Tetrabenzononacene: “Butterfly Wings” Stabilize the Core

In combination with bulky substituents at the core, fourfold benzannulation at the cata‐positions stabilizes a nonacene sufficiently to allow its isolation and characterization by 1H NMR and X‐ray analysis. The four benzo units blueshift the absorption spectrum in comparison to a solely linear nonac...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-01, Vol.59 (5), p.1966-1969
Main Authors: Müller, Matthias, Maier, Steffen, Tverskoy, Olena, Rominger, Frank, Freudenberg, Jan, Bunz, Uwe H. F.
Format: Article
Language:English
Subjects:
Absorption spectra
acenes
benzannulation
Cava reaction
Communication
Communications
NMR
nonacene
Nuclear magnetic resonance
X-ray diffraction
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Summary:In combination with bulky substituents at the core, fourfold benzannulation at the cata‐positions stabilizes a nonacene sufficiently to allow its isolation and characterization by 1H NMR and X‐ray analysis. The four benzo units blueshift the absorption spectrum in comparison to a solely linear nonacene, but significantly increase the stability in the solid state. Attachment of four benzo units electronically stabilizes a nonacene core without heteroatom substitution at/on the aromatic backbone. The four benzo units blueshift the absorption spectrum in comparison to a linear nonacene and significantly increase the stability in the solid state.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201909614