Serendipitous isolation of a triazinone-based air stable organic radical: synthesis, crystal structure, and computation

Abstract

Here we report the synthesis, isolation, and characterization of a dication salt, namely 4,6-bis(4,4′-bipyridinium)-1,3,5-triazin-2-one {1²⁺(PF₆)₂²⁻·2H₂O1(PF₆)₂·2H₂O}, and its radical cation salt, namely 4,6-bis(4,4′-bipyridinium)-1,3,5-triazin-2-one (1⁺˙PF₆⁻1˙PF₆). The easily synthesized, robust air-stable radical cation 1⁺· was confirmed by electron paramagnetic resonance (EPR), variable temperature magnetic studies as well as spin-density calculations.