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Synthesis 2017; 49(12): 2632-2639
DOI: 10.1055/s-0036-1589006
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© Georg Thieme Verlag Stuttgart · New York

Azobenzene Macrocycles: Synthesis of a Z-Stable Azobenzenophane

Andreas H. Heindl
a   Institut für Organische Chemie, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany
,
Luca Schweighauser
a   Institut für Organische Chemie, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany
,
Christian Logemann
b   Institut für Anorganische und Analytische Chemie, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Gießen, Germany   Email: hermann.a.wegner@org.chemie.uni-giessen.de
,
Hermann A. Wegner*
a   Institut für Organische Chemie, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany
› Author Affiliations
Further Information

Publication History

Received: 06 March 2017

Accepted after revision: 27 March 2017

Publication Date:
03 May 2017 (online)

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Abstract

Azobenzenes have attracted increasing attention in the past years due to their application as molecular switches. In this report, we present a macrocyclic bisazobenzene that exists as the stable Z-isomer. The synthetic efforts as well as the successful strategy are discussed. Final ring closure under continuous irradiation gave the (Z,Z)-bisazobenzenophane. This Z-azobenzene does not show any isomerization under either heating or prolonged irradiation. The thermal stability of the Z-form has also been supported by computations. The prepared bisazobenzenophane represents one of the few azobenzenes in which the Z-isomer is more stable than the E-isomer.

Key words

azobenzene - molecular switches - macrocycles - cyclophanes - photochemistry

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589006.
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