Schatz, DominicDominicSchatzBaumert, Marcel E.Marcel E.BaumertKersten, Marie C.Marie C.KerstenSchneider, Finn M.Finn M.SchneiderNielsen, Mogens BrøndstedMogens BrøndstedNielsenHansmann, Max M.Max M.HansmannWegner, Hermann A.Hermann A.Wegner2024-10-072024-10-072024https://jlupub.ub.uni-giessen.de/handle/jlupub/19638https://doi.org/10.22029/jlupub-18996Azobenzenes (ABs) are versatile compounds featured in numerous applications for energy storage systems, such as solar thermal storages or phase change materials. Additionally, the reversible one-electron reduction of these diazenes to the nitrogen-based radical anion has been used in battery applications. Although the oxidation of ABs is normally irreversible, 4,4’-diamino substitution allows a reversible 2e− oxidation, which is attributed to the formation of a stable bis-quinoidal structure. Herein, we present a system that shows a bipolar redox behaviour. In this way, ABs can serve not only as anolytes, but also as catholytes. The resulting redox potentials can be tailored by suitable amine- and ring-substitution. For the first time, the solid-state structure of the oxidized form could be characterized by X-ray diffraction.enNamensnennung - Nicht kommerziell 4.0 Internationalddc:540