MOF复合材料在固相萃取中的应用进展

doi:10.3969/j.issn.1000-1565.2022.01.007

摘要/Abstract

摘要： 样品前处理是分析过程中不可或缺的一步.无论样品是气态、液态还是固态,只有经过前处理才能进行后续分析,其主要目的是使样品中目标组分浓度升高,提高仪器的灵敏度,去除样品中的其他杂质以得到较为纯净的目标组分.而样品前处理的关键是吸附剂类型的选择,它决定了萃取效率.金属有机骨架化合物(MOF)是一种新型材料,因其组成和结构非常丰富,且比表面积和孔隙率高、孔道性能可调、热稳定性较好等诸多优势,被广泛应用于样品前处理.而MOF与其他材料结合形成的复合物不仅克服了MOF本身的缺点,而且还对MOF的特性进行重大改进.本文主要综述了近年来MOF与磁性材料、碳及聚合物等材料复合后作为固相萃取吸附剂在环境、食品和生物等样品分析方面的应用.

关键词: 金属有机骨架材料, 固相萃取, 复合材料

Abstract: Sample pretreatment is an indispensable step in the analysis process. Whether the sample is gaseous, liquid, or solid, pretreatment must be carried out before the sample analysis. The main purpose of pretreatment is to increase the concentration of the target component, improve the sensitivity of the instrument, and remove other impurities to obtain a purer target component. The key of sample pretreatment is the selection of adsorbent, which determines the extraction efficiency. Metalorganic franework(MOF), as a new kind of cage material, has attracted much attention. Its uniform pore structure shows the molecular sieve effect and shape selectivity in the adsorption process. In addition, MOF has many advantages, such as rich composition and structure, high specific surface area and porosity, adjustable pore performance, good thermal stability, etc. MOFs are widely used in gas storage and capture, catalysis, sample pretreatment and other fields. The composite formed by the combination of MOF and other materials not only overcomes the shortcomings of MOF itself, but also greatly improves the properties of MOF. This paper mainly reviewed the applications of MOF composites(including MOF@magnetic material, MOF@carbon composite, MOF@polymer composite,etc)as solid phase extraction adsorbents in the environmental analysis, food analysis and biological sample analysis.

Key words: metal organic framework(MOF), solid phase extraction, composite material

中图分类号:

刘海燕,韩亚美,王杉. MOF复合材料在固相萃取中的应用进展[J]. 河北大学学报(自然科学版), 2022, 42(1): 44-59.

LIU Haiyan, HAN Yamei, WANG Shan. Application of metal organic framework composites in solid phase extraction[J]. Journal of Hebei University(Natural Science Edition), 2022, 42(1): 44-59.

参考文献

[1] 张晓琼,汪彤,王培怡,等. 金属有机骨架及其复合材料在分离领域中的应用进展[J].色谱,2016,34(12):1176-1185.DOI: 10.3724/sp.J.1123.2016.03.08018.
[2] WEN Y Y, CHEN L, LI J H, et al. Recent advances in solid-phase sorbents for sample preparation prior to chromatographic analysis [J]. Trends in Analytical Chemistry, 2014,59:26-41.DOI: 10.1016/j.trac.2014.03.011.
[3] YAGHI O M, OKEEFFE M, OCKWIG N W, et al. Reticular synthesis and the design of new materials[J]. Nature, 2003, 423(6941): 705-714. DOI:10.1038/nature01650.
[4] KITAGAWA S, KITAURA R, NORO S I. Functional porous coordination polymers[J]. Angewandte Chemie International Edition, 2004, 43(18): 2334-2375. DOI:10.1002/anie.200300610.
[5] FÉREY G. Hybrid porous solids: Past, present, future[J]. Chem Soc Rev, 2008, 37(1): 191-214. DOI:10.1039/b618320b.
[6] YUSUF K, AQEL A, ALOTHMAN Z. Metal-organic frameworks in chromatography[J]. Journal of Chromatography A, 2014, 1348: 1-16. DOI:10.1016/j.chroma.2014.04.095.
[7] KAYAL S, SUN B C, CHAKRA BORTY A. Study of metal-organic framework MIL-101(Cr)for natural gas(methane)storage and compare with other MOFs(metal-organic frameworks)[J]. Chakraborty A Energy, 2015, 91: 772-781. DOI:10.1016/j.energy.2015.08.096.
[8] GAIKWAD S, KIM S J, HAN S. CO₂ capture using amine-functionalized bimetallic MIL-101 MOFs and their stability on exposure to humid air and acid gases[J]. Microporous & Mesoporous Materials, 2019, 277: 253-260. DOI:10.1016/j.micromeso.2018.11.001.
[9] NING X, SUN T H, FU H Y, et al. N-doped porous carbon supported Ni catalysts derived from modified Ni-MOF-74 for highly effective and selective catalytic hydrodechlorination of 1,2-dichloroethane to ethylene[J]. Chemosphere, 2020, 241: 124978. DOI:10.1016/j.chemosphere.2019.124978.
[10] PANG X Y, LIU H Y, YU H, et al. A metal organic framework polymer monolithic column as a novel adsorbent for on-line solid phase extraction and determination of ursolic acid in Chinese herbal medicine[J]. Journal of Chromatography B, 2019,1125: 121715. DOI:10.1016/j.jchromb.2019.121715.
[11] 孟志超,张璐,黄艳凤.金属有机骨架复合材料在样品预处理中的研究进展[J]. 色谱,2018,36(3):216-221. DOI:10.3724/sp.j.1123.2017.11042.
[12] 樊花,刘红妹.金属有机骨架及其复合材料在固相微萃取中的制备及应用[J].分析测试技术与仪器,2019,25(2):78-85. DOI:10.16495/j.1006-3757.2019.02.003.
[13] MAYA F, CABELLO C P, FRIZZARIN R M, et al. Magnetic solid-phase extraction using metal-organic frameworks(MOFs)and their derived carbons[J]. Trends in Analytical Chemistry, 2017, 90: 142-152. DOI:10.1016/j.trac.2017.03.004.
[14] HUO S H, YAN X P. Facile magnetization of metal-organic framework MIL-101 for magnetic solid-phase extraction of polycyclic aromatic hydrocarbons in environmental water samples [J]. Analyst, 2012, 137(15): 3445-3451. DOI:10.1039/c2an35429b.
[15] LI Y J, ZHOU X X, DONG L J, et al. Magnetic metal-organic frameworks nanocomposites for negligible-depletion solid-phase extraction of freely dissolved polyaromatic hydrocarbons[J]. Environmental Pollution, 2019, 252: 1574-1581. DOI:10.1016/j.envpol.2019.04.137.
[16] ZHANG S L, YAO W X, YING J B, et al. Polydopamine reinforced magnetization of zeolitic imidazolate framework ZIF-7 for magnetic solid phase extraction of polycyclic aromatic hydrocarbons from the air-water environment[J]. Journal of Chromatography A, 2016, 1452: 18-26. DOI:10.1016/j.chroma.2016.05.039.
[17] PRISCILL R B, VERóNICA P, JUAN H A, et al. A magnetic-based dispersive micro-solid-phase extraction method using the metal-organic framework HKUST-1 and ultra-high-performance liquid chromatography with fluorescence detection for determining polycyclic aromatic hydrocarbons in waters and fruit tea infusions[J]. Journal of Chromatography A, 2016, 1436: 42-50. DOI:10.1016/j.chroma.2016.01.067.
[18] HU Y L, HUANG Z L, LIAO J, et al. Chemical bonding approach for fabrication of hybrid magnetic metal-organic framework-5: high efficient adsorbents for magnetic enrichment of trace analytes[J]. Analytical Chemistry, 2013, 85(14): 6885-6893. DOI:10.1021/ac4011364.
[19] DU F Y, QIN Q, DENG J C, et al. Magnetic metal-organic framework MIL-100(Fe)microspheres for the magnetic solid-phase extraction of trace polycyclic aromatic hydrocarbons from water samples[J]. Journal of Separation Science, 2016, 39: 2356-2364. DOI:10.1002/jssc.201600100.
[20] TAGHIZADEH M, ASGHARINEZHAD A A, POOLADI M, et al. A novel magnetic metal organic framework nanocomposite for extraction and preconcentration of heavy metal ions, and its optimization via experimental design methodology[J]. Microchimica Acta, 2013, 180(11-12): 1073-1084. DOI: 10.1007/s00604-013-1010-y.
[21] BAGHERI A, TAGHIZADEH M, BEHBAHANI M, et al. Synthesis and characterization of magnetic metal-organic framework(MOF)as a novel sorbent, and its optimization by experimental design methodology for determination of palladium in environmental samples[J]. Talanta, 2012, 99: 132-139. DOI:10.1016/j.talanta.2012.05.030.
[22] SOHRABI M R, MATBOUIE Z, ASGHARINEZHAD A A, et al. Solid phase extraction of Cd(II)and Pb(II)using a magnetic metal-organic framework, and their determination by FAAS[J]. Microchimica Acta, 2013, 180(7-8):589-597. DOI:10.1007/s00604-013-0952-4.
[23] 黄理金.新型纳米磁性多孔材料的制备及其在金属离子吸附中的应用[D].武汉:武汉大学,2017.
[24] WANG Y, XIE J, WU Y C, et al. A magnetic metal-organic framework as a new sorbent for solid-phase extraction of copper(Ⅱ), and its determination by electrothermal AAS[J]. Microchimica Acta, 2014, 181: 949-956. DOI:10.1007/s00604-014-1183-z.
[25] RICCO R, KONSTAS K, STYLES M J, et al. Lead(Ⅱ)Uptake by Aluminium Based Magnetic Framework Composites(MFCs)in Water[J]. Journal of Materials Chemistry A, 2015, 3(39): 19822-19831. DOI:10.1039/c5ta04154f.
[26] WANG Y, XIE J, WU Y C, et al. Preparation of a functionalized magnetic metal-organic framework sorbent for the extraction of lead prior to electrothermal atomic absorption spectrometer analysis[J]. Journal of Materials Chemistry A, 2013, 1(31): 8782. DOI:10.1039/c3ta11178d.
[27] ABBASZADEH A, TADJARODI A. Speciation analysis of inorganic arsenic in food and water samples by electrothermal atomic absorption spectrometry after magnetic solid phase extraction by a novel MOF-199/modified magnetite nanoparticle composite[J]. RSC Advances, 2016, 6(114): 113727-113736. DOI:10.1039/c6ra21819a.
[28] ZOU Z R, WANG S L, JIA J, et al. Ultrasensitive determination of inorganic arsenic by hydride generation-atomic fluorescence spectrometry using Fe₃O₄@ZIF-8 nanoparticles for preconcentration[J]. Microchemical Journal, 2016, 124: 578-583. DOI:10.1016/j.microc.2015.10.005.
[29] XIONG Y H, YE F G, ZHANG C, et al. Synthesis of magnetic porous γ-Fe₂O₃/C@HKUST-1 composites for efficient removal of dyes and heavy metal ions from aqueous solution[J]. RSC Advances, 2015, 5(7): 5164. DOI:10.1039/c4ra12468e.
[30] TADJAROD A, ABBASZADEH A. A magnetic nanocomposite prepared from chelator-modified magnetite(Fe₃O₄)and HKUST-1(MOF-199)for separation and preconcentration of mercury(Ⅱ)[J]. Microchimica Acta, 2016, 183: 1391-1399. DOI:10.1007/s00604-016-1770-2.
[31] HE X, ZHOU Y Y, YANG W, et al. Microwave assisted magnetic solid phase extraction using a novel amino-functionalized magnetic framework composite of type Fe₃O₄-NH₂@MIL101(Cr)for the determination of organochlorine pesticides in soil samples[J]. Talanta, 2019, 196: 572-578. DOI:10.1016/j.talanta.2018.12.019.
[32] HE X, YANG W, LI S J, et al. An amino-functionalized magnetic framework composite of type Fe₃O₄-NH₂@MIL-101(Cr)for extraction of pyrethroids coupled with GC-ECD[J]. Microchim Acta, 2018, 185(2): 125. DOI:10.1007/s00604-018-2672-2.
[33] CHEN X F, DING N, ZANG H, et al. Dominic Chan. Fe₃O₄@MOF core-shell magnetic microspheres for magnetic solid-phase extraction of polychlorinated biphenyls from environmental water samples[J]. Journal of Chromatography A, 2013, 1304: 241-245. DOI:10.1016/j.chroma.2013.06.053.
[34] LIU S Y, LI S, YANG W, et al. Magnetic nanoparticle of metal-organic framework with core-shell structure as an adsorbent for magnetic solid phase extraction of non-steroidal anti-inflammatory drugs[J]. Talanta, 2019, 194: 514-521. doi:10.1016/j.talanta.2018.10.037.
[35] 方刚.磁性金属有机骨架与Au-NaYF₄复合纳米材料的制备及其分析应用[D].北京:北京化工大学,2015.
[36] MA J P, YAO Z D, HOU L W, et al. Metal organic frameworks(MOFs)for magnetic solid-phase extraction of pyrazole/pyrrole pesticides in environmental water samples followed by HPLC-DAD determination[J]. Talanta, 2016, 161: 686-692. DOI:10.1016/j.talanta.2016.09.035.
[37] SU H, LIN Y L, WANG Z H, et al. Magnetic metal-organic framework-titanium dioxide nanocomposite as adsorbent in the magnetic solid-phase extraction of fungicides from environmental water samples[J]. Journal of Chromatography A, 2016, 1466: 21-28. DOI:10.1016/j.chroma.2016.08.066.
[38] 曹晓林.功能化金属有机框架及其杂化印迹识别材料的制备与应用研究[D].北京:中国农业科学院,2018.
[39] LIN K Y A, LEE W D. Self-assembled magnetic graphene supported ZIF-67 as a recoverable and efficient adsorbent for benzotriazole[J]. Chemical Engineering Journal, 2016, 284: 1017-1027. DOI:10.1016/j.cej.2015.09.075.
[40] 刘浩驰.磁性MOF的设计制备及其在水污染物分离分析中的应用研究[D].哈尔滨:东北林业大学,2017.
[41] DADFARNIA S, SHABANI A M H, MORADI S E, et al. Methyl red removal from water by iron based metal-organic frameworks loaded onto iron oxide nanoparticle adsorbent[J]. Applied Surface Science, 2015, 330: 85-93. DOI:10.1016/j.apsusc.2014.12.196.
[42] LI L, LIU X L, GAO M, et al. The adsorption on magnetic hybrid Fe₃O₄ /HKUST-1/GO of methylene blue from water solution[J]. Journal of Materials Chemistry A, 2014, 2(6): 1795-1081. DOI:10.1039/c3ta14225f
[43] ZHAO X L, LIU S L, TANG Z, et al. Synthesis of magnetic metal- organic framework(MOF)for efficient removal of organic dyes from water[J]. Scientific Reprots, 2015, 5: 11849. DOI:10.1038/srep11849.
[44] WANG G H, LEI Y Q, SONG H C. Evaluation of Fe₃O₄@SiO₂-MOF-177 as an advantageous adsorbent for magnetic solid-phase extraction of phenols in environmental water samples[J]. Analytical methods, 2014(19): 7842-7847. DOI:10.1039/C4AY00822G.
[45] JIANG X, CHEN H Y, LIU L L, et al. Fe₃O₄ embedded ZIF-8 nanocrystals with ultra-high adsorption capacity towards hydroquinone[J]. Journal of Alloys and Compounds, 2015, 646(15): 1075-1082. DOI:10.1016/j.jallcom.2015.06.021.
[46] PEN^~A-MéNDEZA E M, MAWALE R M, CONDE-GONZáLEZ J E, et al. Metal organic framework composite, nano-Fe₃O₄@Fe-(benzene-1,3,5-tricarboxylic acid), for solid phase extraction of blood lipid regulators from water[J]. Talanta, 2020, 207: 120275. DOI: 10.1016/j.talanta.2019.120275.
[47] LIU X M, SUN Z W, CHEN G, et al. Determination of phthalate esters in environmental water by magnetic Zeolitic Imidazolate Framework-8 solid-phase extraction coupled with high-performance liquid chromatography[J]. Journal of Chromatography A, 2015, 1409: 46-52. DOI:10.1016/j.chroma.2015.07.068.
[48] DARGAHI R, EBRAHIMZADEH H, ASGHARINEZHAD A A, et al. Dispersive magnetic solid-phase extraction of phthalate esters from water samples and human plasma based on a nanosorbent composed of MIL-101(Cr)metal-organic framework and magnetite nanoparticles before their determination by GC-MS[J]. Journal of Separation Science, 2018, 41(4): 948-957. DOI:10.1002/jssc.201700700.
[49] 王娟强.基于磁固相萃取的样品前处理技术及对黄酮类物质和聚合物添加剂分离分析应用[D].北京:北京化工大学,2018.
[50] EBRAHIM G K. A metal-organic framework nanocomposite made from functionalized magnetite nanoparticles and HKUST-1(MOF-199)for preconcentration of Cd(Ⅱ), Pb(Ⅱ), and Ni(Ⅱ)[J]. Microchim Acta, 2016, 183(9): 2639-2647. DOI:10.1007/s00604-016-1896-2.
[51] BABAZADEH M, HOSSEINZADEH-KHANMIRI R, ABOLHASANI J, et al. Solid phase extraction of heavy metal ions from agricultural samples with the aid of a novel functionalized magnetic metal-organic framework[J]. RSC Advances, 2015, 5(26): 19884-19892. DOI:10.1039/c4ra15532g.
[52] HASSANPOUR A, KHANMIRI R H, BABAZADEH M, et al. Determination of heavy metal ions in vegetable samples using a magnetic metal-organic framework nanocomposite sorbent[J]. Food Additives & Contaminants: Part A, 2015, 32(5): 725-736. DOI:10.1080/19440049.2015.1007397.
[53] BABAZADEH M, KHANMIRI R H, ABOLHASANI J, et al. Synthesis and Application of a Novel Functionalized Magnetic Metal-Organic Framework Sorbent for Determination of Heavy Metal Ions in Fish Samples[J]. Bulletin of the Chemical Society of Japan, 2015, 88: 871-879. DOI:10.1246/bcsj.20140380.
[54] GHORBANI-KALHOR E, HOSSEINZADEH-KHANMIRI R, BABAZADEH M, et al. Synthesis and application of a novel magnetic metal-organic framework nanocomposite for determination of Cd, Pb, and Zn in baby food samples[J]. Canadian Journal of Chemistry, 2015, 93(5): 518-525. DOI:10.1139/cjc-2014-0474.
[55] WANG Y, CHEN H H, TANG J, et al. Preparation of magnetic metal organic frameworks adsorbent modified with mercapto groups for the extraction and analysis of lead in food samples by flame atomic absorption spectrometry[J]. Food Chem, 2015, 181: 191-197. DOI:10.1016/j.foodchem.2015.02.080.
[56] WEI X X, WANG Y Z, CHEN J, et al. Poly(deep eutectic solvent)-functionalized magnetic metal-organic framework composites coupled with solid-phase extraction for the selective separation of cationic dyes[J]. Analytica Chimica Acta, 2019, 1056: 47-61. DOI:10.1016/j.aca.2018.12.049.
[57] ZHOU Z H, FU Y Q, QIN Q, et al. Synthesis of magnetic mesoporous metal-organic framework-5 for the effective enrichment of malachite green and crystal violet in fish samples[J]. Journal of Chromatography A, 2018, 1560: 19-25. DOI:10.1016/j.chroma.2018.05.016.
[58] JIA Y Q, WANG Y H, YAN M, et al. Fabrication of iron oxide@MOF-808 as a sorbent for magnetic solid phase extraction of benzoylurea insecticides in tea beverages and juice samples[J]. Journal of Chromatography A, 2020, 1615: 460766. DOI:10.1016/j.chroma.2019.460766.
[59] 鹿萌. 新型 MOFs 固相萃取吸附剂的制备及果蔬中农药残留检测应用[D]. 邯郸:河北工程大学,2020.
[60] BAGHERI A R, GHAEDI M. Magnetic metal organic framework for pre-concentration of ampicillin from cow milk samples[J]. Journal of Pharmaceutical Analysis, 2020, 10(4): 365-375. DOI:10.1016/j.jpha.2020.02.006.
[61] 宁鹏,程云辉,许宙,等.金属-有机框架材料在活性肽富集中的应用[J]. 化学进展,2020,32(4):497-504. DOI:10.7536/pc190816.
[62] 傅寅旭,许雨熙,诸葛黔,等.金属有机骨架材料在生物样品前处理中的应用进展[J].材料导报,2019,33(z1):408-411.
[63] XIE Y Q, DENG C H, LI Y. Designed synthesis of ultra-hydrophilic sulfo-functionalized metal-organic frameworks with a magnetic core for highly efficient enrichment of the N-linked glycopeptides[J]. Journal of Chromatography A, 2017, 1508: 1-6. DOI:10.1016/j.chroma.2017.05.055.
[64] CHEN Y J, XIONG Z C, PENG L, et al. Facile preparation of core shell magnetic metal organic framework nanoparticles for the selective capture of phosphopeptides[J]. ACS Applied Materials & Interfaces, 2015, 7(30): 16338-16347. DOI:10.1021/acsami.5b03335.
[65] XIONG Z C, JI Y S, FANG C L, et al. Facile preparation of core-shell magnetic metal-organic framework nanospheres for the selective enrichment of endogenous peptides[J]. Chemistry-A European Journal, 2014, 20: 1-8. DOI:10.1002/chem.201400389.
[66] ZHAO M, DENG C H, ZHANG X M. The design and synthesis of a hydrophilic core-shell-shell structured magnetic metal-organic framework as a novel immobilized metal ion affinity platform for phosphoproteome research[J]. Chemical Communications, 2014, 50(47): 6228-6231. DOI:10.1039/c4cc01038h.
[67] WEI J P, QIAO B, SONG W J, et al. Synthesis of magnetic framework composites for the discrimination of Escherichia coli at the strain level[J]. Analytica Chimica Acta, 2015, 868: 36-44. DOI:10.1016/j.aca.2015.02.018.
[68] ZHANG S L, JIAO Z, YAO W X. A simple solvothermal process for fabrication of a metal-organic framework with an iron oxide enclosure for the determination of organophosphorus pesticides in biological samples[J]. Journal of Chromatography A, 2014, 1371: 74-81. DOI:10.1016/j.chroma.2014.10.088.
[69] ZHANG W M, YAN Z M, GAO J, et al. Metal-organic framework UiO-66 modified magnetite@silica core-shell magnetic microspheres for magnetic solid-phase extraction of domoic acid from shellfish samples[J]. Journal of Chromatography A, 2015, 1400: 10-18. DOI:10.1016/j.chroma.2015.04.061.
[70] RAHIMPOOR R, BAHRAMI A, NEMATOLLAHI D, et al. Sensitive determination of urinary muconic acid using magnetic dispersive-solid-phase extraction by magnetic amino-functionalised UiO-66[J]. International Journal of Environmental Analytical Chemistry, 2020:1-14. DOI:10.1080/03067319.2020.1727460.
[71] LIANG X J, LIU S J, WANG S, et al. Carbon-based sorbents: Carbon nanotubes[J]. Journal of Chromatography A, 2014, 1357: 53-67. DOI:10.1016/j.chroma.2014.04.039.
[72] WANG X Y, DENG C H. Preparation of magnetic graphene @polydopamine @Zr-MOF material for the extraction and analysis of bisphenols in water samples[J]. Talanta, 2015, 144: 1329-1335. DOI:10.1016/j.talanta.2015.08.014.
[73] LIU G Y, LI L Y, HUANG X D, et al. Determination of triazole pesticides in aqueous solution based on magnetic graphene oxide functionalized MOF-199 as solid phase extraction sorbents[J]. Microporous and Mesoporous Materials, 2018, 270: 258-264. DOI:10.1016/j.micromeso.2018.05.023.
[74] ZHANG X Q, LIANG Q L, HAN Q, et al. Metal-organic frameworks @ graphene hybrid aerogels for solid-phase extraction of nonsteroidal anti-inflammatory drugs and selective enrichment of proteins[J].Analyst, 2016, 141(13): 4219-4226. DOI:10.1039/c6an00353b.
[75] SAMUEL M S, VASUDEVAN S, JAYANTA B, et al. A GO-CS@MOF [Zn(BDC)(DMF)] material for the adsorption of chromium(VI)ions from aqueous solution[J]. Composites Part B: Engineering, 2018, 152: 116-125. DOI:10.1016/j.compositesb.2018.06.034.
[76] YANG P P, LIU Q, LIU J Y, et al. Interfacial growth of metal-organic framework(UiO-66)on the functionalized of graphene oxide(GO)as a suitable seawater adsorbent for extraction of uranium(Ⅵ)[J]. Journal of Materials Chemistry A, 2017, 5(34): 17933-17942. DOI:10.1039/c6ta10022h.
[77] JALILIAN N, EBRAHIMZADEH H, ASGHARINEZHAD A A. Preparation of magnetite/multiwalled carbon nanotubes/metal-organic framework composite for dispersive magnetic micro solid phase extraction of parabens and phthalate esters from water samples and various types of cream for their determination with liquid chromatography[J]. Journal of Chromatography A, 2019, 1608: 460426. DOI:10.1016/j.chroma.2019.460426.
[78] JIA X N, ZHAO P, YE X, et al. 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[J]. Talanta, 2017, 169: 227-238. DOI:10.1016/j.talanta.2016.08.086.
[79] WANG Y D, DAI X P, HE X, et al. MIL-101(Cr)@GO for dispersive micro-solid-phase extraction of pharmaceutical residue in chicken breast used in microwave-assisted coupling with HPLC-MS/MS detection[J]. Journal of Pharmaceutical and Biomedical Analysis, 2017, 145: 440-446. DOI:10.1016/j.jpba.2017.07.010.
[80] ZHANG S H, YANG Q, WANG W C, et al. Covalent bonding of metal-organic framework-5/graphene oxide hybrid composite to stainless steel fiber for solid-phase microextraction of triazole fungicides from fruit and vegetable samples[J]. Journal of Agricultural and Food Chemistry, 2016, 64(13): 2792-2801. DOI:10.1021/acs.jafc.5b05831.
[81] ZHANG S H, YANG Q, LI Z, et al. Solid phase microextraction of phthalic acid esters from vegetable oils using iron(III)-based metal-organic framework/graphene oxide coating[J]. Food Chemistry, 2018, 263: 258-264. DOI:10.1016/j.foodchem.2018.04.132.
[82] WANG Y, WU Y C, GE H L, et al. Fabrication of metal-organic frameworks and graphite oxide hybrid composites for solid-phase extraction and preconcentration of luteolin[J]. Talanta, 2014, 122: 91-96. DOI:10.1016/j.talanta.2014.01.049.
[83] JIN R R, JI F Q, LIN H Q, et al. The synthesis of Zr-metal-organic framework functionalized magnetic graphene nanocomposites as an adsorbent for fast determination of multi-pesticide residues in tobacco samples[J]. Journal of Chromatography A, 2018, 1577: 1-7. DOI:10.1016/j.chroma.2018.09.041.
[84] QIN Z C, JIANG Y X, PIAO H L, et al. MIL-101(Cr)MWCNTs-functionalized melamine sponges for solid-phase extraction of triazines from corn samples, and their subsequent determination[J]. Talanta, 2020, 211: 120676. DOI:10.1016/j.talanta.2019.120676.
[85] JIANG J B, LI J J, ZHU J L, et al. Synthesis of sandwich-structured magnetic graphene-Zn-MOFs composites for quantitative determination of acarbose in rat plasma[J]. Talanta, 2020, 209: 120514. DOI:10.1016/j.talanta.2019.120514.
[86] LIU J W, ZHANG Y, CHEN X W, et al. Graphene oxide-rare earth metal-organic framework composites for the selective isolation of hemoglobin [J]. ACS Appl Mater Interfaces, 2014, 6(13): 10196-10204. DOI:10.1021/am503298v.
[87] WANG J X, LI J, WANG Y N, et al. Development of versatile metal-organic framework functionalized magnetic graphene core-shell biocomposite for highly specific recognition of glycopeptides[J]. ACS Appl Mater Interfaces, 2016, 8(41): 27482-27489. DOI:10.1021/acsami.6b08218.
[88] WEI X X, WANG Y Z, CHEN J, et al. Preparation of ionic liquid modified magnetic metal-organic frameworks composites for the solid-phase extraction of α-chymotrypsin[J]. Talanta, 2018, 182: 484-491. DOI:10.1016/j.talanta.2018.02.022.
[89] KITAO T, ZHANG Y Y, KITAGAWA S, et al. Hybridization of MOFs and polymers[J]. Chemical Society Reviews, 2017, 46(11): 3108-3133. DOI:10.1039/c7cs00041c.
[90] WANG Y D, ZHANG Y, CUI J N, et al. Fabrication and characterization of metal organic frameworks/ polyvinyl alcohol cryogel and their application in extraction of non-steroidal anti-inflammatory drugs in water samples[J]. Analytica Chimica Acta, 2018, 1022: 45-52. DOI:10.1016/j.aca.2018.03.056.
[91] WANG Y D, JIA M T, WU X, et al. PEG modified column MIL-101(Cr)/PVA cryogel as a sorbent in stir bar solid phase extraction for determination of non-steroidal anti-inflammatory drugs in water samples[J]. Microchemical Journal, 2019, 146: 214-219. DOI:10.1016/j.microc.2018.12.045.
[92] FOTOVAT H, KHAJEH M, OVEISI A R, et al. A hybrid material composed of an amino-functionalized zirconium-based metal-organic framework and a urea-based porous organic polymer as an efficient sorbent for extraction of uranium(Ⅵ)[J]. Microchimica Acta, 2018, 185: 469. DOI:10.1007/s00604-018-2991-3.
[93] 杨成雄,杨雪清,严秀平.金属-有机骨架MIL-101(Cr)掺杂聚合物整体柱的制备及其用于酚类化合物的在线固相萃取[J].色谱,2019,37(8):824-830.
[94] JIA Y Q, SU H, WANG Z H, et al. Metal-organic framework@microporous organic network as adsorbent for solid-phase microextraction[J]. Analytical Chemistry, 2016, 88(19): 9364. DOI:10.1021/acs.analchem.6b03156.
[95] LIU H L, MU L, CHEN X M, et al. Core-shell metal-organic frameworks/molecularly imprinted nanoparticles as absorbents for the detection of pyrraline in milk and milk powder[J]. Journal of Agricultural and Food Chemistry, 2017, 65(4): 986-992. DOI:10.1021/acs.jafc.6b05429.
[96] YAN Z M, WU M, HU B Q, et al. Electrospun UiO-66/polyacrylonitrile nanofibers as efficient sorbent for pipette tip solid phase extraction of phytohormones in vegetable samples[J]. Journal of Chromatography A, 2018, 1542: 19-27. DOI:10.1016/j.chroma.2018.02.030.
[97] LAN H Z, GAN N, PAN D D, et al. Development of a novel magnetic molecularly imprinted polymer coating using porous zeolite imidazolate framework-8 coated magnetic iron oxide as carrier for automated solid phase microextraction of estrogens in fish and pork samples[J]. Journal of Chromatography A, 2014, 1365: 35-44. DOI:10.1016/j.chroma.2014.08.096.
[98] PANG X Y, LIU H Y, YU H, et al. A metal organic framework polymer monolithic column as a novel adsorbent for on-line solid phase extraction and determination of ursolic acid in Chinese herbal medicine[J]. J Chromatogr B, 2019, 1125: 121715. DOI:10.1016/j.jchromb.2019.121715.
[99] PANG X Y, LIU H Y, YU H, et al. Monolithic column prepared with UiO-66-2COOH MOF as monomer for enrichment and Purification of ursolic acid in plants by online solid-phase extraction[J]. Chromatographia, 2020, 83(9): 1121-1131. DOI:10.1007/s10337-020-03931-x.
[100] ZHANG M M, LIU H Y, HAN Y M, et al. On-line enrichment and determination of aristolochic acid in medicinal plants using a MOF-based composite monolith as adsorbent[J]. J Chromatogr B, 2020, 1159: 122343. DOI:10.1016/j.jchromb.2020.122343.
[101] GHIASVAND A R, GHAEDRAHMATI L, HEIDARI N, et al. Synthesis and characterization of MIL-101(Cr)intercalated by polyaniline composite, doped with silica nanoparticles and its evaluation as an efficient solid-phase extraction sorbent[J]. Journal of Separation Science, 2018, 41(20): 3910-3617. DOI:10.1002/jssc.201800498.
[102] ASIABI M, MEHDINIA A, JABBARI A. Preparation of water stable methyl-modified metal-organic framework-5/polyacrylonitrile composite nanofibers via electrospinning and their application for solid-phase extraction of two estrogenic drugs in urine samples[J]. Journal of Chromatography A, 2015, 1426: 24-32. DOI:10.1016/j.chroma.2015.11.036.
[103] WANG Y L, QIU X Z, LI Y Y, et al. Synthesis of a molecularly imprinted polymer on NH₂-MIL-101(Cr)for specific recognition of diclofenac sodium[J]. J Nanosci Nanotechnol, 2020, 20(3): 1807-1813. DOI:info:doi/10.1166/jnn.2020.17352.
[104] LIU F L, XU H. Development of a novel polystyrene/metal-organic framework-199 electrospun nanofiber adsorbent for thin film microextraction of aldehydes in human urine[J]. Talanta, 2017, 162: 261-267. DOI:10.1016/j.talanta.2016.09.065.
[105] SOHRABI M R. Preconcentration of mercury(Ⅱ)using a thiol-functionalized metal-organic framework nanocomposite as a sorbent[J]. Microchim Acta, 2014, 181(3-4): 435-444. DOI:10.1007/s00604-013-1133-1.
[106] ASIABI M, MEHDINIAB A, JABBARI A. Electrospun biocompatible Chitosan/MIL-101(Fe)composite nanofibers for solid-phase extraction of △9-tetrahydrocannabinol in whole blood samples using Box-Behnken experimental design[J]. Journal of Chromatography A, 2017, 1479: 71-80. DOI:10.1016/j.chroma.2016.12.024.
[107] LIANG X T, LIU S Q, ZHU R, et al. Highly sensitive analysis of polycyclic aromatic hydrocarbons in environmental water with porous cellulose/zeolitic imidazolate framework-8 composite microspheres as a novel adsorbent coupled with high-performance liquid chromatography[J]. Journal of Separation Science, 2016, 39(14): 2806-2814. DOI:10.1002/jssc.201600348.
[108] YOHANNES A, YAO S. Preconcentration of tropane alkaloids by a metal organic framework(MOF)-immobilized ionic liquid with the same nucleus for their quantitation in Huashanshen tablets[J]. The Analyst, 2019, 144(23): 6989-7000. DOI:10.1039/c9an01362h. (