随着光学纯化合物需求的不断增加,手性分离的研究在医药、化学、生物学等领域具有重要意义。膜分离法是近年来发展的一种新型节能技术,具有连续操作、易于放大、无污染等优点,被认为是一种具有潜力的大规模拆分对映异构体的方法。大多数一维聚合物手性分离膜的选择性与通量之间呈反向关系,且耐溶剂性差,导致分离性能不稳定,通量较低。有机多孔材料具有较大的比表面积和永久孔隙率,对有机溶剂具有极高的稳定性,在合成过程中引入手性官能团制备出手性材料可以实现在手性分离膜领域的应用。
With the increasing demand for optically pure compounds,chiral separation is of great significance in medicine,chemistry,biology and other industries.Membrane separation is a new energy-saving technology developed in recent years.It has the advantages of continuous operation,easy amplification and no pollution.It is considered to be a potential method for large-scale enantiomeric separation.The selectivity of most one-dimensional polymer chiral membranes is inversely related to the flux,and the poor solvent resistance leads to unstable separation performance and low flux.Organic porous materials have large specific surface area,permanent porosity and high stability in organic solvents,which can be used in chiral membrane separation by introducing chiral groups in the synthesis process.
[1] Shen J,Okamoto Y.Efficient separation of enantiomers using stereoregular chiral polymers.Chemical Reviews,2015,116(8):1094-1138.
[2] Kotelnikova E,Isakov A,Kryuchkova L,et al.Acids with chiral molecules as essential organic compounds of biogenic-abiogenic systems[J].Processes and Phenomena on the Boundary Between Biogenic and Abiogenic Nature,2020,10(6):69-72.
[3] Navarrosanchez J,Argentegarcia A,Molinermartinez Y,et al.Peptide metal-organic frameworks for enantioselective separation of chiral drugs[J].Journal of the American Chemical Society,2017,139(12):4294-4297.
[4] Gu L,Chen Q,Li X,et al.Amino acid modified carbon nanotubes with optimal pore size for chiral separation[J].Molecular Simulation,2019,45(13):1051-1057.
[5] Gao B,Li Y,Cui K,et al.Molecularly imprinted membrane with innovative structure and high performance for chiral separation of amino acids[J].International Journal of Polymeric Materials,2018,67(8):517-527.
[6] Zang Y,Qu Y,Aoki T.Simultaneous improvement of permeability and selectivity in enantioselective permeation through solid chiral membranes from a newly synthesized one-handed helical polyphenylacetylene with aldehyde pendant groups by enantioselective reaction[J].Polymer,2019,171(34):45-49.
[7] Yuan L M,Ma W,Xu M,et al.Optical resolution and mechanism using enantioselective cellulose,sodium alginate and hydroxypropyl-β-cyclodextrin membranes[J].Chirality,2017,29(5):315-324.
[8] Amarajothi D,Zhaohui L,Hermenegildo G.Catalysis and photocatalysis by metal organic frameworks[J].Chemical Society Reviews,2018,47(10):62-65.
[9] Kashani T,Jahanshahi M,Rahimpour A,et al.Nanopore molecularly imprinted polymer membranes for environmental usage:selective separation of 2,4-dichlorophenoxyacetic acid as a toxic herbicide from water[J].Polymer-Plastics Technology and Engineering,2016,55(16):1700-1712.
[10] Gao B,Cui K,Li Y,et al.Preparation of molecule imprinted membrane of single enantiomer of amino acid with an innovative strategy and study on its chiral recognition and resolution properties[J].Journal of Chemical Technology & Biotechnology,2017,92(7):1566-1576.
[11] Zhang J,Lu H,Lu H,et al.Porous bimetallic Mo-W oxide nanofibers fabricated by electrospinning with enhanced acetone sensing performances[J].Journal of Alloys and Compounds,2019,779(13):531-542.
[12] Xiong C,Li B,Lin X,et al.The recent progress on three-dimensional porous graphene-based hybrid structure for supercapacitor[J].Composites Part B-Engineering,2019,165(4):10-46.
[13] Roy S,Bandyopadhyay A,Das M,et al.Redox-active and semi-conducting donor-acceptor conjugated microporous polymers as metal-free ORR catalysts[J].Journal of Materials Chemistry,2018,6(14):5587-5591.
[14] Yulia F,Zulys A,Ruliandini R.Metal-organic framework based chromium terephthalate (MIL-101 Cr) growth for carbon dioxide capture:a review[J].Journal of Advanced Research in Fluid Mechanics and Thermal Sciences,2019,57(4):158-174.
[15] Liu Z,Yang X,Lu B,et al.Delicate topotactic conversion of coordination polymers to Pd porous nanosheets for high-efficiency electrocatalysis[J].Applied Catalysis B-Environmental,2019,243(12):86-93.
[16] Chaoui N,Trunk M,Dawson R,et al.Trends and challenges for microporous polymers[J].Chemical Society Reviews,2017,46(6):3302-3321.
[17] Ji X,Yao Y,Li J,et al.A Supramolecular cross-linked conjugated polymer network for multiple fluorescent sensing[J].Journal of the American Chemical Society,2013,135(1):74-77.
[18] Fuoco A,Rizzuto C,Tocci E,et al.The origin of size-selective gas transport through polymers of intrinsic microporosity[J].Journal of Materials Chemistry A,2019,7(36):20121-20126.
[19] Jansen J C,Esposito E,Fuoco A,et al.Microporous organic polymers:synthesis,aharacterization,and applications[J].Polymers,2019,11(54):844-847.
[20] Wang H,Zeng Z,Xu P,et al.Recent progress in covalent organic framework thin films:fabrications,applications and perspectives[J].Chemical Society Reviews,2019,48(28):488-516.
[21] Wei J,Zhang X,Zhao Y,et al.Chiral conjugated microporous polymers as novel chiral fluorescence sensors for amino alcohols[J].Macromolecular Chemistry & Physics,2013,214(19):2232-2238.
[22] Li C,Liu Y,Li J,et al.Conjugated microporous polymers with chiral BINAP ligand built-in as efficient catalysts for asymmetric hydrogenation[J].Catalysis Science & Technology,2015,23(6):45-47.
[23] Huang H,Miao Q,Kang Y,et al.Synthesis and fluorescent properties of a chiral conjugated polymer based on (S)-2,2′-binaphtho-20-crown-6[J].Bulletin of the Chemical Society of Japan,2008,23(4):22-25.
[24] Kokado Kenta,Tokoro Yuichiro,Chujo Yoshiki.Luminescent and axially chiral π-conjugated polymers linked by carboranes in the main chain[J].Macromolecules,2009,45(6):444-446.
[25] Wang L,Zhou J,Lan Y,et al.Divergent synthesis of chiral covalent organic frameworks[J].Angewandte Chemie,2019,58(28):9443-9447.
[26] Ma H C,Zhao C C,Chen G J,et al.Photothermal conversion triggered thermal asymmetric catalysis within metal nanoparticles loaded homochiral covalent organic framework[J].Nature Communications,2019,10(1):3368-3370.
[27] Fang L,Qian H,Cheng Y,et al.Room-temperature preparation of a chiral covalent organic framework for the selective adsorption of amino acid enantiomers[J].RSC Advances,2010,65(6):121-124.
[28] Wang X,Han X,Jie Z,et al.Homochiral 2D porous covalent organic frameworks for heterogeneous asymmetric catalysis[J].Journal of the American Chemical Society,2016,23(5):164-166.
[29] Xu H,Chen X,Gao J,et al.Catalytic covalent organic frameworks via pore surface engineering[J].Chemical Communications,2014,50(11):1292-1294.
[30] Xu S,Wang Y,Li W,et al.Covalent organic framework incorporated chiral polymer monoliths for capillary electrochromatography[J].Journal of Chromatography A,2019,1602:481-488.
[31] Chen X,Qiao Z,Hou B,et al.Chiral metal-organic frameworks with tunable catalytic selectivity in asymmetric transfer hydrogenation reactions[J].Nano Research,2020,23(4):34-36.
[32] Guo J,Zhang Y,Zhu Y,et al.Ultrathin chiral metal-organic-framework nanosheets for efficient enantioselective separation[J].Angewandte Chemie International Edition,2018,57(23):6873-6877.
[33] Das S,Xu S,Ben T,et al.Chiral recognition and separation by chirality-enriched metal-organic frameworks[J].Angewandte Chemie,2018,130(28):8765-8769.
[34] Zhang J,Chen S,Wu T,et al.Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis[J].Journal of the American Chemical Society,2016,130(39):12882-12883.
[35] Zhang S Y,Li D,Guo D,et al.Synthesis of a chiral crystal form of MOF-5,CMOF-5,by chiral induction[J].Journal of the American Chemical Society,2015,137(49):15406-15409.
[36] Bai J,Zhang W,Ma X,et al.Synthesis of novel hyper-cross-linked chiral porous polymers and their applications in enantioselective adsorption of amino acids[J].Microporous and Mesoporous Materials,2019,65(1):23-25.
[37] Kenta K,Yuichiro T,Yoshiki C.Luminescent and axially chiral π-conjugated polymers linked by carboranes in the main chain[J].Macromolecules,2009,13(4):12-15.
[38] Bai J,Zhang W,Ma X,et al.Synthesis of novel hyper-cross-linked chiral porous polymers and their applications in enantioselective adsorption of amino acids[J].Microporous and Mesoporous Materials,2020,10(9):111-114.
[39] Ma L,Wanderley M M,Lin W,et al.Highly porous cross-linked polymers for catalytic asymmetric diethylzinc addition to aldehydes[J].ACS Catalysis,2011,1(7):691-697.
[40] Liu Y,Li P,Xie L,et al.β-cyclodextrin modified silica nanochannel membrane for chiral separation[J].Journal of Membrane Science,2014,453(12):12-17.
[41] Shiomi K,Yoshikawa M.Multi-stage chiral separation with electrospun chitin nanofiber membranes[J].Separation and Purification Technology,2013,65(1):300-304.
[42] Kashani T,Jahanshahi M,Rahimpour A,et al.Nano pore molecularly imprinted polymer membranes for environmental usage:selective separation of 2,4-dichlorophenoxyacetic acid as a toxic herbicide from water[J].Polymer-Plastics Technology and Engineering,2016,65(3):19-23.
[43] Gao B,Cui K,Li Y,et al.Preparation of molecule imprinted membrane of single enantiomer of amino acid with an innovative strategy and study on its chiral recognition and resolution properties[J].Journal of Chemical Technology & Biotechnology,2017,92(7):1566-1576.
[44] Wang W J,Dong X L,Nan J P,et al.A homochiral metal-organic framework membrane for enantioselective separation[J].Chemical Communications,2012,48(56):7022-7024.
[45] Gu Z G,Grosjean S,Brse S,et al.Enantioselective adsorption in homochiral metal-organic frameworks:the pore size influence[J].Chemical Communications,2015,51(7):19-23.
[46] Seo J S,Whang D,Lee H,et al.A homochiral metal-organic porous material for enantioselective separation and catalysis[J].Nature,2000,404(6781):982-986.
[47] Kang Z,Xue M,Fan L,et al.‘Single nickel source’ in situ fabrication of a stable homochiral MOF membrane with chiral resolution properties[J].Chemical Communications,2013,49(90):10569-10571.
[48] Huang K,Dong X,Ren R,et al.Fabrication of homochiral metal-organic framework membrane for enantioseparation of racemic Diols[J].Aiche Journal,2013,59(11):65-68.
[49] Guo J,Zhang Y,Zhu Y,et al.Ultrathin chiral metal-organic-framework nanosheets for efficient enantioselective separation[J].Angewandte Chemie International Edition,2018,56(3):25-28.
[50] Lu Y,Zhang H,Chan J Y,et al.Homochiral mOF-polymer mixed matrix membranes for efficient separation of chiral molecules[J].Angewandte Chemie,2019,131(47):69-72.
[51] Chan J Y,Zhang H,Nolvachai Y.Incorporation of homochirality into zeolitic imidazole framework membrane for efficient chiral separation[J].Angewandte Chemie International Edition,2018,57(6):96-100.
[52] Gu Z,Fu W,Liu M,et al.Surface-Mounted MOF templated fabrication of homochiral polymer thin film for enantioselective adsorption of drug[J].Chemical Communications,2017,53(9):1470-1473.
[53] Weng X,Baez J E,Khiterer M,et al.Chiral polymers of intrinsic microporosity:selective membrane permeation of enantiomers[J].Angewandte Chemie,2015,54(38):11214-11218.
基金资助
国家自然科学基金(52173202);黑龙江省省属高等学校基本科研业务费青年创新人才项目(135409201);黑龙江省人力资源保障厅留学回国人员择优资助项目([2017]No.490);齐齐哈尔大学2019年三年制研究生创新科研项目(YJSCX2019065)