Process in preparation and application of covalent organic frameworks

Expand
  • Shanghai Research Institute of Petrochemical Technology,SINOPEC,Shanghai 201208

Received date: 2020-04-07

  Revised date: 2021-04-12

  Online published: 2021-08-19

Abstract

The covalent organic frameworks (COFs) are a class of crystalline porous polymers connected by organic building units through covalent bonds such as carbon-carbong bond,imine bond,hydrazone bond and so on.They exhibit low densities,large specific surfaces and high crystallinities.The main preparing methods of COFs such as solvent method,ion heat method,microwave method,surface synthesis method and mechanical grinding method were briefly introduced,and summarized the advantages and limitations of these synthesis methods.Then focused on the study on modify the stability of COFs.After that,emphatically introduced recent research about their application in heterogeneous catalysis,gas adsorption and separation,new electrochemical energy storage materials,treatment of pollutants such as heavy metals in water,high sensitivity sensors,loading and delivery of pharmaceutical molecules.At the end,the key problems of preparation and application process,the main research direction were put forward.After all,the future development trend of COFs was prospected.

Cite this article

Wang Xiaochen . Process in preparation and application of covalent organic frameworks[J]. New Chemical Materials, 2021 , 49(7) : 208 -215 . DOI: 10.19817/j.cnki.issn 1006-3536.2021.07.047

References

[1] Tin P S,Chung T S,Jiang L,et al.Carbon-zeolite composite membranes for gas separation[J].Carbon,2005,43:2025-2027.
[2] Asefa T,Maclachalan M J,Coombs N,et al.Periodic mesoporousorganosilicas with organic groups inside the channel walls[J].Nature,1999,402:867-871.
[3] Lai C Y,Trewyn B G,Jefinija D M,et al.A mesoporous silica nanosphere-based carrier system with chemically removable cds nanoparticle caps for stimuli-responsive controlled release of neurotransmitters and drug molecules[J].Journal of the American Chemical Society,2003,125:4451-4459.
[4] O'Keeffe M,Yaghi O M.Deconstructing the crystal structures of metal-organic frameworks and related materials into their underlying nets[J].Chemical Reviews,2012,112(2):675-702.
[5] Jiang J X,Su F,Trewin A.Conjugated microporouspoly(aryleneethynylene) networks[J].AngewanteChemieInernational Edition,2007,119(45):8574-8578.
[6] Cooper A I.Conjugated microporouspolymers[J].Advanced Material,2009,21(12):1291-1295.
[7] Diercks C S,Yaghi O M.The atom,the molecule,and the covalent organic framework[J].Science,2017,355:eaal1585.
[8] Bisbey R P,Dichtel W R.Covalent organic frameworks as a platform for multidimensional polymerization[J].ACS Central Sciety,2017,3:533-543.
[9] Côté A P,Benin A I,Ockwig N W,et al.Porous,crystalline,covalent organic frameworks[J].Science,2005,310:1166-1170.
[10] Deblase C R,Dichtel W R.Moving beyond boron:the emergence of new linkage chemistries in covalent organic frameworks[J].Macromolecules,2016,49:5297-5305.
[11] Liu G,Sheng J,Zhao Y.Chiral covalent organic frameworks for asymmetric catalysis and chiral separation[J].Sci China Chem,2017,60:1015-1022.
[12] Chen R F,Shi J L,Ma Y,et al.Designed synthesis of a 2D porphyrin-based sp2 carbon conjugated covalent organic framework for heterogeneous photocatalysis[J].Angewandte,2019,58(19):6430-6434.
[13] Ei-Kaderi H M,Hunt J R,Mendoza-Cortes J L,et al.Designed synthesis of 3D covalent organic frameworks[J].Science,2009,316:268-272.
[14] Song Y,Sun Q,Aguila B,et al.Opportunities of covalent organic frameworks for advanced applications[J].Advance Science,2019,6(2):1801410.
[15] Yahiaoui O,Fitch A N,Hoffmann F,et al.3D anionic silicate covalent organic framework with srstopology[J].Journal of the American Chemical Society,2018,140:5330-5333.
[16] Jin E,Asada M,Xu Q,et al.Two-dimensional sp2 carbon-conjugated covalent organic frameworks[J].Science,2017,357:673-676.
[17] Smith B J,Overholts A C,Hwang N,et al.Insight into the crystallization of amorphous imine-linked polymer networks to 2D covalent organic frameworks[J].Chemical Communication,2016,52:3690-3693.
[18] Baldwin L A,Crowne J W,Pyles D A,et al.Metalation of a mesoporous three-dimensional covalent organic framework[J].Journal of the American Chemical Society,2016,138:15134-15137.
[19] Peng Y,Wang W K,Hu Z,et al.Room temperature batch and continuous flow synthesis of water-stable covalent organic frameworks[J].Chemistry of Materials,2016,28(14):5095-5101.
[20] Zhang K,Cai S L,Yan Y L,et al.Construction of a hydrazone-linked chiral covalent organic framework-silica composite as the stationary phase for high performance liquid chromatography[J].Journal of Chromatograhy A,2017,1519:100-109.
[21] Tylianakis E,Klontzas E,Froudakis G E.Multi-scale theoretical investigation of hydrogenstorage in covalent organic frameworks[J].Nanoscale,2011,3:856-869.
[22] Yang C X,Liu C,Cao Y M,et al.Facile room-temperature solution-phase synthesis of a spherical covalent organic framework for high-resolution chromatographic separation[J].Chemical Communication,2015,51:12254-12257.
[23] Zhang J,Han X,Wu X,et al.Multivariate chiral covalent organic frameworks with controlled crystallinity and stability for asymmetric catalysis[J].Journal of the American Chemical Society,2017,139:8277-8285
[24] Liu L H,Yang C X,Yang X P,et al.Methacrylate-bonded covalent-organic framework monolithic columns for high performance liquid chromatography[J].Journal of Chromatograhy,2017,1479:137-144.
[25] Qian H L,Yang C X,Yan X P.Bottom-up synthesis of chiral covalent organic frameworks and their bound capillaries for chiral separation[J].Nature Communication,2016,7:12104.
[26] Valentino L,Matsumoto M,Dichtel W R,et al.Development and performance characterization of a polyimine covalent organic framework thin-film composite nanofiltration membrane[J].Environmental Science & Technology,2017,51(24):14352-14359.
[27] Jiang S Y,Gan S X,Zhang X,et al.Aminal-linkedcovalent organic frameworks through condensation of secondary amine with aldehyde[J].Journal of the American Society,2019,141(38):14981-14986.
[28] Deblase C R,Hernández-Burgos K,Silberstein K E,et al.Rapid and efficient redox processes within 2D covalent organic framework thin films[J].ACS Nano,2015,9:3178-3183.
[29] Dienstmaier J F,Medina D D,Dogru M,et al.Isoreticular two-dimensional covalent organic frameworks synthesized by on-surface condensation of diboronic acids[J].ACS Nano,2012,6:7234-7242.
[30] Tan J,Supawadee N,Kong W F,et al.Manipulation of amorphous-to-crystalline transformation:towards the construction of covalent organic framework hybrid microspheres with NIR photothermal conversion ability[J].AngewandteChemie,2016,55(45):13979-13984.
[31] Medina D D,Rotter J M,Hu Y,et al.Room temperature synthesis of covalent-organic framework films through vapor-assisted conversion[J].Journal of the American Chemical Society,2015,137:1016-1019.
[32] Liang R R,Xu S Q,Qi Q Y,et al.Fabrication organic nanotubes through selective disassembly of two-dimensional covalent organic frameworks[J].Journal of the American Chemical Society,2020,142(1):70-74.
[33] Zhang Y B,Su Jie,Hiroyasu Furukawa,et al.Single-crystal structure of a covalent organic framework[J].Journal of American Chemical Society,2013,135(44):16336-16339.
[34] Ding S Y,Gao J,Wang Q,et al.Construction of covalent organic framework for catalysis:Pd/COF-LZUL in Suzuki-miyaura coupling reaction[J].Journal of American Chemical Society,2011,133(49):19816-19822.
[35] Lin S,Diercks C S,Zhang Y B,et al.Covalent organic frameworks comprising cobalt porphyrins for catalytic reduction in water[J].Science,2015,349(6253):1208-1213.
[36] Ma L,Wang S,Feng X,et al.Recent advances of covalent organic frameworks:a type of two-dimensional conducting polymers[J].Chinese Chemical Letters,2016,27(8):1395-1404.
[37] Biswal B P,Chandra S,Kandambeth S,et al.Mechanochemical synthesis of chemically stable isoreticular covalent organic frameworks[J].Journal of the American Society,2013,35:5328-5331.
[38] Kuhn P,Antonietti M,Thomas A.Porous,covalent triazine-based frameworks prepared by ionothermalsynthesis[J].Microporous Polymers,2008,47(18):3450-3453.
[39] Cambell N L,Clowers R,Ritchie L K,er al.Rapid microwave synthesis and purification of porous covalent organic frameworks[J].Chemistry of Materials,2009,21(2):204-206.
[40] Zwaneveld N A A,Pawlak R,Able M,et al.Orgnized formation of 2D extended covalent organic frameworks at surfaces[J].Journal of the American Chemical Society,2008,130(21):6678-6679.
[41] Banerjee T,Haase F,Lotsch,et al.Single-site photocatalytic H2 evolution from covalent organic frameworks with molecular cobaloxime co-catalysts[J].Journal of the American Society,2017,139:16228-16234.
[42] Ma T Q,Eugenne A,Kapustin,et al.Single-crystal x-ray diffraction structures of covalent organic frameworks[J].Science,2018,361(6397):48-52.
[43] Xu H,Luo Y,Li X,et al.Single crstal of a one-dimensional metallo-covalent organic framework.Nature Communications 11,1434(2020).https://doi.org/10.1038/s41467-020-15281-1.
[44] Wang P L,Ding S Y,Zhang Z C,et al.Constructingrobust covalent organic frameworks via multicomponent reactions[J].Journal of the American Chemical Society,2019,141(45):18004-18008.
[45] Rogges M J,A Bavykina,Hajek,et al.Metal-organic and covalent organic frameworks as single-site catalysts[J].Chemical Society Review,2017,46:3134-3184
[46] Chidharth K,Himanshu S J,Karen L,et al.Covalent triazine frameworks-a sustainable perspective[J].Green Chemistry,2020,22:1038-1071.
[47] Jose L Segura,Sergio Royuela,M,Mar Ramos.Post-synthetic modification of covalent organic frameworks[J].Chemical Society,2019,48:3903-3945.
[48] Laura M B,Sergio R,Felix Z M,et al.Thiol grafted imine-based covalent organic frameworks for water remediation through selective removal of Hg(Ⅱ)[J].Journal of Materials Chemistry A,2017,5:17973-17981.
[49] Yuan S S,Li X,Zhu J Y,et al.Covalent organic frameworks for membrane separation[J].Chemical Society Reviews,2019,48:2664-2681.
[50] Harsh V,Aymann N,Abdullum M,et al.Pore surface engineering of covalent organic frameworks:structural diversity and applications[J].Nanoscale,2019,11:21679-21708.
[51] Chen X,Huang N,Gao J,et al.Towards covalent organic frameworks with predesignable and alighed open docking sites[J].Chemical Communication,2014,50:6161-6163.
[52] Wu Y,Xu H,Chen X,et al.A π-electronic covalent organic framework catalyst:π-walls as catalytic beds for Diels-Alder reactions uder ambient conditions[J].Chemical Communication,2015,51:10096-10098.
[53] Haug W K,Wolfson E R,Mornan B T,et al.A nickel-doped dehydrobenzoannulene-based two-dimensional covalent organic framework for the reductive cleavage of inert aryl C—S bonds[J].Journal of the American Society,2020,142(12):5521-5525.
[54] Bidhan C P,SaubK Das,Arnab G,et al.Covalent organic framework based microspheres as an anode material for rechargeable sodium batteries[J].Journal of Materials Chemistry A,2018,6:16655-16663.
[55] Linus S,Katherina S,Lotsch A,et al.A hydrazine-based covalent organic framework for photocatalytic hydrogen production[J].Chemical Science,2014,5:2789-2793.
[56] Banerjee T,Frederrik H,Lotsch,et al.Single-site photocatalytic H2 evolution from covalent organic frameworks with molecular cobaloxime co-catalysts[J].Journal of the American Society,2017,139:16228-16234.
[57] Bishnu P,Biswal,Hugo A,et al.Sustained solar H2 evolution from Thiazolo[5,4-D]Thiazole-bridged covalent organic framework and nickel-thiolate cluster in water[J].Journal of the American Society,2019,141:11082-11092.
[58] Yang S Z,Hu W H,Zhang X,et al.2D covalent organic frameworks as intrinsic photocatalysts for visible light-driven CO2 reduction[J].Journal of the American Chemical Society,2018,140:14614-14618.
[59] Wang S,Sun Q,Chen W,et al.Programming covalent organic frameworks for photocatalysis:investigation of chemical and structural variations[J].Matter,2019,11:1650-1662.
[60] Wang Y C,Liu H,Pan Q Y,et al.Construction of fully conjugated covalent organic framework via facile linkage conversion for efficientphotozymaticcatalysis[J].Journal of the American Chemical Society,2020,142(13):5958-5963.
[61] Wang H,Zeng X F,Wang W C,et al.Selective capture of trace sulfur gas by porous covalent-organic materials[J].Chemical Engineering Science,2015,135:373-380.
[62] Chen W,Huang L,Yi X F,et al.Lithium doping on 2D squaraine-bridged covalent organic polymers for enhancing adsorption properties:a theoretical study[J].Physical Chemistry Chemical Physics,2018,20(9):6487-6499.
[63] 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 Society,2020,142(9):4472-4480.
[64] 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 Society,2020,142(15):6872-6877.
[65] Ding X S,Feng X,Saeki,et al.Conducting metallophalocyanine 2D covalent organic frameworks:the role of central metals in controlling p-electronic functions[J].Chemical Communication,2012,48(71):8952-8954.
[66] Sun J H,Klechikov Alexey,Moise Calin,et al.A molecular pillar approach to grow veitical covalent organic framework nanosheets on grapheme:hybrid materials for energy storage[J].Angewandte Chemie International Edition,2017,57(4):1034-1038.
[67] Mulzer C R,Shen L,Bisbey R P,et al.Superior charge storage and power density of a conductingpolymer-modified covalent organic framework[J].ACS Central Science,2016,2(9):667-673.
[68] Xu J S,He Y F,Bi S,et al.An olefin-linked covalent organic framework as a flexible thin-film electrode for a high-performance micro-supercapacitor[J].AngewandteChemie,2019,131(350):12193-12197.
[69] Yursan,Li H,Guan X Y,et al.Exfoliated mesoporous 2D covalent organic frameworks for high-rate electrochemical double-layer capacitors[J].Advanced Materials,2020,32(8):1907289.
[70] Wang T,Kailasam K,Xiao P,et al.Adsorption removal of organic dyes on covalent triazine framework(CTF)[J].Microporous & Mesoporous Materials,2014,187:63-70.
[71] Hou Y X,Zhang X M,Wang C M,et al.Novel imine-linked porphyrin covalent organic frameworks with good adsorption removing property of RhB[J].New Journal of Chemistry,2017,41(14):5145-6151.
[72] Wang W,Deng S B,Ren L,et al.Stablecovalent organic framewoks as efficient adsorbents for high and selective removal of an aryl-organophosphorous flame retardant from water[J].Applied Materials & Interfaces,2018,10(36):30265-30272.
[73] Guo L,Jia S,Christian S,et al.Amidation,esterification,and thioesterification of a carboxyl-functionalized covalent organic framework[J].AngewandteChemie,2020,59(5):2023-2027.
[74] Ding S Y,Dong M,Wang Y W,et al.Thioether-based fluorescent covalent organic framework for selective detection and facile removal of mercury(Ⅱ)[J].Journal of the American Society,2016,138(9):3031-3037.
[75] Peng Y,Huang Y,Zhu Y,et al.Ultrahin two-dimensional covalent organic framework nanosheets:preparation and application in highly sensitive and selective DNA detection[J].Journal of the American Society,2017,139(25):8698-8704.
[76] 白茹燕,张帅,张坤蕾,等.以Pt/COF-LZUI为固定基底和Pd NPs/MnO2为标记物的C反应蛋白免疫传感器的研制[J].理化检验-化学分册,2017,53(10):1129-1135.
[77] Cui W,Zhang C,Jiang W,et al.Regenerable and stable sp2 carbon-conjugated covalent organic frameworks for selective detection and extraction of uranium[J].Nature Communication,2020,11,436:14289.
[78] Fang Q,Wang J,Gu S,et al.3D porous crystalline polyimide covalent organic frameworks for drug delivery[J].Journal of the American Society,2015,137(26):8352-8355.
[79] Vyas V S M,Vishwakarma I,Moudrakovski F,et al.Exploiting noncovalent interactions in animine-based covalent organic framework for quercetindelivery[J].Advanced Materials,2019,28(39):8749-8754.
[80] Tan J,Supawadee N,Kong W F,et al.Manipulation of amorphous-to-crystalline transformation:towards the construction of covalent organic framework hybrid microspheres with NIR photothermal conversion ability[J].Angewandte,2016,55(45):13979-13984.
[81] Zhang G Y,Gong K,JiaX D,et al.Water-disperible PEG-curcumin/amine-functionalized covalent organic framework nanocomposites as smart carriers for in vivo drug deliver[J].Nature Communication,2018,9,2785.
[82] 刘小舟,王钰杰,刘耀祖,等.一种高比表面积共价有机框架材料的合成及药物缓释性能[J].高等学校化学学报,2019,9:1813-1817.
[83] Li M M,Qiao S,Zheng Y L,et al.Fabricate covalent organic framework capsules with commodious microenvironment for enzymes[J].Journal of the American Society,2020,142(14):6675-6681.
Options
Outlines

/