Synthesis and High Alkaline Chemical Stability of Polyionic Liquids with Methylpyrrolidinium, Methylpiperidinium, Methylazepanium, Methylazocanium, and Methylazonanium Cations

Abstract

Herein, we present the synthesis of five styrene-based poly(ionic liquids) (PILs) containing (covalently linked) saturated <i>N</i>-heterocyclic cations with various ring sizes (i.e., methylpyrrolidinium, methylpiperidinium, methylazepanium, methylazocanium, and methylazonanium). High alkaline chemical stability was confirmed by ¹H NMR spectroscopy after 4 weeks in 40 mol equiv of KOH (1.0 M KOH in D₂O) at 80 °C for PILs with 5-, 6-, 7-, and 8-membered ring cations; a requirement for polymer electrolyte separators in long-lasting alkaline fuel cells. Additionally, ion conductivity of PILs increased by 4 orders of magnitude with increasing water content, where a master percolation power law curve was observed, that is, similar conductivity versus water volume fraction for all PILs, regardless of cation size.