Res. Chem. Intermed.
, Vol. 34, No. 2–3, pp. 137–145 (2008)
Koninklijke Brill NV, Leiden, 2008.
Also available online - www.brill.nl/rci
Self-assembly of soluble anthracene, tetracene and
ALEXANDRE G. L. OLIVE
, ANDRÉ DEL GUERZO
, COLETTE BELIN
, HENNING HOPF
Groupe NEO “Nanostructures Organiques”, Université Bordeaux 1, Institut de Sciences
Moléculaires ISM (CNRS–UMR 5255), F-33405 Talence, France
Groupe “Spectroscopie”, Université Bordeaux 1, Institut de Sciences Moléculaires ISM
(CNRS–UMR 5255), F-33405 Talence, France
Institut für Organische Chemie, TU-Braunschweig, D-38106 Braunschweig, Germany
Received 10 November 2006; accepted 16 January 2007
Abstract—New soluble disubstituted acenes (tetracene, pentacene) have been designed in order to
mimic 2,3-alkoxy derivatives of anthracene. They have been shown to self-assemble and gellify a large
variety of organic solvents. This process involves the formation of nano-ﬁbres through non-covalent
molecular interactions (van der Waals, π–π stacking), weaving a three-dimensional supramolecular
network. Efﬁcient transfer of excitation energy through these nano-structures has been evidenced in
an anthracene light-harvesting matrix doped with less than 1 mol% of a tetracene energy trap.
Keywords: Organogel; linear acenes; energy transfer; nanoﬁbres.
The development of nanostructures with designed optical properties represents a
major interest for applications in photonics, OLEDs, optoelectronics, photovoltaics
and biomimetic light-harvesting. Linear acenes, i.e., linear condensed aromatic
hydrocarbons such as anthracene, tetracene and pentacene, have been appreciated
for years in solid-state photonics for their exceptional optical properties, and in
the design of optically active molecular constituents for their efﬁcient ﬂuorescence
and photochemistry [1–8]. Furthermore, tetracene and pentacene have raised much
interest due to their high charge mobility in the solid state [9–14], showing potential
as organic semiconductors for the fabrication of organic thin-ﬁlm transistors,
electronic papers and ﬂexible displays. Until recently, the limited solubility of pure
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