Tetrabenzononacene: "Butterfly Wings" Stabilize the Core

Matthias Müller; Steffen Maier; Olena Tverskoy; Frank Rominger; Jan Freudenberg; Uwe H F Bunz

doi:10.1002/anie.201909614

Tetrabenzononacene: "Butterfly Wings" Stabilize the Core

Angew Chem Int Ed Engl. 2020 Jan 27;59(5):1966-1969. doi: 10.1002/anie.201909614. Epub 2019 Dec 17.

Authors

Matthias Müller¹, Steffen Maier¹, Olena Tverskoy¹, Frank Rominger¹, Jan Freudenberg^{1

2}, Uwe H F Bunz^{1

3}

Affiliations

¹ Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
² InnovationLab, Speyerer Straße 4, 69115, Heidelberg, Germany.
³ Centre for Advanced Materials, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany.

Abstract

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 ¹ H 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.

Keywords: Cava reaction; X-ray diffraction; acenes; benzannulation; nonacene.

Publication types

Research Support, Non-U.S. Gov't

Abstract

Publication types

Grants and funding