Alkaline stability of poly(phenylene)‐based anion exchange membranes with various cations

Anion exchange membranes comprised of a poly(phenylene) backbone and one of five different cationic head‐groups are prepared, briefly characterized, and tested for stability in 4 M KOH at 90 °C. The two membranes with resonance‐stabilized cations (benzyl pentamethylguanidinium and benzyl N ‐methylimidazolium) show large (>25%) decreases in both conductivity and ion exchange capacity (IEC) after just one day of testing. The membrane with benzyl trimethylammonium cations shows a 33% loss of conductivity (14% decrease in IEC) after 14 days while the membrane with trimethylammonium cations attached by a hexamethylene spacer shows the least degradation: a 5% loss of conductivity over 14 days with no accompanying loss in IEC. A similar membrane which has a six‐carbon spacer and a ketone adjacent to the phenyl ring shows much lower stability, suggesting that the ketone takes part in degradation reactions. © 2012 Wiley Periodicals, Inc. J. Polym. Sci., Part B: Polym. Phys. 2013, 51, 1736–1742, 2013