Halogenated Symmetrical Tetraazapentacenes: Synthesis, Structures, and Properties

The Journal of Organic Chemistry
Jens U EngelhartUwe H F Bunz

Abstract

We herein describe the synthesis and property evaluation of several brominated and chlorinated tetraazapentacenes. The targets were obtained by thermal condensation of 2,5-dihydroxyquinone with 4,5-dichloro-, 2,6-dichloro-, and 4,5-dibromo-1,2-phenylenediamine, followed by oxidation with hot acidic dichromate. Double alkynylation, reductive deoxygenation, and subsequent oxidation using MnO2 furnishes the target compounds. Absorption spectra, electrochemistry, and single crystal structures of the targets are reported. The 1,4,8,11-tetrachlorotetraazapentacene (1,4,8,11-tetrachloroquinoxalino[2,3-b]phenazine) carrying its chlorine atoms in the peri-positions packs in a herringbone type arrangement, while the isomer (2,3,9,10-tetrachloroquinoxalino[2,3-b]phenazine, with the chlorine atoms in the east and west positions) packs in one-dimensional stacks. In all cases, the reduction potentials and the calculated LUMO-positions are decreased by the introduction of the halogen atoms.

References

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Oct 9, 2014·Journal of the American Chemical Society·Jens U EngelhartUwe H F Bunz
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May 15, 2015·Accounts of Chemical Research·Uwe H F Bunz
Nov 13, 2015·The Journal of Organic Chemistry·Florian L GeyerUwe H F Bunz

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Citations

Mar 16, 2017·Chemistry : a European Journal·Matthias MüllerUwe H F Bunz
Aug 23, 2016·Physical Chemistry Chemical Physics : PCCP·Ramachandran Rakhi, Cherumuttathu H Suresh
Jun 1, 2018·Angewandte Chemie·Hilmar ReissUwe H F Bunz
Oct 29, 2019·Chemistry : a European Journal·Lukas AhrensUwe H F Bunz
Jun 12, 2019·Accounts of Chemical Research·Uwe H F Bunz, Jan Freudenberg

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