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化学进展 2021, Vol. 33 Issue (5): 838-854 DOI: 10.7536/PC200622 前一篇   后一篇

• 研究论文 •

共轭微孔聚合物的制备与应用

王玉冰1, 陈杰2, 延卫1,*(), 崔建文3   

  1. 1 西安交通大学环境科学与工程系 西安 710049
    2 福州大学环境与资源学院 福州 350116
    3 新疆知信科技有限公司 乌鲁木齐 830011
  • 收稿日期:2020-06-08 修回日期:2020-08-05 出版日期:2021-05-20 发布日期:2020-12-22
  • 通讯作者: 延卫
  • 作者简介:
    * Corresponding author e-mail:
  • 基金资助:
    国家自然科学基金项目(51978569)
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Preparation and Application of Conjugated Microporous Polymers

Yubing Wang1, Jie Chen2, Wei Yan1,*(), Jianwen Cui3   

  1. 1 Department of Environmental Science and Engineering, Xi'an Jiaotong University,Xi'an 710049, China
    2 College of Environment and Resources, Fuzhou University,Fuzhou 350116, China
    3 Xinjiang Zhixin Technology Co.Ltd, Urumqi 830011, China
  • Received:2020-06-08 Revised:2020-08-05 Online:2021-05-20 Published:2020-12-22
  • Contact: Wei Yan
  • Supported by:
    National Natural Science Foundation of China(51978569)

共轭微孔聚合物(CMPs)是一类有机多孔聚合物,与常规共轭聚合物或多孔材料相比,其最大的特点是既有π共轭骨架又具有大量微孔。这类材料在解决能源和环境问题方面显示出巨大的潜力,已在气体吸附、非均相催化、发光材料、化学传感器、电能存储和生物杂化物等领域显示出巨大的应用前景。目前已开发出多种用于CMPs结构单元设计与合成的新方法,用于制备具有不同结构和特定性质的多种CMPs,有效推动了该领域的快速发展。本综述总结了CMPs的理论模型和结构设计,合成原理、常用合成方法和影响因素分析,以及CMPs在各领域的应用。

关键词： 共轭微孔聚合物, 多功能材料, 合成方法, 气体吸附, 催化

As a unique class within the versatile family of microporous materials, compared with ordinary conjugated polymers or porous materials, conjugated microporous polymers(CMPs) not only have π-conjugated framework but also have many micropores. Since their discovery in 2007, CMPs have been intensively studied as an important subclass of porous materials, and various interesting properties and possible applications have been discovered and described. A wide range of chemical reactions, building blocks and synthetic method offer a tremendous number of CMPs with different properties and specific structures, which drives the rapid growth of the field. CMPs have shown great potential in solving energy and environmental problems, in particular, they have demonstrated huge application prospect in gas adsorption, heterogeneous catalysis, light emittance, sensing, energy storage and biological applications. Since first discovered, CMPs are unparalleled among porous materials because they possess extended π-conjugated backbones along with the chemical and thermal stability. Nowadays, the possibility to produce solvent processable CMPs or to generate thin films on electrodes all makes CMPs an exciting field for further research. In this review, we present the recent significant breakthroughs and the conventional functions and practices in the field of CMPs to find useful applications. We start with an initial historical look at origins of porous materials and a briefly contrast between CMPs and other porous materials. Then, we present an exhaustive analysis of the design strategies with special emphasis on the topologies of amorphous porous organic materials. As following, we discuss the chemical synthesis of CMPs that gives access to a range of potential applications, with a focus on the up-to-date overview of the main fields. Finally, we give an outlook of the challenges and restrictions which CMPs research in the future. We also draw some comparisons between CMPs and the growing range of conjugated crystalline covalent organic frameworks(COFs).

Contents

1 Introduction

2 Design of conjugated microporous polymers

2.1 Topology design

2.2 Structure design of conjugated microporous polymers

3 Synthesis of conjugated microporous polymers

3.1 Synthetic reaction principles

3.2 Synthetic methods

3.3 The influence of various variables on the synthesis products during the reaction

4 Applications of conjugated microporous polymers

4.1 Gas adsorption and storage

4.2 Gas separation

4.3 Adsorption of heavy metal, dyes, solvents and other chemicals

4.4 Heterogeneous catalysis

4.5 Light emitters

4.6 Chemosensors

4.7 Electrical energy storage

4.8 Biocomplex

5 Conclusion and outlook

Key words: conjugated microporous polymers, multifunctional material, synthesis methods, gas adsorption, catalysis
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图1 组分为A2O3的玻璃网络。黑圈为A原子,白圈为O原子[32]
Fig. 1 Glass network bearing composition of A2O3. Black circles represent A atoms, and white circles represent oxygen atoms[32]. Copyright 1932 American Chemical Society.
图2 (a) 具有金刚石拓扑结构的PAF-1模型[15];(b) 非晶硅的CRN模型,黄色为硅原子,红色为氧原子;(c) PAF-1的非晶模型[33]
Fig. 2 (a) Structural model for PAF-1 with dia topology[15]. Copyright 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim;(b) CRN model for amorphous silica. Silicon and oxygen atoms are colored yellow and red, respectively.;(c) Amorphous model of PAF-1 [33]. Copyright 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
图3 CMPs合成的常用合成机理
Fig. 3 Schematic representation of reactions for the synthesis of CMPs
图4 可溶性CMP合成示意图[49]
Fig. 4 Schematic representation of the synthesis of a soluble CMP[49]. Copyright 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
图5 (左)CMT前驱体分子结构;(右)直径为47 mm的独立CMT膜[57]
Fig. 5 (left) The structure of 3-TBTBP(precursor of CMT);(right) A free-standing CMT membrane with a diameter of ~47 mm[57]. Copyright 2020, Springer Nature
图6 具有氨基官能团的微孔有机纳米管网络的制备[73]
Fig. 6 Preparation of the microporous organic nanotube networks with amino functionality[73]. Copyright 2016, Royal Society of Chemistry(Great Britain)
图7 不同结构的连接单元合成螺二芴基CMP示意图[74]
Fig. 7 Schematic representation of the synthesis of spirobifluorene-based CMPs using linkers of different geometries[74]. Copyright 2009, Elsevier
图8 三嗪基多孔聚合物合成示意图[75]
Fig. 8 Schematic representation of the synthesis of triazine-based porous polymers[75]. Copyright? 2009, American Chemical Society
图9 PTPA合成示意图[79]
Fig. 9 Schematic representation of the synthesis of PTPA[79]. Copyright 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
表1 部分CMPs储氢能力汇总
Table 1 Hydrogen storage with some CMPs
CMPs SBET(m2·g-1) Vtotal(cm3·g-1) P(bar) T(K) H2(wt%) ref
CMP-G1 997 1.32 20 77 2.69 98
CMP-G2 786 0.87 20 77 2.14 98
CP-CMP5 2241 2.07 1.13 77.3 2.24 99
S-450 292.8 0.44 1.01 77 0.77 100
S-500 459.3 0.53 1.01 77 0.86 100
S-520 564.9 0.31 1.01 77 1.08 100
S-550 579.2 0.59 1.01 77 0.39 100
RN4-Az-OH 340 0.55 1.01 77 1.1 101
RN4-OH 720 0.71 1.01 77 2.0 101
RN4-F 1230 0.95 1.01 77 1.4 101
P-Fo 611 1.00 1.1 77 118a 102
PBT-C1 685 1.60 1.1 77 124a 102
Si-HCP-1 1205 1.67 1.12 77.3 1.25 103
表2 部分CMPs储二氧化碳能力汇总
Table 2 Carbon dioxide storage in some CMPs
CMPs SBET(m2·g-1) Vtotal(cm3·g-1) T(K) CO2(mmol·g-1) ref
PTPA-NaF 1134 0.89 273 3.23 79
PTPA-NaI 1075 0.69 3.6 79
CP-CMP5 2241 2.07 77.3 2.24 99
PAQCB-900 1077 0.61 273 14.1a 104
PAQCB-1000 686 0.36 273 12.8a 104
PAQTB-900 1165 0.65 273 13.4a 104
RN4-F 1230 0.95 273 11.4 101
CTF-Cl-1 516 0.32 273 40.0 105
CTF-Cl-2 599 0.40 273 43.4 105
CTF-PF-3 590 0.38 273 41.1 105
CTF-PF-4 889 0.58 273 44.7 105
NCA-700 615 0.29 273 17.3a 106
NCA-800 913 0.46 273 20.9a 106
NCA-900 1541 0.72 273 26.7a 106
NCA-1000 2356 1.12 273 15.8a 106
P-Fo 611 1.00 273 45b 102
PBT-C1 685 1.60 273 46b 102
TMP-3 709 0.89 273 157c 107
PAN-NH2 612 0.50 273 12.2a 108
PAN-NH-NH2 665 0.80 273 9.7a 108
PAN-NH-CH3 748 0.57 273 14.9a 108
pTOC 929 0.61 273 43.5b 109
FCDTPA-K-700 2065 1.08 273 6.51 110
Si-HCP-1 1205 1.67 298.1 1.71 103
SN-@CMP-6 1172 1.16 273 86.5b 111
表3 部分CMPs储甲烷能力汇总
Table 3 Methane storage in some CMPs
CMPs SBET(m2·g-1) Vtotal(cm3·g-1) P(bar) T(K) CH4(cm3·g-1) ref
P-Fo 611 1.0 1.1 273 18.91 102
PBT-C1 685 1.6 1.1 273 20.51 102
TMP-1 452 0.741 1 273 14a 107
TMP-2 613 0.864 1 273 18.3a 107
TMP-3 709 0.893 1 273 22.2a 107
图10 (左)CMPAO结构示意图;(右)CMPAO-4吸附铀酰前后暴露在紫外线下的照片[142]
Fig. 10 (left) The structure of CMPAO;(right) The photographs of CMPAO-4 in the column exposed to UV light before and after uranyl adsorption[142]. Copyright 2019, Royal Society of Chemistry
图11 石墨烯基共轭微孔聚合物合成示意图[149]
Fig. 11 Schematic representation of Graphene-Based Conjugated Microporous Polymers.[149] Copyright 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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摘要

共轭微孔聚合物的制备与应用