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DOI: 10.1055/s-0029-1216785
Core-Tetrasubstituted Naphthalene Diimides by Stille Cross-Coupling Reactions and Characterization of Their Optical and Redox Properties
Publication History
Publication Date:
30 April 2009 (online)

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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