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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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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cited_by cdi_FETCH-LOGICAL-c5714-d32baf1d816a96602fe03705b9ce17509b81c01f50b568cf3d8a81d6e9ceca293
cites cdi_FETCH-LOGICAL-c5714-d32baf1d816a96602fe03705b9ce17509b81c01f50b568cf3d8a81d6e9ceca293
container_end_page 1969
container_issue 5
container_start_page 1966
container_title Angewandte Chemie International Edition
container_volume 59
creator Müller, Matthias
Maier, Steffen
Tverskoy, Olena
Rominger, Frank
Freudenberg, Jan
Bunz, Uwe H. F.
description 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.
doi_str_mv 10.1002/anie.201909614
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issn 1433-7851
1521-3773
language eng
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source Wiley
subjects Absorption spectra
acenes
benzannulation
Cava reaction
Communication
Communications
NMR
nonacene
Nuclear magnetic resonance
X-ray diffraction
title Tetrabenzononacene: “Butterfly Wings” Stabilize the Core
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