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A Stable Hexakis(guanidino)benzene: Realization of the Strongest Neutral Organic Four‐Electron Donor
Author(s) -
Eberle Benjamin,
Kaifer Elisabeth,
Himmel HansJörg
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201611189
Subject(s) - redox , chemistry , electron , benzene , sublimation (psychology) , electron donor , nitrogen , photochemistry , inorganic chemistry , organic chemistry , catalysis , psychology , physics , quantum mechanics , psychotherapist
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.