Macromolecules
Article
tethered cations on the PILs, suggesting that small molecule
studies may not provide a solid basis for comparison of relative
cation stability as a preliminary screening tool for determining
the most promising cations.
(14) Vandiver, M. A.; Caire, B. R.; Poskin, Z.; Li, Y.; Seifert, S.;
Knauss, D. M.; Herring, A. M.; Liberatore, M. W. Durability and
Performance of Polystyrene-b-poly(vinylbenzyl trimethylammonium)
Diblock Copolymer and Equivalent Blend Anion Exchange Mem-
branes. J. Appl. Polym. Sci. 2015, 132, 41596.
(
15) Yan, J.; Hickner, M. A. Anion Exchange Membranes by
ASSOCIATED CONTENT
Supporting Information
■
Bromination of Benzylmethyl-Containing Poly(sulfone)s. Macro-
molecules 2010, 43, 2349−2356.
*
S
(16) 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. J. Polym. Sci., Part B: Polym. Phys.
1
Additional H NMR data (PDF)
2
013, 51, 1751−1760.
AUTHOR INFORMATION
Notes
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(17) Sturgeon, M. R.; Macomber, C. S.; Engtrakul, C.; Long, H.;
Pivovar, B. S. Hydroxide based Benzyltrimethylammonium Degrada-
tion: Quantification of Rates and Degradation Technique Develop-
ment. J. Electrochem. Soc. 2015, 162, F366−F372.
*
(
18) Choe, Y.-K.; Fujimoto, C.; Lee, K.-S.; Dalton, L. T.; Ayers, K.;
The authors declare no competing financial interest.
Henson, N. J.; Kim, Y. S. Alkaline Stability of Benzyl Trimethyl
Ammonium Functionalized Polyaromatics: A Computational and
Experimental Study. Chem. Mater. 2014, 26, 5675−5682.
ACKNOWLEDGMENTS
This work is supported in part by the U.S. Army Research
Office under Grant W911NF-14-0310.
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(
19) Chen, D.; Hickner, M. A. Ion Clustering in Quaternary
Ammonium Functionalized Benzylmethyl Containing Poly(arylene
ether ketone)s. Macromolecules 2013, 46, 9270−9278.
(20) Hibbs, M. R. Alkaline Stability of Poly(phenylene)-based Anion
Exchange Membranes with Various Cations. J. Polym. Sci., Part B:
Polym. Phys. 2013, 51, 1736−1742.
(21) Arges, C. G.; Ramani, V. Investigation of Cation Degradation in
Anion Exchange Membranes Using Multi-Dimensional NMR Spec-
troscopy. J. Electrochem. Soc. 2013, 160, F1006−F1021.
(22) Arges, C. G.; Ramani, V. Two-dimensional NMR Spectroscopy
Reveals Cation-triggered Backbone Degradation in Polysulfone-based
Anion Exchange Membranes. Proc. Natl. Acad. Sci. U. S. A. 2013, 110,
REFERENCES
■
(
1) Varcoe, J. R.; Slade, R. C. T. Prospects for Alkaline Anion-
Exchange Membranes in Low Temperature Fuel Cells. Fuel Cells 2005,
5
(
, 187−200.
2) Ye, Y.; Sharick, S.; Davis, E. M.; Winey, K. I.; Elabd, Y. A. High
Hydroxide Conductivity in Polymerized Ionic Liquid Block Copoly-
mers. ACS Macro Lett. 2013, 2, 575−580.
3) Nykaza, J. R.; Ye, Y.; Elabd, Y. A. Polymerized Ionic Liquid
Diblock Copolymers with Long Alkyl Side-chain Length. Polymer
014, 55, 3360−3369.
4) Ye, Y.; Elabd, Y. A. Relative Chemical Stability of Imidazolium-
Based Alkaline Anion Exchange Polymerized Ionic Liquids. Macro-
molecules 2011, 44, 8494−8503.
5) Chen, D.; Hickner, M. A. Degradation of Imidazolium- and
Quaternary Ammonium-Functionalized Poly(fluorenyl ether ketone
sulfone) Anion Exchange Membranes. ACS Appl. Mater. Interfaces
012, 4, 5775−5781.
6) Qiu, B.; Lin, B.; Si, Z.; Qiu, L.; Chu, F.; Zhao, J.; Yan, F. Bis-
imidazolium-based Anion-Exchange Membranes for Alkaline Fuel
Cells. J. Power Sources 2012, 217, 329−335.
7) Ran, J.; Wu, L.; Varcoe, J. R.; Ong, A. L.; Poynton, S. D.; Xu, T.
Development of Imidazolium-type Alkaline Anion Exchange Mem-
branes for Fuel Cell Application. J. Membr. Sci. 2012, 415, 242−249.
8) Li, W.; Fang, J.; Lv, M.; Chen, C.; Chi, X.; Yang, Y.; Zhang, Y.
Novel Anion Exchange Membranes Based on Polymerizable
Imidazolium Salt for Alkaline Fuel Cell Applications. J. Mater. Chem.
011, 21, 11340−11346.
9) Lin, B.; Dong, H.; Li, Y.; Si, Z.; Gu, F.; Yan, F. Alkaline Stable
C2-Substituted Imidazolium-Based Anion-Exchange Membranes.
Chem. Mater. 2013, 25, 1858−1867.
10) Gu, F.; Dong, H.; Li, Y.; Si, Z.; Yan, F. Highly Stable N3-
(
2
(
2
(
490−2495.
23) Arges, C. G.; Kulkarni, S.; Baranek, A.; Pan, K.-J.; Jung, M.-S.;
Patton, D.; Mauritz, K. A.; Ramani, V. Quarternary Ammonium and
Phosphonium Based Anion Exchange Membranes for Alkaline Fuel
Cells. ECS Trans. 2010, 33, 1903−1913.
(
(
24) Noonan, K. J. T.; Hugar, K. M.; Kostalik, H. A.; Lobkovsky, E.
B.; Abrun
̃
a, H. D.; Coates, G. W. Phosphonium-Functionalized
2
(
Polyethylene: A New Class of Base-Stable Alkaline Anion Exchange
Membranes. J. Am. Chem. Soc. 2012, 134, 18161−18164.
(
Y. A Soluble and Highly Conductive Ionomer for High-Performance
Hydroxide Exchange Membrane Fuel Cells. Angew. Chem., Int. Ed.
2
(
25) Gu, S.; Cai, R.; Luo, T.; Chen, Z.; Sun, M.; Liu, Y.; He, G.; Yan,
(
009, 48, 6499−6502.
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. Macromolecules 2010, 43, 3890−3896.
2
(
(
27) Liu, L.; Li, Q.; Dai, J.; Wang, H.; Jin, B.; Bai, R. A Facile Strategy
for the Synthesis of Guanidinium-functionalized Polymer as Alkaline
Anion Exchange Membrane with Improved Alkaline Stability. J.
Membr. Sci. 2014, 453, 52−60.
(
(
28) Kim, D. S.; Labouriau, A.; Guiver, M. D.; Kim, Y. S.
Substituted Imidazolium-Based Alkaline Anion Exchange Membranes:
Experimental Studies and Theoretical Calculations. Macromolecules
014, 47, 208−216.
11) Qiu, B.; Lin, B.; Qiu, L.; Yan, F. Alkaline Imidazolium- and
Quaternary Ammonium-Functionalized Anion Exchange Membranes
for Alkaline Fuel Cell Applications. J. Mater. Chem. 2012, 22, 1040−
045.
Guanidinium-Functionalized Anion Exchange Polymer Electrolytes
via Activated Fluorophenyl-Amine Reaction. Chem. Mater. 2011, 23,
2
(
3
(
795−3797.
29) Sajjad, S. D.; Hong, Y.; Liu, F. Synthesis of Guanidinium-based
Anion Exchange Membranes and their Stability Assessment. Polym.
Adv. Technol. 2014, 25, 108−116.
1
(
12) Zhang, F.; Zhang, H.; Qu, C. Imidazolium Functionalized
Polysulfone Anion Exchange Membrane for Fuel Cell Application. J.
(30) Gu, F.; Dong, H.; Li, Y.; Sun, Z.; Yan, F. Base Stable
Pyrrolidinium Cations for Alkaline Anion Exchange Membrane
Applications. Macromolecules 2014, 47, 6740−6747.
Mater. Chem. 2011, 21, 12744−12752.
1
(
13) Nun
̃
ez, S. A.; Hickner, M. A. Quantitative H NMR Analysis of
(31) Price, S. C.; Williams, K. S.; Beyer, F. L. Relationships between
Structure and Alkaline Stability of Imidazolium Cations for Fuel Cell
Membrane Applications. ACS Macro Lett. 2014, 3, 160−165.
Chemical Stabilities in Anion-Exchange Membranes. ACS Macro Lett.
2
013, 2, 49−52.
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