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Influence of linear and branched perfluoroalkylated side chains on the π–π stacking behaviour of hexa-peri-hexabenzocoronene and thermotropic properties

  • Alameddine, Bassam Department of Mathematics and Natural Sciences, Gulf University for Science andTechnology, Hawally, Kuwait
  • Aebischer, Olivier F. BASF Pharma (Evionnaz) SA, Evionnaz, Valais, Switzerland
  • Heinrich, Benoît Institut de Physique et Chimie des Matériaux de Strasbourg, Université de Strasbourg), France
  • Guillon, Daniel Institut de Physique et Chimie des Matériaux de Strasbourg, Université de Strasbourg), France
  • Donnio, Bertrand Institut de Physique et Chimie des Matériaux de Strasbourg, Université de Strasbourg), France
  • Jenny, Titus A. Department of Chemistry, University of Fribourg, Switzerland
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    2014
Published in:
  • Supramolecular Chemistry. - 2014, vol. 26, no. 2, p. 125–137
English The thermotropic properties and self-assembly of two different series of hexa-peri-hexabenzocoronenes (HBC) bearing either linear or branched perfluoroalkylated side chains, each with a wide range of alkyl spacer and perfluorinated tail lengths, have been studied. Correlations between thermogravimetric analysis, differential scanning calorimetry, polarised optical microscopy and small-angle X-ray scattering experiments revealed, as expected, that the transition temperatures and phase stability are influenced by the determining roles of the aliphatic spacer length and odd/even nature, as well as the size and structure (linear vs. bifurcation) of the perfluorinated sections. Most of the investigated HBC derivatives showed a single-column hexagonal columnar phase, where the columns are structured by a double segregation process between HBC aromatic cores and aliphatic spacers, on the one hand, and between aliphatic spacers and fluorinated tails, on the other hand. For the derivatives with long linear spacers, cores of untilted or quasi-untilted HBC stacks are surrounded by a cylindrical aliphatic envelope segregated from the fluorinated periphery, whereas for those with shorter linear spacers, the same structure is kept, except that the aliphatic envelope deviates from cylindricality and causes a symmetry break to rectangular envelope for the first term of the series. Of the four HBC with branched spacers, two are amorphous, whereas a columnar phase is maintained for the other two derivatives, but with tilted HBC stacks. Consequently, the evolution of the polymorphism in the series could be correlated with the variation of both interface areas.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/303535
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