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Progress in Chemistry 2023, Vol. 35 Issue (3): 475-495 DOI: 10.7536/PC220810 Previous Articles   Next Articles

• Review •

The Stability Enhancement of Covalent Organic Frameworks and Their Applications in Radionuclide Separation

Zhang Huidi1,2, Li Zijie1(), Shi Weiqun1()   

  1. 1. Laboratory of Nuclear Energy Chemistry, Institute of High Energy Physics, Chinese Academy of Sciences,Beijing 100049,China
    2. State Key Laboratory of Featured Metal Materials and Life-cycle Safety for Composite Structures, School of Resources, Environment and Materials, Guangxi University,Nanning 530004, China
  • Received: Revised: Online: Published:
  • Contact: *e-mail: lizijie@ihep.ac.cn(Zijie Li);shiwq@ihep.ac.cn(Weiqun Shi)
  • Supported by:
    National Science Fund for Distinguished Young Scholars(21925603); National Science Foundation of China(11975016)
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Covalent organic frameworks (COFs) are a class of crystalline organic porous polymers with long-range ordered structures prepared by reversible reactions. Due to high radiation resistance, structural designability and functionalization, COFs are expected to play a role in the efficient adsorption of radionuclides and the exploration of interaction mechanism. However, the reversibility of typical linkage bonds causes the limited chemical stability of COFs. This paper reviews the improvement strategies towards chemical stability of COFs (including the decrease of reversibility of linkage bonds, the post synthetic transformation from reversible bonds to irreversible ones, and the construction of hydrophobic environment around linkage bonds), crystalline control (including the influence of synthesis conditions, in layer coplanar and interlayer interaction for two-dimensional COFs and the crystallization of amorphous polymers), functionalization methods and the applications of COFs in the separation and enrichment of radionuclides. The interaction between radionuclides and COFs could be optimized by enhancing the strength of COFs skeleton, introducing special functional groups or changing the size of monomers. The application prospect and research focus of COFs in radionuclide separation are prospected.

Contents

1 Introduction

2 Typical reversible reactions of COFs

2.1 B—O bond formation

2.2 C=N bond formation

2.3 C—N bond formation

2.4 C—O bond formation

2.5 C=C bond formation

2.6 Others

3 Improvement of COFs linkage stability

3.1 COFs linkage cyclization reaction

3.2 Oxidation or reduction of imine linkage

3.3 COF to COF transformation via monomer exchange

3.4 Others

4 Regulation of crystallinity

4.1 Effect of synthesis conditions on crystallinity

4.2 Intralayer coplanarity of 2D COFs

4.3 Interlayer stacking force of 2D COFs

4.4 Crystallization of amorphous polymer

5 Functionalized syntheses of COFs

6 Applications of COFs in separation and enrichment of radionuclides

6.1 UO 2 2 +

6.2 I2 vapor

6.3 TcO 4 -/ ReO 4 -

7 Conclusion and outlook

Key words: covalent organic framework, chemical stability, crystallinity control, functionalization, radionuclide
Scheme 1 Reversible reactions used in COFs synthesis
Scheme 2 Several stabilization strategies towards COFs linkage
Fig. 1 “COF to COF” transformation via monomer exchange[54]. Copyright 2017, American Chemical Science
Fig.2 The enhanced interlayer interaction of TPB-DMeTP-COF by hyperconjugation and induced effects[60]. Copyright 2020, Springer Nature
Fig. 3 Synthesis and structure of alkyl modified CCOF-3/4[62]. Copyright 2017, American Chemical Science
Scheme 3 Reversible molecular structure rearrangement for the improvement of crystallinity[67]
Fig. 4 Effect of reaction solvent on the topological structure of COF[70]. Copyright 2010, Chinese Chemical Society
Fig. 5 The coplanarity of COF layers enhanced by intralayer hydrogen bond[73]
Fig. 6 Structure and synthesis route of TPE-COF-OH and TPE-COF-OMe[76]. Copyright 2020, American Chemical Science
Fig. 7 Interlayer hydrogen bond enhances the stacking force of PDC-MA-COF layers[79]. Copyright 2019, American Chemical Science
Fig. 8 Structure and synthesis route of COF-IHEP1 and COF-IHEP2[16]. Copyright 2019, Chinese Chemical Society
Fig. 9 (a) Adsorption of U(Ⅵ) by COF-IHEP1 under different acidic conditions. (b) Adsorption of Pu(Ⅳ) by COF-IHEP1/2 under different acidic conditions[16]. Copyright 2019, Chinese Chemical Society
Table 1 The application of COFs in the separation and enrichment of various radionuclides and involved adsorption mechanism
COFs Linkages Metal ions Functional group/Sorption
mechanism		 Absorption capacity (mg/g) /Conditions Recyclability ref
COF-HBI Amide U(VI) HBI 211 (pH 4.5) / 95
TpPa-1 β-ketoenamine U(VI) Chemical adsorption 152 (pH 6.0) 4 96
[NH4]+[COF- SO 3 -] β-ketoenamine U(VI) Ion-exchange/Coordination 851 (pH 5.0) / 97
COF-TpDb-AO β-ketoenamine U(VI) AO 394 (pH 6.0) / 98
IHEP1/11 Hydrazone U(VI) Phosphonate 160/147 (pH 1.0) 4 16,88
IHEP2/10/ COF-JLU4 Hydrazone U(VI) Phosphonate 140/127/102 (pH 1.0) / 16,88
TFPT-BTAN-AO C=C bond U(VI) AO 427 (pH 4.0) 6 99
MPCOF P—N bond U(VI) Physical adsorption 123 (pH 1.5) / 38
ACOF β-ketoenamine U(VI)
U(VI)		 Hydroquinone/Redox reaction
Size-matching effect		 169 (pH 4.5)
40 (pH 1.5)		 / 102
Redox-COF1 Hydrazone U(VI) Hydroquinone/Redox reaction 60 (pH 2) / 104
NDA-TN-AO C=C bond U(VI) AO/Photocatalytic reduction 589 (pH=5) 6 105
SIOC-COF-7 Imine I2 Physical adsorption (hollow microspheres) 4810 (75 ℃) 5 107
Meso-COF-3 Imine I2 Pores/Channels 4000 (75 ℃) / 108
BTT-TAPT-COF Imine I2 Electron donor atoms (N/S)/Chemical adsorption 2760 (78 ℃) 5 109
TJNU-201/202 Imine I2 Chemical/Physical adsorption 5625/4820 (150 ℃) / 110
SCU-COF-1 β-ketoenamine ReO 4 - Viologen-N+Cl-/Anion-exchange 367.6 (27 ℃) / 111
[C2vimBr]136%-
TbDa-COF		 Imine ReO 4 - C2vimBr-N+Br-/Anion-exchange 952 / 93
Fig. 10 Structures of COFs with four different pore sizes and their adsorption for I2 vapor[108]. Copyright 2019, American Chemical Science
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