共价有机框架(COFs)是一种新兴的晶体多孔聚合物,因其组成多样化、孔径可调、高稳定性等优点已在很多领域表现出优异的应用前景。随着疏水材料的不断发展,疏水型COFs材料备受关注,其结构类型的设计、开发及应用研究已有相关报道。鉴于此,从C(主要包括含氟类、长链烷烃类及其他芳香烃类疏水型COFs材料)及合成策略方面综述了近年来疏水型共价有机框架相关研究进展。此外,简要介绍了疏水型COFs材料在油水分离、固相微萃取与吸附领域的应用。
Covalent organic frameworks (COFs),as an emerging crystal porous polymer,have exhibited excellent application prospects in various fields because of its advantages of abundant constitution,controllable aperture,high stability and so on.With the continuous development of hydrophobic materials,hydrophobic COFs materials have been paid much attention.More recently,the corresponding research about the structural designation and synthesis,as well as the application have been reported widely.In view of these,the recent progress on hydrophobic COFs materials was reviewed in this paper,mainly including the classification (such as fluorine-containing,long chain alkyl groups,and aromatic hydrocarbon) and the synthetic strategy.In addition,its application in the fields of the oil/water separation,the solid phase microextraction and adsorption were also introduced briefly.
[1] 彭华乔,石涛,薛森,等.用于油水分离超疏水材料的研究进展[J].化工新型材料,2021,49(7):39-41,51.
[2] 陈立,周才龙,杜京城,等.超疏水多孔材料的研究进展[J].化工学报,2020,71(10):4502-4519.
[3] 赵亚梅,丁思奇,曹婷婷,等.超疏水材料的制备及其在海洋领域中应用的研究进展[J].化工新型材料,2022,50(1):34-38.
[4] Levkin P A,Svec F,Frechet J M J.Porous polymer coatings:a versatile approach to superhydrophobic surfaces[J].Advanced Functional Materials,2009,19(12):1993-1998.
[5] Liu C Y,Liu Q,Huang A S.A superhydrophobic zeolitic imidazolate framework (ZIF-90) with high steam stability for efficient recovery of bioalcohols[J].Chemical Communications,2016,52(16):3400-3402.
[6] Liu R C,Young S,Dangwal S,et al.Boron substituted MFI-type zeolite-coated mesh for oil-water separation[J].Colloids and Surfaces A-physicochemical and Engineering Aspects,2018,550(5):108-114.
[7] Huang J Y,Li S H,Ge M Z,et al.Robust superhydrophobic TiO2@fabrics for UV shielding,self-cleaning and oil-water separation[J].Journal of Materials Chemistry A,2015,3(6):2825-2832.
[8] 侯成敏,李娜,董海涛,等.水溶性含氟聚合物杂化纳米SiO2制备超疏水材料及性能[J].功能材料,2019,50(8):8091-8096.
[9] 郑旺,赵冰,阚伟,等.手性共价有机框架的合成及应用研究进展[J].化工新型材料,2022,50(4):41-46.
[10] Cote A P,Benin A I,Ockwig N W,et al.Porous,crystalline,covalent organic frameworks[J].Science,2005,310(5751):1166-1170.
[11] Nagai A,Chen X,Feng X,et al.A squaraine-linked mesoporous covalent organic framework[J].Angewandte Chemie-International Edition,2013,52(13):3770-3774.
[12] Dalapati S,Addicoat M,Jin S B,et al.Rational design of crystalline supermicroporous covalent organic frameworks with triangular topologies[J].Nature Communications,2015,6:7786.
[13] Du Y,Yang H S,Whiteley J M,et al.Ionic covalent organic frameworks with spiroborate linkage[J].Angewandte Chemie-international Edition,2016,55(5):1737-1741.
[14] Pachfule P,Panda M K,Kandambeth S,et al.Multifunctional and robust covalent organic framework-nanoparticle hybrids[J].Journal of Materials Chemistry A,2014,2(21):7944-7952.
[15] Ding S Y,Gao J,Wang Q,et al.Construction of covalent organic framework for catalysis:Pd/COF-LZU1 in suzuki-miyaura coupling reaction[J].Journal of the American Chemical Society,2011,133(49):19816-19822.
[16] Wei P F,Qi M Z,Wang Z P,et al.Benzoxazole-linked ultrastable covalent organic frameworks for photocatalysis[J].Journal of the American Chemical Society,2018,140(13):4623-4631.
[17] Li Z P,Zhi Y F,Shao P P,et al.Covalent organic framework as an efficient,metal-free,heterogeneous photocatalyst for organic transformations under visible light[J].Applied Catalysis B-environmental,2019,245:334-342.
[18] Wang X Y,Chen L J,Chong S Y,et al.Sulfone-containing covalent organic frameworks for photocatalytic hydrogen evolution from water[J].Nature Chemistry,2018,10(12):1180-1189.
[19] Wei S C,Zhang F,Zhang W B,et al.Semiconducting 2D triazine-cored covalent organic frameworks with unsubstituted olefin linkages[J].Journal of the American Chemical Society,2019,141(36):14272-14279.
[20] Chandra S,Kundu T,Kandambeth S,et al.Phosphoric acid loaded azo (—NN—) based covalent organic framework for proton conduction[J].Journal of the American Chemical Society,2014,136(18):6570-6573.
[21] Ma H P,Liu B L,Li B,et al.Cationic covalent organic frameworks:a simple platform of anionic exchange for porosity tuning and proton conduction[J].Journal of the American Chemical Society,2016,138(18):5897-5903.
[22] DeBlase C R,Silberstein K E,Truong T T,et al.Beta-ketoenamine-linked covalent organic frameworks capable of pseudocapacitive energy storage[J].Journal of the American Chemical Society,2013,135(45):16821-16824.
[23] Duhovic S,Dinca M.Synthesis and electrical properties of covalent organic frameworks with heavy chalcogens[J].Chemistry of Materials,2015,27(16):5487-5490.
[24] Lv J Q,Tan Y X,Xie J F,et al.Direct solar-to-electrochemical energy storage in a functionalized covalent organic framework[J].Angewandte Chemie-international Edition,2018,57(39):12716-12720.
[25] Wu C Y,Liu Y M,Liu H,et al.Highly conjugated three-dimensional covalent organic frameworks based on spirobifluorene for perovskite solar cell enhancement[J].Journal of the American Chemical Society,2018,140(31):10016-10024.
[26] Vitaku E,Gannett C N,Carpenter K L,et al.Phenazine-based covalent organic framework cathode materials with high energy and power densities[J].Journal of the American Chemical Society,2020,142(1):16-20.
[27] Peng Y W,Huang Y,Zhu Y H,et al.Ultrathin two-dimensional covalent organic framework nanosheets:preparation and application in highly sensitive and selective DNA detection[J].Journal of the American Chemical Society,2017,139(25):8698-8704.
[28] Ascherl L,Evans E W,Gorman J,et al.Perylene-based covalent organic frameworks for acid vapor sensing[J].Journal of the American Chemical Society,2019,141(39):15693-15699.
[29] Meng Z,Stolz R M,Mirica K A.Two-dimensional chemiresistive covalent organic framework with high intrinsic conductivity[J].Journal of the American Chemical Society,2019,141(30):11929-11937.
[30] Cao X C,Wang Z,Qao Z H,et al.Penetrated COF channels:amino environment and suitable size for CO2 preferential adsorption and transport in mixed matrix membranes[J].ACS Applied Materials & Interfaces,2019,11(5):5306-5315.
[31] Li L T,Li A R,Zhao B,et al.Multi-sulfonated functionalized hydrophilic covalent organic framework for highly efficient dye removal from real samples[J].New Journal of Chemistry,46(35):17016-17025.
[32] Ji W,Xiao L L,Ling Y H,et al.Removal of genx and perfluorinated alkyl substances from water by amine-functionalized covalent organic frameworks[J].Journal of the American Chemical Society,2018,140(40):12677-12681.
[33] Ding L G,Yao B J,Li F,et al.Ionic liquid-decorated COF and its covalent composite aerogel for selective CO2 adsorption and catalytic conversion[J].Journal of Materials Chemistry A,2019,7(9):4689-4698.
[34] Jansone-Popova S,Moinel A,Schott J A,et al.Guanidinium-based ionic covalent organic framework for rapid and selective removal of toxic Cr(Ⅵ) oxoanions from water[J].Environmental Science & Technology,2019,53(2):878-883.
[35] Da H J,Yang C X,Qian H L,et al.A knot-linker planarity control strategy for constructing highly crystalline cationic covalent organic frameworks:decoding the effect of crystallinity on adsorption performance[J].Journal of Materials Chemistry A,2020,8(25):12657-12664.
[36] Li J H,Zhang H X,Zhang L Y,et al.Two-dimensional covalent-organic frameworks for ultrahigh iodine capture[J].Journal of Materials Chemistry A,2020,8(19):9523-9527.
[37] Baldwin L A,Crowe J W,Pyles D A,et al.Metalation of a mesoporous three-dimensional covalent organic framework[J].Journal of the American Chemical Society,2016,138(46):15134-15137.
[38] Yang Y J,Faheem M,Wang L L,et al.Surface pore engineering of covalent organic frameworks for ammonia capture through synergistic multivariate and open metal site approaches[J].ACS Central Science,2018,4(6):748-754.
[39] Fan H W,Peng M H,Strauss I,et al.High-flux vertically aligned 2D covalent organic framework membrane with enhanced hydrogen separation[J].Journal of the American Chemical Society,2018,142(15):6872-6877.
[40] Ying Y P,Tong M M,Ning S C,et al.Ultrathin two-dimensional membranes assembled by ionic covalent organic nanosheets with reduced apertures for gas separation[J].Journal of the American Chemical Society,2020,142(9):4472-4480.
[41] Furukawa H,Yaghi O M.Storage of hydrogen,methane,and carbon dioxide in highly porous covalent organic frameworks for clean energy applications[J].Journal of the American Chemical Society,2009,131(25):8875-8883.
[42] Liao Q B,Ke C,Huang X,et al.Catalyst-free and efficient fabrication of highly crystalline fluorinated covalent organic frameworks for selective guest adsorption[J].Journal of Materials Chemistry A,2019,7(32):18959-18970.
[43] Han N,Zhang Z X,Gao H K,et al.Superhydrophobic covalent organic frameworks prepared via pore surface modifications for functional coatings under harsh conditions[J].ACS Applied Materials & Interfaces,2020,12(2):2926-2934.
[44] Wu X W,Hong Y L,Xu B Q,et al.Perflfluoroalkyl-functionalized covalent organic frameworks with superhydrophobicity for anhydrous proton conduction[J].Journal of the American Chemical Society,2020,142(33):14357-14364.
[45] Li Y X,Liu H Z,Wu X,et al.Positively charged covalent organic framework and its application in the dispersive solidphase extraction of ultraviolet-filters from food packaging material migrants[J].Journal of Liquid Chromatography & Related Technologies,2019,43(5-6):156-163.
[46] Ma Y C,Wang Y J,Li H,Three-Dimensional chemically stable covalent organic frameworks via hydrophobic engineering[J].Angewandte Chemie International Edition,2020,59(44):19633-19638.
[47] Chen A,Guo H Y,Zhou J H,et al.Polyacrylonitrile nanofifibers coated with covalent organic frameworks for oil/water separation[J].ACS Applied Nano Materials,2022,5(3):3925-3936.
[48] Mohammed A K,Al Khoori A A,Addicoat M A,et al.Solvent influenced fragmentations in free-standing three-dimensional covalent organic framework membranes for hydrophobicity switching[J].Angewandte Chemie International Edition,2022,61(13):905.
[49] Wang Y C,Xie J S,Ren Z H,et al.Postsynthetically modified hydrophobic covalent organic frameworks for enhanced oil/water and CH4/C2H2 separation[J].Chemical Engineering Journal,2022,448:137687.
[50] Wang H,Wang M K,Wang Y L,et al.Synergistic effects of COF and GO on high flux oil/water separation performance of superhydrophobic composites[J].Separation and Purification Technology,2021,276:119268.
[51] Chen L,Du J C,Zhou W,et al.Microwave-assisted solvothermal synthesis of covalent organic frameworks (COFs) with stable superhydrophobicity for oil/water separation[J].Chemistry-An Asian Journal,2020,15(21):3421-3427.
[52] Liu Y H,Li W,Yuan C,et al.Two-dimensional fluorinated covalent organic frameworks with tunable hydrophobicity for ultrafast oil-water separation[J].Angewandte Chemie International Edition,2021,62(2):13348.
[53] 张鹏玲.基于共价有机骨架的固相微萃取纤维的制备并应用于生物胺与拟除虫菊酯的检测[D].烟台:烟台大学,2022.
[54] Ma J C,Yu Z D,Liu S T,et al.Efficient extraction of trace organochlorine pesticides from environmental samples by a polyacrylonitrile electrospun nanofiber membrane modified with covalent organic framework[J].Journal of Hazardous Materials,2021,424:127455.
[55] Sun X W,Ji W H,Hou S H,et al.Facile synthesis of trifluoromethyl covalent organic framework for the efficient microextraction of per-and polyfluorinated alkyl substances from milk products[J].Journal of Chromatography A,2020,1623:461197.
[56] Hou Y J,Deng J W,He K L,et al.Covalent organic frameworks-based solid-phase microextraction probe for rapid and ultrasensitive analysis of trace per- and polyfluoroalkyl substances using mass spectrometry[J].Analytical Chemistry,2020,92(15):10213-10217.
[57] Zhao Y X,Sui Z Y,Chang Z S,et al.A trifluoromethyl-grafted ultra-stable fluorescent covalent organic framework for adsorption and detection of pesticides[J].Journal of Materials Chemistry A,2020,8(47):25156-25164.
[58] Zang L J,He M,Wu Z K,et al.Imine-linked covalent organic frameworks coated stir bar sorptive extraction of non-steroidal anti-inflammatory drugs from environmental water followed by high performance liquid chromatography-ultraviolet detection[J].Journal of Materials Chemistry A,2021,1659:462647.
[59] Yi S M,Zhang C R,Jiang W,et al.Ionic liquid modified covalent organic frameworks for efficient detection and adsorption of ReO-4/TcO-4[J].Journal of Environmental Chemical Engineering,2022,10(3):107666.
基金资助
国家自然科学基金(21978140);黑龙江省自然科学基金项目(GZ20210064);黑龙江省省属本科高校基本科研业务费科研项目(135309116)
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