Thiadiazolo-Azaacenes.

Authors :: Müller M
Koser S
Tverskoy O
Rominger F
Freudenberg J
Bunz UHF
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2019 Apr 26; Vol. 25 (24), pp. 6082-6086. Date of Electronic Publication: 2019 Mar 26.
Publication Year :: 2019
Abstract: 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.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)