Thiadiazolo‐Azaacenes

This work reports the synthesis and characterization of bis‐ and tetrakis(thiadiazolo)‐appended di‐ and tetraazaacenes, displaying up to seven catenated benzene/pyrazine rings. The targets are obtained by condensation of benzo‐bis(thiadiazole)‐4,5‐dione with aromatic di‐ and tetraamines. The condens...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-04, Vol.25 (24), p.6082-6086
Main Authors: Müller, Matthias, Koser, Silke, Tverskoy, Olena, Rominger, Frank, Freudenberg, Jan, Bunz, Uwe H. F.
Format: Article
Language:English
Subjects:
Benzene
building blocks
Chemistry
Condensates
Condensation
Condensation products
Diketones
heteroacenes
Pyrazine
thiadiazole
X-ray crystallography
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Summary:This work reports the synthesis and characterization of bis‐ and tetrakis(thiadiazolo)‐appended di‐ and tetraazaacenes, displaying up to seven catenated benzene/pyrazine rings. The targets are obtained by condensation of benzo‐bis(thiadiazole)‐4,5‐dione with aromatic di‐ and tetraamines. The condensation products—up to a heptacene‐like species—are stable but can be insoluble. Soluble derivatives are readily processible, but do not show enhanced electron affinities, as the two or four attached benzothiadiazole units are effectively resonance‐separated from the acene body, maximizing the number of Clar‐sextets. Stabilizing wings: A tetraazaheptacene stabilized by four thiadiazolo‐“aprons”.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201900462