Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (10): 1112-1126.DOI: 10.11944/j.issn.1000-0518.2020.10.200095
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FU Fengyan*, CHENG Jingquan, ZHANG Jie, GAO Zhihua
Received:
2020-04-01
Published:
2020-10-01
Online:
2020-09-30
Contact:
FU Fengyan, lecturer; Tel:0318-6016533; E-mail:1374195561@qq.com; Research interests:polymer chemistry
Supported by:
FU Fengyan, CHENG Jingquan, ZHANG Jie, GAO Zhihua. Recent Development in Ionic Exchange Groups-Based Anion Exchange Membrane[J]. Chinese Journal of Applied Chemistry, 2020, 37(10): 1112-1126.
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URL: http://yyhx.ciac.jl.cn/EN/10.11944/j.issn.1000-0518.2020.10.200095
[1] Merle G,Wessling M,Nijmeijer K. Anion Exchange Membranes for Alkaline Fuel Cells:A Review[J]. J Membr Sci,2011,377(1/2):1-35. [2] Matsumoto K,Fujigaya T,Yanagi H,et al. Very High Performance Alkali Anion Exchange Membrane Fuel Cell[J]. Adv Funct Mater,2011,21(6):1089-1094. [3] Kruusenberg I,Matisen L,Shah Q,et al. Non-platinum Cathode Catalysts for Alkaline Membrane Fuel Cell[J]. Int J Hydrogen Energy,2012,37(5):4406-4412. [4] Maurya S,Shin S H,Kim Y,et al. A Review on Recent Developments of Anion Exchange Membranes for Fuel Cells and Redox Flow Batteries[J]. RSC Adv,2015,5(47):37206-37230. [5] Dekel D R. Review of Cell Performance in Anion Exchange Membrane Fuel Cells[J]. J Power Sources,2018,375:158-169. [6] Meek K M,Nykaza J R,Elabd Y A. Alkaline Chemical Stability and Ion Transport in Polymerized Ionic Liquids with Various Backbones and Cations[J]. Macromolecules,2016,49(9):3382-3394. [7] Cheng J,Yang G,Zhang K,et al. Guanidimidazole Quanternized and Cross-linked Alkaline Polymer Electrolyte Membrane for Fuel Cell Application[J]. J Membr Sci,2016,501:100-108. [8] 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]. J Membr Sci,2017,523:216-224. [9] Zhang B,Kaspar R B,Gu S,et al. A New Alkali Stable Phosphonium Cation Based on Fundamental Understangding of Degradation Mechanisms[J]. ChemSusChem,2016,9(17):2374-2379. [10] Zha Y P,Disabb-Miller M L,Johnson Z D,et al. Metal-Cation-Based Anion Exchange Membranes[J]. J Am Chem Soc,2012,134(10):4493-4496. [11] Wei Y,Kevin J T N,Geoffrey W C. Alkaline-Stable Anion Exchange Membranes:A Review of Synthetic Approaches[J]. Prog Polym Sci,2020,100:101177. [12] Dong X,Hou S,Mao H,et al. Novel Hydrophilic-Hydrophobic Block Copolymer Based on Cardo Poly(arylene ether sulfone)s with Bis-Quaternary Ammonium Moieties for Anion Exchange Membranes[J]. J Membr Sci,2016,518:31-39. [13] Sun Z,Pan J,Guo J,et al. The Alkaline Stability of Anion Exchange Membrane for Fuel Cell Applications:The Effects of Alkaline Media[J]. Adv Sci,2018,5(8):1800065. [14] Edson J,Macomber C,Pivovar B,et al. Hydroxide Based Decomposition Pathways of Alkyltrimethylammonium Cations[J]. J Membr Sci,2012,399:49-59. [15] Li N,Leng Y,Hickner M A,et al. Highly Stable, Anion Conductive, Comb-Shaped Copolymers for Alkaline Fuel Cells[J]. J Am Chem Soc,2013,135(27):10124-10133. [16] Zhu L,Pan J,Christensen C M,et al. Functionalization of Poly(2,6-dimethyl-1,4-phenylene oxide)s with Hindered Fluorene Side Chains for Anion Exchange Membranes[J]. Macromolecules,2016,49(9):3300-3309. [17] Dang H S,Jannasch P. Exploring Different Cationic Alkyl Side Chain Designs for Enhanced Alkaline Stability and Hydroxide Ion Conductivity of Anion-Exchange Membranes[J]. Macromolecules,2015,48(16):5742-5751. [18] Zhang M,Shan C R,Liu L,et al. Facilitating Anion Transport in Polyolefin-Based Anion Exchange Membranes via Bulky Side Chains[J]. ACS Appl Mater Interfaces,2016,8(35):23321-23330. [19] Jeon J Y,Park S,Han J,et al. Synthesis of Aromatic Anion Exchange Membranes by Friedel-Crafts Bromoalkylation and Cross-linking of Polystyrene Block Copolymers[J]. Macromolecules,2019,52(5):2139-2147. [20] Lin B C,Xu F,Su Y,et al. Facile Preparation of Anion-Exchange Membrane Based on Polystyrene-b-Polybutadiene-b-Polystyrene for the Application of Alkaline Fuel Cells[J]. Ind Eng Chem Res,2019,58(49):22299-22305. [21] Peng J W,Liang M H,Liu Z C,et al. Poly(arylene ether sulfone) Crosslinked Networks with Pillar [5] arene Units Grafted by Multiple Long-Chain Quaternary Ammonium Salts for Anion Exchange Membranes[J]. Chem Commun,2020,56(6):928-931. [22] Fu F Y,Xu H L,Dong Y,et al. Design of Polyphosphazene-Based Graft Copolystyrenes with Alkylsulfonate Branch Chains for Proton Exchange Membranes[J]. J Membr Sci,2015,489:119-128. [23] Fu F Y,Xu H L,Dong Y,et al. Polyphosphazene-based Copolymers Containing Pendant Alkylsulfonic Acid Groups as Proton Exchange Membranes[J]. Solid State Ionics,2015,278:58-64. [24] GAO Li,WU Xuemei,YAN Xiaoming,et al. Alkali Stability of Anion Exchange Membrane[J]. Chinese Sci Bull,2019,64:145-152(in Chinese). 高莉,吴雪梅,焉晓明,等. 碱性阴离子交换膜的碱稳定性[J]. 科学通报,2019,64:145-152. [25] XUE Boxin,ZHENG Jifu,ZHANG Suobo. Advances in Alkaline Stable Guanidinium Based Anion Exchange Membranes[J]. Chinese Sci Bull,2019,64:134-144(in Chinese). 薛博欣,郑吉富,张所波. 耐碱的胍盐阴离子交换膜研究进展[J]. 科学通报,2019,64:134-144. [26] 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. [27] Lin X,Wu L,Liu Y,et al. Alkali Resistant and Conductive Guanidinium-Based Anion-Exchange Membranes for Alkaline Polymer Electrolyte Fuel Cells[J]. J Power Sources,2012,217:373-380. [28] Qu C,Zhang H,Zhang F,et al. A High-Performance Anion Exchange Membrane Based on Bi-Guanidinium Bridged Polysilsesquioxane for Alkaline Fuel Cell Application[J]. J Mater Chem,2012,22(17):8203-8207. [29] Sajjada S,HongY,Liu F. Synthesis of Guanidinium-Based Anion Exchange Membranes and Their Stability Assessment[J]. Polym Adv Technol,2014,25(1):108-116. [30] Kim D,Fujimoto C,Hibbs M,et al. Resonance Stabilized Perfluorinated Ionomers for Alkaline Membrane Fuel Cells[J]. Macromolecules,2013,46(19):7826-7833. [31] Cheng J, Yang G, Zhang K,et al. Guanidimidazole-Quanternized and Cross-linked Alkaline Polymer Electrolyte Membrane for Fuel Cell Application[J]. J Membr Sci,2016,501:100-108. [32] Xue B,Dong X,Li Y,et al. Synthesis of Novel Guanidinium-Based Anion-Exchange Membranes with Controlled Microblock Structures[J]. J Membr Sci,2017,537:151-159. [33] Xue B X,Wang F,Zheng J F,et al. Highly Stable Polysulfone Anion Exchange Membranes Incorporated with Bulky Alkyl Substituted Guanidinium Cations[J]. Mol Syst Des Eng,2019,4(5):1039-1047. [34] Xue B X,Wang Q,Zheng J F,et al. Bi-guanidinium-Based Crosslinked Anion Exchange Membranes:Synthesis, Characterization, and Properties[J]. J Membr Sci,2020,601:117923. [35] 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]. J Mater Chem A,2015,3(35):18105-18114. [36] Lee B,Yun D Y,Lee S,et al. Development of Highly Alkaline Stable OH--Conductors Based on Imidazolium Cations with Various Substituents for Anion Exchange Membrane-Based Alkaline Fuel Cells[J]. J Phys Chem C,2019,123(22):13508-13518. [37] Guo D, Lai A N, Lin C X,et al. Imidazolium-Functionalized Poly(arylene ether sulfone) Anion-Exchange Membranes Densely Grafted with Flexible Side Chains for Fuel Cells [J]. ACS Appl Mater Interfaces,2016,8(38):25279-25288. [38] Holl czki O,Terleczky P,Szieberth D,et al. Hydrolysis of Imidazole-2-ylidenes[J]. J Am Chem Soc,2011,133(4):780-789. [39] Lin B C,Dong H L,Li Y Y,et al. Alkaline Stable C2-Substituted Imidazolium-Based Anion-Exchange Membranes[J]. Chem Mater,2013,25(9):1858-1867. [40] Price S C,Williams K S,Beyer F L. Relationships Between Structure and Alkaline Stability of Imidazolium Cations for Fuel Cell Membrane Applications[J]. ACS Macro Lett,2014,3(2):160-165. [41] 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. [42] Gu F L,Dong H L,Li Y Y,et al. Highly Stable N3-Substituted Imidazolium-Based Alkaline Anion Exchange Membranes:Experimental Studies and Theoretical Calculations[J]. Macromolecules,2014,47(1):208-216. [43] Zhu Y,He Y B,Ge X L,et al. Benzyltetramethylimidazolium-Based Membrane with Exceptional Alkaline Stability in Fuel Cell:Role of Structure in Alkaline Stability[J]. J Mater Chem A,2018,6:527-534. [44] Wang J,Gu S,Kaspar R B,et al. Stabilizing the Imidazolium Cation in Hydroxide-Exchange Membranes for Fuel Cells[J]. ChemSusChem,2013,6(11):2079-2082. [45] Thomas O D,Soo K J W Y,Peckham T J P,et al. Anion Conducting Poly(dialkyl benzimidazolium) Salts[J]. Polym Chem,2011,2(8):1641-1643. [46] 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. [47] Lin B C,Xu F,Su Y,et al. Ether-free Polybenzimidazole Bearing Pendant Imidazolium Groups for Alkaline Anion Exchange Membrane Fuel Cells Application[J]. ACS Appl Energy Mater,2020,3(1):1089-1098. [48] Ye Y S,Stokes K K,Beyer F L,et al. Development of Phosphonium-Based Bicarbonate Anion Exchange Polymer Membranes[J]. J Membr Sci,2013,443:93-99. [49] 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]. J Am Chem Soc,2012,134(44):18161-18164. [50] Womble C T,Coates G W,Matyjaszewski K,et al. Tetrakis(dialkylamino)phosphonium Polyelectrolytes Prepared by Reversible Addition-Fragmentation Chain Transfer Polymerization[J]. ACS Macro Lett,2016,5(2):253-257. [51] Cotanda P,Sudre G,Modestino M A,et al. High Anion Conductivity and Low Water Uptake of Phosphonium Containing Diblock Copolymer Membranes[J]. Macromolecules,2014,47(21):7540-7547. [52] Zhang B Z,Long H,Kaspar R B. Relating Alkaline Stability to the Structure of Quaternary Phosphonium Cations[J]. RSC Adv,2018,8(47):26640-26645. [53] Wan W,Yang X Y,Smith R C. Convenient Route to Tetraarylphosphonium Polyelectrolytes via Metal-Catalysed P—C Coupling Polymerisation of Aryl Dihalides and Diphenylphosphine[J]. Chem Commun,2017,53(1):252-254. [54] Han H S,Ma H M,Yu J H,et al. Preparation and Performance of Novel Tetraphenylphosphonium-Functionalized Polyphosphazene Membranes for Alkaline Fuel Cells[J]. Eur Polym J,2019,114:109-117. [55] Liu Y,Zhang B,Kinsinger C,et al. 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. [56] Barnes U M,Du Y F,Zhang W X,et al. Phosphonium-Containing Block Copolymer Anion Exchange Membranes:Effect of Quaternization Level on Bulk and Surface Morphologies at Hydrated and Dehydrated States[J]. Macromolecules,2019,52(16):6097-6106. [57] Ran J,Wu L,He Y B,et al. Ion Exchange Membranes:New Developments and Applications[J]. J Membr Sci,2017,522:267-291. [58] Zha Y,Disabb-Miller M L,Johnson Z D,et al. Metal-Cation-Based Anion Exchange Membranes[J]. J Am Chem Soc,2012,134(10):4493 4496. [59] Disabb-Miller M L, Zha Y P, DeCarlo A J,et al. Water Uptake and Ion Mobility in Cross-Linked Bis(terpyridine)ruthenium-Based Anion Exchange Membranes[J]. Macromolecules,2013,46(23):9279-9287. [60] Kwasny M T,Tew G N. Expanding Metal Cation Options in Polymeric Anion Exchange Membranes[J]. J Mater Chem A,2017,5(4):1400-1405. [61] Zhu T,Xu S,Rahman A,et al. Cationic Metallo-Polyelectrolytes for Robust Alkaline Anion-Exchange Membranes[J]. Angew Chem Int Ed,2018,57:2388-2392. [62] Zhu T Y,Sha Y,Firouzjaie H A,et al. Rational Synthesis of Metallo-Cations Toward Redox- and Alkaline-Stable Metallo-Polyelectrolytes[J]. J Am Chem Soc,2020,142(2):1083-1089. [63] Gu S,Wang J,Kaspar R B,et al. Permethyl Cobaltocenium (Cp*2Co+) as an Ultra-stable Cation for Polymer Hydroxide-Exchange Membranes[J]. Sci Rep,2015,5:11668. [64] Wu B,Ge L,Yu D,et al. Cationic Metal-Organic Framework Porous Membranes with High Hydroxide Conductivity and Alkaline Resistance for Fuel Cells[J]. J Mater Chem A,2016,4(38):14545-14549. [65] Olsson J S,Pham T H,Jannasch P. Poly(arylene piperidinium) Hydroxide Ion Exchange Membranes: Synthesis, Alkaline stability, and Conductivity[J]. Adv Funct Mater,2017,28(2):1702758. [66] Döbbelin M,Azcune I,Bedu M,et al. Synthesis of Pyrrolidinium-Based Poly(ionic liquid) Electrolytes with Poly(ethylene glycol) Side Chains[J]. Chem Mater,2012,24(9):1583-1590. [67] Pham T H,Olsson J S,Jannasch P. N-Spirocyclic Quaternary Ammonium Ionenes for Anion-Exchange Membranes[J]. J Am Chem Soc,2017,139( 8):2888-2891. [68] Olsson J S,Pham T H,Jannasch P. Poly(N,N-diallylazacycloalkane)s for Anion-Exchange Membranes Functionalized with N-Spirocyclic Quaternary Ammonium Cations[J]. Macromolecules,2017,50(7):2784-2793. [69] Pham T H,Olsson J S,Jannasch P. Poly(arylene alkylene)s with Pendant N-Spirocyclic Quaternary Ammonium Cations for Anion Exchange Membranes[J]. J Mater Chem A,2018,6(34):16537-16547. [70] Chen N J,Long C,Li Y X,et al. Ultrastable and High Ion-Conducting Polyelectrolyte Based on Six-Membered N-Spirocyclic Ammonium for Hydroxide Exchange Membrane Fuel Cell Applications[J]. ACS Appl Mater Interfaces,2018,10(18):15720-15732. [71] Chen N J,Lu C R,Li Y X,et al. Robust Poly(aryl piperidinium)/N-Spirocyclic Poly(2,6-dimethyl-1,4-phenyl) for Hydroxide-Exchange Membranes[J]. J Membr Sci,2019,572:246-254. [72] Chu X M,Liu L,Huang Y D,et al. Practical Implementation of Bis-six-membered N-Cyclic Quaternary Ammonium Cations in Advanced Anion Exchange Membranes for Fuel Cells:Synthesis and Durability[J]. J Membr Sci,2019,578:239-250. [73] Zhang Y,Chen W T,Yan X M,et al. Ether Spaced N-Spirocyclic Quaternary Ammonium Functionalized Crosslinked Polysulfone for High Alkaline Stable Anion Exchange Membranes [J]. J Membr Sci,2020,598:117650. [74] Lin C X,Yu D M,Wang J X,et al. Facile Construction of Poly(arylene ether)s-Based Anion Exchange Membranes Bearing Pendent N-Spirocyclic Quaternary Ammonium for Fuel Cells[J]. Int J Hydrogen Energy,2019,44(48):26565-26576. [75] Gu F L,Dong H L,Li Y Y,et al. Base Stable Pyrrolidinium Cations for Alkaline Anion Exchange Membrane Applications[J]. Macromolecules,2014,47(19):6740-6747. [76] Dong X,Lv D,Zheng J F,et al. Pyrrolidinium-Functionalized Poly(arylene ether sulfone)s for Anion Exchange Membranes:Using Densely Doncentrated Ionic Groups and Block Design to Improve Membrane Performance[J]. J Membr Sci,2017,535:301-311. [77] Fujimoto C,Kim D S,Hibbs M,et al. Backbone Stability of Quaternized Polyaromatics for Alkaline Membrane Fuel Cells[J]. J Membr Sci,2012,423:438 449. [78] Lee W H,Mohanty A D,Bae C,et al. Fluorene-Based hydroxide Ion Conducting Polymers for Chemically Stable Anion Exchange Membrane Fuel Cells[J]. ACS Macro Lett,2015,4(4):453 457 . [79] Lee W H,Kim Y S,Bae C. Robust Hydroxide Ion Conducting Poly(biphenyl alkylene)s for Alkaline Fuel Cell Membranes[J]. ACS Macro Lett,2015,4(8):814-818. [80] Olsson J S,Pham T H,Jannasch P. Poly(arylene piperidinium) Hydroxide Ion Exchange Membranes:Synthesis, Alkaline Stability, and Conductivity[J]. Adv Funct Mater,2017,28(2):1702758. [81] Wang J H,Zhao Y,Brian P,et al. Poly(aryl piperidinium) Membranes and Ionomers for Hydroxide Exchange Membrane Fuel Cells[J]. Nat Energy,2019,4(5):392-398. [82] Chu X M,Shi Y,Liu L,et al. Piperidinium-Functionalized Anion Exchange Membranes and Their Application in Alkaline Fuel Cells and Water Electrolysis[J]. J Mater Chem A,2019,7(13):7717-7727. [83] Wang F,Xue B X,Zhou S Y,et al. Synthesis and Property of Novel Anion Exchange Membrane Based on Poly(aryl ether sulfone)s Bearing Piperidinium Moieties[J]. J Membr Sci,2019,591:117334. |
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