N3-adamantyl imidazolium cations: Alkaline stability assessment and the corresponding comb-shaped anion exchange membranes

Varcoe, 2014, Anion-exchange membranes in electrochemical energy systems, Energy Environ. Sci., 7, 3135, 10.1039/C4EE01303D Merle, 2011, Anion exchange membranes for alkaline fuel cells: a review, J. Membr. Sci., 377, 1, 10.1016/j.memsci.2011.04.043 Soloveichik, 2015, Flow batteries: current status and trends, Chem. Rev., 115, 11533, 10.1021/cr500720t Noack, 2015, The chemistry of redox-flow batteries, Angew. Chem. Int. Ed., 54, 9776, 10.1002/anie.201410823 Largier, 2017, Random quaternary ammonium Diels-Alder poly(phenylene) copolymers for improved vanadium redox flow batteries, J. Power Sources, 352, 149, 10.1016/j.jpowsour.2017.03.130 Strathmann, 2010, Electrodialysis, a mature technology with a multitude of new applications, Desalination, 264, 268, 10.1016/j.desal.2010.04.069 Kamcev, 2017, Effect of fixed charge group concentration on equilibrium ion sorption in ion exchange membranes, J. Mater. Chem. A, 5, 4638, 10.1039/C6TA07954G Yang, 2015, Poly(2,6-dimethyl-1,4-phenylene oxide)-b-poly(vinylbenzyltrimethylammonium) diblock copolymers for highly conductive anion exchange membranes, Macromolecules, 48, 4471, 10.1021/acs.macromol.5b00459 Mahmoud, 2017, High hydroxide ion conductivity with enhanced alkaline stability of partially fluorinated and quaternized aromatic copolymers as anion exchange membranes, Macromolecules, 50, 4256, 10.1021/acs.macromol.7b00401 Xue, 2017, Synthesis of novel guanidinium-based anion-exchange membranes with controlled microblock structures, J. Membr. Sci., 537, 151, 10.1016/j.memsci.2017.05.030 Liu, 2016, Anion conducting multiblock copolymer membranes with partial fluorination and long head-group tethers, J. Mater. Chem. A, 4, 16233, 10.1039/C6TA06653D Hou, 2016, Wittig reaction constructed an alkaline stable anion exchange membrane, J. Membr. Sci., 518, 282, 10.1016/j.memsci.2016.07.020 Pan, 2014, Constructing ionic highway in alkaline polymer electrolytes, Energy Environ. Sci., 7, 354, 10.1039/C3EE43275K Lin, 2016, Side-chain-type anion exchange membranes bearing pendent imidazolium-functionalized poly(phenylene oxide) for fuel cells, J. Membr. Sci., 513, 206, 10.1016/j.memsci.2016.04.054 Lin, 2016, Side-chain-type anion exchange membranes bearing pendant quaternary ammonium groups via flexible spacers for fuel cells, J. Mater. Chem. A, 4, 13938, 10.1039/C6TA05090E Li, 2012, Comb-shaped polymers to enhance hydroxide transport in anion exchange membranes, Energy Environ. Sci., 5, 7888, 10.1039/c2ee22050d Yang, 2017, Highly anion conductive, alkyl-chain-grafted copolymers as anion exchange membranes for operable alkaline H2/O2 fuel cells, J. Mater. Chem. A, 5, 10301, 10.1039/C7TA00481H Lee, 2017, Highly conductive and durable poly(arylene ether sulfone) anion exchange membrane with end-group cross-linking, Energy Environ. Sci., 10, 275, 10.1039/C6EE03079C Hugar, 2015, Imidazolium cations with exceptional alkaline stability: a systematic study of structure-stability relationships, J. Am. Chem. Soc., 137, 8730, 10.1021/jacs.5b02879 Mondal, 2017, Click mediated high-performance anion exchange membranes with improved water uptake, J. Mater. Chem. A, 5, 1022, 10.1039/C6TA09114H Lin, 2013, Alkaline stable C2-substituted imidazolium-based anion-exchange membranes, Chem. Mater., 25, 1858, 10.1021/cm400468u Ye, 2011, Relative chemical stability of imidazolium-based alkaline anion exchange polymerized ionic liquids, Macromolecules, 44, 8494, 10.1021/ma201864u Wang, 2016, Alkaline stability of poly(phenylene oxide) based anion exchange membranes containing imidazolium cations, J. Electrochem. Soc., 163, F824, 10.1149/2.0551608jes Weissbach, 2016, Simultaneous, synergistic control of ion exchange capacity and cross-linking of sterically-protected poly(benzimidazolium)s, Chem. Mater., 28, 8060, 10.1021/acs.chemmater.6b03902 Chen, 2017, Comb-shaped guanidinium functionalized poly(ether sulfone)s for anion exchange membranes: effects of the spacer types and lengths, J. Polym. Sci. Part A: Polym. Chem., 55, 1313, 10.1002/pola.28496 Wang, 2010, Novel hydroxide-conducting polyelectrolyte composed of an poly(arylene ether sulfone) containing pendant quaternary guanidinium groups for alkaline fuel cell applications, Macromolecules, 43, 3890, 10.1021/ma100260a Liu, 2014, A facile strategy for the synthesis of guanidinium-functionalized polymer as alkaline anion exchange membrane with improved alkaline stability, J. Membr. Sci., 453, 52, 10.1016/j.memsci.2013.10.054 Kim, 2011, Guanidinium-functionalized anion exchange polymer electrolytes via activated fluorophenyl-amine reaction, Chem. Mater., 23, 3795, 10.1021/cm2016164 Noonan, 2012, Phosphonium-functionalized polyethylene: a new class of base-stable alkaline anion exchange membranes, J. Am. Chem. Soc., 134, 18161, 10.1021/ja307466s Liu, 2016, Anion exchange membranes composed of a poly(2,6-dimethyl-1, 4-phenylene oxide) random copolymer functionalized with a bulky phosphonium cation, J. Membr. Sci., 506, 50, 10.1016/j.memsci.2016.01.042 Gu, 2009, A soluble and highly conductive ionomer for high-performance hydroxide exchange membrane fuel cells, Angew. Chem. Int. Ed., 48, 6499, 10.1002/anie.200806299 Chen, 2017, Cobaltocenium-containing polybenzimidazole polymers for alkaline anion exchange membrane applications, Polym. Chem., 8, 1381, 10.1039/C6PY01936F Zha, 2012, Metal-cation-based anion exchange membranes, J. Am. Chem. Soc., 134, 4493, 10.1021/ja211365r Gu, 2015, Permethyl cobaltocenium (Cp-2*Co+) as an ultra-stable cation for polymer hydroxide-exchange membranes, Sci. Rep., 5, 11668, 10.1038/srep11668 Parrondo, 2015, Synthesis and alkaline stability of solubilized anion exchange membrane binders based on poly(phenylene oxide) functionalized with quaternary ammonium groups via a hexyl spacer, J. Electrochem. Soc., 162, F1236, 10.1149/2.0891510jes Nuñez, 2016, N-alkyl interstitial spacers and terminal pendants influence the alkaline stability of tetraalkylammonium cations for anion exchange membrane fuel cells, Chem. Mater., 28, 2589, 10.1021/acs.chemmater.5b04767 Thomas, 2011, Anion conducting poly(dialkyl benzimidazolium) salts, Polym. Chem., 2, 1641, 10.1039/c1py00142f Wright, 2016, Hexamethyl-p-terphenyl poly(benzimidazolium): a universal hydroxide-conducting polymer for energy conversion devices, Energy Environ. Sci., 9, 2130, 10.1039/C6EE00656F Wright, 2014, Hydroxide-stable ionenes, ACS Macro Lett., 3, 444, 10.1021/mz500168d Wang, 2014, Density functional theory study of hydroxide-ion induced degradation of imidazolium cations, Int. J. Hydrog. Energy, 39, 14355, 10.1016/j.ijhydene.2014.03.053 Gu, 2014, Highly stable N3-substituted imidazolium-based alkaline anion exchange membranes: experimental studies and theoretical calculations, Macromolecules, 47, 208, 10.1021/ma402334t Yang, 2015, Highly alkaline stable N1-alkyl substituted 2-methylimidazolium functionalized alkaline anion exchange membranes, J. Mater. Chem. A, 3, 8559, 10.1039/C5TA00562K Yang, 2016, Preparation and investigation of various imidazolium-functionalized poly(2,6-dimethyl-1,4-phenylene oxide) anion exchange membranes, Electrochim. Acta, 207, 112, 10.1016/j.electacta.2016.04.176 Wang, 2017, Adamantammonium as a novel functional group for anion exchange membranes with excellent comprehensive performances, Polymer, 112, 288, 10.1016/j.polymer.2017.02.030 Raenko, 2001, Adamantylation of imidazoles and benzimidazole, Russ. J. Org. Chem., 37, 1153, 10.1023/A:1013148532518 Wang, 2015, Constructing pendent imidazolium-based poly(phenylene oxide)s for anion exchange membranes using a click reaction, RSC Adv., 5, 93415, 10.1039/C5RA17748K Handy, 2005, The 2-position of imidazolium ionic liquids: substitution and exchange, J. Org. Chem., 70, 1915, 10.1021/jo0480850 Deraedt, 2015, Alkynyl-functionalized imidazolium for “click” dendrimer functionalisation and palladium nanoparticle stabilization, Eur. J. Inorg. Chem., 2015, 1345, 10.1002/ejic.201403045 Lu, 2017, Effects of non-planar hydrophobic cyclohexylidene moiety on the structure and stability of poly(arylene ether sulfone)s based anion exchange membranes, J. Membr. Sci., 533, 210, 10.1016/j.memsci.2017.03.011 Chang, 2015, Hydrogen bond cross-linked sulfonated poly(imino ether ether ketone) (PIEEK) for fuel cell membranes, J. Power Sources, 282, 401, 10.1016/j.jpowsour.2015.02.077 Zhu, 2016, Functionalization of poly(2,6-dimethyl-1,4-phenylene oxide)s with hindered fluorene side chains for anion exchange membranes, Macromolecules, 49, 3300, 10.1021/acs.macromol.6b00578 Lin, 2013, Alkaline polymer electrolytes containing pendant dimethylimidazolium groups for alkaline membrane fuel cells, J. Mater. Chem. A, 1, 7262, 10.1039/c3ta10308k Yang, 2015, Comparison of alkaline stability of quaternary ammonium- and 1,2-methylimidazolium-based alkaline anion exchange membranes, J. Membr. Sci., 487, 12, 10.1016/j.memsci.2015.03.067 Tanaka, 2011, Anion conductive block poly(arylene ether)s: synthesis, properties, and application in alkaline fuel cells, J. Am. Chem. Soc., 133, 10646, 10.1021/ja204166e Yang, 2016, Stability challenge in anion exchange membrane for fuel cells, Curr. Opin. Chem. Eng., 12, 22, 10.1016/j.coche.2016.01.009 Miyanishi, 2016, Ether cleavage-triggered degradation of benzyl alkylammonium cations for polyethersulfone anion exchange membranes, Phys. Chem. Chem. Phys., 18, 12009, 10.1039/C6CP00579A Ran, 2012, Development of imidazolium-type alkaline anion exchange membranes for fuel cell application, J. Membr. Sci., 415, 242, 10.1016/j.memsci.2012.05.006 Lin, 2016, Comb-shaped phenolphthalein-based poly(ether sulfone)s as anion exchange membranes for alkaline fuel cells, RSC Adv., 6, 17269, 10.1039/C5RA22774G Zhu, 2016, Multication side chain anion exchange membranes, Macromolecules, 49, 815, 10.1021/acs.macromol.5b02671 Han, 2017, Elastic long-chain multication cross-linked anion exchange membranes, Macromolecules, 50, 3323, 10.1021/acs.macromol.6b01140