4′-Bromo-2′,3′,5′,6′-tetrafluorostilbazole

Donor and acceptor site for halogen bonding and π-stacking in one rigid-rod-type molecule

André C B Lucassen, Maida Vartanian, Gregory Leitus, Milko van der Boom

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

The title compound, a new fluorinated stilbazole-based chromophore combines hydrocarbon (HC) donor and perfluorocarbon (PFC) acceptor sites in one rigid-rod-type conjugated molecule. The bifunctional stilbazole derivative combines several possibilities of weak, medium, and strong intermolecular interactions leading to an attractive crystal packing. The chromophore shows strong π-π stacking behavior in solution, while its crystal structure consists of an infinite unimolecular network involving both interchain π-π stacking and N⋯Br halogen bonding. The latter Lewis acid-base interactions do not play a dominant role in controlling the solution optical properties. In the solid state, the molecules are aligned in one-dimensional infinite head-to-tail chains as a result of attractive halogen bonding. Adjacent chains are oriented in opposite directions.

Original languageEnglish
Pages (from-to)1671-1673
Number of pages3
JournalCrystal Growth and Design
Volume5
Issue number5
DOIs
Publication statusPublished - Sep 2005

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Halogens
Chromophores
halogens
chromophores
rods
Fluorocarbons
Lewis Acids
Molecules
Hydrocarbons
molecules
Optical properties
hydrocarbons
Crystal structure
interactions
Derivatives
solid state
optical properties
Crystals
acids
crystal structure

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

4′-Bromo-2′,3′,5′,6′-tetrafluorostilbazole : Donor and acceptor site for halogen bonding and π-stacking in one rigid-rod-type molecule. / Lucassen, André C B; Vartanian, Maida; Leitus, Gregory; van der Boom, Milko.

In: Crystal Growth and Design, Vol. 5, No. 5, 09.2005, p. 1671-1673.

Research output: Contribution to journalArticle

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abstract = "The title compound, a new fluorinated stilbazole-based chromophore combines hydrocarbon (HC) donor and perfluorocarbon (PFC) acceptor sites in one rigid-rod-type conjugated molecule. The bifunctional stilbazole derivative combines several possibilities of weak, medium, and strong intermolecular interactions leading to an attractive crystal packing. The chromophore shows strong π-π stacking behavior in solution, while its crystal structure consists of an infinite unimolecular network involving both interchain π-π stacking and N⋯Br halogen bonding. The latter Lewis acid-base interactions do not play a dominant role in controlling the solution optical properties. In the solid state, the molecules are aligned in one-dimensional infinite head-to-tail chains as a result of attractive halogen bonding. Adjacent chains are oriented in opposite directions.",
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