1,3,6,8-Tetraphenylpyrene Derivatives: Towards Fluorescent Liquid-Crystalline Columns?

Authors

  • V. de Halleux,

    1. Laboratoire de Chimie des Polymères, Université Libre de Bruxelles CP 206/01, Bld du Triomphe, 1050 Bruxelles, Belgium
    Search for more papers by this author
  • J.-P. Calbert,

    1. Service de Chimie des Matériaux Nouveaux, Centre de Recherche en Electronique et Photonique Moléculaires, Université de Mons-Hainaut, Place du Parc 20, 7000 Mons, Belgium
    Search for more papers by this author
  • P. Brocorens,

    1. Service de Chimie des Matériaux Nouveaux, Centre de Recherche en Electronique et Photonique Moléculaires, Université de Mons-Hainaut, Place du Parc 20, 7000 Mons, Belgium
    Search for more papers by this author
  • J. Cornil,

    1. Service de Chimie des Matériaux Nouveaux, Centre de Recherche en Electronique et Photonique Moléculaires, Université de Mons-Hainaut, Place du Parc 20, 7000 Mons, Belgium
    2. Second address: School of Chemistry and Biochemistry, Georgia Institute of Technology, 770 State Street, Atlanta, GA 30332-0400, USA.
    Search for more papers by this author
  • J.-P. Declercq,

    1. Unité de Chimie Structurale, Université Catholique de Louvain, 1, Place Louis Pasteur, 1348 Louvain-la-Neuve, Belgium
    Search for more papers by this author
  • J.-L. Brédas,

    1. Service de Chimie des Matériaux Nouveaux, Centre de Recherche en Electronique et Photonique Moléculaires, Université de Mons-Hainaut, Place du Parc 20, 7000 Mons, Belgium
    2. Second address: School of Chemistry and Biochemistry, Georgia Institute of Technology, 770 State Street, Atlanta, GA 30332-0400, USA.
    Search for more papers by this author
  • Y. Geerts

    Search for more papers by this author

  • This work was financially supported by the Belgian National Science Foundation (FNRS-FRFC no. 2.4560.00, FNRS ‘crédit aux chercheurs’ no. 1.5.074.00), Université Libre de Bruxelles, Banque Nationale de Belgique, Communauté Française de Belgique (ARC no. 00/05-257), and European Union (DISCEL G5RD-CT-2000–00321). The work in Mons is partly supported by the Belgian Federal Government ‘Interuniversity Attraction Pole in Supramolecular Chemistry and Catalysis’ (PAI 5/3) and by FNRS/FRFC. The work at Atlanta is partly supported by the US National Science Foundation, the Office of Naval Research Fund, and the IBM Shared University Research Program. J.-P. C. and V. d. H. acknowledge FRIA for a fellowship; J. C. is an FNRS Research Associate.

Abstract

Tetraphenylpyrene has been selected as a discotic core to promote liquid-crystalline fluorescent columns in view of its high fluorescence quantum yield in solution and ease of substitution by flexible lateral side chains. The synthesis and characterization of ten new derivatives of pyrene have been carried out; the pyrene core has been substituted at the 1,3,6,8-positions by phenylene rings bearing alkoxy, ester, thioether, or tris(alkoxy)benzoate groups on the para position; the compounds have been characterized by mass spectrometry and 1H NMR and UV-vis spectroscopies. In order to generate liquid-crystalline phases, the nature, number, and size of the side chains as well as the degree of polarity around the tetraphenylpyrene core have been varied. However, the desired liquid-crystalline behavior has not been observed. The supramolecular order together with the absorption and emission properties in solution and the solid state are discussed and compared to theoretical predictions. Quantum-chemical calculations rationalize the high solid-state fluorescence of a tetraphenylpyrene derivative for which the crystal structure has been determined.

Ancillary