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Updated: Jan 21, 2026

Investigating the Three-dimensional Flow Separation Induced by a Model Vocal Fold Polyp
Published on: February 3, 2014
An azobenzene container showing a definite folding - synthesis and structural investigation
Abdulselam Adam1, Saber Mehrparvar1, Gebhard Haberhauer1
1Institut für Organische Chemie, Universität Duisburg-Essen, Universitätsstr. 7, D-45117 Essen, Germany.
Abstract:
The combination of photo-switchable units with macrocycles is a very interesting field in supramolecular chemistry. Here, we present the synthesis of a foldable container consisting of two different types of Lissoclinum macrocyclic peptides which are connected via two azobenzene units. The container is controllable by light: irradiation with UV light causes a switching process to the compact cis,cis-isomer, whereas by the use of visible light the stretched trans,trans-isomer is formed. By means of quantum chemical calculations and CD spectroscopy we could show that the trans→cis isomerization is spatially directed; that means that one of the two different macrocycles performs a definite clockwise rotation to the other, caused by irradiation with UV light. For the cis→trans isomerization counterclockwise rotations are found. Furthermore, quantum chemical calculations reveal that the energy of the cis,cis-isomer is only slightly higher than the energy of the cis,trans-isomer. This effect can be explained by the high dispersion energy in the compact cis,cis-isomer.
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