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

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;

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

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References

1 Kelly TW. Baude PF. Gerlach C. Ender DE. Muyres D. Haase MA. Vogel DE. Theiss SD. Chem. Mater. 2004, 16: 4413 ; and references therein

2a de Boer RWI. Jochemsen M. Klapwijk TM. Morpurgo AF. Niemax J. Tripathi AK. Pflaum J. J. Appl. Phys. 2004, 95: 1196

2b Endres RG. Fong CY. Yang LH. Witte G. Wöll C. Comput. Mater. Sci. 2004, 29: 362

2c Innone M. Scott GW. Chem. Phys. Lett. 1990, 171: 569 ; and references quoted

3a Odom SA. Parkin SR. Anthony JE. Org. Lett. 2003, 5: 4245

3b Anthony JE. Eaton DL. Parkin SR. Org. Lett. 2002, 4: 15

3c Reichwagen J. Hopf H. Del Guerzo A. Desvergne J.-P. Bouas-Laurent H. Org. Lett. 2004, 6: 1899

3d Reichwagen J. Hopf H. Del Guerzo A. Belin C. Bouas-Laurent H. Desvergne J.-P. Org. Lett. 2005, 7: 971

4 Desvergne J.-P. Brotin T. Meerschaut D. Clavier G. Placin F. Pozzo J.-L. Bouas-Laurent H. New J. Chem. 2004, 28: 234

5 Placin F. Desvergne J.-P. Belin C. Buffeteau T. Desbats B. Ducasse L. Lassègues J.-C. Langmuir 2003, 19: 4563

6 Pozzo J.-L. Clavier GM. Colomès M. Bouas-Laurent H. Tetrahedron 1997, 53: 6377

7 Zhang X. Fox BW. Hadfield JA. Synth. Commun. 1996, 26: 49

8 Mallouli A. Lepage Y. Synthesis 1980, 689

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.