Luminescent ionic liquid crystals from self-assembled BODIPY disulfonate and imidazolimn frameworks

Jean Hubert Olivier, Franck Camerel, Gilles Ulrich, Joaquín Barberá, Raymond Ziessel

Research output: Contribution to journalArticle

53 Scopus citations

Abstract

A series of modular mesogenic salts based on the combination of anionic 4,4-difluoro-4-bora-3a,4a-diazas-indacene (F-BODIPY) 2,6-disulfonate dyes and trialkoxybenzyl-functionalised imidazolium cations has been designed and synthesised. Each salt contains a rigid dianionic BODIPY core associated with two imidazolium cations functionalised by 1,2,3-trialkoxybenzyl (alkyl = n-C8, n-C12 or n-C16) units or, in one case, with imidazolium cations functionalised by a trialkylgallate (3,4,5-trialkoxybenzoate) unit in which the 3,5-dialkyl groups are terminated with a polymerisable acrylate entity. All these compounds were highly fluorescent in solution with quantum yields ranging from 54 to 62%. In the solid state, the width of the emission band observed at around 650 nm is a clear signature of aggregation. With the trialkoxybenzylimidazolium cations, polarised optical microscopy (POM) and X-ray scattering experiments showed that columnar mesophases were formed. Differential scanning calorimetry (DSC) studies confirmed the mesomorphic behaviour from room temperature to about 130°C for salts with alkyl chains containing 8, 12 and 16 carbon atoms. The strong luminescence of the BODIPY unit was maintained in the mesophase and fluorescence measurements confirmed the presence of J aggregates in all cases. The salt containing the gallate-functionalised imidazolium cations showed no mesomorphism but the acrylate terminal units could be used to engender photoinitiated polymerisation thereby allowing the material to be immobilised on glass plates. The polymerisation process was followed by FTIR spectroscopy and the fixed and patterned films were highly fluorescent with a solid-state emission close to that of the complex in the solid state.

Original languageEnglish (US)
Pages (from-to)7134-7142
Number of pages9
JournalChemistry - A European Journal
Volume16
Issue number24
DOIs
StatePublished - Jun 25 2010
Externally publishedYes

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Keywords

  • Aggregation
  • Fluorescence
  • Liquid crystals
  • Polymerization
  • Self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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