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Updated: Mar 7, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
A Stable Hexakis(guanidino)benzene: Realization of the Strongest Neutral Organic Four-Electron Donor
Benjamin Eberle1, Elisabeth Kaifer1, Hans-Jörg Himmel1
1Anorganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Abstract:
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.
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