Asymmetric flavone-based liquid crystals: synthesis and properties

Daren J. Timmons, Abraham J. Jordan, Angelo A. Kirchon, N. Sanjeeva Murthy, Troy J. Siemers, Daniel P. Harrison, Carla Slebodnick

Research output: Contribution to journalArticlepeer-review

Abstract

A series of flavones (n-F) substituted at the 4′, and 6 positions was prepared, characterised by NMR (1H,13C), HRMS, and studied for liquid crystal properties. The 4′-alkoxy,6-methoxyflavones (4-F–16-F) exhibit varying ranges of nematic and smectic A phases as evidenced by polarised optical microscopy and differential scanning calorimetry (DSC). As the tail length is increased, the smectic phase becomes more prevalent. Smectic phases for (8-F–16-F) were further analysed by powder X-ray diffraction (XRD), and the rate of structural transformations was explored by combined DSC/XRD studies. Flavonol 6-F–OH was also prepared but no mesogenic behaviour was observed. The molecular structures of 6-F and 6-F–OH were determined by single-crystal XRD and help to explain the differences in material properties. Additionally, fluorescence and electrochemical studies were conducted on solutions of n-F.

Original languageAmerican English
Pages (from-to)1436-1449
Number of pages14
JournalLiquid Crystals
Volume44
Issue number9
DOIs
StatePublished - Jul 15 2017

ASJC Scopus subject areas

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics

Keywords

  • Liquid crystal
  • combined DSC/XRD
  • flavone
  • fluorescence
  • heterocycle
  • thermotropic

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