Skip to main content
SpringerLink
Log in

Monohydroxycucurbit[7]uril-coated stir-bar sorptive extraction coupled with high-performance liquid chromatography for the determination of apolar and polar organic compounds

  • Original Paper
  • Published:
Microchimica Acta Aims and scope Submit manuscript

Abstract

A detailed study has been carried out on monohydroxycucurbit[7]uril-based stir-bar sorptive extraction (SBSE). A polydimethylsiloxane coating was produced by a sol–gel technique and doped with monohydroxycucurbit[7]uril ((HO)1Q [7]) as a selective sorbent phase. (HO)1Q [7] was chemically bound to the sol–gel silica substrate through hydrolysis and polycondensation. The coating possesses a porous surface, shows strong solvent resistance and good thermal stability, and has a long lifespan. Four groups of compounds, with polarities ranging from apolar polycyclic aromatic hydrocarbons to polar ketones, aromatic amines and phenols, were selected as test analytes. They were extracted with the coated stir bar, then desorbed with methanol and quantified by high-performance liquid chromatography with ultraviolet detection. The limits of detection range between 1.3 and 15 μg L−1, the linear ranges extend from 5 to 10,000 μg L−1, and the relative recoveries from spiked samples range between 76.4 and 97.9%. The intraday relative standard deviations range from 2.3 to 8.6% (for n = 3, at 500 μg L−1). Compared with a commercial PDMS-coated stir bar and a polyether sulfone-coated stir bar, the new stir bar shows wider applicability and better extraction efficiency for each group of compounds. In addition, the stir bar can simultaneously extract mixtures of chemicals of different polarities. This endows it with the potential for recovering a broad group of polar organic compounds.

A stir bar for sorptive extraction based on monohydroxycucurbit[7]uril has been prepared by a sol–gel technique. The stir bar coupled with HPLC with UV detection allows for the determination of a variety of polar compounds and multicomponent mixtures, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. He M, Chen B, Hu B (2013) Recent development in stir bar sorptive extraction. Anal Bioanal Chem 406:2001–2026

    Article  Google Scholar 

  2. Gilart N, Marce RM, Borrull F, Fontanals N (2014) Coatings for stir bar sorptive extraction of polar emerging organic contaminants. TrAC Trends Anal Chem 54:11–23

    Article  CAS  Google Scholar 

  3. Faraji H, Husain SW, Helalizadeh M (2011) β-cyclodextrin-bonded silica particles as novel sorbent for stir bar sorptive extraction of phenolic compounds. J Chromatogr Sci 49:482–487

    Article  CAS  Google Scholar 

  4. Huang X, Lin J, Yuan D (2011) Preparation of cation-extrange stir bar sorptive extraction based on monolithic material and its application to the analysis of soluble cations in milk by ion chromatography. Analyst 36:4289–4294

    Article  Google Scholar 

  5. Hu C, He M, Chen B, Zhong C, Hu B (2013) Polydimethylsiloxane/metal-organic frameworks coated stir bar sorptive extraction coupled to high performance liquid chromatography-ultraviolet detector for the determination of estrogens in environmental water samples. J Chromatogr A 1310:21–30

    Article  CAS  Google Scholar 

  6. Neng NR, Pinto ML, Pires J, Nogueira JMF (2007) Development, optimization and application of polyurethane foams as new polymeric phase for stir bar sorptive extraction. J Chromatogr A 1171:8–14

    Article  CAS  Google Scholar 

  7. David F, Ochiai N, Sandra P (2019) Two decades of stir bar sorptive extraction: a retrospective and future outlook. TrAC Trends Anal Chem 112:102–111

    Article  CAS  Google Scholar 

  8. Zeng J, Zhao C, Chen J, Subhan F, Luo L, Yu J, Cui B, Xing W, Chen X, Yan Z (2014) Ordered mesoporous carbaon/Nafion as a versatile and selective solid-phase microextraction coating. J Chromatogr A 1365:29–34

    Article  CAS  Google Scholar 

  9. Chong SL, Wang DX, Hayes JD, Wilhite BW, Malik A (1997) Sol-gel coating technology for the preparation of solid-phase microextraction fibers of enhanced thermal stability. Anal Chem 69:3889–3898

    Article  CAS  Google Scholar 

  10. Kumar A, Gaurav A, Malik K, Tewary DK, Singh B (2008) A review on development of solid phase microextraction fibers by sol-gel methods and their applications. Anal Chim Acta 610:1–14

    Article  CAS  Google Scholar 

  11. Lee JW, Samal S, Selvapalam N, Kim HJ, Kim K (2003) Cucurbituril homologues and derivations: new opportunities in supramolecular chemistry. Acc Chem Res 36:621–630

    Article  CAS  Google Scholar 

  12. Mock WL, Shin NY (1986) Structure and selectivity in host-guest complexes of cucurbituril. J Org Chem 51:4440–4446

    Article  CAS  Google Scholar 

  13. Kim E, Kim D, Jung H, Lee J, Paul S, Selvapalam N, Yang Y, Lim N, Park CG, Kim K (2010) Facile, template-free synthesis of stimuli-responsive polymer nanocapsule for targeted drug delivery. Angew Chem Int Ed 49:4405–4408

    Article  CAS  Google Scholar 

  14. Jeon WS, Ziganshina AY, Lee JW, Ko YH, Kang JK, Lee C, Kim K (2003) A[2]pseudorotaxane-based molecular machine: reversible formation of a molecular loop driven by electrochemical and photochemical stimuli. Angew Chem Int Ed 42:4097–4100

    Article  CAS  Google Scholar 

  15. Dong N, Li T, Luo YJ, Shao L, Tao Z, Zhu C (2016) A solid-phase microextraction coating of sol-gel-derived perhydroxy cucurbit[6]uril and its application on to the determination of polycyclic aromatic hydrocarbon. J Chromatogr A 1470:9–18

    Article  CAS  Google Scholar 

  16. Cong H, Ni XL, Xiao X, Huang Y, Zhu QJ, Xue SF, Tao Z, Lindoy LF, Wei G (2016) Synthesis and separation of cucurbit[n]urils and their derivatives. Org Biomol Chem 14:4335–4364

    Article  CAS  Google Scholar 

  17. Ma D, Hettiarachchi G, Nguyen D, Zhang B, Wittenberg JB, Zavalij PY, Briken V, Isaacs L (2012) Acyclic curcubit[n]uril molecular contaniers enhance the solubility and bioactivity of poorly soluble pharmaceutical. Nat Chem 4:503–510

    Article  CAS  Google Scholar 

  18. Ghale G, Ramalingam V, Urbach AR, Nau WM (2011) Determination protease substrate selectivity and inhibition by label-free supramolecular tandem enzyme assays. J Am Chem Soc 133:7528–7535

    Article  CAS  Google Scholar 

  19. Jon SJ, Selvapalam N, Oh DH, Kang JK, Kim SY, Jeon YJ, Lee JW, Kim K (2003) Facil synthesis of cucurbit[n]uril derivatives via direct functionalization: expanding utilization of cucurbit[n]uril. J Am Chem Soc 125:10186–10187

    Article  CAS  Google Scholar 

  20. Vinciguerra B, Cao L, Cannon JR, Zavalij PY, Fenselau C, Isaacs L (2012) Synthesis and self-assembly processes of monofunctionalized cucurbit[7]uril. Am Chem Soc 134:13133–13140

    Article  CAS  Google Scholar 

  21. Zeng Z, Qiu W, Huang Z (2001) Solid-phase microextraction using fused-silica fibers coated with sol-gel-derived hydroxy-crown ether. Anal Chem 73:2429–2436

    Article  CAS  Google Scholar 

  22. Dong N, He J, Li T, Peralta A, Avei MR, Ma MF, Kaifer AE (2018) Synthesis and binding properties of monohydroxycucurbit[7]uril: a key derivative for the functionalization of cucurbituril hosts. J Org Chem 83:5467–5473

    Article  CAS  Google Scholar 

  23. Lei Y, Chen B, You L, He M, Hu B (2017) Polydimethylsiloxane/MIL-100(Fe) coated stir bar sorptive extraction-high performance liquid chromatography for the determination of triazines in environmental water samples. Talanta 175:158–167

    Article  CAS  Google Scholar 

  24. Mourdikoudis S, Montes-García V, Rodal-Cedeira S, Winckelmans N, Pérez-Juste L, Wu H, Bals S, Pérez-Juste J, Patoriza-Santos I (2019) Highly porous palladium nanodenedrites: wet-chemical synthesis, electron tomography and catalytic activity. Dalton Trans 48:3758–3767

    Article  CAS  Google Scholar 

  25. Shu J, Xie P, Lin D, Chen R, Wang J, Zhang B, Liu M, Liu H, Liu F (2014) Two highly stable and selective solid phase microextraction fibers coated with crown ether functionalized ionic liquids by different sol-gel reaction approaches. Anal Chim Acta 806:152–164

    Article  CAS  Google Scholar 

  26. Zheng L (2018) Nanoporous silica-dye microspheres for enhanced colorimetric detection of cyclohexanoe. Chemosnesors 6:1–11

    Article  Google Scholar 

  27. Zou X, Wang H, Lu Y, Huang C, Xia L, Chen X, Shen C, Chu Y (2015) Rapid analysis of residrual cyclohexanone in pvc infusion set by extractive electrospray ionization-mass spectrometer/mass spectrometer. Acta Chim Sin 73:851–855

    CAS  Google Scholar 

  28. Khalfi F, Dine T, Luyckx M, Gressier B, Brunet C, Ballester L, Cazin M, Cazin JC (1998) Determination of cyclohexanone after derivatization with 2,4- dinitrophenyl hydrazine in intravenous solution stored in pvc bags by high performace liquid chromatography. Biomed Chromatogr 12:69–72

    Article  CAS  Google Scholar 

  29. Ni XN, Xiao X, Cong H, Zhu QJ, Xue SF, Tao Z (2014) Self-assemblies based on the “outer-surface interactions” of cucurbit[n]urils: new opportunities for supramoloecular architectures and materials. Acc Chem Res 47:1386–1395

    Article  CAS  Google Scholar 

  30. Pinjari RV, Khedkar JK, Gejji SP (2010) Cavity diameter and height of cyclodextrins and cucurbit[n]urils from the molecular electrostatic potential topography. J Incl Phenom Macro 66:371–380

    Article  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NO.21665005).

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Guizhou University, Guiyang, 550025, China

    Nan Dong, Lingxue Zhang, Jianmei Yao, Peijian Ma, Jing He & Tao Li

  2. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guiyang, 550025, China

    Nan Dong

  3. Resource and Environmental Engineering College, Guizhou University, Guiyang, 550025, China

    Yuan Wang

Authors
  1. Nan Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lingxue Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jianmei Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Peijian Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jing He
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tao Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yuan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nan Dong.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

ESM 1

(DOC 24.5 mb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dong, N., Zhang, L., Yao, J. et al. Monohydroxycucurbit[7]uril-coated stir-bar sorptive extraction coupled with high-performance liquid chromatography for the determination of apolar and polar organic compounds. Microchim Acta 186, 846 (2019). https://doi.org/10.1007/s00604-019-3910-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00604-019-3910-y

Keywords

Search

Navigation