Highly stable hydroxide conducting membranes are necessary for solid-state alkaline fuel cells to have long performance lifetimes. In this study, we used solid-state chemistry to synthesize Nafion-based anion exchange membranes (AEMs) with a variety of covalently attached cations, including trimethylammonium, trimethylphosphonium, piperazinium, pyrrolidinium, pyridinium, and quaternized 1,4-diazabicyclo[2.2.2]octane. Infrared spectroscopy confirms a partial asymmetric functionalization of all cations with the exception of pyridinium. The AEMs that were successfully synthesized all exhibited sufficient water uptake and conductivity. The effect of cation type on AEM chemical and thermal stability was investigated as a function of various conditions (e.g., hydration levels, temperature, and pH). High chemical and thermal stability was observed for all successfully synthesized AEMs with the exception of the trimethylphosphonium cation AEM. (C) 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2012