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+PF6-1PF6). 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.