Synthesis of 2,3-Di-n-hexadecyloxypentacene

Jens Reichwagen; Henning Hopf; Jean-Pierre Desvergne; André Del Guerzo; Henri Bouas-Laurent

doi:10.1055/s-2005-918434

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Synthesis 2005(20): 3505-3507
DOI: 10.1055/s-2005-918434

SHORTPAPER

Synthesis of 2,3-Di-n-hexadecyloxypentacene

Jens Reichwagen^a, Henning Hopf*^a, Jean-Pierre Desvergne*^b, André Del Guerzo^b, Henri Bouas-Laurent^b
^a Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
Fax: +49(531)3915388; e-Mail: H.Hopf@tu-bs.de;
^b , Laboratoire de Chimie Organique et Organométallique, CNRS, UMR 5802, Université Bordeaux 1, 33405 Talence, Cedex, France
Fax: +33(5)40006646; e-Mail: jp.desvergne@lcoo.u-bordeaux1.fr;

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Publication History

Received 4 April 2005
Publication Date:
25 October 2005 (online)

Abstract
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Abstract

The six-step synthesis of 2,3-di-n-hexadecyloxypentacene from benzoquinone as starting material is described. This rod-shaped molecule (ca 3.6 nm in the extended form) was shown to self-assemble into a fibrillar network.

Key words

cycloadditions - aldol reactions - linear acenes - Meerwein-Ponndorf reductions - pentacene derivatives

References

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9

Gelation test: Solvent (1 mL) was added to a weighed amount of gelator in a septum-capped test tube (ca 6 cm length and 0.7 cm diameter) in order to obtain the desired concentration. The mixture was warmed (to the bp) until the solid dissolved. Then the mixture was allowed to cool to r.t. When a gel was formed (ca several min), the sample did not flow when the tube was inverted.