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The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles.

Authors
Type
Published Article
Journal
Beilstein Journal of Organic Chemistry
1860-5397
Publisher
Beilstein-Institut
Publication Date
Volume
10
Pages
910–920
Identifiers
DOI: 10.3762/bjoc.10.89
PMID: 24991240
Source
Medline
Keywords
  • X-Ray Scattering
  • Discotic Liquid Crystals
  • Shape-Persistent Macrocycles
  • Templates

Abstract

A series of shape-persistent phenylene-ethynylene-naphthylene-butadiynylene macrocycles with different extraannular alkyl groups and intraannular bridges is synthesized by oxidative Glaser-coupling of the appropriate precursors. The intraannular bridges serve in this case as templates that reduce the oligomerization even when the reaction is not performed under pseudo high-dilution conditions. The extraannular as well as the intraannular substituents have a strong influence on the thermal behavior of the compounds. With branched alkyl chains at the periphery, the macrocycles exhibit liquid crystalline (lc) phases when the interior is empty or when the length of the alkyl bridge is just right to cross the ring. With a longer alkyl or an oligoethylene oxide bridge no lc phase is observed, most probably because the mesogene is no longer planar.

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