共轭微孔聚合物膜的制备策略及其分离应用

doi:10.6023/A21110505

摘要/Abstract

降低工业分离过程的能耗为缓解全球能源紧缺问题提供了有效途径. 相比传统工业分离技术, 膜分离技术能耗低、经济效益高, 开发高效的膜材料是提升膜分离性能的重要手段. 共轭微孔聚合物(CMP)膜具有刚性永久超微孔道、高孔隙率、孔结构及化学环境可调控、交联骨架稳定性好等优势, 在分离领域具有良好的应用前景. 概述了近年来CMP膜的制备方法并简要对比了其优缺点, 阐述了CMP膜在气体分离、有机溶剂纳滤、离子筛分和手性分离等领域的分离机理和研究进展, 为开发新型具有良好分离性能的CMP膜材料提供研究思路.

关键词: 多孔材料, 共轭微孔聚合物膜, 薄膜制备, 分离机理, 分子筛分

Saving the energy consumption of the industrial separation process provides an effective way to alleviate the global energy shortage issue. Compared with traditional separation technology, membrane separation possesses low energy consumption and high economic benefits. The exploration of high-efficiency membrane materials is the key strategy to elevate membrane separation performance. Conjugated microporous polymer (CMP) membranes exhibit merits such as rigid and permanent micropores, high porosity, adjustable pore structure and pore environment, and good structural stability, which play vibrant role in molecular separation. In this review, we summarized the fabrication methods of CMP membranes with their advantages and challenges; introduced the research progress and mechanism in molecular separation field, including gas separation, organic solvent nanofiltration, ion sieving and chiral separation, over the recent years, which may provide ideas for designing new CMP membranes with high performance for crucial separation processes.

Key words: porous materials, conjugated microporous polymer membranes, membrane fabrication, separation mechanism, molecular sieving

引用此文

张蒙茜, 冯霄. 共轭微孔聚合物膜的制备策略及其分离应用[J]. 化学学报, 2022, 80(2): 168-179.

Mengxi Zhang, Xiao Feng. Fabrication Strategies of Conjugated Microporous Polymer Membranes for Molecular Separation[J]. Acta Chimica Sinica, 2022, 80(2): 168-179.

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图/表 17

图1. CMPs的合成路线示意图[13a]

Figure 1. Reaction schemes for the synthesis of CMPs[13a]

图2. (a)两步法合成SCMP1的路线图及其溶解在四氢呋喃中的照片; (b) SCMP1粉末和通过溶剂挥发法制备的SCMP1膜的照片及相应的SEM图像[31]

Figure 2. (a) Two-step synthesis of a soluble conjugated microporous polymer, SCMP1 and a solution of SCMP1 in THF; (b) photographs and corresponding SEM images of SCMP1 powder and SCMP1 film prepared by solvent evaporation method[31]

图3. (a) CMP的构筑单元及其层层组装合成路线示意图; (b) CMP膜转移过程示意图及膜表面SEM图像[32]

Figure 3. (a) Illustration of monomer structure and layer-by-layer synthesis route; (b) illustration of CMP film transfer process and top-view SEM image[32]

图4. (a) CMP膜的合成示意图. p-CMP的(b)照片、(c) SEM图像、(d) AFM图像及(e)相应厚度[33a]

Figure 4. (a) The illustration of synthesis route of CMP membranes. The (b) photograph, (c) SEM images, (d) AFM image and (e) corresponding height profile of a p-CMP membrane[33a]

图5. CMP-1~CMP-4及Imine-CMP纳米膜的合成[34a]

Figure 5. Syntheses of CMP-1~CMP-4 and Imine-CMP-nanofilms[34a]

Polymer network	Nanofilm
Polymer network	S_BET^a/(m²•g^–1)	Pore diameter^b/nm
CMP-1	750	0.52
CMP-2	759	0.58
CMP-3	1038	1.80
CMP-4	680	1.40
Imine-CMP	22	1.30

表1. 所得CMP膜材料的比表面积及孔径[34a]

Table 1. The surface area and pore size of obtained CMP films[34a]

图6. (a) CMP@PSU膜界面聚合示意图; (b)所选单体的化学结构[34b]

Figure 6. (a) Illustration of interfacial polymerization of CMP@PSU film. (b) The chemical structures of monomers[34b]

图7. (a) BTT和TTB的结构, 蓝色箭头表示在反应中形成C—C键的位置; (b)三电极电化学反应体系示意图, CMP膜沉积在ITO表面; (c) BTT-CMP和TTB-CMP膜的孔结构和膜照片[35b]

Figure 7. (a) The structures of BTT and TTB, the blue arrow indicates the position of the C—C bond formed in the reaction; (b) the schematic diagram of the three-electrode electrochemical reaction system, with the CMP film deposited on the ITO surface; (c) structure and film photos of BTT-CMP and TTB-CMP films[35b]

图8. TTB-CMP膜的(a)褶皱和(b)放大的表面和横截面SEM图像, (c) AFM图像和(d)相应的膜厚. (e) TTB-CMP膜转移到PDMS上并受压缩应力时形成褶皱的AFM图像. (f)通过PFQNM测试的TTB-CMP的杨氏模量[39a]

Figure 8. The (a) wrinkles and (b) magnified surface and cross-section SEM, (c) AFM image and (d) corresponding height profile of TTB-CMP. (e) AFM images of the formed wrinkles when TTB-CMP membrane is transferred onto PDMS substrate and subjected to an applied compressive stress. (f) Young’s modulus tested for TTB-CMP by PFQNM method[39a]

图9. 电聚合制备CMPs的单体结构[42]

Figure 9. Monomer structures of CMPs prepared by electropolymerization[42]

成膜方法	优点	不足
旋涂法	成膜方法简单易操作	仅限于可溶性骨架
层层组装法	成膜厚度可控	单体种类少合成过程复杂膜均匀程度不高
表面引发法	成膜厚度可控易进一步官能化	需要特定表面修饰单体种类少
界面聚合	成膜厚度可控反应条件温和膜可自支撑	反应类型较少膜转移时易被破坏
电聚合	成膜厚度可控反应条件温和无需催化剂	难完整从基底剥离多数膜刚性强、易碎
离子化“溶解”法	成膜厚度可控易于官能化	单体种类较少

表2. 现有CMP成膜方法的优点与不足

Table 2. Advantages and shortcomings of CMP film fabrication methods

图10. 77 K条件下(a) SCMP1粉末和(b) SCMP1薄膜的N2及H2等温吸附曲线; (c)在273 K条件下SCMP1薄膜的N2、CH4、Xe和CO2吸附等温线[31]

Figure 10. N2 and H2 adsorption isotherms of (a) SCMP1 powder and (b) SCMP1 film at 77 K; (c) N2, CH4, Xe and CO2 adsorption isotherms of SCMP1 film at 273 K[31]

图11. (a)自支撑共聚膜的照片; (b) CMP膜在298 K和0.1 MPa下的单一气体渗透率和气体动力学直径的关系图; (c) H2/CO2、(d) H2/N2、(e) H2/CH4与现有聚合物膜分离性能的对比, 黑线代表聚合物膜的Robeson上限(2008年)[37a]

Figure 11. (a) Photographs of freestanding copolymeric membranes; (b) single gas permeabilities of the obtained membranes at 298 K and 0.1 MPa as a function of the gas kinetic diameter. Comparisons of the (c) H2/CO2, (d) H2/N2, and (e) H2/CH4 gas separation performance of the co-polymeric membranes to those of the state-of-the-art polymeric membranes, black lines represent the Robeson upper bound (2008) of polymeric membranes[37a]

图12. (a) BILP-101x膜的制备过程示意图; (b)在氧化铝基底上形成的BILP-101x膜的横截面SEM图像(ca. 400 nm厚); (c) H2/CO2分离性能与现有聚合物膜的对比; (d)在423 K干湿混合气下H2/CO2分离的长循环稳定性[37d]

Figure 12. (a) Illustration of the preparation process of BILP-101x membrane; (b) cross-sectional SEM image of BILP-101x membrane formed on alumina substrate (ca. 400 nm); (c) H2/CO2 separation performance compared with reported polymer membranes; (d) long-term stability of H2/CO2 separation under dry and wet mixed gas atmosphere at 423 K[37d]

图13. (a)电聚合制膜过程示意图; (b)膜材料的横截面SEM图像; (c)在0.1 MPa条件下膜材料对极性和非极性有机溶剂的渗透率; (d)在0.1 MPa条件下膜材料的对不同分子量染料的截留率; (e) CNT-EP- PC15膜对CR/甲醇混合溶液过滤的长时间测试; (f) CNT-EP-PC15膜与已报道的纳滤膜的性能对比[39d]

Figure 13. (a) Illustration of the electropolymerization process; (b) the cross-sectional SEM image of the membrane; (c) the organic solvents permeability of CMP membranes at 0.1 MPa; (d) rejection of dyes with different molecular weights at 0.1 MPa; (e) long-term filtration test of the CR/methanol solution on the CNT-EP-PC15 membrane; (f) performance comparison of the CNT-EP-PC15 membrane with some reported nanofiltration membranes[39d]

图14. (a)共电聚合制备的i-CMP膜的示意图; (b) i-CMP膜的3D结构及膜中离子通道图,以实现快速和选择性离子传输; (c) i-CMP膜的离子渗透率与水合离子直径的关系图[38b]

Figure 14. (a) Schematic diagram of i-CMP membrane prepared by co-electropolymerization; (b) 3D structure and ion channels of i-CMP membrane to achieve fast and selective ion transmission; (c) the ion permeation rate of i-CMP membrane as a function of the hydrated diameter[38b]

图15. CCMP及CCMP/SiO2膜的表面引发聚合示意图[45]

Figure 15. Synthesis of CCMP and CCMP/SiO2 membranes by surface- initiated polymerization[45]

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