碱性阴离子交换膜的碱稳定性
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摘要
碱性阴离子交换膜(AEMs)是碱性阴离子交换膜燃料电池的核心部件之一,目前已成为制约碱性阴离子交换膜燃料电池发展的关键因素.离子传导基团在碱性条件下,容易受到氢氧根离子的攻击发生降解.本文主要从以下3个方面介绍了近期AEMs在耐碱稳定性方面的研究成果:(1)开发稳定的离子传导基团,并通过提高离子传导基团的电子密度和增大缺电子位置的空间位阻提高离子基团的稳定性;(2)在离子传导基团与聚合物主链之间引入长烷基侧链;(3)合成不含醚氧键的聚合物主链,改善AEMs的耐碱稳定性.
Anion exchange membrane fuel cells(AEMFCs) are attractive alternatives to proton exchange membrane fuel cells due to using non-noble metal catalysts and faster cathode reaction kinetics. Anion exchange membranes(AEMs) are one of the key materials composed of AEMFCs. The hydroxide conductivity of AEMs has been able to meet operating requirements of fuel cells. Although the hydroxide conductivity is no longer a problem, the stability of AEMs is still a notable challenge. This work mainly introduces the development of alkaline stability of AEMs. AEMs mainly consist of functional groups, side chains and polymer backbones. The degradation of functional groups causes by attacking of hydroxide ion through Hofmann elimination, nucleophilic substitution and ylide-intermediate degradation pathways. Numerous functional groups have been developed in order to improve the alkaline stability of AEMs. The introductions of appropriate electron donors and steric shielding are effective ways to weaken the attack of hydroxide ion. Developing new functional groups is a very important way. In addition, the development of novel stable groups is an important way for long-lived AEMs. For example, hetero-cycloaliphatic quaternary ammonium cations(QAs) are proved to be especially stable in both model compound studies and even AEM studies. The most commonly studied AEMs were synthesized by chloromethylation/bromination of the aromatic backbones, followed by a Menshutkin reaction to introduce QAs. Benzylic groups, electron-withdrawing groups, are prone to degrade by nucleophilic substitution on the benzylic carbon/α-carbon, Hofmann elimination and N-ylide intermediate formation in the presence of hydroxide ion. Therefore, the tethering linkage between the polymer backbone and functional groups is quite important. Recent studies have mainly introduced long side chains between functional groups and polymer backbones, leaving functional groups away from the benzene ring of the polymer backbone. The all-alkyl, amineand ether-containing branched-chain structures are proved to be stable. Poly(arylene ether)s have been extensively studied in AEMs due to the advantages of good thermal stability, high mechanical property and easy modification. Frequently employed polyaromatic electrolytes are quaternized poly(aryl ether sulfone)s, which are prepared via the nucleophilic polycondensation reaction. The introduction of functional groups leads to degrade of these main chains containing aryl ether bonds, which are unable to avoid in the polycondensation reaction. It is necessary that main chains are devoid of aryl ether bonds so as to develop AEMs with excellent alkaline stability. Diels-Alder reaction, coupling reaction and acid-catalyzed Friedel-Craft polycondensation are effective methods for synthesizing aromatic backbones devoid of aryl ether bonds. In addition, aliphatic backbones, such as poly(ethylene-co-tetrafluoroethylene), are proved to have good stability in alkaline conditions, so its modification for AEMs has also become an important research direction. At present, the alkaline stability of AEMs has made great progress. Three major aspects have been studied in an effort to develop stable AEMs:(1) screening stable functional groups such as five-or six-membered cyclic amines, substituted imidazoles;(2) developing effective linkages between functional groups and polymer backbones;(3) designing aryl ether-free aromatic backbones and stable aliphatic backbones. The designed AEMs can remain for hundreds of hours without degradation in alkaline solution, which is a significant advancement in increasing alkaline stability of AEMs.
Anion exchange membrane fuel cells(AEMFCs) are attractive alternatives to proton exchange membrane fuel cells due to using non-noble metal catalysts and faster cathode reaction kinetics. Anion exchange membranes(AEMs) are one of the key materials composed of AEMFCs. The hydroxide conductivity of AEMs has been able to meet operating requirements of fuel cells. Although the hydroxide conductivity is no longer a problem, the stability of AEMs is still a notable challenge. This work mainly introduces the development of alkaline stability of AEMs. AEMs mainly consist of functional groups, side chains and polymer backbones. The degradation of functional groups causes by attacking of hydroxide ion through Hofmann elimination, nucleophilic substitution and ylide-intermediate degradation pathways. Numerous functional groups have been developed in order to improve the alkaline stability of AEMs. The introductions of appropriate electron donors and steric shielding are effective ways to weaken the attack of hydroxide ion. Developing new functional groups is a very important way. In addition, the development of novel stable groups is an important way for long-lived AEMs. For example, hetero-cycloaliphatic quaternary ammonium cations(QAs) are proved to be especially stable in both model compound studies and even AEM studies. The most commonly studied AEMs were synthesized by chloromethylation/bromination of the aromatic backbones, followed by a Menshutkin reaction to introduce QAs. Benzylic groups, electron-withdrawing groups, are prone to degrade by nucleophilic substitution on the benzylic carbon/α-carbon, Hofmann elimination and N-ylide intermediate formation in the presence of hydroxide ion. Therefore, the tethering linkage between the polymer backbone and functional groups is quite important. Recent studies have mainly introduced long side chains between functional groups and polymer backbones, leaving functional groups away from the benzene ring of the polymer backbone. The all-alkyl, amineand ether-containing branched-chain structures are proved to be stable. Poly(arylene ether)s have been extensively studied in AEMs due to the advantages of good thermal stability, high mechanical property and easy modification. Frequently employed polyaromatic electrolytes are quaternized poly(aryl ether sulfone)s, which are prepared via the nucleophilic polycondensation reaction. The introduction of functional groups leads to degrade of these main chains containing aryl ether bonds, which are unable to avoid in the polycondensation reaction. It is necessary that main chains are devoid of aryl ether bonds so as to develop AEMs with excellent alkaline stability. Diels-Alder reaction, coupling reaction and acid-catalyzed Friedel-Craft polycondensation are effective methods for synthesizing aromatic backbones devoid of aryl ether bonds. In addition, aliphatic backbones, such as poly(ethylene-co-tetrafluoroethylene), are proved to have good stability in alkaline conditions, so its modification for AEMs has also become an important research direction. At present, the alkaline stability of AEMs has made great progress. Three major aspects have been studied in an effort to develop stable AEMs:(1) screening stable functional groups such as five-or six-membered cyclic amines, substituted imidazoles;(2) developing effective linkages between functional groups and polymer backbones;(3) designing aryl ether-free aromatic backbones and stable aliphatic backbones. The designed AEMs can remain for hundreds of hours without degradation in alkaline solution, which is a significant advancement in increasing alkaline stability of AEMs.
引文
1 Liu J G,Sun G Q.A survey of fuel cells(in Chinese).Physics,2004,33:70-84[刘建国,孙公权.燃料电池概述.物理,2004,33:70-84]
2 Yu H M,Yi B L.Current status of vehicle fuel cells and electrocatalysis(in Chinese).Sci Sin Chim,2012,42:480-494[俞红梅,衣宝廉.车用燃料电池现状与电催化.中国科学:化学,2012,42:480-494]
3 Zhuang L.Alkaline polymer electrolyte fuel cells completely free from noble metal catalysts(in Chinese).China Basic Sci,2009,6:28-29[庄林.完全不使用贵金属催化剂的聚合物电解质燃料电池.中国基础科学,2009,6:28-29]
4 Couture G,Alaaeddine A,Boschet F,et al.Polymeric materials as anion-exchange membranes for alkaline fuel cells.Prog Polym Sci,2011,36:1521-1557
5 Shin D W,Guiver M D,Lee Y M.Hydrocarbon-based polymer electrolyte membranes:Importance of morphology on ion transport and membrane stability.Chem Rev,2017,117:4759-4805
6 Gottesfeld S,Dekel D R,Page M,et al.Anion exchange membrane fuel cells:Current status and remaining challenges.J Power Sources,2018,375:170-184
7 Arges C,Zhang L.Anion exchange membranes’evolution towards high hydroxide ion conductivity and alkaline resiliency.ACS Appl Energy Mater,2018,1:2991-3012
8 Ge Q Q,Ran J,Miao J B,et al.Click chemistry finds its way in constructing an ionic highway in anion-exchange membrane.ACS Appl Mater Interfaces,2015,7:28545-28553
9 He S,Liu L,Wang X,et al.Azide-assisted self-crosslinking of highly ion conductive anion exchange membranes.J Membrane Sci,2016,509:48-56
10 Dong X,Xue B X,Qian H D,et al.Novel quaternary ammonium microblock poly(p-phenylene-co-aryl ether ketone)s as anion exchange membranes for alkaline fuel cells.J Power Sources,2017,342:605-615
11 Wu X,Chen W,Yan X,et al.Enhancement of hydroxide conductivity by the di-quaternization strategy for poly(ether ether ketone)based anion exchange membranes.J Mater Chem A,2014,2:12222-12231
12 Chen W T,Hu M M,Wang H C,et al.Dimensionally stable hexamethylenetetramine functionalized polysulfone anion exchange membranes.J Mater Chem A,2017,5:15038-15047
13 Li X H,Yu Y F,Liu Q F,et al.Synthesis and characterization of anion exchange membranes based on poly(arylene ether sulfone)s containing various cations functioned tetraphenyl methane moieties.Int J Hydrogen Energy,2013,38:11067-11073
14 Pan J,Chen C,Li Y,et al.Constructing ionic highway in alkaline polymer electrolytes.Energy Environ Sci,2014,7:354-360
15 Hugar K M,Kostalik H A T,Coates G W.Imidazolium cations with exceptional alkaline stability:A systematic study of structure-stability relationships.J Am Chem Soc,2015,137:8730-8737
16 Liu Y,Wang J,Yang Y,et al.Anion transport in a chemically stable,sterically bulkyα-C modified imidazolium functionalized anion exchange membrane.J Phys Chem C,2014,118:15136-15145
17 Wang J,Wei H,Yang S,et al.Constructing pendent imidazolium-based poly(phenylene oxide)s for anion exchange membranes using a click reaction.RSC Adv,2015,5:93415-93422
18 Si Z H,Sun Z,Gu F L,et al.Alkaline stable imidazolium-based ionomers containing poly(arylene ether sulfone)side chains for alkaline anion exchange membranes.J Mater Chem A,2014,2:4413-4421
19 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.Macromolecules,2010,43:3890-3896
20 Cheng J,Yang G Q,Zhang K B,et al.Guanidimidazole-quanternized and cross-linked alkaline polymer electrolyte membrane for fuel cell application.J Membr Sci,2016,501:100-108
21 Qu C,Zhang H M,Zhang F X,et al.A high-performance anion exchange membrane based on bi-guanidinium bridged polysilsesquioxane for alkaline fuel cell application.J Mater Chem,2012,22:8203-8207
22 Gu S,Cai R,Luo T,et al.A soluble and highly conductive ionomer for high-performance hydroxide exchange membrane fuel cells.Angew Chem Int Ed,2009,48:6499-6502
23 Zhang B Z,Gu S,Wang J H,et al.Tertiary sulfonium as a cationic functional group for hydroxide exchange membranes.RSC Adv,2012,2:12683-12685
24 Gu S,Wang J,Kaspar R B,et al.Permethyl cobaltocenium(Cp*2Co+)as an ultra-stable cation for polymer hydroxide-exchange membranes.Sci Rep,2015,5:11668
25 Zha Y P,Disabb-Miller M L,Johnson Z D,et al.Metal-cation-based anion exchange membranes.J Am Chem Soc,2012,134:4493-4496
26 Ge X,He Y,Guiver M D,et al.Alkaline anion-exchange membranes containing mobile ion shuttles.Adv Mater,2016,28:3467-3472
27 Si Z H,Qiu L H,Dong H L,et al.Effects of substituents and substitution positions on alkaline stability of imidazolium cations and their corresponding anion-exchange membranes.ACS Appl Mater Interfaces,2014,6:4346-4355
28 Wright A G,Weissbach T,Holdcroft S.Poly(phenylene)and m-terphenyl as powerful protecting groups for the preparation of stable organic hydroxides.Angew Chem Int Ed,2016,55:4818-4821
29 Marino M G,Kreuer K D.Alkaline stability of quaternary ammonium cations for alkaline fuel cell membranes and ionic liquids.ChemSusChem,2015,8:513-523
30 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
31 Pan Y,Zhang Q D,Yan X M,et al.Hydrophilic side chain assisting continuous ion-conducting channels for anion exchange membranes.J Membr Sci,2018,552:286-294
32 Yan X M,Deng R L,Pan Y,et al.Improvement of alkaline stability for hydroxide exchange membranes by the interactions between strongly polar nitrile groups and functional cations.J Membr Sci,2017,533:121-129
33 Gao L,He G,Pan Y,et al.Poly(2,6-dimethyl-1,4-phenylene oxide)containing imidazolium-terminated long side chains as hydroxide exchange membranes with improved conductivity.J Membr Sci,2016,518:159-167
34 Yan X,Gao L,Zheng W,et al.Long-spacer-chain imidazolium functionalized poly(ether ether ketone)as hydroxide exchange membrane for fuel cell.Int J Hydrog Energy,2016,41:14982-14990
35 Gong X,Yan X,Li T,et al.Design of pendent imidazolium side chain with flexible ether-containing spacer for alkaline anion exchange membrane.J Membr Sci,2017,523:216-224
36 Hou J,Wang X,Liu Y,et al.Wittig reaction constructed an alkaline stable anion exchange membrane.J Membr Sci,2016,518:282-288
37 Dang H S,Jannasch P.Exploring different cationic alkyl side chain designs for enhanced alkaline stability and hydroxide ion conductivity of anion-exchange membranes.Macromolecules,2015,48:5742-5751
38 Lin B,Qiu L,Qiu B,et al.A soluble and conductive polyfluorene ionomer with pendant imidazolium groups for alkaline fuel cell applications.Macromolecules,2011,44:9642-9649
39 You W,Hugar K M,Coates G W.Synthesis of alkaline anion exchange membranes with chemically stable imidazolium cations:Unexpected cross-linked macrocycles from ring-fused romp monomers.Macromolecules,2018,51:3212-3218
40 Zhuo Y Z,Lai A L,Zhang Q G,et al.Enhancement of hydroxide conductivity by grafting flexible pendant imidazolium groups into poly(arylene ether sulfone)as anion exchange membranes.J Mater Chem A,2015,3:18105-18114
41 Fujimoto C,Kim D S,Hibbs M,et al.Backbone stability of quaternized polyaromatics for alkaline membrane fuel cells.J Membr Sci,2012,423:438-449
42 Arges C G,Ramani V.Two-dimensional NMR spectroscopy reveals cation-triggered backbone degradation in polysulfone-based anion exchange membranes.Proc Natl Acad Sci USA,2013,110:2490-2495
43 Mohanty A D,Tignor S E,Krause J A,et al.Systematic alkaline stability study of polymer backbones for anion exchange membrane applications.Macromolecules,2016,49:3361-3372
44 Miyanishi S,Yamaguchi T.Ether cleavage-triggered degradation of benzyl alkylammonium cations for polyethersulfone anion exchange membranes.Phys Chem Chem Phys,2016,18:12009-12023
45 Hibbs M R.Alkaline stability of poly(phenylene)-based anion exchange membranes with various cations.J Polym Sci Pol Phys,2013,51:1736-1742
46 Fan J T,Wright A G,Britton B,et al.Cationic polyelectrolytes,stable in 10 M KOHaq at 100oC.ACS Macro Lett,2017,6:1089-1093
47 Lee W H,Kim Y S,Bae C.Robust hydroxide ion conducting poly(biphenyl alkylene)s for alkaline fuel cell membranes.ACS Macro Lett,2015,4:814-818
48 Lee W H,Mohanty A D,Bae C.Fluorene-based hydroxide ion conducting polymers for chemically stable anion exchange membrane fuel cells.ACS Macro Lett,2015,4:453-457
49 Pham T H,Olsson J S,Jannasch P.N-spirocyclic quaternary ammonium ionenes for anion-exchange membranes.J Am Chem Soc,2017,139:2888-2891
50 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
51 Ponce-González J,Whelligan D K,Wang L Q,et al.High performance aliphatic-heterocyclic benzyl-quaternary ammonium radiationgrafted anion-exchange membranes.Energy Environ Sci,2016,9:3724-3735
52 Noonan K J T,Hugar K M,Kostalik H A,et al.Phosphonium-functionalized polyethylene:A new class of base-stable alkaline anion exchange membranes.J Am Chem Soc,2012,134:18161-18164
53 Zhu T Y,Xu S C,Rahman A,et al.Cationic metallo-polyelectrolytes for robust alkaline anion-exchange membranes.Angew Chem Int Ed,2018,57:2388-2392
54 Liu X,Gao H,Chen X,et al.Poly(tetrafluoroethylene-co-perfluorovinyl ether sulfonamide)for anion exchange membranes.Polym Chem,2016,7:2904-2912
55 Olsson J S,Pham T H,Jannasch P.Poly(N,N-diallylazacycloalkane)s for anion-exchange membranes functionalized with N-spirocyclic quaternary ammonium cations.Macromolecules,2017,50:2784-2793
2 Yu H M,Yi B L.Current status of vehicle fuel cells and electrocatalysis(in Chinese).Sci Sin Chim,2012,42:480-494[俞红梅,衣宝廉.车用燃料电池现状与电催化.中国科学:化学,2012,42:480-494]
3 Zhuang L.Alkaline polymer electrolyte fuel cells completely free from noble metal catalysts(in Chinese).China Basic Sci,2009,6:28-29[庄林.完全不使用贵金属催化剂的聚合物电解质燃料电池.中国基础科学,2009,6:28-29]
4 Couture G,Alaaeddine A,Boschet F,et al.Polymeric materials as anion-exchange membranes for alkaline fuel cells.Prog Polym Sci,2011,36:1521-1557
5 Shin D W,Guiver M D,Lee Y M.Hydrocarbon-based polymer electrolyte membranes:Importance of morphology on ion transport and membrane stability.Chem Rev,2017,117:4759-4805
6 Gottesfeld S,Dekel D R,Page M,et al.Anion exchange membrane fuel cells:Current status and remaining challenges.J Power Sources,2018,375:170-184
7 Arges C,Zhang L.Anion exchange membranes’evolution towards high hydroxide ion conductivity and alkaline resiliency.ACS Appl Energy Mater,2018,1:2991-3012
8 Ge Q Q,Ran J,Miao J B,et al.Click chemistry finds its way in constructing an ionic highway in anion-exchange membrane.ACS Appl Mater Interfaces,2015,7:28545-28553
9 He S,Liu L,Wang X,et al.Azide-assisted self-crosslinking of highly ion conductive anion exchange membranes.J Membrane Sci,2016,509:48-56
10 Dong X,Xue B X,Qian H D,et al.Novel quaternary ammonium microblock poly(p-phenylene-co-aryl ether ketone)s as anion exchange membranes for alkaline fuel cells.J Power Sources,2017,342:605-615
11 Wu X,Chen W,Yan X,et al.Enhancement of hydroxide conductivity by the di-quaternization strategy for poly(ether ether ketone)based anion exchange membranes.J Mater Chem A,2014,2:12222-12231
12 Chen W T,Hu M M,Wang H C,et al.Dimensionally stable hexamethylenetetramine functionalized polysulfone anion exchange membranes.J Mater Chem A,2017,5:15038-15047
13 Li X H,Yu Y F,Liu Q F,et al.Synthesis and characterization of anion exchange membranes based on poly(arylene ether sulfone)s containing various cations functioned tetraphenyl methane moieties.Int J Hydrogen Energy,2013,38:11067-11073
14 Pan J,Chen C,Li Y,et al.Constructing ionic highway in alkaline polymer electrolytes.Energy Environ Sci,2014,7:354-360
15 Hugar K M,Kostalik H A T,Coates G W.Imidazolium cations with exceptional alkaline stability:A systematic study of structure-stability relationships.J Am Chem Soc,2015,137:8730-8737
16 Liu Y,Wang J,Yang Y,et al.Anion transport in a chemically stable,sterically bulkyα-C modified imidazolium functionalized anion exchange membrane.J Phys Chem C,2014,118:15136-15145
17 Wang J,Wei H,Yang S,et al.Constructing pendent imidazolium-based poly(phenylene oxide)s for anion exchange membranes using a click reaction.RSC Adv,2015,5:93415-93422
18 Si Z H,Sun Z,Gu F L,et al.Alkaline stable imidazolium-based ionomers containing poly(arylene ether sulfone)side chains for alkaline anion exchange membranes.J Mater Chem A,2014,2:4413-4421
19 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.Macromolecules,2010,43:3890-3896
20 Cheng J,Yang G Q,Zhang K B,et al.Guanidimidazole-quanternized and cross-linked alkaline polymer electrolyte membrane for fuel cell application.J Membr Sci,2016,501:100-108
21 Qu C,Zhang H M,Zhang F X,et al.A high-performance anion exchange membrane based on bi-guanidinium bridged polysilsesquioxane for alkaline fuel cell application.J Mater Chem,2012,22:8203-8207
22 Gu S,Cai R,Luo T,et al.A soluble and highly conductive ionomer for high-performance hydroxide exchange membrane fuel cells.Angew Chem Int Ed,2009,48:6499-6502
23 Zhang B Z,Gu S,Wang J H,et al.Tertiary sulfonium as a cationic functional group for hydroxide exchange membranes.RSC Adv,2012,2:12683-12685
24 Gu S,Wang J,Kaspar R B,et al.Permethyl cobaltocenium(Cp*2Co+)as an ultra-stable cation for polymer hydroxide-exchange membranes.Sci Rep,2015,5:11668
25 Zha Y P,Disabb-Miller M L,Johnson Z D,et al.Metal-cation-based anion exchange membranes.J Am Chem Soc,2012,134:4493-4496
26 Ge X,He Y,Guiver M D,et al.Alkaline anion-exchange membranes containing mobile ion shuttles.Adv Mater,2016,28:3467-3472
27 Si Z H,Qiu L H,Dong H L,et al.Effects of substituents and substitution positions on alkaline stability of imidazolium cations and their corresponding anion-exchange membranes.ACS Appl Mater Interfaces,2014,6:4346-4355
28 Wright A G,Weissbach T,Holdcroft S.Poly(phenylene)and m-terphenyl as powerful protecting groups for the preparation of stable organic hydroxides.Angew Chem Int Ed,2016,55:4818-4821
29 Marino M G,Kreuer K D.Alkaline stability of quaternary ammonium cations for alkaline fuel cell membranes and ionic liquids.ChemSusChem,2015,8:513-523
30 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
31 Pan Y,Zhang Q D,Yan X M,et al.Hydrophilic side chain assisting continuous ion-conducting channels for anion exchange membranes.J Membr Sci,2018,552:286-294
32 Yan X M,Deng R L,Pan Y,et al.Improvement of alkaline stability for hydroxide exchange membranes by the interactions between strongly polar nitrile groups and functional cations.J Membr Sci,2017,533:121-129
33 Gao L,He G,Pan Y,et al.Poly(2,6-dimethyl-1,4-phenylene oxide)containing imidazolium-terminated long side chains as hydroxide exchange membranes with improved conductivity.J Membr Sci,2016,518:159-167
34 Yan X,Gao L,Zheng W,et al.Long-spacer-chain imidazolium functionalized poly(ether ether ketone)as hydroxide exchange membrane for fuel cell.Int J Hydrog Energy,2016,41:14982-14990
35 Gong X,Yan X,Li T,et al.Design of pendent imidazolium side chain with flexible ether-containing spacer for alkaline anion exchange membrane.J Membr Sci,2017,523:216-224
36 Hou J,Wang X,Liu Y,et al.Wittig reaction constructed an alkaline stable anion exchange membrane.J Membr Sci,2016,518:282-288
37 Dang H S,Jannasch P.Exploring different cationic alkyl side chain designs for enhanced alkaline stability and hydroxide ion conductivity of anion-exchange membranes.Macromolecules,2015,48:5742-5751
38 Lin B,Qiu L,Qiu B,et al.A soluble and conductive polyfluorene ionomer with pendant imidazolium groups for alkaline fuel cell applications.Macromolecules,2011,44:9642-9649
39 You W,Hugar K M,Coates G W.Synthesis of alkaline anion exchange membranes with chemically stable imidazolium cations:Unexpected cross-linked macrocycles from ring-fused romp monomers.Macromolecules,2018,51:3212-3218
40 Zhuo Y Z,Lai A L,Zhang Q G,et al.Enhancement of hydroxide conductivity by grafting flexible pendant imidazolium groups into poly(arylene ether sulfone)as anion exchange membranes.J Mater Chem A,2015,3:18105-18114
41 Fujimoto C,Kim D S,Hibbs M,et al.Backbone stability of quaternized polyaromatics for alkaline membrane fuel cells.J Membr Sci,2012,423:438-449
42 Arges C G,Ramani V.Two-dimensional NMR spectroscopy reveals cation-triggered backbone degradation in polysulfone-based anion exchange membranes.Proc Natl Acad Sci USA,2013,110:2490-2495
43 Mohanty A D,Tignor S E,Krause J A,et al.Systematic alkaline stability study of polymer backbones for anion exchange membrane applications.Macromolecules,2016,49:3361-3372
44 Miyanishi S,Yamaguchi T.Ether cleavage-triggered degradation of benzyl alkylammonium cations for polyethersulfone anion exchange membranes.Phys Chem Chem Phys,2016,18:12009-12023
45 Hibbs M R.Alkaline stability of poly(phenylene)-based anion exchange membranes with various cations.J Polym Sci Pol Phys,2013,51:1736-1742
46 Fan J T,Wright A G,Britton B,et al.Cationic polyelectrolytes,stable in 10 M KOHaq at 100oC.ACS Macro Lett,2017,6:1089-1093
47 Lee W H,Kim Y S,Bae C.Robust hydroxide ion conducting poly(biphenyl alkylene)s for alkaline fuel cell membranes.ACS Macro Lett,2015,4:814-818
48 Lee W H,Mohanty A D,Bae C.Fluorene-based hydroxide ion conducting polymers for chemically stable anion exchange membrane fuel cells.ACS Macro Lett,2015,4:453-457
49 Pham T H,Olsson J S,Jannasch P.N-spirocyclic quaternary ammonium ionenes for anion-exchange membranes.J Am Chem Soc,2017,139:2888-2891
50 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
51 Ponce-González J,Whelligan D K,Wang L Q,et al.High performance aliphatic-heterocyclic benzyl-quaternary ammonium radiationgrafted anion-exchange membranes.Energy Environ Sci,2016,9:3724-3735
52 Noonan K J T,Hugar K M,Kostalik H A,et al.Phosphonium-functionalized polyethylene:A new class of base-stable alkaline anion exchange membranes.J Am Chem Soc,2012,134:18161-18164
53 Zhu T Y,Xu S C,Rahman A,et al.Cationic metallo-polyelectrolytes for robust alkaline anion-exchange membranes.Angew Chem Int Ed,2018,57:2388-2392
54 Liu X,Gao H,Chen X,et al.Poly(tetrafluoroethylene-co-perfluorovinyl ether sulfonamide)for anion exchange membranes.Polym Chem,2016,7:2904-2912
55 Olsson J S,Pham T H,Jannasch P.Poly(N,N-diallylazacycloalkane)s for anion-exchange membranes functionalized with N-spirocyclic quaternary ammonium cations.Macromolecules,2017,50:2784-2793
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