Ionic liquid crystals formed by self-assembly around an anionic anthracene core

Jean Hubert Olivier, Franck Camerel, Joaquín Barberá, Pascal Retailleau, Raymond Ziessel

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

We have designed and synthesised a series of modular, mesogenic complexes based on anthracene-2,6-di-sulfonate and trialkoxybenzyl-functionalised imidazolium cations. Each complex contains a central, rigid, dianionic anthracene core and two flexible monocations bearing paraffin chains anchored on imidazolium rings. Anthracene-2, 6-disulfonate can be crystallised with various simple alkylammonium ions and, in the case of +N(CH 3)2-(C16H33)2, a crystal structure determination has shown that the long paraffinic chains are intercalated between the anthracene moieties. The dianion forms columnar mesophases with trialkoxy-benzylimidazolium cations, as identified by polarising optical microscopy and X-ray scattering measurements. Differential scanning calorimetry studies confirmed mesomorphic behaviour from room temperature to about 200 °C for alkyl chains containing 8, 12 and 16 carbon atoms. The strong luminescence of anthracene is maintained in the mesophase and fluorescence measurements confirmed the presence of J aggregates in all cases. The new functional materials described herein provide an easy access to stable and luminescent mesomorphic materials engineered by an ionic self-assembly process.

Original languageEnglish (US)
Pages (from-to)8163-8174
Number of pages12
JournalChemistry - A European Journal
Volume15
Issue number33
DOIs
StatePublished - Aug 17 2009
Externally publishedYes

Keywords

  • Anthracene
  • Liquid crystals
  • Luminescence
  • Mesophases
  • Self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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