Magnetic nanoparticles coated with poly(p-phenylenediamine-co-thiophene) as a sorbent for preconcentration of organophosphorus pesticides

Abstract

The authors describe the preparation of Fe3O4 nanoparticles coated with poly(p-phenylenediamine-co-thiophene). The resulting nanoparticles (NPs) are shown to be viable sorbents for use in magnetic solid-phase extraction (MSPE) of organophosphorus pesticides (OPPs). The coated NPs were characterized by BET, FTIR, scanning electron microscopy and transmission electron microscopy. Following sorption of OPPs and subsequent desorption with dichloromethane, the OPPs were quantified by GC in combination with FID. Under optimal conditions, the preconcentration factors range from 118 to 163. Other figures of merit include (a) a linear response between 0.3 and 500 ng mL−1; (b) detection limits (at an S/N ratio of 3) between 0.1 and 0.3 ng mL−1, and (c) a precision (for n = 5) between 4.7 and 8.1% at concentration levels of 1, 10 and 100 ng mL−1). The nanocomposites can be reused up to 8 times. The method was applied to the analysis of spiked environmental water samples and fruit juices and gave relative recoveries in the range of 88.1 to 99.2%.

Schematic presentation of the synthesis of core-shell magnetic nanoparticles (MNPs) of the type poly(pPDA-co-Th)@Fe3O4, and their application as a sorbent for magnetic solid-phase extraction (MSPE) of organophosphorus pesticides.

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References

  1. 1.

    Li Q, Nagahara N, Takahashi H, Takeda K, Okumura K, Minami M (2002) Organophosphorus pesticides markedly inhibit the activities of natural killer, cytotoxic T lymphocyte and lymphokine-activated killer: a proposed inhibiting mechanism via granzyme inhibition. Toxicology 172:181–190

    CAS  Article  Google Scholar 

  2. 2.

    Wang X, Ma X, Wang H, Huang P, Du X, Lu X (2017) A zinc(II) benzenetricarboxylate metal organic framework with unusual adsorption properties, and its application to the preconcentration of pesticides. Microchim Acta 184:3681–3687

    CAS  Article  Google Scholar 

  3. 3.

    You X, Xing Z, Liu F, Jiang N (2013) Air-assisted liquid-liquid microextraction used for the rapid determination of organophosphorus pesticides in juice samples. J Chromatogr A 1311:41–47

    CAS  Article  Google Scholar 

  4. 4.

    Salemi A, Rasoolzadeh R, Nejad MM, Vosough M (2013) Ultrasonic assisted headspace single drop micro-extraction and gas chromatography with nitrogen-phosphorus detector for determination of organophosphorus pesticides in soil. Anal Chim Acta 769:121–126

    CAS  Article  Google Scholar 

  5. 5.

    Sun X, Zhu F, Xi J, Lu T, Liu H, Tong Y, Ouyang G (2011) Hollow fiber liquid-phase microextraction as clean-up step for the determination of organophosphorus pesticides residues in fish tissue by gas chromatography coupled with mass spectrometry. Mar Pollut Bull 63:102–107

    CAS  Article  Google Scholar 

  6. 6.

    Jafari MT, Saraji M, Sherafatmand H (2014) Polypyrrole/montmorillonite nanocomposite as a new solid phase microextraction fiber combined with gas chromatography–corona discharge ion mobility spectrometry for the simultaneous determination of diazinon and fenthion organophosphorus pesticides. Anal Chim Acta 814:69–78

    CAS  Article  Google Scholar 

  7. 7.

    Farajzadeh MA, Bahram M, Vardast MR, Bamorowat M (2011) Dispersive liquid-liquid microextraction for the analysis of three organophosphorus pesticides in real samples by high performance liquid chromatography-ultraviolet detection and its optimization by experimental design. Microchim Acta 172:465–470

    CAS  Article  Google Scholar 

  8. 8.

    Wierucka M, Biziuk M (2014) Application of magnetic nanoparticles for magnetic solid-phase extraction in preparing biological, environmental and food samples. Trends Anal Chem 59:50–58

    CAS  Article  Google Scholar 

  9. 9.

    Giakisikli G, Anthemidis AN (2013) Magnetic materials as sorbents for metal/metalloid preconcentration and/or separation. A review. Anal Chim Acta 789:1–16

    CAS  Article  Google Scholar 

  10. 10.

    Yang G, He Z, Liu X, Liu C, Zhan J, Liu D, Wang P, Zhou Z (2016) Polymer-coated magnetic nanospheres for preconcentration of organochlorine and pyrethroid pesticides prior to their determination by gas chromatography with electron capture detection. Microchim Acta 183:1187–1194

    CAS  Article  Google Scholar 

  11. 11.

    Li H, Xie T, Ye L, Wang Y, Xie C (2017) Core-shell magnetic molecularly imprinted polymer nanoparticles for the extraction of triazophos residues from vegetables. Microchim Acta 184:1011–1019

    CAS  Article  Google Scholar 

  12. 12.

    Bouri M, Gurau M, Salghi R, Cretescu I, Zougagh M, Rios Á (2012) Ionic liquids supported on magnetic nanoparticles as a sorbent preconcentration material for sulfonylurea herbicides prior to their determination by capillary liquid chromatography. Anal Bioanal Chem 404:1529–1538

    CAS  Article  Google Scholar 

  13. 13.

    Amiri A, Zonoz FM, Targhoo A, Saadati-Moshtaghin HR (2017) Enrichment of phenolic compounds from water samples by using magnetic Fe3O4 nanoparticles coated with a Keggin type heteropoly acid of type H6[BFe(OH2)W11O39] as a sorbent. Microchim Acta 184:1093–1101

    CAS  Article  Google Scholar 

  14. 14.

    Ballesteros-Gómez A, Rubio S (2009) Hemimicelles of alkyl carboxylates chemisorbed onto magnetic nanoparticles: study and application to the extraction of carcinogenic polycyclic aromatic hydrocarbons in environmental water samples. Anal Chem 81:9012–9020

    Article  Google Scholar 

  15. 15.

    Rezvani-Eivari M, Amiri A, Baghayeri M, Ghaemi F (2016) Magnetized graphene layers synthesized on the carbon nanofibers asnovel adsorbent for the extraction of polycyclic aromatic hydrocarbons from environmental water samples. J Chromatogr A 1465:1–8

    CAS  Article  Google Scholar 

  16. 16.

    Mehdinia A, Rouhani S, Mozaffari S (2016) Microwave-assisted synthesis of reduced graphene oxide decorated with magnetite and gold nanoparticles, and its application to solid-phase extraction of organochlorine pesticides. Microchim Acta 183:1177–1185

    CAS  Article  Google Scholar 

  17. 17.

    Tahmasebi E, Yamini Y, Moradi M, Esrafili A (2013) Polythiophene-coated Fe3O4 superparamagnetic nanocomposite: synthesis and application as a new sorbent for solid-phase extraction. Anal Chim Acta 770:68–74

    CAS  Article  Google Scholar 

  18. 18.

    Pan C, Sugiyasu K, Aimi J, Sato A, Takeuchi M (2014) Picket-fence Polythiophene and its Diblock copolymers that afford microphase separations comprising a stacked and an isolated Polythiophene ensemble. Angew Chem Int Ed 53:8870–8875

    CAS  Article  Google Scholar 

  19. 19.

    Cogal S, Kiristi M, Ocakoglu K, Oksuz L, Oksuz AU (2015) Electrochromic properties of electrochemically synthesized porphyrin/3-substituted polythiophene copolymers. Mater Sci Semicond Process 31:551–560

    CAS  Article  Google Scholar 

  20. 20.

    Boudouris BW, Frisbie CD, Hillmyer MA (2010) Polylactide−Polythiophene−Polylactide triblock copolymers. Macromolecules 43:3566–3569

    CAS  Article  Google Scholar 

  21. 21.

    Cianga I, Mercore VM, Grigoras M, Yagci Y (2007) Poly(thienyl-phenylene)s with macromolecular side chains by oxidative polymerization of well-defined macromonomers. J Polym Sci A Polym Chem 45:848–865

    CAS  Article  Google Scholar 

  22. 22.

    Chen X, Gholamkhass B, Han X, Vamvounis G, Holdcroft S (2007) Polythiophene-graft-styrene and Polythiophene-graft-(styrene-graft-C60) copolymers. Macromol Rapid Commun 28:1792–1797

    CAS  Article  Google Scholar 

  23. 23.

    Bilal S, Shah A-HA, Holze R (2011) Spectroelectrochemistry of poly(o-phenylenediamine): polyaniline-like segments in the polymer structure. Electrochim Acta 56:3353–3358

    CAS  Article  Google Scholar 

  24. 24.

    Amiri A, Baghayeri M, Nori S (2015) Magnetic solid-phase extraction using poly(para-phenylenediamine) modified with magnetic nanoparticles as adsorbent for analysis of monocyclic aromatic amines in water and urine samples. J Chromatogr A 1415:20–26

    CAS  Article  Google Scholar 

  25. 25.

    Li XG, Huang MR, Duan W, Yang Y (2002) Novel multifunctional polymers from aromatic diamines by oxidative polymerizations. Chem Rev 102:2925–3030

    CAS  Article  Google Scholar 

  26. 26.

    Amiri A, Baghayeri M, Kashmari M (2016) Magnetic nanoparticles modified with polyfuran for the extraction of polycyclic aromatic hydrocarbons prior to their determination by gas chromatography. Microchim Acta 183:149–156

    CAS  Article  Google Scholar 

  27. 27.

    Wang C, Schindler JL, Kannewurf CR, Kanatzidis MG (1995) Poly(3,4-ethylenedithiathiophene). A new soluble conductive polythiophene derivative. Chem Mater 7:58–68

    CAS  Article  Google Scholar 

  28. 28.

    Yildiz UH, Sahin E, Akhmedov IM, Tanyeli C, Toppare L (2006) A new soluble conducting polymer and its electrochromic devices. J Polym Sci Part A: Polym Chem 44:2215–2225

    CAS  Article  Google Scholar 

  29. 29.

    Nicho ME, Hu H, Lopez-Mata C, Escalante J (2004) Synthesis of derivatives of polythiophene and their application in an electrochromic device. Sol Energy Mater Sol Cells 82:105–118

    CAS  Article  Google Scholar 

  30. 30.

    Farajzadeh MA, Afshar Mogaddam MR, Rezaee Aghdam S, Nouri N, Bamorrowat M (2016) Application of elevated temperature–dispersive liquid–liquid microextraction for determination of organophosphorus pesticides residues in aqueous samples followed by gas chromatography– flame ionization detection. Food Chem 2012:198–204

    Article  Google Scholar 

  31. 31.

    Farajzadeh MA, Asghari A, Feriduni B (2016) An efficient, rapid and microwave-accelerated dispersive liquid–liquid microextraction method for extraction and pre-concentration of some organophosphorus pesticide residues from aqueous samples. J Food Compos Anal 48:73–80

    CAS  Article  Google Scholar 

  32. 32.

    Ayazi Z, Jaafarzadeh R, Matin AA (2017) Montmorillonite/polyaniline/polyamide nanocomposite as a novel stir bar coating for sorptive extraction of organophosphorous pesticides in fruit juices and vegetables applying response surface methodology. Anal Methods 9:4547–4557

    CAS  Article  Google Scholar 

  33. 33.

    Pinheiro AS, de Andrade JB (2009) Development, validation and application of a SDME/GC-FID methodology for the multiresidue determination of organophosphate and pyrethroid pesticides in water. Talanta 79:1354–1359

    CAS  Article  Google Scholar 

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Correspondence to Amirhassan Amiri.

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Targhoo, A., Amiri, A. & Baghayeri, M. Magnetic nanoparticles coated with poly(p-phenylenediamine-co-thiophene) as a sorbent for preconcentration of organophosphorus pesticides. Microchim Acta 185, 15 (2018). https://doi.org/10.1007/s00604-017-2560-1

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Keywords

  • Emulsion polymerization
  • Brunauer-Emmett-teller adsorption
  • Conductive polymer
  • Polythiophene
  • Poly(p-phenylenediamine)