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Ionic Liquid Crystals Formed by Self‐Assembly around an Anionic Anthracene Core
Author(s) -
Olivier JeanHubert,
Camerel Franck,
Barberá Joaquín,
Retailleau Pascal,
Ziessel Raymond
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900721
Subject(s) - anthracene , mesophase , ionic liquid , differential scanning calorimetry , chemistry , alkyl , crystallography , ionic bonding , luminescence , mesogen , columnar phase , polymer chemistry , materials science , ion , organic chemistry , polymer , phase (matter) , liquid crystalline , physics , optoelectronics , thermodynamics , catalysis
We have designed and synthesised a series of modular, mesogenic complexes based on anthracene‐2,6‐disulfonate 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 (C 16 H 33 ) 2 , a crystal structure determination has shown that the long paraffinic chains are intercalated between the anthracene moieties. The dianion forms columnar mesophases with trialkoxybenzylimidazolium 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.