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Synthesis 2009(11): 1841-1845  
DOI: 10.1055/s-0029-1216785
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Core-Tetrasubstituted Naphthalene Diimides by Stille Cross-Coupling Reactions and Characterization of Their Optical and Redox Properties

Sabin-Lucian Suraru, Frank Würthner*
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Fax: +49(931)3184756; e-Mail: wuerthner@chemie.uni-wuerzburg.de;
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Publication History

Received 18 November 2008
Publication Date:
30 April 2009 (online)

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Abstract

The palladium-catalyzed cross-coupling reaction of 2,3,6,7-tetrabromonaphthalene diimide with various aryl- and alkynylstannanes afforded a series of hitherto unknown tetraaryl- and tetraethynyl-substituted naphthalene diimides (NDIs). UV/Vis spectroscopic studies revealed that the absorption maxima of ethynyl-substituted NDIs are significantly bathochromically shifted compared to those of unsubstituted and tetraaryl-substituted NDIs. Cyclic voltammetry investigations showed that ethynyl substituents shift the reduction potentials of NDIs anodically, thus these NDI derivatives are interesting candidates for air-stable n-channel organic field-effect transistors.

Key words

chromophores - arylenes - cross-coupling - Stille reaction - catalysis

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