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Shape-persistent macrocycles with intraannular alkyl groups: some structural limits of discotic liquid crystals with an inverted structure

Sigurd Höger1*, Jill Weber2, Andreas Leppert2 and Volker Enkelmann3

Author Affiliations

1 Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany

2 Institut für Technische Chemie und Polymerchemie, Universität Karlsruhe (TH), Engesserstr. 18, 76131 Karlsruhe, Germany

3 Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128 Mainz, Germany

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Beilstein Journal of Organic Chemistry 2008, 4:1  doi:10.1186/1860-5397-4-1

Published: 9 January 2008


The synthesis and thermal properties of new shape-persistent macrocycles of different sizes decorated with intraannular alkyl chains are described. The alkyl chain length is in all cases sufficient to cross the rings and to fill their interior completely. The investigation of the thermal behavior has shown that the smaller cycles do not exhibit thermotropic mesophases. Single crystal x-ray analysis indicates that the anisotropy in these compounds is too small to describe them as plates rather than spheres. For the larger macrocycles it is shown that longer adaptable substituents decrease the phase transition temperatures compared to previously described structures.

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Graphical abstract