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.
1,3,6,8-Tetraphenylpyrene Derivatives: Towards Fluorescent Liquid-Crystalline Columns?†
Article first published online: 22 JUL 2004
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Advanced Functional Materials
Volume 14, Issue 7, pages 649–659, July, 2004
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
- Issue published online: 22 JUL 2004
- Article first published online: 22 JUL 2004
- Manuscript Received: 29 DEC 2003
- Fluorescing materials;
- Liquid crystals, discotic;
- Quantum-chemical calculations;
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.