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

  1. V. de Halleux1,
  2. J.-P. Calbert2,
  3. P. Brocorens2,
  4. J. Cornil2,4,
  5. J.-P. Declercq3,
  6. J.-L. Brédas2,4,
  7. Y. Geerts

Article first published online: 22 JUL 2004

DOI: 10.1002/adfm.200400006

Issue

Advanced Functional Materials

Advanced Functional Materials

Volume 14, Issue 7, pages 649–659, July, 2004

Additional Information

How to Cite

de Halleux, V., Calbert, J.-P., Brocorens, P., Cornil, J., Declercq, J.-P., Brédas, J.-L. and Geerts, Y. (2004), 1,3,6,8-Tetraphenylpyrene Derivatives: Towards Fluorescent Liquid-Crystalline Columns?. Adv. Funct. Mater., 14: 649–659. doi: 10.1002/adfm.200400006

Author Information

  1. 1

    Laboratoire de Chimie des Polymères, Université Libre de Bruxelles CP 206/01, Bld du Triomphe, 1050 Bruxelles, Belgium

  2. 2

    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

  3. 3

    Unité de Chimie Structurale, Université Catholique de Louvain, 1, Place Louis Pasteur, 1348 Louvain-la-Neuve, Belgium

  4. 4

    Second address: School of Chemistry and Biochemistry, Georgia Institute of Technology, 770 State Street, Atlanta, GA 30332-0400, USA.

  1. †

    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.

Publication History

  1. Issue published online: 22 JUL 2004
  2. Article first published online: 22 JUL 2004
  3. Manuscript Received: 29 DEC 2003

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Keywords:

  • Fluorescing materials;
  • Liquid crystals, discotic;
  • Quantum-chemical calculations;
  • Tetraphenylpyrenes

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.

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