A Stable Hexakis(guanidino)benzene: Realization of the Strongest Neutral Organic Four-Electron Donor

The growing demand for efficient batteries has stimulated the search for redox-active organic compounds with multistage redox behavior, as materials with large charge capacity. Herein we report the synthesis and properties of the first hexakis(guanidino) benzene derivative: a strong neutral organic electron donor with reversible multistage redox behavior and a record low redox potential for donation of four electrons. Detailed structural and spectroscopic characterization of three redox states (0, + 2, and + 4) reveal its unique electronic features. Despite its nitrogen richness, the compound is thermally robust and can be readily purified by sublimation.