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Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships

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Hugar, Kristina M., Kostalik, Henry A., Coates, Geoffrey W.·2015·Journal of the American Chemical Society

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Abstract

Highly base-stable cationic moieties are a critical component of anion exchange membranes (AEMs) in alkaline fuel cells (AFCs); however, the commonly employed organic cations have limited alkaline stability. To address this problem, we synthesized and characterized the stability of a series of imidazolium cations in 1, 2, or 5 M KOH/CD3OH at 80 °C, systematically evaluating the impact of substitution on chemical stability. The substituent identity at each position of the imidazolium ring has a dramatic effect on the overall cation stability. We report imidazolium cations that have the highest alkaline stabilities reported to date, >99% cation remaining after 30 days in 5 M KOH/CD3OH at 80 °C.

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Borup, R., Meyers, J., Pivovar, B., Kim, Y. S., Mukundan, R., Garland, N., Myers, D., Wilson, M., Garzon, F., Wood, D., et al. (2007) · Chemical Reviews · doi:10.1021/cr050182l · Cited by 3,402
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Hickner, M. A., Ghassemi, H., Kim, Y. S., Einsla, B. R., & McGrath, J. E. (2004) · Chemical Reviews · doi:10.1021/cr020711a · Cited by 2,834
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Dunn, S. (2002) · International Journal of Hydrogen Energy · doi:10.1016/s0360-3199(01)00131-8 · Cited by 1,520
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Alkaline polymer electrolyte fuel cells completely free from noble metal catalysts
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Hydroxide Degradation Pathways for Imidazolium Cations: A DFT Study
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(2012) · doi:10.1016/j.polymer.2012.11.023 · Cited by 110
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Phosphonium cation-containing polymers: From ionic liquids to polyelectrolytes
Jangu, C., & Long, T. E. (2014) · Polymer · doi:10.1016/j.polymer.2014.04.015 · Cited by 90
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Tsai, T., Maes, A. M., Vandiver, M. A., Versek, C., Seifert, S., Tuominen, M. T., Liberatore, M. W., Herring, A. M., & Coughlin, E. B. (2012) · Journal of Polymer Science Part B Polymer Physics · doi:10.1002/polb.23170 · Cited by 89
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From curiosity to “power to change the world®”
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Macomber, C. S., Boncella, J. M., Pivovar, B. S., & Rau, J. (2008) · Journal of Thermal Analysis and Calorimetry · doi:10.1007/s10973-007-8930-x · Cited by 84
Thermal and ion transport properties of hydrophilic and hydrophobic polymerized styrenic imidazolium ionic liquids
Weber, R. L., Ye, Y., Banik, S. M., Elabd, Y. A., Hickner, M. A., & Mahanthappa, M. K. (2011) · Journal of Polymer Science Part B Polymer Physics · doi:10.1002/polb.22319 · Cited by 82
Alkaline stable imidazolium-based ionomers containing poly(arylene ether sulfone) side chains for alkaline anion exchange membranes
Si, Z., Sun, Z., Gu, F., Qiu, L., & Yan, F. (2014) · Journal of Materials Chemistry A · doi:10.1039/c3ta15178f · Cited by 80
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Amel, A., Zhu, L. J., Hickner, M. A., & Ein‐Eli, Y. (2014) · Journal of The Electrochemical Society · doi:10.1149/2.044405jes · Cited by 79
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Wu, L., Xu, T., & Yang, W. (2006) · Journal of Membrane Science · doi:10.1016/j.memsci.2006.09.035 · Cited by 79
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Hydroxide-ion induced degradation pathway for dimethylimidazolium groups in anion exchange membranes
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Hossain, M. A., Lim, Y., Lee, S., Jang, H., Choi, S.-Y., Jeon, Y., Lee, S., Ju, H., & Kim, W. G. (2013) · Solid State Ionics · doi:10.1016/j.ssi.2013.09.036 · Cited by 25
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(2013) · doi:10.1007/s00289-013-1028-7 · Cited by 21
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See all 465

Authors: Hugar, K. M., Kostalik, H. A., & Coates, G. W.
Venue: Journal of the American Chemical Society
Publisher: American Chemical Society (ACS)
Published: 2015-07-01
Volume: 137
Issue: 27
Pages: 8730-8737
ISSN: 0002-7863 (ISSN-L)
1520-5126
DOI: 10.1021/jacs.5b02879
OpenAlex: W2235633166
Cited by: 465
References: 143
FWCI: 18.60
Type: journal article
Language: en
Open access: hybrid

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Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships

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