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Stable Radical Cations of N,N'-Diarylated Dihydrodiazapentacenes.

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.

SUBMITTER: Xie G

PROVIDER: S-EPMC6973034 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Stable Radical Cations of N,N'-Diarylated Dihydrodiazapentacenes.

Xie Gaozhan G Brosius Victor V Han Jie J Rominger Frank F Dreuw Andreas A Freudenberg Jan J Bunz Uwe H F UHF

Chemistry (Weinheim an der Bergstrasse, Germany) 20191216 1

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 an ...[more]

PMID: 31538683

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