Vinylic-addition Polynorbornene-based Anion-Exchange Membranes with Semi-Interpenetrating Polymer Networks for Water Electrolysis

Ting Wang; Yu Wang; Wei You

doi:10.1007/s10118-024-3225-2

Your Location：

Home >

Browse articles >

Vinylic-addition Polynorbornene-based Anion-Exchange Membranes with Semi-Interpenetrating Polymer Networks for Water Electrolysis

RESEARCH ARTICLE | Updated：2024-12-03

- Vinylic-addition Polynorbornene-based Anion-Exchange Membranes with Semi-Interpenetrating Polymer Networks for Water Electrolysis
- Vinylic-addition Polynorbornene-based Anion-Exchange Membranes with Semi-Interpenetrating Polymer Networks for Water Electrolysis
- 高分子科学（英文版） 2024年42卷第12期页码：1888-1896
- Affiliations：
  
  a.Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
  b.University of Chinese Academy of Sciences, Beijing 100049, China
- Author bio：
  
  ywang507@iccas.ac.cn (Y.W.)
  weiyou@iccas.ac.cn (W.Y.)
- Funds：
  
  This work was financially supported by the Ministry of Science and Technology of China under the National Key R&D Program of China (No. 2023YFB3811200) and the National Natural Science Foundation of China (No. 22075292).;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-024-3225-2.
- DOI：10.1007/s10118-024-3225-2
  中图分类号：
- 收稿：2024-08-03，
  
  修回：2024-09-04，
  
  录用：2024-09-05，
  
  网络首发：2024-11-07，
  
  纸质出版：2024-12-01
- Accepted：
Scan QR Code
Wang, T.; Wang, Y.; You, W. Vinylic-addition polynorbornene-based anion-exchange membranes with semi-interpenetrating polymer networks for water electrolysis. Chinese J. Polym. Sci. 2024, 42, 1888–1896

Ting Wang, Yu Wang, Wei You. Vinylic-addition Polynorbornene-based Anion-Exchange Membranes with Semi-Interpenetrating Polymer Networks for Water Electrolysis[J]. Chinese Journal of Polymer Science, 2024, 42(12): 1888-1896.
Wang, T.; Wang, Y.; You, W. Vinylic-addition polynorbornene-based anion-exchange membranes with semi-interpenetrating polymer networks for water electrolysis. Chinese J. Polym. Sci. 2024, 42, 1888–1896 DOI： 10.1007/s10118-024-3225-2.

Ting Wang, Yu Wang, Wei You. Vinylic-addition Polynorbornene-based Anion-Exchange Membranes with Semi-Interpenetrating Polymer Networks for Water Electrolysis[J]. Chinese Journal of Polymer Science, 2024, 42(12): 1888-1896. DOI： 10.1007/s10118-024-3225-2.

摘要

A semi-interpenetrating polymer network (s-IPN) strategy is proposed to prepare high-performance anion-exchange membranes (AEMs) with vinylic addition polynorbornene backbones. The synthesis involves easily accessible starting materials including poly(5-vinyl-2-norbornene) (PVNB).

Abstract

Anion-exchange membranes (AEMs) with high conductivity and stability are essential components of hydrogen related water electrolysis and fuel cell applications. During the past decades

polynorbornene (PNB)-based AEMs have shown excellent performance due to their saturated all-carbon-based backbones and diverse strategies to prepare cross-linked membranes. However

nearly all previously reported PNB-based AEMs rely on the alkyl-substituted norbornene monomers

whose low-yielding synthesis leads to high-cost of the AEMs. In addition

the cross-linked PNB-based AEMs usually suffered from mechanical brittleness. Herein

we propose a novel semi-interpenetrating polymer network (s-IPN) strategy to simultaneously enhance mechanical modulus and ionic conductivity

while using commercial 5-vinyl-2-norbornene (VNB) as the single norbornene derivatives to prepare high-performance AEMs. A diallylphenol quaternary ammonium salt was used for photo-induced cross-linking with poly-VNB and various dithiols to produce AEMs with s-IPN structures. The resultant membranes have excellent hydroxide conductivities and alkaline stability in 1 mol/L KOH at 80 °C

and are successfully applied in alkaline anion-exchange membrane water electrolyzers to stably operate for over 150 h.

关键词

Keywords

references

Du, N.; Roy, C.; Peach, R.; Turnbull, M.; Thiele, S.; Bock, C. Anion-exchange membrane water electrolyzers. Chem. Rev. 2022 , 122 , 11830−11895..

Yang, Y.; Peltier, C. R.; Zeng, R.; Schimmenti, R.; Li, Q.; Huang, X.; Yan, Z.; Potsi, G.; Selhorst, R.; Lu, X.; Xu, W.; Tader, M.; Soudackov, A. V.; Zhang, H.; Krumov, M.; Murray, E.; Xu, P.; Hitt, J.; Xu, L.; Ko, H. Y.; Ernst, B. G.; Bundschu, C.; Luo, A.; Markovich, D.; Hu, M.; He, C.; Wang, H.; Fang, J.; DiStasio, R. A., Jr.; Kourkoutis, L. F.; Singer, A.; Noonan, K. J. T.; Xiao, L.; Zhuang, L.; Pivovar, B. S.; Zelenay, P.; Herrero, E.; Feliu, J. M.; Suntivich, J.; Giannelis, E. P.; Hammes-Schiffer, S.; Arias, T.; Mavrikakis, M.; Mallouk, T. E.; Brock, J. D.; Muller, D. A.; DiSalvo, F. J.; Coates, G. W.; Abruna, H. D. Electrocatalysis in alkaline media and alkaline membrane-based energy technologies. Chem. Rev. 2022 , 122 , 6117−6321..

Yang, Y.; Li, P.; Zheng, X.; Sun, W.; Dou, S. X.; Ma, T.; Pan, H. Anion-exchange membrane water electrolyzers and fuel cells. Chem. Soc. Rev. 2022 , 51 , 9620−9693..

Park, E. J.; Arges, C. G.; Xu, H.; Kim, Y. S. Membrane strategies for water electrolysis. ACS Energy Lett. 2022 , 7 , 3447−3457..

Santoro, C.; Lavacchi, A.; Mustarelli, P.; Di Noto, V.; Elbaz, L.; Dekel, D. R.; Jaouen, F. What is next in anion-exchange membrane water electrolyzers? Bottlenecks, benefits, and future. ChemSusChem 2022, 15 , e202200027|1–17..

Wan, L.; Xu, Z.; Xu, Q.; Pang, M. B.; Lin, D. C.; Liu, J.; Wang, B. G. Key components and design strategy of the membrane electrode assembly for alkaline water electrolysis. Energy Environ. Sci. 2023 , 16 , 1384−1430..

Varcoe, J. R.; Atanassov, P.; Dekel, D. R.; Herring, A. M.; Hickner, M. A.; Kohl, P. A.; Kucernak, A. R.; Mustain, W. E.; Nijmeijer, K.; Scott, K.; Xu, T. W.; Zhuang, L. Anion-exchange membranes in electrochemical energy systems. Energy Environ. Sci. 2014 , 7 , 3135−3191..

Chen, N.; Lee, Y. M. Anion exchange polyelectrolytes for membranes and ionomers. Prog. Polym. Sci. 2021 , 113 , 101345..

You, W.; Noonan, K. J. T.; Coates, G. W. Alkaline-stable anion exchange membranes: a review of synthetic approaches. Prog. Polym. Sci. 2020 , 100 , 101177..

Nie, G. H.; Wu, W. J.; Yue, X.; Liao, S. J.; Li, X. H. Synthesis and properties of hydroxide conductive polymers carrying dense aromatic side-chain quaternary ammonium groups. Chinese J. Polym. Sci. 2017 , 35 , 823−836..

Pan, Y.; Wang, T. Y.; Yan, X. M.; Xu, X. W.; Zhang, Q. D.; Zhao, B. L.; El Hamouti, I.; Hao, C.; He, G. H. Benzimidazolium functionalized polysulfone-based anion exchange membranes with improved alkaline stability. Chinese J. Polym. Sci. 2017 , 36 , 129−138..

Xiong, L.; Hu, Y. F.; Zheng, Z. G.; Xie, Z. L.; Chen, D. Y. Chloromethylation and quaternization of poly(aryl ether ketone sulfone)s with clustered electron-rich phenyl groups for anion exchange membranes. Chinese J. Polym. Sci. 2019 , 38 , 278−287..

Liu, M.; Hu, X.; Hu, B.; Liu, L.; Li, N. Soluble poly(aryl piperidinium) with extended aromatic segments as anion exchange membranes for alkaline fuel cells and water electrolysis. J. Membr. Sci. 2022 , 642 , 119966..

Chu, X.; Shi, Y.; Liu, L.; Huang, Y.; Li, N. Piperidinium-functionalized anion exchange membranes and their application in alkaline fuel cells and water electrolysis. J. Mater. Chem. A 2019 , 7 , 7717−7727..

Cao, D. F.; Yang, F.; Sheng, W. B.; Zhou, Y. F.; Zhou, X. X.; Lu, Y. G.; Nie, F. M.; Li, N. W.; Pan, L.; Li, Y. S. Polynorbornene-based anion exchange membranes with hydrophobic large steric hindrance arylene substituent. J. Membr. Sci . 2022, 641 , 119938..

Chen, N.; Hu, C.; Wang, H. H.; Kim, S. P.; Kim, H. M.; Lee, W. H.; Bae, J. Y.; Park, J. H.; Lee, Y. M. Poly(alk yl-terphenyl piperidinium) ionomers and membranes with an outstanding alkaline-membrane fuel-cell performance of 2.58 W cm -2 . Angew. Chem. Int. Ed. 2021 , 60 , 7710−7718..

Wu, X. Y.; Chen, N. J.; Klok, H. A.; Lee, Y. M.; Hu, X. L. Branched poly(aryl piperidinium) membranes for anion-exchange membrane fuel cells. Angew. Chem. Int. Ed . 2022, 61 , e202114892|1–8..

Chen, N.; Wang, H. H.; Kim, S. P.; Kim, H. M.; Lee, W. H.; Hu, C.; Bae, J. Y.; Sim, E. S.; Chung, Y. C.; Jang, J. H.; Yoo, S. J.; Zhuang, Y.; Lee, Y. M. Poly(fluorenyl aryl piperidinium) membranes and ionomers for anion exchange membrane fuel cells. Nat. Commun . 2021, 12 , 2367|1–12..

Wang, J.; Zhao, Y.; Setzler, B. P.; Rojas-Carbonell, S.; Ben Yehuda, C.; Amel, A.; Page, M.; Wang, L.; Hu, K.; Shi, L.; Gottesfeld, S.; Xu, B.; Yan, Y. Poly(aryl piperidinium) membranes and ionomers for hydroxide exchange membrane fuel cells. Nat. Energy 2019 , 4 , 392−398..

Olsson, J. S.; Pham, T. H.; Jannasch, P. Poly(arylene piperidinium) hydroxide ion exchange membranes: synthesis, alkaline stability, and conductivity. Adv. Funct. Mater. 2018 , 28 , 1702758..

Wang, T.; Zhang, Y.; Wang, Y.; You, W. Transition-metal-free preparation of polyethylene-based anion exchange membranes from commercial EVA. Polymer 2022 , 262 , 125439..

Wang, T.; Wang, Y.; You, W. Dithiol cross-linked polynorbornene-based anion-exchange membranes with high hydroxide conductivity and alkaline stability. J. Membr. Sci. 2023 , 685 , 121916..

Wang, T.; Wang, Y.; You, W. Polycyclic norbornene based anion-exchange membranes with high ionic conductivity and chemical stability. J. Membr. Sci . 2024, 702 , 122747|1–10..

Zhang, F.; Li, T.; Chen, W.; Yan, X.; Wu, X.; Jiang, X.; Zhang, Y.; Wang, X.; He, G. High-Performance Anion Exchange Membranes with Para-Type Cations on Electron-Withdrawing C═O Links Free Backbone. Macromolecules 2020 , 53 , 10988−10997..

Kwasny, M. T.; Zhu, L.; Hickner, M. A.; Tew, G. N. Thermodynamics of counterion release is critical for anion exchange membrane conductivity. J. Am. Chem. Soc. 2018 , 140 , 7961−7969..

Zeng, M.; He, X.; Wen, J.; Zhang, G.; Zhang, H.; Feng, H.; Qian, Y.; Li, M. N-methylquinuclidinium-based anion exchange membrane with ultrahigh alkaline stability. Adv. Mater. 2023 , 35 , 2306675..

Zhang, H.; Wang, X.; Wang, Y.; Zhang, Y.; Zhang, W.; You, W. Alkaline-stable anion-exchange membranes with barium [2.2.2 ] cryptate cations: the importance of high binding constants. Angew. Chem. Int. Ed. 2023 , 62 , e202217742..

Wang, W.; Cao, D. F.; Sun, X. W.; Pan, L.; Ma, Z.; Li, Y. S. The influence of various cationic group on polynorbornene based anion exchange membranes with hydrophobic large steric hindrance arylene substituent. Chinese J. Polym. Sci. 2022 , 41 , 278−287..

Ge, X.; He, Y.; Guiver, M. D.; Wu, L.; Ran, J.; Yang, Z.; Xu, T. Alkaline anion-exchange membranes containing mobile ion shuttles. Adv. Mater. 2016 , 28 , 3467−3472..

Zhu, Y.; Ding, L.; Liang, X.; Shehzad, M. A.; Wang, L.; Ge, X.; He, Y.; Wu, L.; Varcoe, J. R.; Xu, T. Beneficial use of rotatable-spacer side-chains in alkaline anion exchange membranes for fuel cells. Energy Environ. Sci. 2018 , 11 , 3472−3479..

Zhang, J.; Zhang, K.; Liang, X.; Yu, W.; Ge, X.; Shehzad, M. A.; Ge, Z.; Yang, Z.; Wu, L.; Xu, T. Self-aggregating cationic-chains enable alkaline stable ion-conducting channels for anion-exchange membrane fuel cells. J. Mater. Chem. A 2021 , 9 , 327−337..

Yu, W.; Zhang, J.; Liang, X.; Ge, X.; Wei, C.; Ge, Z.; Zhang, K.; Li, G.; Song, W.; Shehzad, M. A.; Wu, L.; Xu, T. Anion exchange membranes with fast ion transport channels driven by cation-dipole interactions for alkaline fuel cells. J. Membr. Sci. 2021 , 634 , 119404..

Ma, L.; Hussain, M.; Li, L.; Qaisrani, N. A.; Bai, L.; Jia, Y.; Yan, X.; Zhang, F.; He, G. Octopus-like side chain grafted poly(arylene piperidinium) membranes for fuel cell application. J. Membr. Sci. 2021 , 636 , 119529..

Jeon, S.; Han, S.; Lee, J.; Min, K.; Nam, S. Y.; Kim, T. H. Crosslinked high-performance anion exchange membranes based on poly(dibenzyl -methyl piperidine) and pentafluorobenzoyl-substituted SEBS. J. Mater. Chem. A 2024 , 12 , 18593−18603..

Lee, Y.; Min, K.; Choi, J.; Choi, G.; Kim, H.; Kim, T. H. Development of highly conductive anion exchange membranes based on crosslinked PIM-SEBS with high free volume. J. Mater. Chem. A 2023 , 11 , 25008−25019..

Min, K.; Jeong, I.; Kim, H.; Kim, T. H. Polycarbazole-SEBS-crosslinked AEMs based on two spacer polymers for high-performance AEMWE. J. Mater. Chem. A 2023 , 12 , 343−353..

Guo, D.; Zhuo, Y. Z.; Lai, A. N.; Zhang, Q. G.; Zhu, A. M.; Liu, Q. L. Interpenetrating anion exchange membranes using poly(1-vinylimidazole) as bifunctional crosslinker for fuel cells. J. Membr. Sci. 2016 , 518 , 295−304..

Pan, J.; Zhu, L.; Han, J.; Hickner, M. A. Mechanically tough and chemically stable anion exchange membranes from rigid-flexible semi-interpenetrating networks. Chem. Mater. 2015 , 27 , 6689−6698..

Zeng, L.; Liao, Y.; Wang, J.; Wei, Z. Construction of highly efficient ion channel within anion exchange membrane based on interpenetrating polymer network for H 2 /Air (CO 2 -free) alkaline fuel cell. J. Power Sources 2021, 486 , 229377..

Zeng, L. P.; Yuan, W.; He, Q.; Ma, X. Q.; Zhang, L.; Wang, J. C.; Wei, Z. D. Dual-Cation interpenetrating polymer network anion exchange membrane for fuel cells and water electrolyzers. Macromolecules 2022 , 55 , 4647−4655..

Han, J.; Liu, C.; Deng, C.; Zhang, Y.; Song, W.; Zheng, X.; Liu, X.; Zhang, Y.; Yang, X.; Ren, Z.; Hu, M.; Xiao, L.; Zhuang, L. Mechanically robust and highly conductive semi-interpenetrating network anion exchange membranes for fuel cell applications. J. Power Sources 2022 , 548 , 232097..

Xue, J.; Liu, L.; Liao, J.; Shen, Y.; Li, N. Semi-interpenetrating polymer networks by azide–alkyne cycloaddition as novel anion exchange membranes. J. Mater. Chem. A 2018 , 6 , 11317−11326..

Matanovic, I.; Maurya, S.; Park, E. J.; Jeon, J. Y.; Bae, C.; Kim, Y. S. Adsorption of polyaromatic backbone impacts the performance of anion exchange membrane fuel cells. Chem. Mater. 2019 , 31 , 4195−4204..

Mandal, M.; H uang, G.; Kohl, P. A. Highly conductive anion-exchange membranes based on cross-linked poly(norbornene): vinyl addition polymerization. ACS Appl. Energy Mater. 2019 , 2 , 2447−2457..

Gaitor, J. C.; Yang-Neyerlin, A. C.; Markovich, D.; Fors, B. P.; Coates, G. W.; Kourkoutis, L. F.; Pivovar, B. S.; Kowalewski, T.; Noonan, K. J. T. Comparing ammonium and tetraaminophosphonium anion-exchange membranes derived from vinyl-addition polynorbornene copolymers. ACS Appl. Energy Mater. 2024 , 7 , 1517−1526..

Mandal, M.; Huang, G.; Kohl, P. A. Anionic multiblock copolymer membrane based on vinyl addition polymerization of norbornenes: applications in anion-exchange membrane fuel cells. J. Membr. Sci . 2019, 570−571 , 394−402..

Xie, Y.; Wang, G.; Tang, H.; Wang, G.; Xiao, L.; Zhuang, L. An efficient approach towards highly chemically stable poly(norbornene) membrane for alkaline polyelectrolyte fuel cells. J. Membr. Sci. 2024 , 709 , 123057..

Zhegur-Khais, A.; Kubannek, F.; Krewer, U.; Dekel, D. R. Measuring the true hydroxide conductivity of anion exchange membranes. J. Membr. Sci. 2020 , 612 , 118461..

Ziv, N.; Dekel, D. R. A practical method for measuring the true hydroxide conductivity of anion exchange membranes. Electrochem. Commun. 2018 , 88 , 109−113..

Zhu, M.; Su, Y.; Wu, Y.; Zhang, M.; Wang, Y.; Chen, Q.; Li, N. Synthesis and properties of quaternized polyolefins with bulky poly(4-phenyl-1-butene) moieties as anion exchange membranes. J. Membr. Sci. 2017 , 541 , 244−252..

Ma, Y.; Hu, C.; Yi, G.; Jiang, Z.; Su, X.; Liu, Q.; Lee, J. Y.; Lee, S. Y.; Lee, Y. M.; Zhang, Q. Durable multiblock poly(biphenyl alkylene) anion exchange membranes with microphase separation for hydrogen energy conversion. Angew. Chem. Int. Ed. 2023 , 62 , e202311509..

Mohanty, A. D.; Bae, C. Mechanistic analysis of ammonium cation stability for alkaline exchange membrane fuel cells. J. Mater. Chem. A 2014 , 2 , 17314−17320..

Peltier, C. R.; You, W.; Fackovic Volcanjk, D.; Li, Q.; Macbeth, A. J.; Abruña, H. D.; Coates, G. W. Quaternary ammonium-functionalized polyethylene-based anion exchange membranes: balancing performance and stability. ACS Energy Lett. 2023 , 8 , 2365−2372..

Hsu, J. H.; Peltier, C. R.; Treichel, M.; Gaitor, J. C.; Li, Q.; Girbau, R.; Macbeth, A. J.; Abruna, H. D.; Noonan, K. J. T.; Coates, G. W.; Fors, B. P. Direct insertion polymerization of ionic monomers: rapid production of anion exchange membranes. Angew. Chem. Int. Ed. 2023 , 62 , e202304778..

Dang, H. S.; Jannasch, P. A comparative study of anion-exchange membranes tethered with different hetero-cycloaliphatic quaternary ammonium hydroxides. J. Mater. Chem. A 2017 , 5 , 21965−21978..

Li, D.; Motz, A. R.; Bae, C.; Fujimoto, C.; Yang, G.; Zhang, F. Y.; Ayers, K. E.; Kim, Y. S. Durability of anion exchange membrane water electrolyzers. Energy Environ. Sci. 2021 , 14 , 3393−3419..

浏览量

244

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Robust and Self-healable Antibiofilm Multilayer Coatings

pH-Responsive L-Cysteine-conjugated Polydopamine Nanocarriers for Controlled Release of Emamectin Benzoate against Pieris brassicae

Squaramide-directed Cooperative One-dimensional Assembly in Telechelic Polydimethylsiloxane for Hierarchical Network Formation

Advances in Polymer-based Circularly Polarized Luminescent Materials

Preparation and Chiral Recognition Ability of Crystalline Cellulose Phenylcarbamate