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Updated: Jan 19, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Stable Radical Cations of N,N'-Diarylated Dihydrodiazapentacenes
Gaozhan Xie1, Victor Brosius1, Jie Han2
1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Abstract:
A series of quinoidal N,N'-diaryldiaza-N,N'-dihydropentacenes (Quino) was prepared in a two-step reaction, starting from quinacridone. Oxidation of Quino furnishes stable radical cations, isoelectronic to the radical anions of the azaacenes, whereas the dicationic species are isoelectronic to neutral azapentacenes. The spectroscopic properties of the diaryldiazapentacenes and their oxidized mono- and dications are equivalent to that of the dianion of tetraazapentacene (TAP), its radical anion and the neutral TAP.
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