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Pure Appl. Chem., 2006, Vol. 78, No. 4, pp. 707-719

Self-assembling and spectroscopic properties of soluble linear acenes

Jean-Pierre Desvergne1, André Del Guerzo1, Henri Bouas-Laurent1, Colette Belin2, Jens Reichwagen3 and Henning Hopf3

1 LCOO - CNRS UMR 5802, Université Bordeaux 1, F-33405, Talence, France
2 Laboratoire de Physico-Chimie Moléculaire (CNRS, UMR 5803) Université Bordeaux 1, F-33405 Talence, France
3 Institut für Organische Chemie,TU-Braunschweig, D-38106 Braunschweig, Germany

Abstract: The gelling and spectroscopic properties of new soluble disubstituted acenes (anthracene, tetracene, pentacene) are reported. It is shown that the 2,3-alkoxy derivatives gel a large variety of organic solvents, a process that is related to the linear shape of the molecule. The gelation involves the formation of nanofibers through noncovalent interactions (van der Waals, π-π stacking), weaving a 3D supramolecular network or a deposit made of isolated fibers on surfaces (mica or graphite). Transport of photons through this type of nanostructure has been evidenced by the observation of an efficient energy transfer occurring from an anthracene light-harvesting matrix to a tetracene energy trap doping agent.