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 language | English (US) |
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Pages (from-to) | 8163-8174 |
Number of pages | 12 |
Journal | Chemistry - A European Journal |
Volume | 15 |
Issue number | 33 |
DOIs | |
State | Published - Aug 17 2009 |
Externally published | Yes |
Keywords
- Anthracene
- Liquid crystals
- Luminescence
- Mesophases
- Self-assembly
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Organic Chemistry