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化学进展 2023, Vol. 35 Issue (3): 475-495 DOI: 10.7536/PC220810 前一篇   后一篇

• 综述 •

共价有机框架稳定性提高及其在放射性核素分离中的应用

张慧迪1,2, 李子杰1,*(), 石伟群1,*()   

  1. 1.中国科学院高能物理研究所 核能放射化学实验室 北京 100049
    2.广西大学资源环境与材料学院 省部共建特色金属材料与组合结构全寿命安全国家重点实验室 南宁 530004
  • 收稿日期:2022-08-15 修回日期:2022-10-03 出版日期:2023-03-24 发布日期:2023-02-16
  • 作者简介:

    李子杰 中国科学院高能物理研究所副研究员,主要从事新型纳米材料在放射性核素分离、富集中应用研究。

    石伟群 中国科学院高能物理研究所研究员, 国家杰出青年科学基金获得者,长期致力于核燃料循环化学与锕系元素化学相关基础研究,在JACS、Angew. Chem、Chem、CCS Chem.、Nat. Commun、Adv. Mater.、Environ. Sci. Technol. 等国际知名期刊发表SCI论文200余篇,成果被国内外同行广泛关注和引用。

  • 基金资助:
    国家杰出青年科学基金项目(21925603); 国家自然科学基金项目(11975016)
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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:2022-08-15 Revised:2022-10-03 Online:2023-03-24 Published:2023-02-16
  • 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)

共价有机框架(Covalent Organic Frameworks, COFs)是一类通过可逆反应制备的具有长程有序结构的晶态有机多孔聚合物,因其良好的耐辐照性、结构可设计性及可功能化特点有望在放射性核素高效吸附及作用机理探讨中发挥作用。但连接键可逆性降低了COFs的化学稳定性,本文系统地综述了COFs化学稳定性提高(包括连接键可逆性的降低、合成后可逆连接键向不可逆转化及连接键周围疏水环境构建)、晶型调控(包括合成条件、二维COFs层内共平面及层间堆叠作用力的影响及无定形聚合物结晶化)、功能化方法和其在放射性核素分离富集方面中的应用。通过增强COFs骨架的强度,引入特殊的功能化官能团或改变单体大小通过尺寸匹配效应来增强放射性核素离子与COFs的相互作用,并就COFs在该领域应用前景和研究方向进行了展望。

关键词： 共价有机框架, 化学稳定性, 晶型调控, 功能化, 放射性核素

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
()
图式1 应用于COFs合成的可逆反应
Scheme 1 Reversible reactions used in COFs synthesis
图式2 若干COFs连接键稳定化处理方法
Scheme 2 Several stabilization strategies towards COFs linkage
图1 基于单体交换的“COF-to-COF”转化[54]
Fig. 1 “COF to COF” transformation via monomer exchange[54]. Copyright 2017, American Chemical Science
图2 超共轭和诱导效应增强TPB-DMeTP-COF层间相互作用[60]
Fig.2 The enhanced interlayer interaction of TPB-DMeTP-COF by hyperconjugation and induced effects[60]. Copyright 2020, Springer Nature
图3 烷基修饰的CCOF-3/4合成和结构[62]
Fig. 3 Synthesis and structure of alkyl modified CCOF-3/4[62]. Copyright 2017, American Chemical Science
图式3 可逆的分子结构重排来提高结晶性[67]
Scheme 3 Reversible molecular structure rearrangement for the improvement of crystallinity[67]
图4 反应溶剂对COF拓扑结构的影响[70]
Fig. 4 Effect of reaction solvent on the topological structure of COF[70]. Copyright 2010, Chinese Chemical Society
图5 层内氢键增强共平面效应[73]
Fig. 5 The coplanarity of COF layers enhanced by intralayer hydrogen bond[73]
图6 TPE-COF-OH和TPE-COF-OMe结构及合成路线[76]
Fig. 6 Structure and synthesis route of TPE-COF-OH and TPE-COF-OMe[76]. Copyright 2020, American Chemical Science
图7 PDC-MA-COF层间氢键增强层层堆叠作用力[79]
Fig. 7 Interlayer hydrogen bond enhances the stacking force of PDC-MA-COF layers[79]. Copyright 2019, American Chemical Science
图8 COF-IHEP1和COF-IHEP2结构及合成路线[16]
Fig. 8 Structure and synthesis route of COF-IHEP1 and COF-IHEP2[16]. Copyright 2019, Chinese Chemical Society
图9 (a) COF-IHEP1 在不同酸性条件下对U(Ⅵ)的吸附;(b) COF-IHEP1/2 在不同酸性条件下对Pu(Ⅳ)的吸附[16]
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
表1 COFs在放射性核素分离富集中的应用及其作用机理
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
图10 四种不同孔径COFs结构及其对I2蒸气的吸附[108]
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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