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A Stable Bis(benzocyclobutadiene)‐Annelated Tetraazapentacene Derivative
Author(s) -
Biegger Philipp,
Schaffroth Manuel,
Tverskoy Olena,
Rominger Frank,
Bunz Uwe H. F.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602675
Subject(s) - cyclobutadiene , ring (chemistry) , cleavage (geology) , biphenylene , derivative (finance) , reagent , chemistry , condensation , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , physics , materials science , molecule , thermodynamics , phenylene , fracture (geology) , financial economics , economics , composite material , polymer
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.