共价有机框架的设计及质子传导性能研究进展

doi:10.6023/A25040135

化学学报 ›› 2025, Vol. 83 ›› Issue (11): 1435-1450.DOI: 10.6023/A25040135 上一篇下一篇

综述

共价有机框架的设计及质子传导性能研究进展

班渺寒^a^,^b, 双亚洲^a, 杨安平^a, 郑长勇^b, 张伟^b^,^*(), 徐飞^a^,^*()

^a 西北工业大学材料学院西安 710072
^b 西北化工研究院有限公司陕西省石油精细化学品重点实验室西安 710065

投稿日期:2025-04-28 发布日期:2025-06-09
通讯作者: 张伟, 徐飞

作者简介:

班渺寒, 西北工业大学材料学院在职博士, 西北化工研究院有限公司工程师. 研究方向为质子交换膜燃料电池关键材料的开发.

张伟, 西北化工研究院, 精细化工研究中心主任、教授级高级工程师, 三秦学者. 2009年于中科院大连化物所获理学博士学位. 负责、参加国家863、国家自然科学基金、中科院领域前沿创新、中科院重要方向性、振兴东北重点、中石化科技、中石油技术开发、陕西省重点研发计划等43项. 发表论文63篇, 主持编写标准3件; 申请授权专利57件. 主要从事煤、石油、清洁能源、天然气深加工及含氟精细化学品等领域的应用和基础研究.

徐飞, 西北工业大学材料学院教授、博士生导师、国家基金委优青、洪堡学者. 于2015年在中山大学获得博士学位, 2012~2014年在日本分子科学研究所从事联合培养博士研究, 2018~2020年在德累斯顿工业大学从事洪堡博士后研究. 主要研究方向为功能多孔聚合物和炭材料的创新制备及在新能源等领域的应用.

基金资助:
项目受国家自然科学基金面上项目(52473220); 陕西省重点研发计划(2025CY-YBXM-444)

Advances in Covalent Organic Frameworks Design for Proton Conduction

Ban Miaohan^a^,^b, Shuang Yazhou^a, Yang Anping^a, Zheng Changyong^b, Zhang Wei^b^,^*(), Xu Fei^a^,^*()

^a School of Materials Science and Engineering, Northwestern Polytechnical University, Xi’An 710072, China
^b The Northwest Research Institute of Chemical Industry Co., Ltd., Shaanxi Key Laboratory of Petroleum for Fine Chemicals, Xi’an 710065, China

Received:2025-04-28 Published:2025-06-09
Contact: Zhang Wei, Xu Fei
Supported by:
National Natural Science Foundation of China(52473220); Shaanxi Provincial Key Research and Development Program(2025CY-YBXM-444)

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摘要/Abstract

质子交换膜燃料电池(PEMFCs)通过氢氧电化学反应直接将化学能转化为电能, 为高效清洁能源转化提供了重要的途经. 质子交换膜作为PEMFC的核心功能组件, 通过定向传导质子实现电化学能的连续转换, 对电池性能具有决定性的作用. 共价有机框架(COFs)作为一种新型有机多孔材料, 具有高度结晶性、有序的多孔排列、功能可修饰性、结构可调性以及较高稳定性, 作为质子交换膜具有潜在的优势. COFs可功能修饰的骨架可以定制质子传导功能位点, 规整的孔道可以限域容纳多种质子载体/供体, 周期性分布的孔结构可以构建连续稳定的质子传输通道, 在含水/无水质子传导中均发挥出巨大的作用. 本文系统综述了近年来COFs材料的设计与质子传导性能研究进展, 重点讨论了COF骨架功能化设计、孔内限域和孔结构调控三种策略对质子传导性能的提升与传导机制解析, 并展望了该领域未来发展方向.

关键词: 共价有机框架, 质子传导, 功能化设计, 孔内限域, 孔结构调控

Proton exchange membrane fuel cells (PEMFCs) have emerged as a revolutionary technology in the field of clean energy, enabling the direct conversion of chemical energy to electricity through hydrogen-oxygen electrochemical reactions. This technology fundamentally circumvents the limitations of conventional combustion-based power generation, achieving near-zero greenhouse gas emissions while presenting a critical solution for efficient and environmentally-benign utilization of chemical energy. As the critical component of PEMFCs, the proton exchange membrane (PEM) plays an essential role in determining device-level efficiency and long-term operational stability. The PEM is a proton conductive polymer membrane existing between the anode and cathode, enabling selective proton transport while blocking electrons and gases. The ideal PEM materials must concurrently satisfy two critical operational requirements: (1) establishing efficient proton conduction pathways from anode to cathode with directional specificity, while (2) exhibiting robust resistance to gas and electricity leakage. To address these competing demands, strategic innovations in nanostructured membrane architectures continue to drive progress in next-generation PEMs. Covalent organic frameworks (COFs), a novel class of porous organic crystalline materials, demonstrate exceptional potential as next-generation PEM candidates owing to their inherent advantages including precise structural tunability, periodic pore arrangements, customizable functionality, and remarkable chemical stability. The unique architectural features of COFs provide unprecedented opportunities for proton conduction engineering. Their molecular-designed frameworks allow precise engineering of proton-conductive sites through strategic chemical modifications, while the well-defined nanochannels enable effective confinement of diverse proton carriers/vehicles. The periodic and topological pore nanoarchitectures facilitate the establishment of hierarchical proton transport pathways. These characteristics demonstrate exceptional performances in either hydrated or anhydrous proton conduction systems. This review systematically examines recent advancements in the design and preparation of COF-based proton conducting materials. Beginning with a brief introduction to the PEMFCs and current PEM, the basic knowledge of COFs and their potential structural advantages for proton conduction are discussed. Subsequently, the preparation of COF-based membrane and the key performance evaluation of PEM are summarized. Particular emphasis is placed on design strategies to enhance proton conduction including: (1) Framework design with incorporation of proton-conducting functionalities, (2) Pore nanoconfinement of proton-conducting guest moieties and (3) Pore-structure engineering for building proton conducting superhighways. The proton conductivity under different temperatures and humidities are discussed, along with the correlations to their structures and proton conduction mechanisms. Finally, the summary and perspective in this field are presented, underscoring challenges and opportunities in this burgeoning field. We hope this review would offer valuable insights into designing high-performance COF-based PEMs.

Key words: covalent organic frameworks, proton conduction, framework functionalization, pore nanoconfinement, pore-structure engineering

引用此文

班渺寒, 双亚洲, 杨安平, 郑长勇, 张伟, 徐飞. 共价有机框架的设计及质子传导性能研究进展[J]. 化学学报, 2025, 83(11): 1435-1450.

Ban Miaohan, Shuang Yazhou, Yang Anping, Zheng Changyong, Zhang Wei, Xu Fei. Advances in Covalent Organic Frameworks Design for Proton Conduction[J]. Acta Chimica Sinica, 2025, 83(11): 1435-1450.

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图/表 19

图1. (a)燃料电池示意图; (b~d)质子传导膜的结构分类

Figure 1. (a) Scheme of the fuel cell; (b~d) Classification of the proton conducting structure of the membrane

图2. COF传导质子结构设计示意图: (a)骨架功能化与孔结构设计和(b)孔内限域质子载体

Figure 2. Scheme of COF structure design for proton conduction: (a) framework functionality and pore structure design and (b) pore confinement of proton carriers

图3. (a)直接固相压片成膜, (b)界面聚合法制膜和(c)溶液浇铸法制膜

Figure 3. Membrane prepared by (a) direct solid-phase compaction method, (b) interfacial polymerization method, and (c) solvent casting method

图4. (a)磺化COFs NUS-9(G)和NUS-10(G)的合成路线; (b) NUS-9(R)和NUS-10(R)的质子传导率及Nyquist图

图5. (a) IPC-COF纳米片的自下而上合成示意图以及NUS-9的化学结构; (b) IPC-COF膜组装及孔结构示意图; (c) 40 ℃时IPC-COF膜和Nafion 212的质子传导率随RH的变化; (d)不同类型PEMs的离子传输通道随相对湿度降低的变化示意图

Figure 5. (a) Schematic illustration of the bottom-up synthesis of IPC-COF nanosheets and the chemical structure of NUS-9; (b) Schematic illustration of IPC-COF membrane assembly and pore structures; (c) Proton conductivity of IPC-COF membrane and Nafion 212 versus RH at 40 ℃; (d) Schematic illustration of ion transport channels changes with decreased RH for different types PEMs[38]. Copyright © 2020 Wiley- VCH GmbH

图6. (a) TPB-indazole-COF和BIY-COF制备合成示意图; (b, c)两种COF的质子传导率测试: Nyquist曲线图和Arrhenius图

图7. (a) TFPPY-BT-COF-H2PO3 不对称氢膦酰化反应的化学结构演变; (b) TFPPY-BT-COF-H2PO3在H2O和D2O中(313 K, RH=98%)测得的Nyquist图; (c) TFPPY-BT-COF-H2PO3的模拟质子传导机制示意图

Figure 7. (a) Chemical structure evolution of the asymmetric hydrophosphonylation of TFPPY-BT-COF-H2PO3; (b) Nyquist plots of TFPPY- BT-COF-H2PO3 measured with H2O and D2O (313 K, 98% RH); (c) Illustration for the proposed proton conduction mechanism of TFPPY- BT-COF-H2PO3[55]. Copyright © 2022, American Chemical Society

图8. (a) iCOF拓扑结构的分子模拟; (b) iCOFs骨架中-SO3H基团距离示意图; (c) 在RH=100%条件下, 膜的质子电导率随温度的变化情况; (d) iCOFMs中的质子转移机制: “穿梭”和“转移”示意图, 以及质子跳跃次数随模拟时间的变化情况; (e)质子的易解离行为; (f)质子在水合氢离子域内和域之间的转移; (g)水合氢离子(H3O+)在TpBd-SO3H和TpPa-SO3H中的概率密度分布

Figure 8. (a) The molecule simulation of the iCOF topological structure; (b) Scheme of the -SO3H group distance in iCOFs skeleton; (c) Temperature dependent proton conductivities of the membranes under RH=100%; (d) Proton transfer mechanism in iCOFMs, schematics of a shuttle and a transfer, and the number of proton hopping as a function of the simulation time; (e) Facile proton dissociation behavior; (f) proton transfer in and between hydronium domain; (g) The probability density distribution of H3O+ in TpBd-SO3H and TpPa-SO3H[56]

图9. (a) Tp-Azo和Tp-Stb的合成示意图; (b) COFs中H3PO4掺杂的示意图; (c) 4-[(E)-苯基偶氮基]苯胺二氢磷酸盐的晶体结构; (d)磷酸负载的Tp-Azo(PA@Tp-Azo)在无水条件下的质子传导率

Figure 9. (a) Schematic representation of synthesis of Tp-Azo and Tp-Stb; (b) Schematic representation of H3PO4 doping in COFs; (c) Crystal structure of 4-[(E)-phenyl-diazenyl]anilinium dihydrogen phosphate; (d) Proton conductivity of PA@Tp-Azo in anhydrous condition[67]

图10. (a)自下而上合成COF-Fx (x=6、8、10)的策略; (b)在无水条件下, 负载42% (w) H3PO4的COF-F6-H和COF-42-H的示意图; (c) COF-F6和COF-42在磷酸浸泡处理前后的PXRD图谱; (d) COF-F6-H的二维1H/1D图谱; (e) COF-F6-H的质子传导率长周期测试

Figure 10. (a) A bottom-up strategy for the synthesis of COF-Fx (x=6, 8, 10); (b) Scheme of COF-F6-H and COF-42-H with 42% (w) H3PO4 loading under anhydrous conditions; (c) PXRD patterns of COF-F6 and COF-42 before and after H3PO4 soaking treatments; (d) 2D 1H/1D spectra for COF-F6-H; (e) Long-period test for COF-F6-H[69]. Copyright © 2020, American Chemical Society

图11. (a) NKCOFs的合成路线示意图; (b)在RH=100%, T=60 ℃的条件下, 使用H2/O2单电池组件测得H3PO4@NKCOF-1的燃料电池极化曲线和功率密度曲线; (c) H3PO4@NKCOF-1的OCV和功率密度的循环稳定性测试

Figure 11. (a) Illustration of the synthetic route of NKCOFs; (b) Fuel cell polarization curves and power density curves of H3PO4@NKCOF-1 measured at 60 ℃ using single H2/O2 cell assembly under 100% RH; (c) Cyclic stability of OCV and power density of H3PO4@NKCOF-1[60]. Copyright © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

图12. (a) HFPTP-PDA-COF、HFPTP-BPDA-COF、Py-2,2-BPyPh- COF、TPB-DMTP-COF及Py-TMQPDA-COF的重构单孔结构; (b) H3PO4@COFs材料在不同温度下的无水质子传导率; (c) 160 ℃时H3PO4@COFs的无水质子传导率; (d) H3PO4@COFs的活化能垒

Figure 12. (a) Reconstructed one pore structures of HFPTP-PDA-COF, HFPTP-BPDA-COF, Py-2,2-BPyPh-COF, TPB-DMTP-COF, and Py-TMQPDA-COF; (b) Anhydrous proton conductivity of H3PO4@COFs at different temperatures; (c) Anhydrous proton conductivity of H3PO4@COFs at 160 ℃; (d) Activation energy barriers of H3PO4@COFs[72]. Copyright © 2024 The Author(s). Angewandte Chemie International Edition published by Wiley-VCH GmbH

图13. (a)分级宏-微孔结构m-TpPa-SO3H的合成过程示意图; (b, c)分级结构m-TpPa-SO3H的SEM图和TEM图; (d) m-TpPa-SO₃H、PIL0.2@m-TpPa-SO₃H、PIL0.5@m-TpPa-SO₃H及PIL0.2@s-COF质子传导率随温度变化曲线; (e) PIL0.5@m-TpPa-SO₃H在90 ℃、RH=100%下的质子传导率长期稳定性; (f)在RH=100% 条件下, PIL0.5@m-TpPa-SO3H的质子传导机制示意图

Figure 13. (a) Schematic illustration of the synthesis process of hierarchical macro-microporous m-TpPa-SO3H; (b, c) The SEM images and TEM image of hierarchical m-TpPa-SO3H; (d) Temperature dependence of the proton conductivities of m-TpPa-SO3H, PIL0.2@m-TpPa-SO3H, PIL0.5@m-TpPa-SO3H, and PIL0.2@s-COF; (e) Long-term proton conductivity durability of PIL0.5@m-TpPa-SO3H at 90 ℃ under RH=100%; (f) Schematic illustration of proton conduction mechanism of PIL0.5@m-TpPa-SO3H under RH=100%[73]. Copyright © 2023 Wiley-VCH GmbH

图14. (a)孔径相近但亲水基团数量不同的COF-1、COF-2和COF-3的结构; (b, c) COF-3的二维1H DQ/SQ核磁共振光谱; (d)质子在一维和三维方向上的传导路径示意图; (e) COF-3@PA-30的质子电导率随温度的变化情况

Figure 14. (a) The structure of COF-1, COF-2 and COF-3 with similar pore diameters but different amounts of hydrophilic groups; (b, c) 2D 1H DQ/SQ NMR spectrum of COF-3; (d) Proton conduction pathway schematic illustration in 1D and 3D direction; (e) The temperature-dependent proton conductivity of COF-3@PA-30[31]. Copyright © 2023, Tsinghua University Press

图15. (a)三维COF NUST-28的合成路径; (b) NUST-28与磷酸之间的氢键连接; (c) NUST-28-60%的质子传导长期稳定性

Figure 15. (a) Illustration for the synthesis of NUST-28; (b) The hydrogen bonding between NUST-28 and H3PO4; (c) Long-term proton conduction of NUST-28-60%[64]

图16. (a)使用COF粉末制作MEA的示意图: (1)制备涂有Pt的气体扩散层(GDL, 用作阳极和阴极)、COF压片(用作固体电解质), (2~4)将COF压片夹在两个电极之间, (5~7)将膜电极组件组装成单电池堆; (b)在PEMFC中, 使用H3PO4负载的PA@TpBpy-ST和PA@TpBpy-MC作为固体电解质测得的OCV寿命数据; (c)在50 ˚C下, 使用干燥H2、Pt、C/COF压片/Pt、C、干燥O2的电化学电池测得的燃料电池极化图

Figure 16. (a) Schematic representation of MEA making using pelletized COF powder: (1) Preparation of Pt coated GDL (as anode and cathode), COF pellet (as solid electrolyte), (2~4) Sandwiching of COF pellet between two electrodes, (5~7) Assembly of the MEA into a single cell stack; (b) Lifetime OCV measurement obtained using PA@TpBpy-ST and PA@TpBpy-MC as solid electrolytes in PEMFC; (c) Fuel cell polarization plot obtained at 50 ℃ using dry H2, Pt, C/COF pellet/Pt, C, dry O2 electrochemical cell[47]

图17. (a) EB-COF:Br的合成示意图; (b) EB-COF:Br和EB-COF:PW12的氮气吸附等温线; (c) PW12O40³⁻限域COF的示意图; (d)在RH=97%条件下EB-COF:Br和(e) EB-COF:PW12的质子传导率

Figure 17. (a) Schematic of the synthesis of EB-COF:Br; (b) Nitrogen sorption isotherms for EB-COF:Br and EB-COF:PW12; (c) Schematic of PW12O403- doping in COF; (d) Proton conductivity of EB-COF:Br and (e) EB-COF:PW12 in RH=97% condition[77]. Copyright © 2016, American Chemical Society

COFs	Sources of conductivity	Proton conductivity/(S•cm⁻¹)	T/℃	RH/%
TFPPY-BT-COF-H₂PO₃^[65]	H₃PO₄	1.12×10⁻³	60	98
NUST-28^[74]	H₃PO₄	1.46×10⁻¹	120	0
COF-3@PA-30^[31]	H₃PO₄	1.4	160	0
H₃PO₄@TPB-DMeTPCOF^[68]	H₃PO₄	1.91×10⁻¹	160	0
COF-F6-H^[69]	H₃PO₄	4.2×10⁻²	140	0
H₃PO₄@Tp-Azo-COF^[67]	H₃PO₄	6.70×10⁻⁵	67	0
H₃PO₄@NKCOFs^[70]	H₃PO₄	1.13×10⁻¹	80	98
H₃PO₄@TpBpy-MC^[47]	H₃PO₄	2.50×10⁻³	120	0
Phytic acid@TpPa- (SO₃H-Py)^[75]	Phytic acid	5.00×10⁻⁴	120	0
PTSA@TpAzo^[43]	p-Toluenesulfonic acid	7.8×10⁻²	80	95
EB-COF:PW₁₂^[77]	polyoxometalates	3.32×10⁻³	20	97
trz@TPB-DMTP-COF^[58]	Triazole	1.1×10⁻³	130	0

表1. 负载不同客体分子的COFs材料的质子传导性能

Table 1. The proton conduction properties of COFs materials loaded with different sources

图18. 骨架功能基团修饰COF与限域外源分子COF在不同温度和湿度下的质子传导率

Figure 18. Proton conductivities of COFs with modified skeletal functional groups and confining exogenous molecules under different temperatures and relative humidity

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共价有机框架的设计及质子传导性能研究进展

Advances in Covalent Organic Frameworks Design for Proton Conduction

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