Abstract
A hybrid material was synthesized by growing a covalent organic framework (COF) in-situ on the surface of functionalized metal organic framework (MOF). Specifically, the amino-modified MOF (type MIL-68) was obtained by reacting indium(III) nitrate and 2-aminoterephthalic acid. Subsequently, it was reacted with tris(4-formylphenyl)amine and tris(4-aminophenyl)amine to obtain the final hybrid COF. This material overcomes the disadvantage of MOF concerning poor stability in aqueous solution and it combines the advantages of MOF and COF. This MOF@COF hybrid material is shown to be a viable adsorbent for the extraction of sulfonamides by pipette tip solid-phase extraction). Following elution with acetonitrile, the sulfonamides were quantified by high performance liquid chromatography using variable wavelength detection (HPLC-VWD). The structure and morphology of the material was characterized by various techniques. Extraction parameters such as amount of adsorbent, sampling rate, sample pH, elution solvent and sample volume were investigated. Under the optimum conditions, the sulfonamides tested (sulfadimethoxine sulfamethoxazole, sulfamonomethoxine, sulfamethazine, sulfamerazine and sulfadiazine) can be determined over a wide linear range (10–2000 ng·mL−1), with low limits of detection (1 ng·mL−1) and high precision (RSD <5.2%). The method was applied the determination of sulfonamide residues in (spiked) environmental water, milk and meat samples and gave recoveries in the range from 68.9–103.8%, with RSDs of <6.6%. The packed pipette tip column exhibits excellent stability, reproducibility and high adsorption capacity.
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References
Xi J, Zhang J, Zhao H (2017) Novel uniform Fe3O4hollow spheres for magnetic solid-phase extraction of polycyclic aromatic hydrocarbons. Anal Sci 33:999–1005. https://doi.org/10.2116/analsci.33.999
Ma W, Li XJ, Bai Y, Liu HW (2018) Applications of metal-organic frameworks as advanced sorbents in biomacromolecules sample preparation. TRAC-Trends Anal Chem 109:154–162. https://doi.org/10.1016/j.trac.2018.10.003
Herrero-Latorre C, Barciela-Garcia J, Garcia-Martin S, Pena-Crecente RM (2018) Graphene and carbon nanotubes as solid phase extraction sorbents for the speciation of chromium: a review. Anal Chim Acta 1002:1–17. https://doi.org/10.1016/j.aca.2017.11.042
Kumazawa T, Hasegawa C, Lee X-P, Hara K, Seno H, Suzuki O, Sato K (2007) Simultaneous determination of methamphetamine and amphetamine in human urine using pipette tip solid-phase extraction and gas chromatography–mass spectrometry. J Pharmaceut Biomed Anal 44:602–607. https://doi.org/10.1016/j.jpba.2006.12.025
Shen Q, Gong L, Baibado JT, Dong W, Wang Y, Dai Z, Cheung H-Y (2013) Graphene based pipette tip solid phase extraction of marine toxins in shellfish muscle followed by UPLC–MS/MS analysis. Talanta 116:770–775. https://doi.org/10.1016/j.talanta.2013.07.042
Sun N, Han Y, Yan H, Song Y (2014) A self-assembly pipette tip graphene solid-phase extraction coupled with liquid chromatography for the determination of three sulfonamides in environmental water. Anal Chim Acta 810:25–31. https://doi.org/10.1016/j.aca.2013.12.013
Ma Y, Liu L, Tang W, Zhu T (2017) Sulfonated poly(styrene-divinylbenzene) modified with amines and the application for pipette-tip solid-phase extraction of carbendazim in apples. J Sep Sci 40:3938–3945. https://doi.org/10.1002/jssc.201700594
Wang J, Liu X, Wei Y (2018) Magnetic solid-phase extraction based on magnetic zeolitic imazolate framework-8 coupled with high performance liquid chromatography for the determination of polymer additives in drinks and foods packed with plastic. Food Chem 256:358–366. https://doi.org/10.1016/j.foodchem.2018.02.136
Zhang J, Chen Z (2017) Metal-organic frameworks as stationary phase for application in chromatographic separation. J Chromatogr A 1530:1–18. https://doi.org/10.1016/j.chroma.2017.10.065
Qian HL, Yang CX, Wang WL, Yang C, Yan XP (2018) Advances in covalent organic frameworks in separation science. J Chromatogr A 1542:1–18. https://doi.org/10.1016/j.chroma.2018.02.023
Wang X, Ma R, Hao L, Wu Q, Wang C, Wang Z (2018) Mechanochemical synthesis of covalent organic framework for the efficient extraction of benzoylurea insecticides. J Chromatogr A 1551:1–9. https://doi.org/10.1016/j.chroma.2018.03.053
Liu J-M, Wang X-Z, Zhao C-Y, Hao J-L, Fang G-Z, Wang S (2018) Fabrication of porous covalent organic frameworks as selective and advanced adsorbents for the on-line preconcentration of trace elements against the complex sample matrix. J Hazard Mater 344:220–229. https://doi.org/10.1016/j.jhazmat.2017.10.013
Zhang J, Zhang W, Bao T, Chen Z (2015) Polydopamine-based immobilization of zeolitic imidazolate framework-8 for in-tube solid-phase microextraction. J Chromatogr A 1388:9–16. https://doi.org/10.1016/j.chroma.2015.02.010
Chen Y, Chen Z (2017) COF-1-modified magnetic nanoparticles for highly selective and efficient solid-phase microextraction of paclitaxel. Talanta 165:188–193. https://doi.org/10.1016/j.talanta.2016.12.051
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
Wang Q, Wang Y, Zhang Z, Tong Y, Zhang L (2017) Waxberry-like magnetic porous carbon composites prepared from a nickel-organic framework for solid-phase extraction of fluoroquinolones. Microchim Acta 184:4107–4115. https://doi.org/10.1007/s00604-017-2438-2
Liu GY, Li LY, Huang XD, Zheng SN, Xu DH, Xu XM, Zhang YG, Lin H (2018) Determination of triazole pesticides in aqueous solution based on magnetic graphene oxide functionalized MOF-199 as solid phase extraction sorbents. Microporous Mesoporous Mater 270:258–264. https://doi.org/10.1016/j.micromeso.2018.05.023
Zhang X, Liang Q, Han Q, Wan W, Ding M (2016) Metal–organic frameworks@graphene hybrid aerogels for solid-phase extraction of non-steroidal anti-inflammatory drugs and selective enrichment of proteins. Analyst 141:4219–4226. https://doi.org/10.1039/C6AN00353B
Lin C-L, Lirio S, Chen Y-T, Lin C-H, Huang H-Y (2014) A novel hybrid metal–organic framework–polymeric monolith for solid-phase microextraction. Chem Eur J 20:3317–3321. https://doi.org/10.1002/chem.201304458
Jia Y, Su H, Wang Z, Wong YLE, Chen X, Wang M, Chan TWD (2016) Metal–organic framework@microporous organic network as adsorbent for solid-phase microextraction. Anal Chem 88:9364–9367. https://doi.org/10.1021/acs.analchem.6b03156
Jeremias F, Frohlich D, Janiak C, Henninger SK (2014) Water and methanol adsorption on MOFs for cycling heat transformation processes. New J Chem 38:1846–1852. https://doi.org/10.1039/C3NJ01556D
Li N, Wu D, Hu N, Fan G, Li X, Sun J, Chen X, Suo Y, Li G, Wu Y (2018) Effective enrichment and detection of trace polycyclic aromatic hydrocarbons in food samples based on magnetic covalent organic framework hybrid microspheres. J Agric Food Chem 66:3572–3580. https://doi.org/10.1021/acs.jafc.8b00869
Wu L, Xue M, Qiu S-L, Chaplais G, Simon-Masseron A, Patarin J (2012) Amino-modified MIL-68(In) with enhanced hydrogen and carbon dioxide sorption enthalpy. Microporous Mesoporous Mater 157:75–81. https://doi.org/10.1016/j.micromeso.2011.12.034
Peng Y, Zhao M, Chen B, Zhang Z, Huang Y, Dai F, Lai Z, Cui X, Tan C, Zhang H (2018) Hybridization of MOFs and COFs: anew strategy for construction of MOF@COF hybrid materials. Adv Mater 30. https://doi.org/10.1002/adma.201705454
Chullasat K, Nurerk P, Kanatharana P, Kueseng P, Sukchuay T, Bunkoed O (2017) Hybrid monolith sorbent of polypyrrole-coated graphene oxide incorporated into a polyvinyl alcohol cryogel for extraction and enrichment of sulfonamides from water samples. Anal Chim Acta 961:59–66. https://doi.org/10.1016/j.aca.2017.01.052
Izanloo M, Esrafili A, Behbahani M, Ghambarian M, Sobhi HR (2018) Trace quantification of selected sulfonamides in aqueous media by implementation of a new dispersive solid-phase extraction method using a nanomagnetic titanium dioxide graphene-based sorbent and HPLC-UV. J Sep Sci 41:910–917. https://doi.org/10.1002/jssc.201700814
Li YY, Zhu N, Chen T, Ma YL, Li Q (2018) A green cyclodextrin metal-organic framework as solid-phase extraction medium for enrichment of sulfonamides before their HPLC determination. Microchem J 138:401–407. https://doi.org/10.1016/j.microc.2018.01.038
da Silva MR, Lancas FM (2018) Evaluation of ionic liquids supported on silica as a sorbent for fully automated online solid-phase extraction with LC-MS determination of sulfonamides in bovine milk samples. J Sep Sci 41:2237–2244. https://doi.org/10.1002/jssc.201701148
Wang GN, Zhang L, Song YP, Liu JX, Wang JP (2017) Application of molecularly imprinted polymer based matrix solid phase dispersion for determination of fluoroquinolones, tetracyclines and sulfonamides in meat. J Chromatogr B 1065:104–111. https://doi.org/10.1016/j.jchromb.2017.09.034
Chatzimitakos T, Samanidou V, Stalikas CD (2017) Graphene-functionalized melamine sponges for microextraction of sulfonamides from food and environmental samples. J Chromatogr A 1522:1–8. https://doi.org/10.1016/j.chroma.2017.09.043
Jia X, Zhao P, Ye X, Zhang L, Wang T, Chen Q, Hou X (2017) A novel metal-organic framework composite MIL-101(Cr)@GO as an efficient sorbent in dispersive micro-solid phase extraction coupling with UHPLC-MS/MS for the determination of sulfonamides in milk samples. Talanta 169:227–238. https://doi.org/10.1016/j.talanta.2016.08.086
Nasir ANM, Yahaya N, Zain NNM, Lim V, Kamaruzaman S, Saad B, Nishiyama N, Yoshida N, Hirota Y (2019) Thiol-functionalized magnetic carbon nanotubes for magnetic micro-solid phase extraction of sulfonamide antibiotics from milks and commercial chicken meat products. Food Chem 276:458–466. https://doi.org/10.1016/j.foodchem.2018.10.044
SadeghiS OS (2019) Nanostructured polyaniline based pipette tip solid phase extraction coupled with high-performance liquid chromatography for the selective determination of trace levels of three sulfonamides in honey and milk samples with the aid of experimental design methodology. Microchem J 146:974–985. https://doi.org/10.1016/j.microc.2019.02.020
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This work was financed by the National Natural Science Foundation of China (No. 81503036), the Natural Science Foundation of Hubei Province (No. 2017CFB220) and the Scientific Research Foundation of Wuhan Institute of Technology (K201457).
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Chen, Z., Yu, C., Xi, J. et al. A hybrid material prepared by controlled growth of a covalent organic framework on amino-modified MIL-68 for pipette tip solid-phase extraction of sulfonamides prior to their determination by HPLC. Microchim Acta 186, 393 (2019). https://doi.org/10.1007/s00604-019-3513-7
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DOI: https://doi.org/10.1007/s00604-019-3513-7