Areno-Condensed Annulenes - Extended Discotic Mesogens

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 Col_h and in radiation-induced imaging techniques.

Key words

annulenes - condensation - ring closure - aggregation - photochemistry

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