A stable bis(benzocyclobutadiene)-annelated tetraazapentacene derivative
Abstract 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...
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| Hauptverfasser: | , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
15 September 2016
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| In: |
Chemistry - a European journal
Year: 2016, Jahrgang: 22, Heft: 44, Pages: 15896-15901 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201602675 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201602675 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201602675 
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| Verfasserangaben: | Philipp Biegger, Manuel Schaffroth, Olena Tverskoy, Frank Rominger, and Uwe H. F. Bunz |
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| 520 | |a Abstract 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. | ||
| 650 | 4 | |a aromaticity | |
| 650 | 4 | |a azaheteropolycycle | |
| 650 | 4 | |a condensation | |
| 650 | 4 | |a cyclobutadiene | |
| 650 | 4 | |a tetraazapentacene | |
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