磁性有机骨架材料在生物样品前处理中的应用进展
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摘要
样品前处理是生物样品分析过程中的重要一环,为了去除基质的干扰、富集微量待测物质,通常需要进行合适、高效的前处理。金属有机骨架(MOFs)和共价有机骨架(COFs)是近年来涌现出的两类新型多功能多孔晶体材料,MOFs和COFs因具有比表面积高、孔隙率大、热稳定性好和功能多样化等特点,以及可与磁固相萃取(MSPE)相结合进行有效应用而备受关注。本综述概述了磁性MOFs和COFs的制备方法,总结了磁性MOFs和COFs作为新型吸附剂在生物样品前处理中的应用。此外,还探讨了未来生物样品前处理过程中磁性MOFs和COFs的不足和发展前景,有望促进以磁性MOFs和COFs为新型吸附剂的MSPE领域研究。
Sample pretreatment is an important part of the biological sample analysis process. In order to remove the interference of the matrix and enrich the trace substances to be tested,appropriate and efficient pretreatment is usually required. Metal-organic frameworks(MOFs) and covalent-organic frameworks(COFs) are two new types of multi-functional porous crystal materials emerging in recent years. MOFs and COFs have attracted much attention due to their characteristics of high specific surface area,large porosity,good thermal stability and functional diversification,as well as their effective application in combination with magnetic solid phase extraction(MSPE). This review summarizes the preparation methods of magnetic MOFs and COFs,and summarizes the application of magnetic MOFs and COFs as novel adsorbents in the pretreatment of biological samples. In addition,the shortcomings and development prospects of magnetic MOFs and COFs in the pretreatment of biological samples in the future are also discussed,which is expected to promote the study of magnetic MOFs and COFs as new adsorbents in the field of MSPE.
Sample pretreatment is an important part of the biological sample analysis process. In order to remove the interference of the matrix and enrich the trace substances to be tested,appropriate and efficient pretreatment is usually required. Metal-organic frameworks(MOFs) and covalent-organic frameworks(COFs) are two new types of multi-functional porous crystal materials emerging in recent years. MOFs and COFs have attracted much attention due to their characteristics of high specific surface area,large porosity,good thermal stability and functional diversification,as well as their effective application in combination with magnetic solid phase extraction(MSPE). This review summarizes the preparation methods of magnetic MOFs and COFs,and summarizes the application of magnetic MOFs and COFs as novel adsorbents in the pretreatment of biological samples. In addition,the shortcomings and development prospects of magnetic MOFs and COFs in the pretreatment of biological samples in the future are also discussed,which is expected to promote the study of magnetic MOFs and COFs as new adsorbents in the field of MSPE.
引文
[1]Che D,Jie C,Ji Z,et al.Recent advances and applications of polydopamine-derived adsorbents for sample pretreatment[J].TrAC Trends in Analytical Chemistry,2017(97):1-14.
[2]张圣虎,张易曦,吉贵祥,等.生物样品中烷基酚类内分泌干扰物的前处理和分析方法[J].环境化学,2015(9):1601-1610.
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[6]Wierucka M,Biziuk MJTiAC.Application of magnetic nanoparticles for magnetic solid-phase extraction in preparing biological,environmental and food samples[J].TrAC Trends in Analytical Chemistry,2014,59(2):50-58.
[7]祁晓月,李先江,白玉,等.手性金属有机骨架材料的合成及其在对映异构体选择性分离中的应用[J].色谱,2016,34(1):10-15.
[8]Tadjarodi 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(4):1391-1399.
[9]Wang Y,Xie J,Wu Y,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(9-10):949-956.
[10]邓玉兰,李傲天,王燕飞,等.Mil-53(fe)@聚多巴胺@Fe3O4磁性复合材料的制备及其用于环境水样中磺酰脲类除草剂的磁固相萃取[J].色谱,2018,36(3):253-260.
[11]Liu Y,Ma Y,Zhao Y,et al.Weaving of organic threads into a crystalline covalent organic framework[J].Science,2016,351(6271):365.
[12]Li N,Wu D,Hu N,et al.Effective enrichment and detection of trace polycyclic aromatic hydrocarbons in food samples based on magnetic covalent organic framework hybrid microspheres[J].Journal of Agricultural and Food Chemistry,2018,66(13):3572-3580.
[13]Qian H L,Yang C X,Wang W L,et al.Advances in covalent organic frameworks in separation science[J].Journal of Chromatography A,2018(1542):1-18.
[14]He S,Zeng T,Wang S,et al.Facile synthesis of magnetic covalent organic framework with three-dimensional bouquet-like structure for enhanced extraction of organic targets[J].ACS Applied Materials & Interfaces,2017,9(3):2959-2965.
[15]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.
[16]Na L,Junjie D,Di W,et al.Recent advances in facile synthesis and applications of covalent organic framework materials as superior adsorbents in sample pretreatment[J].TrAC Trends in Analytical Chemistry,2018.
[17]Chen L,He Y,Lei Z,et al.Preparation of core-shell structured magnetic covalent organic framework nanocomposites for magnetic solid-phase extraction of bisphenols from human serum sample [J].Talanta,2018(181):296-304.
[18]Chen Y,Chen Z J T.Cof-1-modified magnetic nanoparticles for highly selective and efficient solid-phase microextraction of paclitaxel [J].Talanta,2017(165):188-193.
[19]Ren J Y,Wang X L,Li X L,et al.Magnetic covalent triazine-based frameworks as magnetic solid-phase extraction adsorbents for sensitive determination of perfluorinated compounds in environmental water samples[J].Analytical and Bioanalytical Chemistry,2018,410(6):1657-1665.
[20]Yaghi O M,Michael O K,Ockwig N W,et al.Reticular synthesis and the design of new materials [J].Nature,2003,423(6941):705-714.
[21]Tan K,Nijem N,Canepa P,et al.Stability and hydrolyzation of metal organic frameworks with paddle-wheel sbus upon hydration [J].Chemistry of Materials,2016,24(16):3153-3167.
[22]Huo S H,Yan X P J A.Facile magnetization of metal-organic framework mil-101 for magnetic solid-phase extraction of polycyclic aromatic hydrocarbons in environmental water samples[J].The Analyst,2012,137(15):3445-3451.
[23]Saikia M,Bhuyan D,Saikia L.Facile synthesis of Fe3O4 nanoparticles on metal organic framework MIL-101(Cr):Characterization and catalytic activity[J].New Journal of Chemistry,2014,39(1):64-67.
[24]Lu G,Li S,Guo Z,et al.Imparting functionality to a metal-organic framework material by controlled nanoparticle encapsulation[J].Nature Chemistry,2012,4(4):310-316.
[25]Sara S,Beatriz Z,Carlos T,et al.Ordered mesoporous silica-(zif-8) core-shell spheres [J].Chemical Communications,2012,48(75):9388-9390.
[26]Torad N L,Ming H,Shinsuke I,et al.Direct synthesis of mof-derived nanoporous carbon with magnetic co nanoparticles toward efficient water treatment [J].Small,2014,10(10):2096-2107.
[27]Salunkhe R R,Kaneti Y V,Yamauchi Y.Metal-organic framework-derived nanoporous metal oxides toward supercapacitor applications:Progress and prospects [J].ACS Nano,2017,11(6):5293.
[28]Maya F,Cabello C,Palomino,et al.Automated growth of metal-organic framework coatings on flow-through functional supports [J].Chem Commun,2015,51(38):8169-8172.
[29]Wang J,Li J,Wang Y,et al.Development of versatile metal-organic framework functionalized magnetic graphene core-shell biocomposite for highly specifically recognizing glycopeptides[J].ACS Applied Materials & Interfaces,2016,8(41):27482-27489.
[30]Zou Z,Wang S,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.
[31]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,2017,41(4):948-957.
[32]Zhang S,Jiao Z,Yao W.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.
[33]Xie Y,Deng C,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.
[34]Ma R,Hao L,Wang J,et al.Magnetic porous carbon derived from a metal-organic framework as a magnetic solid-phase extraction adsorbent for the extraction of sex hormones from water and human urine[J].Journal of Separation Science,2016,39(18):3571-3577.
[35]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.
[36]Wei J P,Wang H,Luo T,et al.Enrichment of serum biomarkers by magnetic metal-organic framework composites[J].Analytical and Bioanalytical Chemistry,2017,409(7):1895-1904.
[37]C?Té A P,Benin AI,Ockwig N W,et al.Porous,crystalline,covalent organic frameworks [J].Science,2005,310(5751):1166-1170.
[38]Long C,Ko F,Jia G,et al.Photoelectric covalent organic frameworks:Converting open lattices into ordered donor-acceptor heterojunctions[J].Journal of the American Chemical Society,2014,136(28):9806-9809.
[39]Pachfule P,Acharjya A,Roeser J,et al.Diacetylene functionalized covalent organic framework (cof) for photocatalytic hydrogen generation[J].Journal of the American Chemical Society,2017,140(4):1423-1427.
[40]Wang X,Han X,Zhang J,et al.Homochiral 2d porous covalent organic frameworks for heterogeneous asymmetric catalysis[J].Journal of the American Chemical Society,2016,138(38):12332-12335.
[41]Ning H,Xiong C,Rajamani K,et al.Two-dimensional covalent organic frameworks for carbon dioxide capture through channel-wall functionalization[J].Angew Chem Int Ed Engl,2015,127(10):3029-3033.
[42]Li Z,Zhang Y,Xia H,et al.A robust and luminescent covalent organic framework as a highly sensitive and selective sensor for the detection of Cu(2+) ions[J].Chemical Communications,2016,52(39):6613-6616.
[43]Niu X,Ding S,Wang W,et al.Separation of small organic molecules using covalent organic frameworks-lzu1 as stationary phase by open-tubular capillary electrochromatography[J].Journal of Chromatography A,2016,1436(7):109-117.
[44]Mohammad Gulam R,Ali Kemal S,Zafer K,et al.A 2d mesoporous imine-linked covalent organic framework for high pressure gas storage applications[J].Chemistry - A European Journal,2013,19(10):3324-3328.
[45]Doonan C J,Tranchemontagne D J,Glover T G,et al.Exceptional ammonia uptake by a covalent organic framework[J].Nature Chemistry,2010,2(3):235-238.
[46]Han X,Huang J,Yuan C,et al.Chiral 3d covalent organic frameworks for high performance liquid chromatographic enantioseparation[J].Journal of the American Chemical Society,2018,140(3):892.
[47]Wang R,Chen Z L.A covalent organic framework-based magnetic sorbent for solid phase extraction of polycyclic aromatic hydrocarbons,and its hyphenation to hplc for quantitation[J].Microchimica Acta,2017(5751):1-8.
[48]Zhang W,Qiu L G,Yuan Y P,et al.Microwave-assisted synthesis of highly fluorescent nanoparticles of a melamine-based porous covalent organic framework for trace-level detection of nitroaromatic explosives[J].Journal of Hazardous Materials,2012,221-222(4):147-154.
[49]Hao W,Shuangzhi C,Nantao H,et al.The microwave-assisted solvothermal synthesis of a crystalline two-dimensional covalent organic framework with high Co2 capacity[J].Chemical Communications,2015,51(61):12178-12181.
[50]Bojdys M J,Jekaterina J,Arne T,et al.Rational extension of the family of layered,covalent,triazine-based frameworks with regular porosity[J].Advanced Materials,2010,22(19):2202-2205.
[51]Pierre K,Markus A,Arne T.Porous,covalent triazine-based frameworks prepared by ionothermal synthesis[J].Angewandte Chemie,2010,47(18):3450-3453.
[52]Xin W,Takaki S,Yamagishi J.Investigating very deep highway networks for parametric speech synthesis[J].Speech Communication,2016,96:166-171.
[53]Lin G,Gao C,Zheng Q,et al.Room-temperature synthesis of core-shell structured magnetic covalent organic frameworks for efficient enrichment of peptides and simultaneous exclusion of proteins[J].Chem Commun,2017,53(26):3649-3652.
[54]Gao C,Guo L,Lei Z,et al.Facile synthesis of core-shell structured magnetic covalent organic framework composite nanospheres for selective enrichment of peptides with simultaneous exclusion of proteins[J].J Mater Chem B,2017,5:7496-7503.
[55]Wang H,Jiao F,Gao F,et al.Facile synthesis of magnetic covalent organic frameworks for the hydrophilic enrichment of n-glycopeptides[J].Journal of Materials Chemistry B,2017,5(22):4052-4059.
[56]Lei C,Zhang M,Fu F,et al.Facile synthesis of magnetic covalent organic framework nanobeads and application to magnetic solid-phase extraction of trace estrogens from human urine[J].Journal of Chromatography A,2018,1567:136-146.
[57]Wang Y,Wang J,Gao M,et al.Functional dual hydrophilic dendrimer-modified metal-organic framework for the selective enrichment of n-glycopeptides[J].Proteomics,2017,17(10):e1700005.
[58]杨成雄,严秀平.共价-有机骨架材料在色谱及样品预处理中的应用[J].色谱,2018,36(11):1075-1080.
[2]张圣虎,张易曦,吉贵祥,等.生物样品中烷基酚类内分泌干扰物的前处理和分析方法[J].环境化学,2015(9):1601-1610.
[3]Andrade-Eiroa A,Canle M,Leroy-Cancellieri V,et al.Solid phase extraction of organic compounds:A critical review.Part ii[J].TrAC Trends in Analytical Chemistry,2016(80):655-667.
[4]Hashemi B,Zohrabi P,Raza N,et al.Metal organic frameworks as advanced sorbents for the extraction and determination of pollutants from environmental,biological,and food media[J].TrAC Trends in Analytical Chemistry,2017(97) :65-82.
[5]Maya F,Cabello C P,Frizzarin R M,et al.Magnetic solid-phase extraction using metal-organic frameworks (mofs) and their derived carbons[J].TrAC Trends in Analytical Chemistry,2017(90):142-152.
[6]Wierucka M,Biziuk MJTiAC.Application of magnetic nanoparticles for magnetic solid-phase extraction in preparing biological,environmental and food samples[J].TrAC Trends in Analytical Chemistry,2014,59(2):50-58.
[7]祁晓月,李先江,白玉,等.手性金属有机骨架材料的合成及其在对映异构体选择性分离中的应用[J].色谱,2016,34(1):10-15.
[8]Tadjarodi 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(4):1391-1399.
[9]Wang Y,Xie J,Wu Y,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(9-10):949-956.
[10]邓玉兰,李傲天,王燕飞,等.Mil-53(fe)@聚多巴胺@Fe3O4磁性复合材料的制备及其用于环境水样中磺酰脲类除草剂的磁固相萃取[J].色谱,2018,36(3):253-260.
[11]Liu Y,Ma Y,Zhao Y,et al.Weaving of organic threads into a crystalline covalent organic framework[J].Science,2016,351(6271):365.
[12]Li N,Wu D,Hu N,et al.Effective enrichment and detection of trace polycyclic aromatic hydrocarbons in food samples based on magnetic covalent organic framework hybrid microspheres[J].Journal of Agricultural and Food Chemistry,2018,66(13):3572-3580.
[13]Qian H L,Yang C X,Wang W L,et al.Advances in covalent organic frameworks in separation science[J].Journal of Chromatography A,2018(1542):1-18.
[14]He S,Zeng T,Wang S,et al.Facile synthesis of magnetic covalent organic framework with three-dimensional bouquet-like structure for enhanced extraction of organic targets[J].ACS Applied Materials & Interfaces,2017,9(3):2959-2965.
[15]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.
[16]Na L,Junjie D,Di W,et al.Recent advances in facile synthesis and applications of covalent organic framework materials as superior adsorbents in sample pretreatment[J].TrAC Trends in Analytical Chemistry,2018.
[17]Chen L,He Y,Lei Z,et al.Preparation of core-shell structured magnetic covalent organic framework nanocomposites for magnetic solid-phase extraction of bisphenols from human serum sample [J].Talanta,2018(181):296-304.
[18]Chen Y,Chen Z J T.Cof-1-modified magnetic nanoparticles for highly selective and efficient solid-phase microextraction of paclitaxel [J].Talanta,2017(165):188-193.
[19]Ren J Y,Wang X L,Li X L,et al.Magnetic covalent triazine-based frameworks as magnetic solid-phase extraction adsorbents for sensitive determination of perfluorinated compounds in environmental water samples[J].Analytical and Bioanalytical Chemistry,2018,410(6):1657-1665.
[20]Yaghi O M,Michael O K,Ockwig N W,et al.Reticular synthesis and the design of new materials [J].Nature,2003,423(6941):705-714.
[21]Tan K,Nijem N,Canepa P,et al.Stability and hydrolyzation of metal organic frameworks with paddle-wheel sbus upon hydration [J].Chemistry of Materials,2016,24(16):3153-3167.
[22]Huo S H,Yan X P J A.Facile magnetization of metal-organic framework mil-101 for magnetic solid-phase extraction of polycyclic aromatic hydrocarbons in environmental water samples[J].The Analyst,2012,137(15):3445-3451.
[23]Saikia M,Bhuyan D,Saikia L.Facile synthesis of Fe3O4 nanoparticles on metal organic framework MIL-101(Cr):Characterization and catalytic activity[J].New Journal of Chemistry,2014,39(1):64-67.
[24]Lu G,Li S,Guo Z,et al.Imparting functionality to a metal-organic framework material by controlled nanoparticle encapsulation[J].Nature Chemistry,2012,4(4):310-316.
[25]Sara S,Beatriz Z,Carlos T,et al.Ordered mesoporous silica-(zif-8) core-shell spheres [J].Chemical Communications,2012,48(75):9388-9390.
[26]Torad N L,Ming H,Shinsuke I,et al.Direct synthesis of mof-derived nanoporous carbon with magnetic co nanoparticles toward efficient water treatment [J].Small,2014,10(10):2096-2107.
[27]Salunkhe R R,Kaneti Y V,Yamauchi Y.Metal-organic framework-derived nanoporous metal oxides toward supercapacitor applications:Progress and prospects [J].ACS Nano,2017,11(6):5293.
[28]Maya F,Cabello C,Palomino,et al.Automated growth of metal-organic framework coatings on flow-through functional supports [J].Chem Commun,2015,51(38):8169-8172.
[29]Wang J,Li J,Wang Y,et al.Development of versatile metal-organic framework functionalized magnetic graphene core-shell biocomposite for highly specifically recognizing glycopeptides[J].ACS Applied Materials & Interfaces,2016,8(41):27482-27489.
[30]Zou Z,Wang S,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.
[31]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,2017,41(4):948-957.
[32]Zhang S,Jiao Z,Yao W.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.
[33]Xie Y,Deng C,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.
[34]Ma R,Hao L,Wang J,et al.Magnetic porous carbon derived from a metal-organic framework as a magnetic solid-phase extraction adsorbent for the extraction of sex hormones from water and human urine[J].Journal of Separation Science,2016,39(18):3571-3577.
[35]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.
[36]Wei J P,Wang H,Luo T,et al.Enrichment of serum biomarkers by magnetic metal-organic framework composites[J].Analytical and Bioanalytical Chemistry,2017,409(7):1895-1904.
[37]C?Té A P,Benin AI,Ockwig N W,et al.Porous,crystalline,covalent organic frameworks [J].Science,2005,310(5751):1166-1170.
[38]Long C,Ko F,Jia G,et al.Photoelectric covalent organic frameworks:Converting open lattices into ordered donor-acceptor heterojunctions[J].Journal of the American Chemical Society,2014,136(28):9806-9809.
[39]Pachfule P,Acharjya A,Roeser J,et al.Diacetylene functionalized covalent organic framework (cof) for photocatalytic hydrogen generation[J].Journal of the American Chemical Society,2017,140(4):1423-1427.
[40]Wang X,Han X,Zhang J,et al.Homochiral 2d porous covalent organic frameworks for heterogeneous asymmetric catalysis[J].Journal of the American Chemical Society,2016,138(38):12332-12335.
[41]Ning H,Xiong C,Rajamani K,et al.Two-dimensional covalent organic frameworks for carbon dioxide capture through channel-wall functionalization[J].Angew Chem Int Ed Engl,2015,127(10):3029-3033.
[42]Li Z,Zhang Y,Xia H,et al.A robust and luminescent covalent organic framework as a highly sensitive and selective sensor for the detection of Cu(2+) ions[J].Chemical Communications,2016,52(39):6613-6616.
[43]Niu X,Ding S,Wang W,et al.Separation of small organic molecules using covalent organic frameworks-lzu1 as stationary phase by open-tubular capillary electrochromatography[J].Journal of Chromatography A,2016,1436(7):109-117.
[44]Mohammad Gulam R,Ali Kemal S,Zafer K,et al.A 2d mesoporous imine-linked covalent organic framework for high pressure gas storage applications[J].Chemistry - A European Journal,2013,19(10):3324-3328.
[45]Doonan C J,Tranchemontagne D J,Glover T G,et al.Exceptional ammonia uptake by a covalent organic framework[J].Nature Chemistry,2010,2(3):235-238.
[46]Han X,Huang J,Yuan C,et al.Chiral 3d covalent organic frameworks for high performance liquid chromatographic enantioseparation[J].Journal of the American Chemical Society,2018,140(3):892.
[47]Wang R,Chen Z L.A covalent organic framework-based magnetic sorbent for solid phase extraction of polycyclic aromatic hydrocarbons,and its hyphenation to hplc for quantitation[J].Microchimica Acta,2017(5751):1-8.
[48]Zhang W,Qiu L G,Yuan Y P,et al.Microwave-assisted synthesis of highly fluorescent nanoparticles of a melamine-based porous covalent organic framework for trace-level detection of nitroaromatic explosives[J].Journal of Hazardous Materials,2012,221-222(4):147-154.
[49]Hao W,Shuangzhi C,Nantao H,et al.The microwave-assisted solvothermal synthesis of a crystalline two-dimensional covalent organic framework with high Co2 capacity[J].Chemical Communications,2015,51(61):12178-12181.
[50]Bojdys M J,Jekaterina J,Arne T,et al.Rational extension of the family of layered,covalent,triazine-based frameworks with regular porosity[J].Advanced Materials,2010,22(19):2202-2205.
[51]Pierre K,Markus A,Arne T.Porous,covalent triazine-based frameworks prepared by ionothermal synthesis[J].Angewandte Chemie,2010,47(18):3450-3453.
[52]Xin W,Takaki S,Yamagishi J.Investigating very deep highway networks for parametric speech synthesis[J].Speech Communication,2016,96:166-171.
[53]Lin G,Gao C,Zheng Q,et al.Room-temperature synthesis of core-shell structured magnetic covalent organic frameworks for efficient enrichment of peptides and simultaneous exclusion of proteins[J].Chem Commun,2017,53(26):3649-3652.
[54]Gao C,Guo L,Lei Z,et al.Facile synthesis of core-shell structured magnetic covalent organic framework composite nanospheres for selective enrichment of peptides with simultaneous exclusion of proteins[J].J Mater Chem B,2017,5:7496-7503.
[55]Wang H,Jiao F,Gao F,et al.Facile synthesis of magnetic covalent organic frameworks for the hydrophilic enrichment of n-glycopeptides[J].Journal of Materials Chemistry B,2017,5(22):4052-4059.
[56]Lei C,Zhang M,Fu F,et al.Facile synthesis of magnetic covalent organic framework nanobeads and application to magnetic solid-phase extraction of trace estrogens from human urine[J].Journal of Chromatography A,2018,1567:136-146.
[57]Wang Y,Wang J,Gao M,et al.Functional dual hydrophilic dendrimer-modified metal-organic framework for the selective enrichment of n-glycopeptides[J].Proteomics,2017,17(10):e1700005.
[58]杨成雄,严秀平.共价-有机骨架材料在色谱及样品预处理中的应用[J].色谱,2018,36(11):1075-1080.