A Stable Bis(benzocyclobutadiene)-Annelated Tetraazapentacene Derivative

Biphenylene‐2,3‐dione is a powerful reagent to build up cyclobutadiene‐containing azapolyheterocycles. The target structures are formed in high yields through classical condensation of suitable aromatic diamines with the biphenylenedione. To achieve the title compound, the biphenylenedione is couple...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-10, Vol.22 (44), p.15896-15901
Main Authors: Biegger, Philipp, Schaffroth, Manuel, Tverskoy, Olena, Rominger, Frank, Bunz, Uwe H. F.
Format: Article
Language:English
Subjects:
Absorption
Accumulation
aromaticity
azaheteropolycycle
Chemistry
Cleavage
Condensation
cyclobutadiene
Derivatives
Diamines
Reagents
tetraazapentacene
Thiadiazoles
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Summary:Biphenylene‐2,3‐dione is a powerful reagent to build up cyclobutadiene‐containing azapolyheterocycles. The target structures are formed in high yields through classical condensation of suitable aromatic diamines with the biphenylenedione. To achieve the title compound, the biphenylenedione is coupled with a diaminobenzothiadiazole derivative. Reductive cleavage of the thiadiazole ring and subsequent condensation with the biphenylenedione gives the title compound in which a central tetraazapentacene is flanked by two benzocyclobutadiene units. This compound is stable despite its extended π‐system and its optical features are blueshifted in comparison to those of the symmetrical tetraazapentacene. Cyclobutadiene‐blues: Upon welding two benzocyclobutadiene groups to the eastern and western sides of a soluble tetraazapentacene, the absorption maximum is significantly blueshifted in comparison to the tetraazapentacene core (see figure). The effect originates through the destabilization of the LUMO of this compound.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201602675