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 E. Van Der Boom

Research output: Contribution to journalArticle

40 Citations (Scopus)


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
Issue number5
Publication statusPublished - Sep 1 2005


ASJC Scopus subject areas

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

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