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Progress in Chemistry 2024, Vol. 36 Issue (1): 48-66 DOI: 10.7536/PC230529 Previous Articles   Next Articles

• Review •

Covalent Organic Frameworks for Proton Exchange Membranes

Weiyu Zhang, Jie Li, Hong Li, Jiaqi Ji, Chenliang Gong(), Sanyuan Ding   

  1. College of Chemistry and Chemical Engineering, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received: Revised: Online: Published:
  • Contact: * e-mail: gongchl@lzu.edu.cn
  • Supported by:
    National Natural Science Foundation of China(21975112)
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Covalent organic frameworks (COFs), as a new type of organic porous materials, are highly crystalline and orderly porous, exhibiting functional modifiability, structural tunability and high stability. The regular pore channels of COFs can accommodate a variety of proton carriers and proton donors to build continuous and stable proton transport channels, playing a great role in both aqueous and anhydrous proton conduction. The application of COFs to the field of proton exchange membranes is of great research significance and value. In this paper, the characteristics of different types of proton exchange membranes, such as COFs solid electrolyte membranes, polymer matrix-COFs composite membranes, COFs self-supporting membranes and the modification methods to improve the performance of COFs proton exchange membranes are summarized from the aspects of COFs as proton exchange membranes for low temperature fuel cells and high temperature fuel cells, respectively. The relevant representative research of COFs in the field of fuel cell proton exchange membranes in recent years is reviewed. Finally, the application prospects of COFs proton exchange membranes are discussed and prospected.

Contents

1 Introduction

2 Covalent organic frameworks

2.1 Structure of COFs

2.2 Synthesis of COFs and COFs membrane

2.3 Application of COFs

3 COFs fuel cell proton exchange membrane

3.1 COFs low-temperature fuel cell proton exchange membranes

3.2 COFs high-temperature fuel cell proton exchange membranes

4 Conclusion and outlook

Key words: covalent organic frameworks, proton exchange membranes, proton conduction
Fig. 1 Topology diagrams for designing COFs[31]. Copyright 2019, Springer Nature
Fig. 2 Synthesis methods of COFs
Fig. 3 Top-down strategies for preparing COFs nanosheets
Fig. 4 Bottom-up strategies for preparing COFs membranes (a) Solvothermal synthesis[38] (b) Laminar assembly polymerization[44] (c) Interfacial polymerization[41]. Ref 38, Copyright 2011, American Association for the Advancement of Science; Ref 44, Copyright 2019, American Association for the Advancement of Science; Ref 41, Copyright 2023, American Chemical Society
Fig. 5 Applications of COFs[54,55,60]. ref 54, Copyright 2018, Royal Society of Chemistry; ref 55, Copyright 2011, American Chemical Society; ref 60, Copyright 2023, American Chemical Society
Fig. 6 （a）Synthetic route of NKCOFs; （b）The hexagonal structural of NKCOFs; （c~f）The side views of NKCOFs, resulting from the eclipsed AA stacking[66]. Copyright 2019, Wiley-VCH
Fig. 7 (a) The synthesis of EB-COF：Br; (b) Top views and side views of the offset AA stacking structure of the EB-COF：Br;(c) Schematic of PW12O403? doping in COF[67]. Copyright 2016, American Chemical Society
Fig. 8 (a)Schematic of proton transfer in composite membranes; (b)SEM images of the cross sections of Nafion membrane and Nafion/H3PO4@S1-15 composite membrane[71]. Copyright 2016, Elsevier
Fig. 9 Synthetic route of SNW-1 and Z-COF[72]
Fig. 10 Structural illustration of SCONs and Nafion molecule[73]. Copyright 2019, Elsevier
Fig. 11 Schematic of proton transfer in SPEEK/HPW@COF composite membranes[74]. Copyright 2020, Elsevier
Fig. 12 (a)Schematic illustration of IPC-COF membrane assembly and pore structures; (b)SEM image of IPC-COF; (c)XRD pattern of IPC-COF; (d)Swelling ratio versus IEC value from IPC-COF membrane and existing PEMs as reported in the literature[76]. Copyright 2020, Wiley-VCH
Fig. 13 Illustration of DABA-TFP-COF-NS synthesis process in single solution-phase[77]. Copyright 2022, Wiley-VCH
Fig. 14 (a~d)Schematic representation of the synthesis of COFMs; (e)PXRD patterns of as-obtained PTSA@COFMs and those obtained after washing with water[78]. Copyright 2018, Wiley-VCH
Table 1 Properties of different COFs proton exchange membranes
COFs Sample type Thermal decomposition temperature (℃) Tensile strength（MPa） Activation energy
(kJ·mol-1)		 σ (S·cm-1) Maximum power density
(mW·cm-2)		 ref
PA@aza-COF-2 Pellet 250 — 45 4.8×10-3 (50°C, 97% RH) — 64
NSU-10（R） Pellet — — — 3.96×10-2 (room temperature, 97% RH) — 65
H3PO4@NKCOF-1 Pellet 260 — 14 1.13×10-1 (80 ℃, 98% RH) 81 (60°C) 66
EB-COF：PW12 Pellet 300~400 — 24 3.32×10-3 (25 ℃, 97% RH) — 67
Nafion/H3PO4@S1-15 Composite membrane 389 — — 6.04×10-2 (80 ℃, 51% RH) 277.8 (60°C) 71
Nafion/Z-COF-10 Composite membrane 359.5 25~28 7.7 2.2×10-1 (80 ℃, 100% RH) — 72
Nafion-SCONs-0.6 Composite membrane 280~350 27.3±0.4 — 2.65×10-1 (80 ℃) 118.2 (80°C) 73
SPEEK/HPW@COF-15 Composite membrane 250~360 75.0 23.76 6.2×10-3 (65 ℃, 40% RH) — 74
IPC-COF Membrane — 91.2±6 12 3.8×10-1 (80 ℃, 98% RH) 1100 (80°C) 76
SPC-COF-NS Membrane — 24.3 — 3.64×10-1 (80 ℃) 891.7 (80°C) 77
SCOF Membrane — — 19 5.4×10-1 (80 ℃) — 75
Fig. 15 (a)The synthesis of TPB-DMeTP-COF; (b)The structure of one hexagonal macrocycle; (c)The structure of a 1D channel (grey, C；green, N；CH3 units and H are omitted for clarity); (d)Nitrogen sorption isotherms of TPB-DMeTP-COF measured at 77 K (circle, adsorption; triangle, desorption)[83]. Copyright 2020, Spring Nature
Fig. 16 (a)The synthesis of TPT-COF; (b)Top and side views of the corresponding refined crystal structures of TPT-COF with the antiparallel stacking model (gray, blue, and white spheres represent C, N, and H atoms, respectively); (c)The PXRD patterns of TPT-COF[84]. Copyright 2022, Wiley-VCH
Fig. 17 (a)Structure of and synthetic route to TB-COF and PIL-TB-COF (b)Schematic illustration of the proton transfer in PIL-TB-COF[87]. Copyright 2022, Royal Society of Chemistry
Fig. 18 (a)Reaction for the in situ growth of COFs in OPBI solution; (b)SEM image of pristine OPBI membrane; (c)SEM image of 40%-COF-OPBI composite membrane[93]. Copyright 2022, Elsevier
Table 2 Properties of different COFs HTPEMs
COFs Sample type Thermal decomposition temperature (°C) Tensile strength(MPa) Activation energy
(kJ·mol-1)		 σ (S·cm-1) Maximum power density
(mW·cm-2)		 ref
H3PO4@TPB-DMeTP-COF Pellet — — 34 1.91×10-1 (160 ℃, 0 RH) — 83
TPT-COF Pellet 525 — 17 1.27×10-2 (160 ℃, 0 RH) — 84
H3PO4@TPB-DABI-COF Pellet — — 17 1.52×10-1 (160 ℃, 0 RH) — 85
im@TPB-DMTP-COF Pellet 220 — 25 4.37×10-3 (130 ℃, 0 RH) — 59
PIL-TB-COF Pellet 221 — 30 2.21×10-3 (120 ℃, 0 RH) — 87
F6-[dema]HSO4-1.5 Pellet 300 — 34 1.33×10-2 (140 ℃, 0 RH) — 88
30%-CTFs-OPBI Membrane 300 7.7 — 7.71×10-2 (160 ℃, 0 RH) 534.3 92
40%-COF-OPBI Membrane 300~400 12.2 — 1.777×10-1 (160 ℃, 0 RH) 774.7 93
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