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The Radical Anion and Dianion of Tetraazapentacene
Author(s) -
Ji Lei,
Haehnel Martin,
Krummenacher Ivo,
Biegger Philipp,
Geyer Florian L.,
Tverskoy Olena,
Schaffroth Manuel,
Han Jie,
Dreuw Andreas,
Marder Todd B.,
Bunz Uwe H. F.
Publication year - 2016
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.201603177
Subject(s) - electron paramagnetic resonance , phenazine , chemistry , ion , potassium , fluorescence , photochemistry , spectroscopy , radical ion , medicinal chemistry , organic chemistry , nuclear magnetic resonance , physics , quantum mechanics
The mono‐ and bis‐reduction of 6,13‐bis((triisopropylsilyl)ethynyl)quinoxalino[2,3‐ b ]phenazine ( 1 ) with potassium anthracenide in THF is reported. Both the radical anion 1 .− and the dianion 1 2− were isolated and characterized by optical and structural (single‐crystal X‐ray diffraction) methods. Solutions of the radical anion 1 . − were stable in air for several hours and characterized by EPR spectroscopy. Dianion 1 2− is highly fluorescent and photostable.