Covalent organic frameworks: Design, synthesis, characterization, and applications

Solomon Oluwaseun Akinnawo

ChemPhysMater ›› 2024, Vol. 3 ›› Issue (1) : 36 -63.

PDF (8021KB)
ChemPhysMater ›› 2024, Vol. 3 ›› Issue (1) :36 -63. DOI: 10.1016/j.chphma.2023.08.003
Research article
research-article
Covalent organic frameworks: Design, synthesis, characterization, and applications
Author information +
History +
PDF (8021KB)

Abstract

Covalent organic frameworks (COFs) have emerged as an interesting class of crystalline porous materials with desirable properties (such as highly ordered porosity, structural versatility, high chemical and thermal stabilities, and facile surface modification) and a broad range of potential applications. This critical review is aimed at providing insight into design strategies and synthetic methodologies for COFs. Unlike previous reviews on COFs, this article also focuses on the characterization of COFs, which is important for understanding the physical and chemical properties of COFs that are essential for practical applications. Furthermore, this review highlights the applications of COFs in various fields, including catalysis, photovoltaic devices, sensors, supercapacitors, wastewater treatment, biomedicine, chromatographic and spectroscopic analyses, and gas separation and storage. Lastly, perspectives on future directions and challenges associated with COFs are provided.

Keywords

Crystalline / Covalent organic framework / Catalysis / Porous material / Wastewater treatment

Cite this article

Download citation ▾
Solomon Oluwaseun Akinnawo. Covalent organic frameworks: Design, synthesis, characterization, and applications. ChemPhysMater, 2024, 3(1): 36-63 DOI:10.1016/j.chphma.2023.08.003

登录浏览全文

4963

注册一个新账户 忘记密码

Declaration of Competing Interests

The author declares that there are no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

References

[1]

H.R. Abuzeid, A.F.M. EL-Mahdy, S.W. Kuo, Covalent organic frameworks: Design principles, synthetic strategies, and diverse applications, Giant 6 (2021) 100054.

[2]

A.P. Côté, A.I. Benin, N.W. Ockwig, M. O’Keeffe, A.J. Matzger, O.M. Yaghi, Porous, crystalline, covalent organic frameworks, Science 310 (2005) 1166-1170.

[3]

J. Gong, R.B. Lin, B. Chen, Conjugated microporous polymers with rigid backbones for organic solvent nanofiltration, Chem. 4 (2018) 2269-2271.

[4]

W.T. Chung, I. Mekhemer, M.G. Abuosoaud, A. Elewa, A. EL-Mahdy, H.H. Chou, S.W. Kuo, K.C.W. Wu, Recent advances in metal/covalent organic frameworks based materials: Their synthesis, structure design and potential applications for hydrogen production, Coord. Chem. Rev. 483 (2023) 215066.

[5]

M.G. Mohamed, T.C. Chen, S.W. Kuo, Solid-state chemical transformations to enhance gas capture in benzoxazine-linked conjugated microporous polymers, Macromolecules 54 (2021) 5866-5877.

[6]

M. Mohamed Samy, I.M.A. Mekhemer, M.G. Mohamed, M. Hammad Elsayed, K.H. Lin, Y.K. Chen,Conjugated microporous polymers incorporating thiazolo[5,4-d]thiazole moieties for sunlight-driven hydrogen production from water, Chem. Eng. J. 446 (2022) 137158.

[7]

M. Ejaz, M.G. Mohamed, S.W. Kuo, Solid state chemical transformation provides a fully benzoxazine-linked porous organic polymer displaying enhanced CO2 capture and supercapacitor performance, Polym. Chem. 14 (2023) 2494-2509.

[8]

M.G. Mohamed, H.Y. Hu, M. Madhu, M.M. Samy, I.M.A. Mekhemer, W.L. Tseng, Ultrastable two-dimensional fluorescent conjugated microporous polymers containing pyrene and fluorene units for metal ion sensing and energy storage, Eur. Polym. J. 189 (2023) 111980.

[9]

M.G. Mohamed, S.U. Sharma, N.Y. Liu, T.H. Mansoure, M.M. Samy, S.V. Chaganti, Ultrastable covalent triazine organic framework based on anthracene moiety as platform for high-performance carbon dioxide adsorption and supercapacitors, Int. J. Mol. Sci. 23 (2022) 3174.

[10]

L. Song, X. Wang, M. Zhang, W. Jia, Q. Wang, W. Ye, A single-component supramolecular organic framework with efficient ultralong phosphorescence, CCS Chem. 3 (2021) 466-472.

[11]

W. Yao, C. Ma, H. Ma, L. Fu, S. Lu, A. Lv, Supramolecular organic frameworks with ultralong phosphorescence via breaking π -conjugated structures, Giant 1 (2020) 1-7.

[12]

B.M. Weckhuysen, J. Yu, Recent advances in zeolite chemistry and catalysis, Chem Soc Rev 44 (2015) 7022-7024.

[13]

S. Akinnawo, Synthesis, modification, applications and challenges of titanium dioxide nanoparticles, Res. J. Nanosci. Eng. 3 (2019) 10-22.

[14]

K.A. Adegoke, S.O. Akinnawo, O.S. Bello, N.W. Maxakato, R.O. Adegoke, R.K. Gupta, T.A. NguyenYasin GBT-M-OF-BN for EC and S, Chapter 6 -MOF-based electrocatalysts for oxygen evolution reactions, Micro and Nano Technologies editors, Elsevier, 2022, pp. 107-134.

[15]

J. Liu, G. Han, D. Zhao, K. Lu, J. Gao, T.S. Chung, Self-standing and flexible covalent organic framework (COF) membranes for molecular separation, Sci. Adv. 6 (2020) 1-9.

[16]

Y. Song, Q. Sun, B. Aguila, S. Ma, Opportunities of covalent organic frameworks for advanced applications, Adv Sci 6 (2019) 1801410.

[17]

N. Liu, L. Shi, X. Han, Q.Y. Qi, Z.Q. Wu, X. Zhao, A heteropore covalent organic framework for adsorptive removal of Cd(II) from aqueous solutions with high efficiency, Chinese Chem. Lett. 31 (2020) 386-390.

[18]

M.S. Lohse, T. Bein, Covalent organic frameworks: Structures, synthesis, and applications, Adv Funct Mater 28 (2018) 1705553.

[19]

S.Y. Ding, W. Wang, Covalent organic frameworks (COFs): From design to applications, Chem Soc Rev 42 (2013) 548-568.

[20]

R.K. Sharma, P. Yadav, M. Yadav, R. Gupta, P. Rana, A. Srivastava, Recent development of covalent organic frameworks (COFs): Synthesis and catalytic (organic-electro-photo) applications, Mater. Horizons 7 (2020) 411-454.

[21]

J. Wang, S. Zhuang, Covalent organic frameworks (COFs) for environmental applications, Coord Chem Rev 400 (2019) 213046.

[22]

Y. Sun, Z. Ning, A. Ishag, Y. Li, H. Wang, H. Guo, P. Mei, Q. Meng, Recent investigations and progress in environmental remediation by using covalent organic framework-based adsorption method: A review, J. Clean. Prod. 277 (2020) 123360.

[23]

M. Gatou, P. Bika, T. Stergiopoulos, P. Dallas, E.A. Pavlatou, Recent advances in covalent organic frameworks for heavy metal removal applications, Energies 14 (2021) 1-26.

[24]

C. Arqueros, F. Zamora, C. Montoro, A Perspective on the application of covalent organic frameworks for detection and water treatment, Nanomaterials 11 (2021) 1-31.

[25]

Z. Xia, Y. Zhao, S.B. Darling, Adv. Mater. Covalent organic frameworks for water treatment, Interfaces. 8 (2021) 2001507.

[26]

J.L. Segura, M.J. Mancheño, F. Zamora, Covalent organic frameworks based on Schiff-base chemistry: Synthesis, properties and potential applications, Chem. Soc. Rev. 45 (2016) 5635-5671.

[27]

F.J. Uribe-Romo, J.R. Hunt, H. Furukawa, C. Klöck, M. O’Keeffe, O.M. Yaghi, A crystalline imine-linked 3-D porous covalent organic framework, J. Am. Chem. Soc. 131 (2009) 4570-4571.

[28]

S. Dalapati, S. Jin, J. Gao, Y. Xu, A. Nagai, D. Jiang, An azine-linked covalent organic framework, J. Am. Chem. Soc. 135 (2013) 17310-17313.

[29]

Y. Li, C. Wang, S. Ma, H. Zhang, J. Ou, Y. Wei, Fabrication of hydrazone-linked covalent organic frameworks using alkyl amine as building block for high adsorption capacity of metal ions, ACS Appl. Mater. Interfaces. 11 (2019) 11706-11714.

[30]

X. Qin, X. Tang, Y. Ma, H. Xu, Q. Xu, W. Yang, Decorating covalent organic frameworks with high-density chelate groups for uranium extraction, Chem. Res. Chinese Univ. 38 (2022) 433-439.

[31]

A. Nagai, Z. Guo, X. Feng, S. Jin, X. Chen, X. Ding, Pore surface engineering in covalent organic frameworks, Nat. Commun. 2 (2011) 536.

[32]

Z. Qu, C. Lai, G. Zhao, A. Knebel, H. Fan, H. Meng, Pore engineering in covalent organic framework membrane for gas separation, Adv. Membr. 2 (2022) 100037.

[33]

X. Xu, X. Wu, K. Xu, H. Xu, H. Chen, N. Huang, Pore partition in two-dimensional covalent organic frameworks, Nat. Commun. 14 (2023) 1-9.

[34]

T. Ma, L. Wei, L. Liang, S. Yin, L. Xu, Diverse crystal size effects in covalent organic frameworks, Nat. Commun. 11 (2020) 1-9.

[35]

C. Liu, Y. Jiang, A. Nalaparaju, J. Jiang, A. Huang, Post-synthesis of a covalent organic framework nanofiltration membrane for highly efficient water treatment, J. Mater. Chem. A. 7 (2019) 24205-24210.

[36]

H. Yang, L. Yang, H. Wang, Z. Xu, Y. Zhao, Y. Luo, Covalent organic framework membranes through a mixed-dimensional assembly for molecular separations, Nat. Commun. 10 (2019) 2101.

[37]

R. Wen, Y. Li, M. Zhang, X. Guo, X. Li, X. Li, Graphene-synergized 2D covalent organic framework for adsorption: A mutual promotion strategy to achieve stabilization and functionalization simultaneously, J. Hazard Mater. 358 (2018) 273-285.

[38]

Z.J. Xia, H.C. Yang, Z. Chen, R.Z. Waldman, Y. Zhao, C. Zhang, Porphyrin covalent organic framework (POF)-based interface engineering for solar steam generation, Adv. Mater. Interfaces. 6 (2019) 1900254.

[39]

J.J. Jarju, A.M. Lavender, B. Espiña, V. Romero, L.M. Salonen, Covalent organic framework composites : Synthesis and analytical applications, Molecules 25 (2020) 1-41.

[40]

L.L. Wang, C.X. Yang, X.P. Yan, In situ growth of covalent organic framework shells on silica microspheres for application in liquid chromatography, Chempluschem 82 (2017) 933-938.

[41]

H.L. Qian, C. Yang, X.P. Yan, Layer-by-layer preparation of 3D covalent organic framework/silica composites for chromatographic separation of position isomers, Chem. Commun. 54 (2018) 11765-11768.

[42]

S. He, T. Zeng, S. Wang, H. Niu, Y. Cai, Facile synthesis of magnetic covalent organic framework with three-dimensional bouquet-like structure for enhanced extraction of organic targets, ACS Appl. Mater. Interfaces. 9 (2017) 2959-2965.

[43]

L. Huang, N. Mao, Q. Yan, D. Zhang, Q. Shuai, Magnetic covalent organic frameworks for the removal of diclofenac sodium from water, ACS Appl. Nano Mater. 3 (2020) 319-326.

[44]

D. Hao, J. Zhang, H. Lu, W. Leng, R. Ge, X. Dai, Fabrication of a COF-5 membrane on a functionalized a-Al2O3 ceramic support using a microwave irradiation method, Chem. Commun. 5 (2014) 1462-1464.

[45]

H. Lu, C. Wang, J. Chen, R. Ge, W. Leng, B. Dong, A novel 3D covalent organic framework membrane grown on a porous a-Al2O3 substrate under solvothermal conditions, Chem. Commun. 51 (2015) 15562-15565.

[46]

H. Fan, J. Gu, H. Meng, A. Knebel, J. Caro, High-flux membranes based on the covalent organic framework COF-LZU1 for selective dye separation by nanofiltration, Angew Chem. Int. Ed. Engl. 57 (2018) 4083-4087.

[47]

H. Fan, M. Peng, I. Strauss, A. Mundstock, H. Meng, J. Caro, High-flux vertically aligned 2D covalent organic framework membrane with enhanced hydrogen separation, J. Am. Chem. Soc. 142 (2020) 6872-6877.

[48]

C. Wang, W. Gao, N. Liu, Y. Xin, X. Liu, X. Wang, Covalent organic framework decorated TiO2 nanotube arrays for photoelectrochemical cathodic protection of steel, Corros. Sci. 176 (2020) 108920.

[49]

S.B. Kalidindi, H. Oh, M. Hirscher, D. Esken, C. Wiktor, T.S. Metal@COFs, Covalent organic frameworks as templates for Pd nanoparticles and hydrogen storage properties of Pd@COF-102 hybrid material, Chem - A. Eur. J. 18 (2012) 10848-10856.

[50]

P. Pachfule, S. Kandambeth, D. Díaz Díaz, R. Banerjee, Highly stable covalent organic framework-Au nanoparticles hybrids for enhanced activity for nitrophenol reduction, Chem. Commun. 50 (2014) 3169-3172.

[51]

P. Pachfule, M.K. Panda, S. Kandambeth, S.M. Shivaprasad, D.D. Díaz, R. Banerjee, Multifunctional and robust covalent organic framework-nanoparticle hybrids, J. Mater. Chem. A. 2 (2014) 7944-7952.

[52]

X. Shi, Y. Yao, Y. Xu, K. Liu, G. Zhu, L. Chi, Imparting catalytic activity to a covalent organic framework material by nanoparticle encapsulation, ACS Appl. Mater. Interfaces. 9 (2017) 7481-7488.

[53]

G.J. Chen, X.B. Li, C.C. Zhao, H.C. Ma, J.L. Kan, Y.B. Xin, Ru nanoparticles-loaded covalent organic framework for solvent-free one-pot tandem reactions in air, Inorg. Chem. 57 (2018) 2678-2685.

[54]

M. Bhadra, H.S. Sasmal, A. Basu, S.P. Midya, S. Kandambeth, P. Pachfule, Pre-designed metal-anchored building block for in situ generation of Pd nanoparticles in porous covalent organic framework: Application in heterogeneous tandem catalysis, ACS Appl. Mater. Interfaces. 9 (2017) 13785-13792.

[55]

C. Hu, Z. Zhang, S. Liu, X. Liu, M. Pang, Monodispersed CuSe sensitized covalent organic framework photosensitizer with an enhanced photodynamic and photothermal effect for cancer therapy, ACS Appl. Mater. Interfaces. 11 (2019) 23072-23082.

[56]

L. Wang, H. Xu, Y. Qiu, X. Liu, W. Huang, N. Yan, Utilization of Ag nanoparticles anchored in covalent organic frameworks for mercury removal from acidic waste water, J. Hazard Mater. 389 (2020) 121824.

[57]

J.X. Guo, H.L. Qian, X. Zhao, C. Yang, X.P. Yan, In situ room-temperature fabrication of a covalent organic framework and its bonded fiber for solid-phase microextraction of polychlorinated biphenyls in aquatic products, J. Mater. Chem. A. 7 (2019) 13249-13255.

[58]

Y. Tian, Y. Hou, Q. Yu, X. Wang, M. Tian, Layer-by-layer self-assembly of a novel covalent organic frameworks microextraction coating for analyzing polycyclic aromatic hydrocarbons from aqueous solutions via gas chromatography, J. Sep. Sci. 43 (2020) 896-904.

[59]

L. Wen, P. Wu, L.L. Wang, L.Z. Chen, M.L. Wang, X. Wang, Solid-phase microextraction using a $\beta$-ketoenamine-linked covalent organic framework coating for efficient enrichment of synthetic musks in water samples, Anal. Methods. 12 (2020) 2434-2442.

[60]

I.A. Kinloch, J. Suhr, J. Lou, R.J. Young, P.M. Ajayan, Composites with carbon nanotubes and graphene: An outlook, Science 362 (2018) 547-553.

[61]

L. Chen, W. Wang, Q. Fang, K. Zuo, G. Hou, Q. Ai, High performance hierarchically nanostructured graphene oxide/covalent organic framework hybrid membranes for stable organic solvent nanofiltration, Appl. Mater. Today. 20 (2020) 100791.

[62]

J. Wang, J. Li, M. Gao, X. Zhang, Self-assembling covalent organic framework functionalized magnetic graphene hydrophilic biocomposites as an ultrasensitive matrix for N-linked glycopeptide recognition, Nanoscale 9 (2017) 10750-10756.

[63]

Y. Lu, B. Wang, C. Wang, Y. Yan, D. Wu, H. Liang, A covalent organic framework-derived hydrophilic magnetic graphene composite as a unique platform for detection of phthalate esters from packaged milk samples, Chromatographia 82 (2019) 1089-1099.

[64]

Y.J. Yu, W. Li, S.B. Ren, X.J. Zhou, D.M. Han, Rational design of COF-MOF composites for ratiometric fluorescence detection of phosphate, New J. Chem. 47 (2023) 6186-6190.

[65]

J. Fu, S. Das, G. Xing, T. Ben, V. Valtchev, S. Qiu, Fabrication of COF-MOF composite membranes and their highly selective separation of H2/CO2, J. Am. Chem. Soc. (2016).

[66]

B.P. Biswal, H.D. Chaudhari, R. Banerjee, U.K. Kharul, Chemically stable covalent organic framework (COF)-polybenzimidazole hybrid membranes: Enhanced gas separation through pore modulation, Chemistry 22 (2016) 4695-4699.

[67]

R. Wang, X. Shi, Z. Zhang, A. Xiao, S.P. Sun, Z. Cui, Undirectional diffusion synthesis of covalent organic frameworks (COFs) on polymeric substrates for dye separation, J. Memb. Sci. 586 (2019) 274-280.

[68]

S.B. Alahakoon, G.T. McCandless, A.A.K. Karunathilake, C.M. Thompson, R.A. Smaldone, Enhanced structural organization in covalent organic frameworks through fluorination, Chemistry 23 (2017) 4255-4259.

[69]

S.B. Alahakoon, C.M. Thompson, A.X. Nguyen, G. Occhialini, G.T. McCandless, R.A. Smaldone, An azine-linked hexaphenylbenzene based covalent organic framework, Chem. Commun. 52 (2016) 2843-2845.

[70]

J. Lu, F. Lin, Q. Wen, Q.Y. Qi, J.Q. Xu, X. Zhao, Large-scale synthesis of azine-linked covalent organic frameworks in water and promoted by water, New J. Chem. 43 (2019) 6116-6120.

[71]

X. Li, Y. Qi, G. Yue, Q. Wu, Y. Li, M. Zhang, Solvent- and catalyst-free synthesis of an azine-linked covalent organic framework and the induced tautomerization in the adsorption of U(vi) and Hg(ii), Green Chem. 21 (2019) 649-657.

[72]

P. Guan, J. Qiu, Y. Zhao, H. Wang, Z. Li, Y. Shi, A novel crystalline azine-linked three-dimensional covalent organic framework for CO2 capture and conversion, Chem. Commun. 55 (2019) 12459-12462.

[73]

S. Kandambeth, A. Mallick, B. Lukose, M.V. Mane, T. Heine, R. Banerjee, Construction of crystalline 2D covalent organic frameworks with remarkable chemical (acid/base) stability via a combined reversible and irreversible route, J. Am. Chem. Soc. 134 (2012) 19524-19527.

[74]

A.F.M. EL-Mahdy, Y.H. Hung, T.H. Mansoure, H.H. Yu, Y.S. Hsu, K.C.W. Wu, Synthesis of [3 + 3] $\beta$-ketoenamine-tethered covalent organic frameworks (COFs) for high-performance supercapacitance and CO2 storageJ. Taiwan Inst. Chem. Eng 103 (2019) 199-208.

[75]

Y. Zhang, X. Shen, X. Feng, H. Xia, Y. Mu, X. Liu, Covalent organic frameworks as pH responsive signaling scaffolds, Chem. Commun. 52 (2016) 11088-11091.

[76]

Y. Wang, Y. Liu, H. Li, X. Guan, M. Xue, Y. Yan, Three-dimensional mesoporous covalent organic frameworks through steric hindrance engineering, J. Am. Chem. Soc. 142 (2020) 3736-3741.

[77]

L. Stegbauer, K. Schwinghammer, B.V. Lotsch, A hydrazone-based covalent organic framework for photocatalytic hydrogen production, Chem. Sci. 5 (2014) 2789-2793.

[78]

Z.J. Li, S.Y. Ding, H.D. Xue, W. Cao, W. Wang, Synthesis of -C = N- linked covalent organic frameworks via the direct condensation of acetals and amines, Chem. Commun. 52 (2016) 7217-7220.

[79]

Q. Fang, Z. Zhuang, S. Gu, R.B. Kaspar, J. Zheng, J. Wang, Designed synthesis of large-pore crystalline polyimide covalent organic frameworks, Nat. Commun. 5 (2014) 4503.

[80]

Q. Fang, J. Wang, S. Gu, R.B. Kaspar, Z. Zhuang, J. Zheng, 3D porous crystalline polyimide covalent organic frameworks for drug delivery, J. Am. Chem. Soc. 137 (2015) 8352-8355.

[81]

C. Montoro, D. Rodríguez-San-Miguel, E. Polo, R. Escudero-Cid, M.L. Ruiz-González, J.A.R. Navarro, Ionic conductivity and potential application for fuel cell of a modified imine-based covalent organic framework, J. Am. Chem. Soc. 139 (2017) 10079-10086.

[82]

S.Y. Ding, J. Gao, Q. Wang, Y. Zhang, W.G. Song, C.Y. Su, Construction of covalent organic framework for catalysis: Pd/COF-LZU1 in Suzuki-Miyaura coupling reaction, J. Am. Chem. Soc. 133 (2011) 19816-19822.

[83]

D.M. Fischbach, G. Rhoades, C. Espy, F. Goldberg, B.J. Smith, Controlling the crystalline structure of imine-linked 3D covalent organic frameworks, Chem. Commun. 55 (2019) 3594-3597.

[84]

X. Wu, B. Wang, Z. Yang, L. Chen, Novel imine-linked covalent organic frameworks: Preparation, characterization and application, J. Mater. Chem. A 7 (2019) 5650-5655.

[85]

M.G. Rabbani, A.K. Sekizkardes, Z. Kahveci, T.E. Reich, R. Ding, H.M. El-Kaderi, A 2D mesoporous imine-linked covalent organic framework for high pressure gas storage applications, Chemistry 19 (2013) 3324-3328.

[86]

W.L. Dong, S.Y. Li, J.Y. Yue, C. Wang, D. Wang, L.J. Wan, Fabrication of bilayer tetrathiafulvalene integrated surface covalent organic frameworks, Phys. Chem. Chem. Phys. 18 (2016) 17356-17359.

[87]

E. Jin, M. Asada, Q. Xu, S. Dalapati, M.A. Addicoat, M.A. Brady, Two-dimensional sp(2) carbon-conjugated covalent organic frameworks, Science 357 (2017) 673-676.

[88]

X. Zhuang, W. Zhao, F. Zhang, Y. Cao, F. Liu, S. Bi, A two-dimensional conjugated polymer framework with fully sp2-bonded carbon skeleton, Polym. Chem. 7 (2016) 4176-4181.

[89]

R. Chen, J.L. Shi, Y. Ma, G. Lin, X. Lang, C. Wang, Designed synthesis of a 2D porphyrin-based sp(2) carbon-conjugated covalent organic framework for heterogeneous photocatalysis, Angew Chem. Int. Ed. Engl. 58 (2019) 6430-6434.

[90]

Y. Zhao, H. Liu, C. Wu, Z. Zhang, Q. Pan, F. Hu, Fully Conjugated two-dimensional sp(2) -carbon covalent organic frameworks as artificial photosystem i with high efficiency, Angew Chem. Int. Ed. Engl. 58 (2019) 5376-5381.

[91]

J. You, Y. Zhao, L. Wang, W. Bao, Recent developments in the photocatalytic applications of covalent organic frameworks: A review, J. Clean Prod. 291 (2021) 125822.

[92]

K. Geng, V. Arumugam, H. Xu, Y. Gao, D. Jiang, Covalent organic frameworks: Polymer chemistry and functional design, Prog. Polym. Sci. 108 (2020) 101288.

[93]

F. Haase, E. Troschke, G. Savasci, T. Banerjee, V. Duppel, S. Dörfler, Topochemical conversion of an imine- into a thiazole-linked covalent organic framework enabling real structure analysis, Nat. Commun. 9 (2018) 2600.

[94]

P.J. Waller, Y.S. AlFaraj, C.S. Diercks, N.N. Jarenwattananon, O.M. Yaghi, Conversion of imine to oxazole and thiazole linkages in covalent organic frameworks, J. Am. Chem. Soc. 140 (2018) 9099-9103.

[95]

P. Kuhn, M. Antonietti, A. Thomas, Porous, covalent triazine-based frameworks prepared by ionothermal synthesis, Angew Chem. Int. Ed. Engl. 47 (2008) 3450-3453.

[96]

X. Chen, M. Addicoat, E. Jin, H. Xu, T. Hayashi, F. Xu, Designed synthesis of double-stage two-dimensional covalent organic frameworks, Sci. Rep. 5 (2015) 1-19.

[97]

Y. Zeng, R. Zou, Z. Luo, H. Zhang, X. Yao, X. Ma, Covalent organic frameworks formed with two types of covalent bonds based on orthogonal reactions, J. Am. Chem. Soc. 137 (2015) 1020-1023.

[98]

H. Li, Q. Pan, Y. Ma, X. Guan, M. Xue, Q. Fang, Three-dimensional covalent organic frameworks with dual linkages for bifunctional cascade catalysis, J. Am. Chem. Soc. 138 (2016) 14783-14788.

[99]

X. Guan, Y. Ma, H. Li, Y. Yusran, M. Xue, Q. Fang, Fast, Ambient temperature and pressure ionothermal synthesis of three-dimensional covalent organic frameworks, J. Am. Chem. Soc. 140 (2018) 4494-4498.

[100]

B.J. Smith, A.C. Overholts, N. Hwang, W.R. Dichtel, Insight into the crystallization of amorphous imine-linked polymer networks to 2D covalent organic frameworks, Chem. Commun. 52 (2016) 3690-3693.

[101]

C. Qian, Q.Y. Qi, G.F. Jiang, F.Z. Cui, Y. Tian, X. Zhao, Toward covalent organic frameworks bearing three different kinds of pores: The strategy for construction and COF-to-COF transformation via heterogeneous linker exchange, J. Am. Chem. Soc. 139 (2017) 6736-6743.

[102]

N. Li, J. Du, D. Wu, J. Liu, N. Li, Z. Sun, Recent advances in facile synthesis and applications of covalent organic framework materials as superior adsorbents in sample pretreatment, TrAC Trends Anal. Chem. 108 (2018) 154-166.

[103]

S. Cao, B. Li, R. Zhu, H. Pang, Design and synthesis of covalent organic frameworks towards energy and environment fields, Chem. Eng. J. 355 (2019) 602-623.

[104]

B.T. Koo, R.F. Heden, P. Clancy, Nucleation and growth of 2D covalent organic frameworks: Polymerization and crystallization of COF monomers, Phys. Chem. Chem. Phys. 19 (2017) 9745-9754.

[105]

V. Singh, S. Jang, N.K. Vishwakarma, D.P. Kim, Intensified synthesis and post-synthetic modification of covalent organic frameworks using a continuous flow of microdroplets technique, NPG Asia Mater. 10 (2018) e456-e456.

[106]

A. Kuchenbuch, R. Giernoth, Ionic liquids beyond simple solvents: Glimpses at the state of the art in organic chemistry, ChemistryOpen 4 (2015) 677-681.

[107]

Y. Gao, C. Wang, H. Hu, R. Ge, M. Lu, J. Zhang, Synthesis of two-dimensional covalent organic frameworks in ionic liquids, Chemistry 25 (2019) 15488-15492.

[108]

J. Gan, A.R. Bagheri, N. Aramesh, I. Gul, M. Franco, Y.Q. Almulaiky, Covalent organic frameworks as emerging host platforms for enzyme immobilization and robust biocatalysis - A review, Int. J. Biol. Macromol. 167 (2021) 502-515.

[109]

M.J. Bojdys, J. Jeromenok, A. Thomas, M. Antonietti, Rational extension of the family of layered, covalent, triazine-based frameworks with regular porosity, Adv. Mater. 22 (2010) 2202-2205.

[110]

L.A. Baldwin, J.W. Crowe, D.A. Pyles, P.L. McGrier, Metalation of a mesoporous three-dimensional covalent organic framework, J. Am. Chem. Soc. 138 (2016) 15134-15137.

[111]

N.L. Campbell, R. Clowes, L.K. Ritchie, A.I. Cooper, Rapid microwave synthesis and purification of porous covalent organic frameworks, Chem. Mater. 21 (2009) 204-206.

[112]

L.K. Ritchie, A. Trewin, A. Reguera-Galan, T. Hasell, A.I. Cooper, Synthesis of COF-5 using microwave irradiation and conventional solvothermal routes, Microporous Mesoporous Mater. 132 (2010) 132-136.

[113]

H. Lyu, B. Gao, F. He, C. Ding, J. Tang, J.C. Crittenden, Ball-milled carbon nanomaterials for energy and environmental applications, ACS Sustain Chem. Eng. 5 (2017) 9568-9585.

[114]

T. Friščić, J. Mater. New opportunities for materials synthesis using mechanochemistry, Chem. 20 (2010) 7599-7605.

[115]

S.L. James, C.J. Adams, C. Bolm, D. Braga, P. Collier, T. Friščić, Mechanochemistry: Opportunities for new and cleaner synthesis, Chem. Soc. Rev. 41 (2012) 413-447.

[116]

B.P. Biswal, S. Chandra, S. Kandambeth, B. Lukose, T. Heine, R. Banerjee, Mechanochemical synthesis of chemically stable isoreticular covalent organic frameworks, J. Am. Chem. Soc. 135 (2013) 5328-5331.

[117]

X. Wang, R. Ma, L. Hao, Q. Wu, C. Wang, Z. Wang, Mechanochemical synthesis of covalent organic framework for the efficient extraction of benzoylurea insecticides, J. Chromatogr. A 1551 (2018) 1-9.

[118]

J.H. Bang, K.S. Suslick, Applications of ultrasound to the synthesis of nanostructured materials, Adv. Mater. 22 (2010) 1039-1059.

[119]

S.T. Yang, J. Kim, H.Y. Cho, S. Kim, W.S. Ahn, Facile synthesis of covalent organic frameworks COF-1 and COF-5 by sonochemical method, RSC Adv. 2 (2012) 10179-10181.

[120]

J. Yoo, S. Lee, S. Hirata, C. Kim, C.K. Lee, T. Shiraki, In situ synthesis of covalent organic frameworks (COFs) on carbon nanotubes and graphenes by sonochemical reaction for CO2 adsorbents, Chem. Lett. 44 (2015) 560-562.

[121]

S. Kim, H.C. Choi, Light-promoted synthesis of highly-conjugated crystalline covalent organic framework, Commun. Chem. 2 (2019) 60, doi: 10.1038/s42004-019-0162-z.

[122]

E. Jin, J. Li, K. Geng, Q. Jiang, H. Xu, Q. Xu, D. Jiang, Designed synthesis of stable light-emitting two-dimensional sp 2 carbon-conjugated covalent organic frameworks, Nat. Commun. 9 (2018) 1-10.

[123]

P. Wang, Q. Wu, L. Han, S. Wang, S. Fang, Z. Zhang, Synthesis of conjugated covalent organic frameworks/graphene composite for supercapacitor electrodes, RSC Adv. 5 (2015) 27290-27294.

[124]

M. Çalıșkan, T. Baran, Design of a palladium nanocatalyst produced from Schiff base modified dialdehyde cellulose and its application in aryl halide cyanation and reduction of nitroarenes, Cellulose 29 (2022) 4475-4493.

[125]

C. Zhu, S. Pang, Z. Chen, L. Bi, S. Wang, C. Liang, Synthesis of covalent organic frameworks (COFs)-nanocellulose composite and its thermal degradation studied by TGA/FTIR, Polymers (Basel) 14 (2022) 3158.

[126]

H. Guo, L. Zhang, R. Xue, B. Ma, W. Yang, Eyes of covalent organic frameworks: Cooperation between analytical chemistry and COFs, Rev. Anal. Chem. 38 (2019) 20170023.

[127]

P. Katekomol, J. Roeser, M. Bojdys, J. Weber, A. Thomas,Covalent triazine frameworks prepared from 1,3,5-tricyanobenzene, Chem. Mater. 25 (2013) 1542-1548.

[128]

H. Ding, Y. Li, H. Hu, Y. Sun, J. Wang, C. Wang, A tetrathiafulvalene-based electroactive covalent organic framework, Chemistry 20 (2014) 14614-14618.

[129]

J. Ma, X.B. Fu, Y. Li, T. Xia, L. Pan, Y.F. Yao, Solid-state NMR study of adsorbed water molecules in covalent organic framework materials, Microporous Mesoporous Mater. 305 (2020) 110287.

[130]

A. Halder, M. Ghosh, M.A. Khayum, S. Bera, M. Addicoat, H.S. Sasmal, Interlayer hydrogen-bonded covalent organic frameworks as high-performance supercapacitors, J. Am. Chem. Soc. 140 (2018) 10941-10945.

[131]

C. Zhang, G. Li, Z. Zhang, A hydrazone covalent organic polymer based micro-solid phase extraction for online analysis of trace Sudan dyes in food samples, J. Chromatogr. A 1419 (2015) 1-9.

[132]

J. Li, X. Yang, C. Bai, Y. Tian, B. Li, S. Zhang, A novel benzimidazole-functionalized 2-D COF material: Synthesis and application as a selective solid-phase extractant for separation of uranium, J. Colloid Interface Sci. 437 (2015) 211-218.

[133]

X. Zhong, W. Liang, Z. Lu, M. Qiu, B. Hu, Ultra-high capacity of graphene oxide conjugated covalent organic framework nanohybrid for U(VI) and Eu(III) adsorption removal, J. Mol. Liq. 323 (2021) 114603.

[134]

W. Li, H.X. Jiang, Y. Geng, X.H. Wang, R.Z. Gao, A.N. Tang, Facile removal of phytochromes and efficient recovery of pesticides using heteropore covalent organic framework-based magnetic nanospheres and electrospun films, ACS Appl. Mater. Interfaces. 12 (2020) 20922-20932.

[135]

X. Wan, X. Wang, G. Chen, C. Guo, B. Zhang, Covalent organic framework/nanofibrillated cellulose composite membrane loaded with Pd nanoparticles for dechlorination of dichlorobenzene, Mater. Chem. Phys. 246 (2020) 122574.

[136]

Y.H. Pang, Q. Yue, Y.Y. Huang, C. Yang, X.F. Shen, Facile magnetization of covalent organic framework for solid-phase extraction of 15 phthalate esters in beverage samples, Talanta 206 (2020) 120194.

[137]

D. Rodríguez-San-Miguel, A. Yazdi, V. Guillerm, J. Pérez-Carvajal, V. Puntes, D. Maspoch, Confining functional nanoparticles into colloidal imine-based COF spheres by a sequential encapsulation-crystallization method, Chemistry 23 (2017) 8623-8627.

[138]

W. Li, L. Huang, D. Guo, Y. Zhao, Y. Zhu, Self-assembling covalent organic framework functionalized poly (styrene-divinyl benzene-glycidylmethacrylate) composite for the rapid extraction of non-steroidal anti-inflammatory drugs in wastewater, J. Chromatogr. A 1571 (2018) 76-83.

[139]

K.M. Koczkur, S. Mourdikoudis, L. Polavarapu, S.E. Skrabalak, Polyvinylpyrrolidone (PVP) in nanoparticle synthesis, Dalt Trans. 44 (2015) 17883-17905.

[140]

T. Zhang, Y. Chen, W. Huang, Y. Wang, X. Hu, A novel AuNPs-doped COFs composite as electrochemical probe for chlorogenic acid detection with enhanced sensitivity and stability, Sensors Actuators B Chem. 276 (2018) 362-369.

[141]

H. Zhu, X. Yang, E.D. Cranston, S. Zhu, Flexible and porous nanocellulose aerogels with high loadings of metal-organic-framework particles for separations applications, Adv. Mater. 28 (2016) 7652-7657.

[142]

A.F.M. EL-Mahdy, C.H. Kuo, A. Alshehri, C. Young, Y. Yamauchi, J. Kim, Strategic design of triphenylamine- and triphenyltriazine-based two-dimensional covalent organic frameworks for CO2 uptake and energy storage, J. Mater. Chem. A. 6 (2018) 19532-19541.

[143]

H. Furukawa, O.M. Yaghi, Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications, J. Am. Chem. Soc. 131 (2009) 8875-8883.

[144]

Y. Zhang, S.N. Riduan, Functional porous organic polymers for heterogeneous catalysis, Chem. Soc. Rev. 41 (2012) 2083-2094.

[145]

R.L. Wang, D.P. Li, L.J. Wang, X. Zhang, Z.Y. Zhou, J.L. Mu, The preparation of new covalent organic framework embedded with silver nanoparticles and its applications in degradation of organic pollutants from waste water, Dalt Trans. 48 (2019) 1051-1059.

[146]

M.Y. Gao, C.C. Li, H.L. Tang, X.J. Sun, H. Dong, F.M. Zhang, Boosting visible-light-driven hydrogen evolution of covalent organic frameworks through compositing with MoS2: A promising candidate for noble-metal-free photocatalysts, J. Mater. Chem. A 7 (2019) 20193-20200.

[147]

P. Verma, J.J.M. Le Brocq, R. Raja, Rational design and application of covalent organic frameworks for solar fuel production, Molecules 26 (2021) 4181.

[148]

D. Wang, H. Zeng, X. Xiong, M.F. Wu, M. Xia, M. Xie, Highly efficient charge transfer in CdS-covalent organic framework nanocomposites for stable photocatalytic hydrogen evolution under visible light, Sci. Bull 65 (2020) 113-122.

[149]

L. Li, Z. Zhou, L. Li, Z. Zhuang, J. Bi, J. Chen, Thioether-functionalized 2D covalent organic framework featuring specific affinity to Au for photocatalytic hydrogen production from seawater, ACS Sustain. Chem. Eng. 7 (2019) 18574-18581.

[150]

Y. Fu, X. Zhu, L. Huang, X. Zhang, F. Zhang, W. Zhu, Azine-based covalent organic frameworks as metal-free visible light photocatalysts for CO2 reduction with H2O, Appl. Catal. B Environ. 239 (2018) 46-51.

[151]

S. Guo, P. Yang, Y. Zhao, X. Yu, Y. Wu, H. Zhang, Direct Z-scheme heterojunction of SnS(2) /sulfur-bridged covalent triazine frameworks for visible-light-driven CO(2) photoreduction, ChemSusChem 13 (2020) 6278-6283.

[152]

Z. Fu, X. Wang, A.M. Gardner, X. Wang, S.Y. Chong, G. Neri, A stable covalent organic framework for photocatalytic carbon dioxide reduction, Chem. Sci. 11 (2020) 543-550.

[153]

K. Guo, X. Zhu, L. Peng, Y. Fu, R. Ma, X. Lu, Boosting photocatalytic CO2 reduction over a covalent organic framework decorated with ruthenium nanoparticles, Chem. Eng. J. 405 (2021) 127011.

[154]

X. Chen, Q. Dang, R. Sa, L. Li, L. Li, J. Bi, Integrating single Ni sites into biomimetic networks of covalent organic frameworks for selective photoreduction of CO2, Chem. Sci. 11 (2020) 6915-6922.

[155]

Y.N. Gong, W. Zhong, Y. Li, Y. Qiu, L. Zheng, J. Jiang, Regulating photocatalysis by spin-state manipulation of cobalt in covalent organic frameworks, J. Am. Chem. Soc. 7 (2020) 142.

[156]

E.L. Spitler, B.T. Koo, J.L. Novotney, J.W. Colson, F.J. Uribe-Romo, G.D. Gutierrez,A 2D covalent organic framework with 4.7-nm pores and insight into its interlayer stacking, J. Am. Chem. Soc. 133 (2011) 19416-19421.

[157]

M. Wang, H. Guo, R. Xue, Q. Li, H. Liu, N. Wu, Covalent organic frameworks: A new class of porous organic frameworks for supercapacitor electrodes, ChemElectroChem 6 (2019) 2984-2997.

[158]

C.R. DeBlase, K. Hernández-Burgos, K.E. Silberstein, G.G. Rodríguez-Calero, R.P. Bisbey, H.D. Abruña, Rapid and efficient redox processes within 2D covalent organic framework thin films, ACS Nano 9 (2015) 3178-3183.

[159]

M.G. Mohamed, A.F.M. El-Mahdy, M.M.M. Ahmed, S.W. Kuo, Direct synthesis of microporous bicarbazole-based covalent triazine frameworks for high-performance energy storage and carbon dioxide uptake, Chempluschem 84 (2019) 1767-1774.

[160]

A.F.M. El-Mahdy, Y.H. Hung, T.H. Mansoure, H.H. Yu, T. Chen, S.W. Kuo, A Hollow Microtubular triazine- and benzobisoxazole-based covalent organic framework presenting sponge-like shells that functions as a high-performance supercapacitor, Chem. Asian J. 14 (2019) 1429-1435.

[161]

A.F.M. EL-Mahdy, C. Young, J. Kim, J. You, Y. Yamauchi, S.W. Kuo, Hollow microspherical and microtubular [3 + 3] carbazole-based covalent organic frameworks and their gas and energy storage applications, ACS Appl. Mater. Interfaces 11 (2019) 9343-9354.

[162]

A.F.M. EL-Mahdy, M.B. Zakaria, H.X. Wang, T. Chen, Y. Yamauchi, S.W. Kuo, Heteroporous bifluorenylidene-based covalent organic frameworks displaying exceptional dye adsorption behavior and high energy storage, J. Mater. Chem. A 8 (2020) 25148-25155.

[163]

A. Solomon, The emergence of nanotechnology and its applications, Res. J. Nanosci. Eng. 2 (2018) 8-12.

[164]

Y.A. Adeshina, A. Solomon, A.F. Ademola, Contamination levels of organochlorine and organophosphorous pesticide residues in water and sediment from river Owena, Nigeria. Curr. J. Appl. Sci. Technol. 34 (2019) 1-11.

[165]

O.A. Ajala, S.O. Akinnawo, A. Bamisaye, D.T. Adedipe, M.O. Adesina, O.A. Okon-Akan, Adsorptive removal of antibiotic pollutants from wastewater using biomass/biochar-based adsorbents, RSC Adv. 13 (2023) 4678-4712.

[166]

S.O. Akinnawo, P.O. Ayadi, M. Temitope, Chemical coagulation and biological techniques for wastewater treatment, Ovidius University Annals of Chemistry 34 (2023) 14-21.

[167]

S.O. Akinnawo, K.A. Adegoke, T.A. Ajala, R.O. Adegoke, W.N. Maxakato, O.S. Bello, Modified biomass adsorbents for removal of organic pollutants : A review of batch and optimization studies, Int. J. Environ. Sci. Technol. 20 (2023) 11615-11644.

[168]

S.O. Akinnawo, Eutrophication : Causes, consequences, physical, chemical and biological techniques for mitigation strategies, Environmental Challenges 12 (2023) 1-18.

[169]

A. Solomon, K. Rasheed, E. Olanipekun,Spatial distribution and speciation of heavy metals in sediment of river Ilaje, Nigeria. Int. Res. J. Pure Appl. Chem. 10 (2015) 1-10.

[170]

K. Rasheed, A. Solomon, A. Aiyesanmi, Chemical speciation and fractionation study of heavy metals in top sediment deposit of Owena river, Nigeria. Phys. Sci. Int. J. 21 (2019) 1-13.

[171]

A. Peter, O. Ajayi, E. Abata, A. Solomon, M. Oluwalope, Chemical fractionation of heavy metals in the soil of auto-mechanic workshops in Akure, Ondo State, Nigeria. Chem. Sci. Int. J. 21 (2018) 1-16.

[172]

A. Solomon, A. Christiana, E. Olanipekun,Seasonal variation in the physico-chem-ical and microbial characterization of sediment and water samples from selected areas in Ondo coastal region, Nigeria. J. Geogr. Environ. Earth Sci. Int. 5 (2016) 1-12.

[173]

K. Adesina, S.O. Akinnawo, O. Aderemi, T. Adewumi, W.N. Maxakato, O.S. Bello, Progress and challenges in batch and optimization studies on the adsorptive removal of heavy metals using modified biomass-based adsorbents, Bioresour. Technol. Reports. 19 (2022) 1-12.

[174]

X.F. Lu, W.H. Ji, L. Yuan, S. Yu, D.S. Guo, Preparation of carboxy-functionalized covalent organic framework for efficient removal of Hg 2+ and Pb 2+ from water, Ind. Eng. Chem. Res. 58 (2019) 17660-17667.

[175]

T. Xu, L. Zhou, Y. He, S. An, C. Peng, J. Hu, Covalent organic framework with triazine and hydroxyl bifunctional groups for efficient removal of lead(II) ions, Ind. Eng. Chem. Res. 58 (2019) 19642-19648.

[176]

Y. Cao, X. Hu, C. Zhu, S. Zhou, R. Li, H. Shi, Sulfhydryl functionalized covalent organic framework as an efficient adsorbent for selective Pb (II) removal, Colloids Surfaces A Physicochem Eng. Asp. 600 (2020) 125004.

[177]

W. Xu, X. Sun, M. Huang, X. Pan, X. Huang, H. Zhuang, Novel covalent organic framework/PVDF ultrafiltration membranes with antifouling and lead removal performance, J. Environ. Manage. 269 (2020) 110758.

[178]

G. Li, J. Ye, Q. Fang, F. Liu, Amide-based covalent organic frameworks materials for efficient and recyclable removal of heavy metal lead (II), Chem. Eng. J. 370 (2019) 822-830.

[179]

K. Leus, K. Folens, N.R. Nicomel, J.P.H. Perez, M. Filippousi, M. Meledina, Removal of arsenic and mercury species from water by covalent triazine framework encapsulated 𝛾-Fe2O3 nanoparticles, J. Hazard Mater. 353 (2018) 312-319.

[180]

B. Sun, J. Liu, A. Cao, W. Song, D. Wang, Interfacial synthesis of ordered and stable covalent organic frameworks on amino-functionalized carbon nanotubes with enhanced electrochemical performance, Chem. Commun. 53 (2017) 6303-6306.

[181]

S. Mondal, S. Chatterjee, S. Mondal, A. Bhaumik, Thioether-functionalized covalent triazine nanospheres: A robust adsorbent for mercury removal, ACS Sustain. Chem. Eng. 7 (2019) 7353-7361.

[182]

M. Afshari, M. Dinari, K. Zargoosh, H. Moradi, Novel triazine-based covalent organic framework as a superadsorbent for the removal of mercury(II) from aqueous solutions, Ind. Eng. Chem. Res. 59 (2020) 9116-9126.

[183]

Z. Ma, F. Liu, N. Liu, W. Liu, M. Tong, Facile synthesis of sulfhydryl modified covalent organic frameworks for high efficient Hg(II) removal from water, J. Hazard Mater. 405 (2021) 124190.

[184]

M. Dinari, M. Hatami, Novel N-riched crystalline covalent organic framework as a highly porous adsorbent for effective cadmium removal, J. Environ. Chem. Eng. 7 (2019) 102907.

[185]

C.H. Yang, J.S. Chang, D.J. Lee, Covalent organic framework EB-COF:Br as adsorbent for phosphorus (V) or arsenic (V) removal from nearly neutral waters, Chemosphere 253 (2020) 126736.

[186]

X. Liu, H. Xu, L. Wang, Z. Qu, N. Yan, Surface nano-traps of FeO/COFs for arsenic(III) depth removal from wastewater in non-ferrous smelting industry, Chem. Eng. J. 381 (2020) 122559.

[187]

S. Jansone-Popova, A. Moinel, J.A. Schott, S.M. Mahurin, I. Popovs, G.M. Veith, Guanidinium-based ionic covalent organic framework for rapid and selective removal of toxic Cr(VI) oxoanions from water, Environ. Sci. Technol. 53 (2019) 878-883.

[188]

F.Z. Cui, R.R. Liang, Q.Y. Qi, G.F. Jiang, X. Zhao, Efficient removal of Cr(VI) from aqueous solutions by a dual-pore covalent organic framework, Adv. Sustain. Syst. 3 (2019) 1800150.

[189]

X. Zhong, Z. Lu, W. Liang, B. Hu, The magnetic covalent organic framework as a platform for high-performance extraction of Cr(VI) and bisphenol a from aqueous solution, J. Hazard Mater. 393 (2020) 122353.

[190]

Y. Lin, X. Jiang, S.T. Kim, S.B. Alahakoon, X. Hou, Z. Zhang, An elastic hydrogen-bonded cross-linked organic framework for effective iodine capture in water, J. Am. Chem. Soc. 139 (2017) 7172-7175.

[191]

P. Wang, Q. Xu, Z. Li, W. Jiang, Q. Jiang, D. Jiang, Exceptional iodine capture in 2D covalent organic frameworks, Adv. Mater. 30 (2018) 1801991.

[192]

Y. Li, Y. Li, Q. Zhao, L. Li, R. Chen, C. He, Cotton fiber functionalized with 2D covalent organic frameworks for iodine capture, Cellulose 27 (2020) 1-13.

[193]

R. Chen, T. Hu, Y. Li, Stable nitrogen-containing covalent organic framework as porous adsorbent for effective iodine capture from water, React Funct. Polym. 159 (2020) 104806.

[194]

L. Suo, J. Li, Y. Meng, H. Li, Graph-based fair resource allocation scheme combining interference alignment in femtocell networks, IET Commun. 9 (2015) 211-218.

[195]

C. Bai, M. Zhang, B. Li, X. Zhao, S. Zhang, L. Wang, Modifiable diyne-based covalent organic framework: A versatile platform for in situ multipurpose functionalization, RSC Adv. 6 (2016) 39150-39158.

[196]

B. Li, Q. Sun, Y. Zhang, C.W. Abney, B. Aguila, W. Lin, S. Ma, Functionalized porous aromatic framework for efficient uranium adsorption from aqueous solutions, ACS Appl. Mater. Interfaces. 9 (2017) 12511-12517.

[197]

Z.D. Li, H.Q. Zhang, X.H. Xiong, F. Luo, U(VI) adsorption onto covalent organic frameworks-TpPa-1, J. Solid State Chem. 277 (2019) 484-492.

[198]

Y. Liang, L. Feng, X. Liu, Y. Zhao, Q. Chen, Z. Sui, Enhanced selective adsorption of NSAIDs by covalent organic frameworks via functional group tuning, Chem. Eng. J. 404 (2021) 127095.

[199]

A. Mellah, S.P.S. Fernandes, R. Rodríguez, J. Otero, J. Paz, J. Cruces, Adsorption of pharmaceutical pollutants from water using covalent organic frameworks, Chem - A Eur. J. 24 (2018) 10601-10605.

[200]

S. Zhuang, R. Chen, Y. Liu, J. Wang, Magnetic COFs for the adsorptive removal of diclofenac and sulfamethazine from aqueous solution: Adsorption kinetics, isotherms study and DFT calculation, J. Hazard Mater. 385 (2020) 121596.

[201]

A. Peter, A. Solomon, Isolation and anti-bacterial activity of the active components from the stem-back of enantial chlorantha, European J. Med. Plants. 22 (2018) 1-7.

[202]

Y. Tang, H. Huang, W. Xue, Y. Chang, Y. Li, X. Guo, Rigidifying induced fluorescence enhancement in 2D porous covalent triazine framework nanosheets for the simultaneously luminous detection and adsorption removal of antibiotics, Chem. Eng. J. 384 (2020) 123382.

[203]

A. Solomon, Determination of organochlorine pesticide residues in water and sediment samples from selected areas of river Ilaje, Nigeria. Chem. Sci. Int. J. 11 (2015) 1-6.

[204]

A. Solomon, Concentration of organophosphorous pesticide residues in water and sediment samples from river Ilaje, Nigeria. Chem. Sci. Int. J. 11 (2015) 1-9.

[205]

V. Romero, S.P.S. Fernandes, P. Kovář, M. Pšenička, Y.V. Kolen’ko, L.M. Salonen, Efficient adsorption of endocrine-disrupting pesticides from water with a reusable magnetic covalent organic framework, Microporous Mesoporous Mater. 307 (2020) 110523.

[206]

W. Wang, S. Deng, L. Ren, D. Li, W. Wang, M. Vakili, Stable covalent organic frameworks as efficient adsorbents for high and selective removal of an aryl-organophosphorus flame retardant from water, ACS Appl. Mater. Interfaces. 10 (2018) 30265-30272.

[207]

X. Zhu, S. An, Y. Liu, J. Hu, H. Liu, C. Tian, Efficient removal of organic dye pollutants using covalent organic frameworks, AIChE J. 63 (2017) 3470-3478.

[208]

Y. Li, C.X. Yang, X.P. Yan, Controllable preparation of core-shell magnetic covalent-organic framework nanospheres for efficient adsorption and removal of bisphenols in aqueous solution, Chem. Commun. 53 (2017) 2511-2514.

[209]

C.H. Yang, C.C. Cheng, D.J. Lee, Excess adsorption of phosphoric acid from extremely acidic solutions by covalent organic framework EB-COF:Br, Chemosphere 257 (2020) 127244.

[210]

H. Wang, H. Wang, H. Jiang, A. Sheng, Z. Wei, Y. Li, Positively charged polysulfonamide nanocomposite membranes incorporating hydrophilic triazine-structured COFs for highly efficient nanofiltration, ACS Appl. Nano Mater. 3 (2020) 9329-9339.

[211]

N.A. Khan, J. Yuan, H. Wu, T. Huang, X. You, A.U. Rahman, Covalent organic framework nanosheets as reactive fillers to fabricate free-standing polyamide membranes for efficient desalination, ACS Appl. Mater. Interfaces. 12 (2020) 27777-27785.

[212]

X. Tan, Y. Fan, S. Wang, Y. Wu, W. Shi, T. Huang,Ultrasensitive and highly selective electrochemical sensing of sodium picrate by Dihydroxylatopillar[6]arene-modified gold nanoparticles and cationic Pillar[6]arene functionalized covalent organic framework, Electrochim Acta 335 (2020) 135706.

[213]

C. Zhang, M. Cui, J. Ren, Y. Xing, N. Li, H. Zhao, Facile synthesis of novel spherical covalent organic frameworks integrated with Pt nanoparticles and multiwalled carbon nanotubes as electrochemical probe for tanshinol drug detection, Chem. Eng. J. 401 (2020) 126025.

[214]

B. Ma, H. Guo, M. Wang, Q. Wang, W. Yang, Y. Wang, Electrocatalysis and simultaneous determination of hydroquinone and acetaminophen using PNCOF/graphene oxide modified electrode, Microchem J 155 (2020) 104776.

[215]

Y. Sun, G.I.N. Waterhouse, L. Xu, X. Qiao, Z. Xu, Three-dimensional electrochemical sensor with covalent organic framework decorated carbon nanotubes signal amplification for the detection of furazolidone, Sensors Actuators B Chem. 321 (2020) 128501.

[216]

X. Tan, Z. Zhang, T. Cao, W. Zeng, T. Huang, G. Zhao, Control assembly of Pillar[6]arene-modified Ag nanoparticles on covalent organic framework surface for enhanced sensing performance toward paraquat, ACS Sustain. Chem. Eng. 7 (2019) 20051-20059.

[217]

Y. Xie, T. Zhang, Y. Chen, Y. Wang, L. Wang, Fabrication of core-shell magnetic covalent organic frameworks composites and their application for highly sensitive detection of luteolin, Talanta 213 (2020) 120843.

[218]

J. Li, C. Zhang, M. Yin, Z. Zhang, Y. Chen, Q. Deng, Surfactant-sensitized covalent organic frameworks-functionalized lanthanide-doped nanocrystals: An ultrasensitive sensing platform for perfluorooctane sulfonate, ACS Omega 4 (2019) 15947-15955.

[219]

L. Guo, Y. Song, K. Cai, L. Wang, On-off” ratiometric fluorescent detection of Hg 2+ based on N-doped carbon dots-rhodamine B@TAPT-DHTA-COF, Spectrochim Acta Part A Mol. Biomol. Spectrosc. 227 (2020) 117703.

[220]

H. Liu, Y. Zhang, D. Zhang, F. Zheng, M. Huang, J. Sun, A fluorescent nanoprobe for 4-ethylguaiacol based on the use of a molecularly imprinted polymer doped with a covalent organic framework grafted onto carbon nanodots, Microchim Acta 186 (2019) 182.

[221]

M. Wang, M. Gao, L. Deng, X. Kang, K. Zhang, Q. Fu,A sensitive and selective fluorescent sensor for 2,4,6-trinitrophenol detection based on the composite material of magnetic covalent organic frameworks, molecularly imprinted polymers and carbon dots, Microchem. J. 154 (2020) 104590.

[222]

P. Sun, J. Hai, S. Sun, S. Lu, S. Liu, H. Liu, Aqueous stable Pd nanoparticles/covalent organic framework nanocomposite: An efficient nanoenzyme for colorimetric detection and multicolor imaging of cancer cells, Nanoscale 12 (2020) 825-831.

[223]

W.R. Cui, C.R. Zhang, W. Jiang, R.P. Liang, S.H. Wen, D. Peng, Covalent organic framework nanosheet-based ultrasensitive and selective colorimetric sensor for trace Hg2+ detection, ACS Sustain. Chem. Eng. 7 (2019) 9408-9415.

[224]

W. Li, Y. Li, H.L. Qian, X. Zhao, C.X. Yang, X.P. Yan, Fabrication of a covalent organic framework and its gold nanoparticle hybrids as stable mimetic peroxidase for sensitive and selective colorimetric detection of mercury in water samples, Talanta 204 (2019) 224-228.

[225]

M. Dogru, T. Bein, On the road towards electroactive covalent organic frameworks, Chem. Commun. 50 (2014) 5531-5546.

[226]

S. Wan, J. Guo, J. Kim, H. Ihee, D. Jiang, A belt-shaped, blue luminescent, and semiconducting covalent organic framework, Angew Chem. Int. Ed. Engl. 47 (2008) 8826-8830.

[227]

S. Wan, J. Guo, J. Kim, H. Ihee, D. Jiang, A photoconductive covalent organic framework: Self-condensed arene cubes composed of eclipsed 2D polypyrene sheets for photocurrent generation, Angew Chem. Int. Ed. Engl. 48 (2009) 5439-5442.

[228]

X. Feng, L. Chen, Y. Honsho, O. Saengsawang, L. Liu, L. Wang, An ambipolar conducting covalent organic framework with self-sorted and periodic electron donor-acceptor ordering, Adv. Mater. 24 (2012) 3026-3031.

[229]

X. Feng, L. Liu, Y. Honsho, A. Saeki, S. Seki, S. Irle, High-rate charge-carrier transport in porphyrin covalent organic frameworks: Switching from hole to electron to ambipolar conduction, Angew Chem. Int. Ed. Engl. 51 (2012) 2618-2622.

[230]

X. Ding, J. Guo, X. Feng, Y. Honsho, J. Guo, S. Seki, Synthesis of metallophthalocyanine covalent organic frameworks that exhibit high carrier mobility and photoconductivity, Angew Chem. Int. Ed. Engl. 50 (2011) 1289-1293.

[231]

X. Ding, X. Feng, A. Saeki, S. Seki, A. Nagai, D. Jiang, Conducting metallophthalocyanine 2D covalent organic frameworks: The role of central metals in controlling π -electronic functions, Chem. Commun. 48 (2012) 8952-8954.

[232]

J.W. Colson, A.R. Woll, A. Mukherjee, M.P. Levendorf, E.L. Spitler, V.B. Shields, Oriented 2D covalent organic framework thin films on single-layer graphene, Science 332 (2011) 228-231.

[233]

H. Wang, Z. Zeng, P. Xu, L. Li, G. Zeng, R. Xiao, Recent progress in covalent organic framework thin films: Fabrications, applications and perspectives, Chem. Soc. Rev. 48 (2019) 488-516.

[234]

D. Cui, D.F. Perepichka, J.M. MacLeod, F. Rosei, Surface-confined single-layer covalent organic frameworks: Design, synthesis and application, Chem. Soc. Rev. 49 (2020) 2020-2038.

[235]

S.L. Cai, Y.B. Zhang, A.B. Pun, B. He, J. Yang, F.M. Toma, Tunable electrical conductivity in oriented thin films of tetrathiafulvalene-based covalent organic framework, Chem. Sci 5 (2014) 4693-4700.

[236]

D.D. Medina, M.L. Petrus, A.N. Jumabekov, J.T. Margraf, S. Weinberger, J.M. Rotter, Directional charge-carrier transport in oriented benzodithiophene covalent organic framework thin films, ACS Nano 11 (2017) 2706-2713.

[237]

M.G. Mohamed, C.C. Lee, A.F.M. EL-Mahdy, J. Lüder, M.H. Yu, Z. Li, Exploitation of two-dimensional conjugated covalent organic frameworks based on tetraphenylethylene with bicarbazole and pyrene units and applications in perovskite solar cells, J. Mater. Chem. A 8 (2020) 11448-11459.

[238]

J.M. Cox, B. Mileson, A. Sadagopan, S.A. Lopez, Molecular recognition and band alignment in 3D covalent organic frameworks for cocrystalline organic photovoltaics, J. Phys. Chem. C 124 (2020) 9126-9133.

[239]

C. Wu, Y. Liu, H. Liu, C. Duan, Q. Pan, J. Zhu, Highly conjugated three-dimensional covalent organic frameworks based on spirobifluorene for perovskite solar cell enhancement, J. Am. Chem. Soc. 140 (2018) 10016-10024.

[240]

S. Park, M.S. Kim, W. Jang, J.K. Park, D.H. Wang, Covalent organic nanosheets for effective charge transport layers in planar-type perovskite solar cells, Nanoscale 10 (2018) 4708-4717.

[241]

K. Sinha Roy, D.R. Goud, A. Mazumder, B. Chandra, A.K. Purohit, M. Palit, Triazine-based covalent organic framework: A promising sorbent for efficient elimination of the hydrocarbon backgrounds of organic sample for GC-MS and 1H NMR analysis of chemical weapons convention related compounds, ACS Appl. Mater. Interfaces. 11 (2019) 16027-16039.

[242]

J. He, F. Xu, Z. Chen, X. Hou, Q. Liu, Z. Long, AuNPs/COFs as a new type of SERS substrate for sensitive recognition of polyaromatic hydrocarbons, Chem. Commun. 53 (2017) 11044-11047, doi: 10.1039/C7CC06440C.

[243]

Y. Su, D. Wu, J. Chen, G. Chen, N. Hu, H. Wang, Ratiometric surface enhanced raman scattering immunosorbent assay of allergenic proteins via covalent organic framework composite material based nanozyme tag triggered Raman signal “turn-on ” and amplification, Anal. Chem. 91 (2019) 11687-11695.

[244]

D. Yao, C. Li, H. Wang, G. Wen, A. Liang, Z. Jiang, A new dual-mode SERS and RRS aptasensor for detecting trace organic molecules based on gold nanocluster-doped covalent-organic framework catalyst, Sensors Actuators B Chem. 319 (2020) 128308.

[245]

W. Cao, W.D. Wang, H.S. Xu, I.V. Sergeyev, J. Struppe, X. Wang, F. Mentink-Vigier, Z. Gan, M.X. Xiao, L.Y. Wang, G.P. Chen, S.Y. Ding, S. Bai, W. Wang, Exploring applications of covalent organic frameworks: Homogeneous reticulation of radicals for dynamic nuclear polarization, J. Am. Chem. Soc. 140 (2018) 6969-6977.

[246]

N. Singh, J. Kim, J. Kim, K. Lee, Z. Zunbul, I. Lee, Covalent organic framework nanomedicines: Biocompatibility for advanced nanocarriers and cancer theranostics applications, Bioact. Mater. 21 (2023) 358-380.

[247]

J.Y. Zeng, X.S. Wang, B.R. Xie, M.J. Li, X.Z. Zhang, Covalent organic framework for improving near-infrared light induced fluorescence imaging through two-photon induction, Angew Chem. Int. Ed. Engl. 59 (2020) 10087-10094.

[248]

G.S. He, L.S. Tan, Q. Zheng, P.N. Prasad, Multiphoton absorbing materials: Molecular designs, characterizations, and applications, Chem. Rev. 108 (2008) 1245-1330.

[249]

J. Wang, L. Zhao, B. Yan, Indicator displacement assay inside dye-functionalized covalent organic frameworks for ultrasensitive monitoring of sialic acid, an ovarian cancer biomarker, ACS Appl. Mater. Interfaces. 12 (2020) 12990-12997.

[250]

D. Liang, X. Zhang, Y. Wang, T. Huo, M. Qian, Y. Xie, Magnetic covalent organic framework nanospheres-based miRNA biosensor for sensitive glioma detection, Bioact. Mater. 14 (2022) 145-151.

[251]

L. Bai, S.Z.F. Phua, W.Q. Lim, A. Jana, Z. Luo, H.P. Tham, Nanoscale covalent organic frameworks as smart carriers for drug delivery, Chem. Commun. 52 (2016) 4128-4131.

[252]

A. Rengaraj, P. Puthiaraj, Y. Haldorai, N.S. Heo, S.K. Hwang, Y.K. Han, Porous covalent triazine polymer as a potential nanocargo for cancer therapy and imaging, ACS Appl. Mater. Interfaces. 8 (2016) 8947-8955.

[253]

S. Liu, C. Hu, Y. Liu, X. Zhao, M. Pang, J. Lin, One-pot synthesis of DOX@covalent organic framework with enhanced chemotherapeutic efficacy, Chemistry 25 (2019) 4315-4319.

PDF (8021KB)

98

Accesses

0

Citation

Detail

Sections
Recommended

/