CAS Key Laboratory of Soft Matter Chemistry, Collaborative Innovation Center of Chemistry for Energy Materials, School of Chemistry and Material Science, University of Science and Technology of China, Hefei 230026, China
Poly(2,6-dimethyl-1,4-phenylene oxide) was tethered with a 1,5-disubstituted tetrazole through a quaternary ammonium linkage. The formation of a tetrazole-ion network in the resulting polymers was found to promote the hydroxide ion transport through the Grotthus-type mechanism.
Borup R, Meyers J, Pivovar B, Kim Y S, Mukundan R, Garland N, Myers D, Wilson M, Garzon F, Wood D, et al.. Scientific aspects of polymer electrolyte fuel cell durability and degradation. Chemical Reviews, 2007, 107(10): 3904–3951 https://doi.org/10.1021/cr050182l
2
McLean G F, Niet T, Prince-Richard S, Djilali N. An assessment of alkaline fuel cell technology. International Journal of Hydrogen Energy, 2002, 27(5): 507–526 https://doi.org/10.1016/S0360-3199(01)00181-1
3
Gair S, Cruden A, McDonald J, Hegarty T, Chesshire M. Fuel cells for power generation and waste treatment. Journal of Power Sources, 2006, 154(2): 472–478 doi:10.1016/j.jpowsour.2005.10.075
4
Varcoe J R, Slade R C T. Prospects for alkaline anion-exchange membranes in low temperature fuel cells. Fuel Cells (Weinheim), 2005, 5(2): 187–200 https://doi.org/10.1002/fuce.200400045
5
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. Energy & Environmental Science, 2014, 7(10): 3135–3191 https://doi.org/10.1039/C4EE01303D
6
Merle G, Wessling M, Nijmeijer K. Anion exchange membranes for alkaline fuel cells: A review. Journal of Membrane Science, 2011, 377(1-2): 1–35 https://doi.org/10.1016/j.memsci.2011.04.043
7
Pan J, Chen C, Li Y, Wang L, Tan L, Li G, Tang X, Xiao L, Lu J, Zhuang L. Constructing ionic highway in alkaline polymer electrolytes. Energy & Environmental Science, 2014, 7(1): 354–360 https://doi.org/10.1039/C3EE43275K
8
Li N, Yan T, Li Z, Thurn-Albrecht T, Binder W H. Comb-shaped polymers to enhance hydroxide transport in anion exchange membranes. Energy & Environmental Science, 2012, 5(7): 7888–7892 https://doi.org/10.1039/c2ee22050d
9
Li N, Leng Y, Hickner M A, Wang C Y. Highly stable, anion conductive, comb-shaped copolymers for alkaline fuel cells. Journal of the American Chemical Society, 2013, 135(27): 10124–10133 https://doi.org/10.1021/ja403671u
10
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. Chemical Communications, 2014, 50(21): 2791–2793 https://doi.org/10.1039/c3cc47897a
11
Ran J, Wu L, Wei B, Chen Y, Xu T. Simultaneous enhancements of conductivity and stability for anion exchange membranes (AEMs) through precise structure design. Scientific Reports, 2014, 4(1): 6486 https://doi.org/10.1038/srep06486
12
Ran J, Wu L, Xu T. Enhancement of hydroxide conduction by self-assembly in anion conductive comb-shaped copolymers. Polymer Chemistry, 2013, 4(17): 4612–4620 https://doi.org/10.1039/c3py00421j
13
Yang Z, Guo R, Malpass-Evans R, Carta M, McKeown N B, Guiver M D, Wu L, Xu T. Highly conductive anion-exchange membranes from microporous Troger’s base polymers. Angewandte Chemie International Edition in English, 2016, 55(38): 11499–11502 https://doi.org/10.1002/anie.201605916
14
Hickner M A, Herring A M, Coughlin E B. Anion exchange membranes: Current status and moving forward. Journal of Polymer Science. Part B, Polymer Physics, 2013, 51(24): 1727–1735 https://doi.org/10.1002/polb.23395
15
He Y, Pan J, Wu L, Zhu Y, Ge X, Ran J, Yang Z, Xu T. A novel methodology to synthesize highly conductive anion exchange membranes. Scientific Reports, 2015, 5(1): 13417 https://doi.org/10.1038/srep13417
16
Si J, Lu S, Xu X, Peng S, Xiu R, Xiang Y. A gemini quaternary ammonium poly(ether ether ketone) anion-exchange membrane for alkaline fuel cell: Design, synthesis, and properties. ChemSusChem, 2014, 7(12): 3389–3395 https://doi.org/10.1002/cssc.201402664
17
Pan J, Zhu L, Han J, Hickner M A. Mechanically tough and chemically stable anion exchange membranes from rigid-flexible semi-interpenetrating networks. Chemistry of Materials, 2015, 27(19): 6689–6698 https://doi.org/10.1021/acs.chemmater.5b02557
18
Ran J, Wu L, Ge Q, Chen Y, Xu T. High performance anion exchange membranes obtained through graft architecture and rational cross-linking. Journal of Membrane Science, 2014, 470: 229–236 https://doi.org/10.1016/j.memsci.2014.07.036
19
Wu L, Pan Q, Varcoe J R, Zhou D, Ran J, Yang Z, Xu T. Thermal crosslinking of an alkaline anion exchange membrane bearing unsaturated side chains. Journal of Membrane Science, 2015, 490: 1–8 https://doi.org/10.1016/j.memsci.2015.04.046
20
Li N, Wang L, Hickner M. Cross-linked comb-shaped anion exchange membranes with high base stability. Chemical Communications, 2014, 50(31): 4092–4095 https://doi.org/10.1039/c3cc49027k
21
Zhang M, Liu J, Wang Y, An L, Guiver M D, Li N. Highly stable anion exchange membranes based on quaternized polypropylene. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2015, 3(23): 12284–12296 https://doi.org/10.1039/C5TA01420D
22
Yang Z, Zhou J, Wang S, Hou J, Wu L, Xu T. A strategy to construct alkali-stable anion exchange membranes bearing ammonium groups via flexible spacers. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2015, 3(29): 15015–15019 https://doi.org/10.1039/C5TA02941D
23
Han J, Peng H, Pan J, Wei L, Li G, Chen C, Xiao L, Lu J, Zhuang L. Highly stable alkaline polymer electrolyte based on a poly(ether ether ketone) backbone. ACS Applied Materials & Interfaces, 2013, 5(24): 13405–13411 https://doi.org/10.1021/am4043257
24
Gu S, Skovgard J, Yan Y S. Engineering the Van der Waals interaction in cross-linking-free hydroxide exchange membranes for low swelling and high conductivity. ChemSusChem, 2012, 5(5): 843–848 https://doi.org/10.1002/cssc.201200057
25
Li N, Guiver M D, Binder W H. Towards high conductivity in anion-exchange membranes for alkaline fuel cells. ChemSusChem, 2013, 6(8): 1376–1383 https://doi.org/10.1002/cssc.201300320
26
Song M K, Li H, Li J, Zhao D, Wang J, Liu M. Tetrazole-based, anhydrous proton exchange membranes for fuel cells. Advanced Materials, 2014, 26(8): 1277–1282 https://doi.org/10.1002/adma.201304121
Karaghiosoff K, Klapötke T M, Mayer P, Sabaté C M, Penger A, Welch J M. Salts of methylated 5-aminotetrazoles with energetic anions. Inorganic Chemistry, 2008, 47(3): 1007–1019 https://doi.org/10.1021/ic701832z
29
Klapötke T M, Miró Sabaté C, Penger A, Rusan M, Welch J M. Energetic salts of low-symmetry methylated 5-aminotetrazoles. European Journal of Inorganic Chemistry, 2009, 2009(7): 880–896 https://doi.org/10.1002/ejic.200800995
30
Lu D, Winter C H. Complexes of the [K(18-Crown-6)]+ fragment with bis(tetrazolyl)borate ligands: unexpected boron-nitrogen bond isomerism and associated enforcement of k3-N,N′,H-ligand chelation. Inorganic Chemistry, 2010, 49(13): 5795–5797 https://doi.org/10.1021/ic100959j
31
Allen F H, Groom C R, Liebeschuetz J W, Bardwell D A, Olsson T S G, Wood P A. The hydrogen bond environments of 1H-tetrazole and tetrazolate rings: The structural basis for tetrazole-carboxylic acid bioisosterism. Journal of Chemical Information and Modeling, 2012, 52(3): 857–866 https://doi.org/10.1021/ci200521k
32
Tsarevsky N V, Bernaerts K V, Dufour B, Du Prez F E, Matyjaszewski K. Well-defined (Co)polymers with 5-vinyltetrazole units via combination of atom transfer radical (Co)polymerization of acrylonitrile and “click chemistry”-type postpolymerization modification. Macromolecules, 2004, 37(25): 9308–9313 https://doi.org/10.1021/ma048207q
33
Tsai T H, Maes A M, Vandiver M A, Versek C, Seifert S, Tuominen M, Liberatore M W, Herring A M, Coughlin E B. Synthesis and structure-conductivity relationship of polystyrene-block-poly(vinyl benzyl trimethylammonium) for alkaline anion exchange membrane fuel cells. Journal of Polymer Science. Part B, Polymer Physics, 2013, 51(24): 1751–1760 https://doi.org/10.1002/polb.23170
34
Xing B, Savadogo O. Hydrogen/oxygen polymer electrolyte membrane fuel cells (PEMFCs) based on alkaline-doped polybenzimidazole (PBI). Electrochemistry Communications, 2000, 2(10): 697–702 https://doi.org/10.1016/S1388-2481(00)00107-7