Benzimidazolium Functionalized Polysulfone-based Anion Exchange Membranes with Improved Alkaline Stability
- Corresponding author: Gao-Hong He, hgaohong@dlut.edu.cn
Citation:
Yu Pan, Ting-Yun Wang, Xiao-Ming Yan, Xiao-Wei Xu, Qi-Dong Zhang, Bao-Lin Zhao, Issam El Hamouti, Ce Hao, Gao-Hong He. Benzimidazolium Functionalized Polysulfone-based Anion Exchange Membranes with Improved Alkaline Stability[J]. Chinese Journal of Polymer Science,
;2018, 36(1): 129-138.
doi:
10.1007/s10118-018-2049-3
Steele B. C. H., Heinzel A.. Materials for fuel-cell technologies[J]. Nature, 2001,414(6816):345-352.
Carrette L., Friedrich K. A., Stimming U.. Fuel cells-fundamentals and applications[J]. Fuel Cells, 2001,1(1):5-39. doi: 10.1002/(ISSN)1615-6854
Mehta V., Cooper J. S.. Review and analysis of PEM fuel cell design and manufacturing[J]. J. Power Sources, 2003,114(1):32-53. doi: 10.1016/S0378-7753(02)00542-6
Zhang S. H., Zhou J., Jian X. G.. Synthesis and properties of sulfonated poly(ether ketone)s containing 3, 5-dimethyl phthalazinone moieties as proton exchange membrane materials[J]. Chinese J. Polym. Sci., 2012,30(4):511-519. doi: 10.1007/s10118-012-1129-z
Lei R., Kang C. Q., Huang Y. J., Qiu X. P., Ji X. L., Xing W., Gao L. X.. Sulfonated polyimides containing pyridine groups as proton exchange membrane materials[J]. Chinese J. Polym. Sci., 2011,29(5):532-539. doi: 10.1007/s10118-011-1063-5
Borup R., Meyers J., Pivovar B., Kim Y. S., Mukundan M., Garland N., Myers D., Wilson M., Garzon F., Wood D., Zelenay P., More K., Stroh K., Zawodzinski T., Boncella J., McGrath J. E., Inaba M., Miyatake K., Hori M., Ota K., Ogumi Z., Miyata S., Nishikata A., Siroma Z., Uchimoto Y., Yasuda K., Kimijima K., Iwashita N.. Scientific aspects of polymer electrolyte fuel cell durability and degradation[J]. Chem. Rev., 2007,107(10):3904-3951. doi: 10.1021/cr050182l
Varcoe J. R., Slade R. C. T.. Prospects for alkaline anion-exchange membranes in low temperature fuel cells[J]. Fuel Cells, 2005,5(2):187-200. doi: 10.1002/fuce.v5:2
Tanaka M., Fukasawa K., Nishino E., Yamaguchi S., Yamada K., Tanaka H., Bae B., Miyatake K., Watanabe M.. Anion conductive block poly(arylene ether)s:synthesis, properties, and application in alkaline fuel cells[J]. J. Am. Chem. Soc., 2011,133(27):10646-10654. doi: 10.1021/ja204166e
Gu S., Cai R., Yan Y. S.. Self-crosslinking for dimensionally stable and solvent-resistant quaternary phosphonium based hydroxide exchange membranes[J]. Chem. Commun., 2011,47:2856-2858. doi: 10.1039/c0cc04335d
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., Zhuang L.. Anion-exchange membranes in electrochemical energy systems[J]. Energy Environ. Sci., 2014,7:3135-3191. doi: 10.1039/C4EE01303D
Wang Y. J., Qiao J., Baker R., Zhang J.. Alkaline polymer electrolyte membranes for fuel cell applications[J]. Chem. Soc. Rev., 2013,42:5768-5787. doi: 10.1039/c3cs60053j
Li Q., Liu L., Miao Q., Jin B., Bai R.. A novel poly(2, 6-dimethyl-1, 4-phenylene oxide) with trifunctional ammonium moieties for alkaline anion exchange membranes[J]. Chem. Commun., 2014,50:2791-2793. doi: 10.1039/c3cc47897a
Zhu L., Zimudzi T. J., Li N., Pan J., Lin B., Hickner M. A.. Crosslinking of comb-shaped polymer anion exchange membranes via thiol-ene click chemistry[J]. Polym. Chem., 2016,7:2464-2475. doi: 10.1039/C5PY01911G
Edson J. B., Macomber C. S., Pivovar B. S., Boncella J. M.. Hydroxide based decomposition pathways of alkyltrimethylammonium cations[J]. J. Membr. Sci., 2012,399:49-59.
Mohanty A. D., Bae C.. Mechanistic analysis of ammonium cation stability for alkaline exchange membrane fuel cells[J]. J. Mater. Chem. A, 2014,2:17314-17320. doi: 10.1039/C4TA03300K
Cheng J., Yang G., Zhang K., He G., Jia J., Yu H., Gai F., Li L., Hao C., Zhang F.. Guanidimidazole-quanternized and cross-linked alkaline polymer electrolyte membrane for fuel cell application[J]. J. Membr. Sci., 2016,501:100-108. doi: 10.1016/j.memsci.2015.12.012
Zhang B., Gu S., Wang J., Liu Y., Herring A. M., Yan Y.. Tertiary sulfonium as a cationic functional group for hydroxide exchange membranes[J]. RSC Adv., 2012,2:12683-12685. doi: 10.1039/c2ra21402d
Vöge A., Deimede V., Kallitsis J. K.. Synthesis and properties of alkaline stable pyridinium containing anion exchange membranes[J]. RSC Adv., 2014,4:45040-45049. doi: 10.1039/C4RA07616H
Kim D. S., Fujimoto C. H., Hibbs M. R., Labouriau A., Choe Y. K., Kim Y. S.. Resonance stabilized perfluorinated ionomers for alkaline membrane fuel cells[J]. Macromolecules, 2013,46(19):7826-7833. doi: 10.1021/ma401568f
Liu L., Li Q., Dai J., Wang H., Jin B., Bai R.. A facile strategy for the synthesis of guanidinium-functionalized polymer as alkaline anion exchange membrane with improved alkaline stability[J]. J. Membr. Sci., 2014,453:52-60. doi: 10.1016/j.memsci.2013.10.054
Chen Y., Tao Y., Wang J., Yang S., Cheng S., Wei H., Ding Y.. Comb-shaped guanidinium functionalized poly(ether sulfone)s for anion exchange membranes:effects of the spacer types and lengths[J]. J. Polym. Sci., Part A:Polym. Chem., 2017,55(8):1313-1321. doi: 10.1002/pola.v55.8
Ye Y., Stokes K. K., Beyer F. L., Elabd Y. A.. Development of phosphonium-based bicarbonate anion exchange polymer membranes[J]. J. Membr. Sci., 2013,443:93-99. doi: 10.1016/j.memsci.2013.04.053
Jangu C., Long T. E.. Phosphonium cation-containing polymers:from ionic liquids to polyelectrolytes[J]. Polymer, 2014,55(16):3298-3304. doi: 10.1016/j.polymer.2014.04.015
Liu Y., Zhang B. Z., Kinsinger C. L., Yang Y., Seifert S., Yan Y., Maupin C. M., Liberatore M. W., Herring A. M.. Anion exchange membranes composed of a poly(2, 6-dimethyl-1, 4-phenylene oxide) random copolymer functionalized with a bulky phosphonium cation[J]. J. Membr. Sci., 2016,506:50-59. doi: 10.1016/j.memsci.2016.01.042
Lin X., Varcoe J. R., Poynton S. D., Liang X., Ong A. L., Ran J., Li Y., Xu T.. Alkaline polymer electrolytes containing pendant dimethylimidazolium groups for alkaline membrane fuel cells[J]. J. Mater. Chem. A, 2013,1:7262-7269. doi: 10.1039/c3ta10308k
Rao A. H. N., Nam S., Kim T. H.. Comb-shaped alkyl imidazolium-functionalized poly(arylene ether sulfone)s as high performance anion-exchange membranes[J]. J. Mater. Chem. A, 2015,3:8571-8580. doi: 10.1039/C5TA01123J
Gao, He, Pan, Zhao, Xu, Liu, Deng, Y, X. Poly(2, 6-dimethyl-1, 4-phenylene oxide) containing imidazolium-terminated long side chains as hydroxide exchange membranes with improved conductivity[J]. J. Membr. Sci., 2016,518:159-167. doi: 10.1016/j.memsci.2016.07.012
Zhang F., Zhang H., Qu C.. Imidazolium functionalized polysulfone anion exchange membrane for fuel cell application[J]. J. Mater. Chem., 2011,21:12744-12752. doi: 10.1039/c1jm10656b
Lin B., Dong H., Li Y., Si Z., Gu F., Yan F.. Alkaline stable C2-substituted Imidazolium-based anion-exchange membranes[J]. Chem. Mater., 2013,25(9):1858-1867. doi: 10.1021/cm400468u
Hugar K. M., Kostalik H. A., Coates G. W.. Imidazolium cations with exceptional alkaline stability:a systematic study of structure-stability relationships[J]. J. Am. Chem. Soc., 2015,137(27):8730-8737. doi: 10.1021/jacs.5b02879
Thomas O. D., Soo K. J. W. Y., Peckham T. J., Kulkarni M. P., Holdcroft S.. Anion conducting poly(dialkyl benzimidazolium) salts[J]. Polym. Chem., 2011,2:1641-1643. doi: 10.1039/c1py00142f
Thomas O. D., Soo K. J. W. Y., Peckham T. J., Kulkarni M. P., Holdcroft S.. A stable hydroxide-conducting polymer[J]. J. Am. Chem. Soc., 2012,134(26):10753-10756. doi: 10.1021/ja303067t
Wright A. G., Weissbach T., Holdcroft S.. Poly(phenylene) and m-terphenyl as powerful protecting groups for the preparation of stable organic hydroxides[J]. Angew. Chem. Int. Ed., 2016,55(15):4818-4821. doi: 10.1002/anie.201511184
Wright A. G., Holdcroft S.. Hydroxide-stable ionenes[J]. ACS Macro Lett., 2014,3(5):444-447. doi: 10.1021/mz500168d
Lin X., Liang X., Poynton S. D., Varcoe J. R., Ong A. L., Ran J., Li Y., Li Q., Xu T.. Novel alkaline anion exchange membranes containing pendant benzimidazolium groups for alkaline fuel cells[J]. J. Membr. Sci., 2013,443:193-200. doi: 10.1016/j.memsci.2013.04.059
Warshawsky A., Deshe A.. Halomethyl octyl ethers:Convenient halomethylation reagents.[J]. J. Polym. Sci., Part A:Polym. Chem., 1985,23(6):1839-1841. doi: 10.1002/pol.1985.170230623
Pilarski B.. A new method for N-alkylation of imidazoles and benzimidazoles[J]. Liebigs Ann. Chem., 1983,6(15):1078-1080.
Xu L., Huang Z. H., Sandoval C. A., Gu L. Q., Huang Z. S.. Asymmetric hydrogenation of 3, 5-bistrifluoromethyl acetophenone in pilot scale with industrially viable ru/diphosphine-benzimidazole complexes[J]. Org. Process Res. Dev., 2014,18(9):1137-1141. doi: 10.1021/op500148k
Weinberger L., Day A. R.. Syntheses of dimethoxybenzimidazoles, dihydroxybenzimidazoles and imidazo-p-benzoquinones[J]. J. Org. Chem., 1959,24(10):1451-1455. doi: 10.1021/jo01092a017
Skibo E. B.. Studies of extended quinone methides[J]. The hydrolysis mechanism of 1-methyl-2-(bromomethyl)-4, 7-dihydroxybenzimidazole. J. Org. Chem., 1986,51(4):522-527.
Yan X., Gao L., Zheng W., Ruan X., Zhang C., Wu X., He G.. Long-spacer-chain imidazolium functionalized poly(ether ether ketone) as hydroxide exchange membrane for fuel cell[J]. Int. J. Hydrogen Energy, 2016,41(33):14982-14990. doi: 10.1016/j.ijhydene.2016.06.030
Zhao, B. ; He, G. ; El Hamouti, I. ; Gao, L. ; Liu, Y. ; Deng, R. ; Yan, X. Int. J. Hydrogen Energy 2017, DOI: 10.1016/j.ijhydene.2017.01.170
G u, S. He G., Wu X., Li C., Liu H., Lin C., Li X.. Synthesis and characteristics of sulfonated poly(phthalazinone ether sulfone ketone) (SPPESK) for direct methanol fuel cell (DMFC)[J]. J. Membr. Sci., 2006,281:121-129. doi: 10.1016/j.memsci.2006.03.021
Wang J., Li S., Zhang S.. Novel hydroxide-conducting polyelectrolyte composed of an poly(arylene ether sulfone) containing pendant quaternary guanidinium groups for alkaline fuel cell applications[J]. Macromolecules, 2010,43(8):3890-3896. doi: 10.1021/ma100260a
Lin B., Qiu L., Lu J., Yan F.. Cross-linked alkaline ionic liquid-based polymer electrolytes for alkaline fuel cell applications[J]. Chem. Mater., 2010,22(24):6718-6725. doi: 10.1021/cm102957g
Pernpointner. M., Hashmi A. S. K. Fully relativistic, comparative investigation of gold and platinum alkyne complexes of relevance for the catalysis of nucleophilic additions to alkynes[J]. J. Chem. Theory Comput., 2009,5(10):2717-2725. doi: 10.1021/ct900441f
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