acta 182:1491–1499CrossRefGoogle Scholar
  6. 6.
    Hou X, Guo Y, Liang X, Wang X, Wang L, Wang L, Liu X (2016) Bis(trifluoromethanesulfonyl)imide-based ionic liquids grafted on graphene oxide-coated solid-phase microextraction fiber for extraction and enrichment of polycyclic aromatic hydrocarbons in potatoes and phthalate esters in food-wrap. Talanta 153:392–400CrossRefPubMedGoogle Scholar
  7. 7.
    Xia S, Dong J, Chen Y, Wang Y, Chen X (2013) Three dimensional phytic acid-induced graphene as a solid-phase microextraction fiber coating and its analytical applications for nerolidol in tea. Chin Chem Lett 29:107–110CrossRefGoogle Scholar
  8. 8.
    Wang X, Sheng WR, Jiao XY, Zhao RS, Wang ML, Lin JM (2018) Zinc(II)-based metal-organic nanotubes coating for high sensitive solid phase microextraction of nitro-polycyclic aromatic hydrocarbons. Talanta 186:561–567CrossRefPubMedGoogle Scholar
  9. 9.
    Amanzadeh H, Yamini Y, Moradi M, Asl YA (2016) Determination of phthalate esters in drinking water and edible vegetable oil samples by headspace solid phase microextraction using graphene/polyvinylchloride nanocomposite coated fiber coupled to gas chromatography-flame ionization detector. J Chromatogr A 1465:38–46CrossRefPubMedGoogle Scholar
  10. 10.
    Asadollahzadeh H, Noroozian E, Maghsoudi S (2010) Solid-phase microextraction of phthalate esters from aqueous media by electrochemically deposited carbon nanotube/polypyrrole composite on a stainless steel fiber. Anal Chim Acta 669:32–38CrossRefPubMedGoogle Scholar
  11. 11.
    Ho TD, Toledo BR, Hantao LW, Anderson JL (2014) Chemical immobilization of crosslinked polymeric ionic liquids on nitinol wires produces highly robust sorbent coatings for solid-phase microextraction. Anal Chim Acta 843:18–26CrossRefPubMedGoogle Scholar
  12. 12.
    Feng J, Sun M, Bu Y, Luo C (2015) Facile modification of multi-walled carbon nanotubes-polymeric ionic liquids-coated solid-phase microextraction fibers by on-fiber anion exchange. J Chromatogr A 1393:8–17CrossRefPubMedGoogle Scholar
  13. 13.
    Zhang B, Xu G, Li L, Wang X, Li N, Zhao RS, Lin J (2018) Facile fabrication of MIL-96 as coating fiber for solid-phase microextraction of trihalomethanes and halonitromethanes in water samples. Chem Eng J 350:240–247CrossRefGoogle Scholar
  14. 14.
    Li QL, Huang F, Wang XL, Wang X, Zhao RS (2017) Multiple-helix cobalt(II)-based metal-organic nanotubes on stainless steel fibers for solid-phase microextraction of chlorophenol and nitrophenols from water samples. Microchim Acta 184:1817–1825CrossRefGoogle Scholar
  15. 15.
    Zhao S, Wu M, Zhao F, Zeng B (2013) Electrochemical preparation of polyaniline-polypyrrole solid-phase microextraction coating and its application in the GC determination of several esters. Talanta 117:146–151CrossRefPubMedGoogle Scholar
  16. 16.
    Hou X, Yu H, Guo Y, Liang X, Wang S, Wang L, Liu X (2015) Polyethylene glycol/graphene oxide coated solid-phase microextraction fiber for analysis of phenols and phthalate esters coupled with gas chromatography. J Sep Sci 38:2700–2707CrossRefPubMedGoogle Scholar
  17. 17.
    Zhang Y, A S ZY, Luo X, Li Z, Xia H, Liu X, Mu Y (2014) Gas uptake, molecular sensing and organocatalytic performances of a multifunctional carbazole-based conjugated microporous polymer. J Mater Chem A 2:13422–13430CrossRefGoogle Scholar
  18. 18.
    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 1015:27–34CrossRefPubMedGoogle Scholar
  19. 19.
    Jin Y, Li Z, Yang L, Xu J, Zhao L, Li Z, Niu J (2017) Porous aromatic framework 48/gel hybrid material coated solid-phase microextraction fiber for the determination of the migration of styrene from polystyrene food contact materials. Anal Chem 89:1290–1298CrossRefPubMedGoogle Scholar
  20. 20.
    Liu S, Chen D, Zheng J, Zeng L, Jiang J, Jiang R, Zhu F, Shen Y, Wu D, Ouyang G (2015) The sensitive and selective adsorption of aromatic compounds with highly crosslinked polymer nanoparticles. Nanoscale 7:16943–16951CrossRefPubMedGoogle Scholar
  21. 21.
    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 1456:34–41CrossRefPubMedGoogle Scholar
  22. 22.
    Zhang S, Yang Q, Li Z, Wang W, Wang C, Wang Z (2017) Covalent organic frameworks as a novel fiber coating for solid-phase microextraction of volatile benzene homologues. Anal Bioanal Chem 409:3429–3439CrossRefPubMedGoogle Scholar
  23. 23.
    Guo H, Chen G, Wu M, Ma J, Jia Q (2017) Preparation of a porous aromatic framework via the Chan-Lam reaction: a coating for solid-phase microextraction of antioxidants and preservatives. Microchim Acta 184:4409–4416CrossRefGoogle Scholar
  24. 24.
    Zhu Y, Wan S, Jin Y, Zhang W (2015) Desymmetrized vertex design for the synthesis of covalent organic frameworks with periodically heterogeneous pore structures. J Am Chem Soc 137:13772–13775CrossRefPubMedGoogle Scholar
  25. 25.
    Zhou TY, Xu SQ, Wen Q, Pang ZF, Zhao X (2014) One-step construction of two different kinds of pores in a 2D covalent organic framework. J Am Chem Soc 136:15885–15888CrossRefPubMedGoogle Scholar
  26. 26.
    Yin ZJ, Xu SQ, Zhan TG, Qi QY, Wu ZQ, Zhao X (2017) Ultrahigh volatile iodine uptake by hollow microspheres formed from a heteropore covalent organic framework. Chem Commun 53:7266–7269CrossRefGoogle Scholar
  27. 27.
    Qian C, Xu SQ, Jiang GF, Zhan TG, Zhao X (2016) Precision construction of 2D heteropore covalent organic frameworks by a multiple-linking-site strategy. Chem Eur J 22:17784–17789CrossRefPubMedGoogle Scholar
  28. 28.
    Xu L, Ding SY, Liu J, Sun J, Wang W, Zheng QY (2016) Highly crystalline covalent organic frameworks from flexible building blocks. Chem Commun 52:4706–4709CrossRefGoogle Scholar
  29. 29.
    Ding SY, Dong M, Wang YW, Chen YT, Wang HZ, Su CY, Wang W (2016) Thioether-based fluorescent covalent organic framework for selective detection and facile removal of mercury(II). J Am Chem Soc 138:3031–3037CrossRefPubMedGoogle Scholar
  30. 30.
    Li Y, Yang CX, Yan XP (2017) Controllable preparation of core-shell magnetic covalent-organic framework nanospheres for efficient adsorption and removal of bisphenols in aqueous solution. Chem Commun 53:2511–2514CrossRefGoogle Scholar
  31. 31.
    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 185:1–10CrossRefGoogle Scholar
  32. 32.
    Wen CY, Chen J, Li M, Xue Y, Aslam S, Subhan F, Zhao R, Yu J, Zeng J, Chen X (2017) Gold nanoparticles deposited on mesoporous carbon as a solid-phase sorbent with enhanced extraction capacity and selectivity for anilines. Microchim Acta 184:3929–3936CrossRefGoogle Scholar
  33. 33.
    He J, Lv R, Zhu J, Lu K (2010) Selective solid-phase extraction of dibutyl phthalate from soybean milk using molecular imprinted polymers. Anal Chim Acta 661:215–221CrossRefPubMedGoogle Scholar
  34. 34.
    Yang J, Li Y, Wang Y, Ruan J, Zhang J, Sun C (2015) Recent advances in analysis of phthalate esters in foods. Trac-Trend Anal Chem 72:10–26CrossRefGoogle Scholar
  35. 35.
    Ye CW, Gao J, Yang C, Liu XJ, Li XJ, Pan SY (2009) Development and application of an SPME/GC method for the determination of trace phthalates in beer using a calix[6]arene fiber. Anal Chim Acta 641:64–74CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.College of ChemistryJilin UniversityChangchunChina

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