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Synthesis 2002(9): 1213-1228
DOI: 10.1055/s-2002-32525
PAPER
© Georg Thieme Verlag Stuttgart · New York

Areno-Condensed Annulenes - Extended Discotic Mesogens

H. Meier*
Institute of Organic Chemistry, Johannes Gutenberg University, Mainz, Germany
Fax: +49(6131)3925396; e-Mail: hmeier@mail.uni-mainz.de;
Further Information

Publication History

Received 24 February 2002
Publication Date:
28 June 2002 (online)

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Abstract

[n]Annulenes (n ≥12) condensed with 2-4 aromatic ring systems (benzenes, naphthalenes, anthracenes, phenanthrenes, chrysenes, pyrenes) can be prepared by cyclocondensation reactions or ring transformations. Due to the local arene aromaticity, the molecules can be regarded as aromatic islands, which are connected by olefinic bridges. The compounds are non-planar, but the majority of the systems shows a fast inversion of the central macrocyclic ring, so that the molecules appear on average as large planar discs, which consist of extended π systems. The aggregation tendency (π stacking) of the compounds can be strengthened by the attachment of flexible saturated chains on the periphery. The discs represent then mesogens for columnar (or nematic) discotic LC phases. Because of the stilbenoid character, the compounds show a variety of interesting photophysical and photochemical properties. They can be applied in photoconductive liquid crystalline phases Colh and in radiation-induced imaging techniques.

Key words

annulenes - condensation - ring closure - aggregation - photochemistry

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