High charge-carrier mobility in π-deficient discotic mesogens: design and structure-property relationship

Matthias Lehmann, Gaël Kestemont, Rafael Gómez Aspe, Claudine Buess-Herman, Michel H.J. Koch, Michael G. Debije, Jorge Piris, Matthijs P. De Haas, John M. Warman, Mark D. Watson, Vincent Lemaur, Jérôme Cornil, Yves Henri Geerts, Raluca Gearba, Dimitri A. Ivanov

Research output: Contribution to journalArticlepeer-review

169 Scopus citations


Hexaazatrinaphthylene (HATNA) derivatives with six alkylsulfanyl chains of different length (hexyl, octyl, decyl and dodecyl) have been designed to obtain new potential electron-carrier materials. The electron-deficient nature of these compounds has been demonstrated by cyclic voltammetry. Their thermotropic behaviour has been studied by means of differential scanning calorimetry and polarised optical microscopy. The supramolecular organisation of these discotic molecules has been explored by temperature-dependent X-ray diffraction on powders and oriented samples. In addition to various liquid crystalline columnar phases (Colhd, Colrd), an anisotropic plastic crystal phase is demonstrated to exist. The charge-carrier mobilities have been measured with the pulse-radiolysis time-resolved microwave-conductivity technique. They are found to be higher in the crystalline than in the liquid crystalline phases, with maximum values of approximately 0.9 and 0.3 cm2V -1s-1, respectively, for the decylsulfanyl derivative. Mobilities strongly depend on the nature of the side chains.

Original languageEnglish
Pages (from-to)3349-3362
Number of pages14
JournalChemistry - A European Journal
Issue number11
StatePublished - May 20 2005


  • Charge-carrier mobility
  • Columnar mesophases
  • Electron-deficient mesogens
  • Liquid crystals
  • X-ray diffraction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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