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Synthesis 2007(12): 1872-1876  
DOI: 10.1055/s-2007-983718
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Optical Properties of Fluorescent Core-Trisubstituted Naphthalene Diimide Dyes

Cornelia Röger, Shahadat Ahmed, Frank Würthner*
Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg, Germany
Fax: +49(931)8884756; e-Mail: wuerthner@chemie.uni-wuerzburg.de;
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Publication History

Received 23 February 2007
Publication Date:
08 June 2007 (online)

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Abstract

Efficient synthetic routes to hitherto unknown core-trisubstituted naphthalene diimides (NDIs) starting with 2,6-dichloro-substituted NDIs 1 are described. The reaction of NDIs 1 with ethylene diamine as solvent, affords the ethylene-diamine-bridged core-trisubstituted NDIs 2 in very good yield. The substitution of the chlorine atom of 2 with alkylamino or alkoxy nucleophiles leads to triamino- or alkoxy-diamino-substituted NDIs. UV/Vis spectroscopy revealed that the electronic properties of NDI chromophores bearing three core substituents are strongly influenced by the nature of the substituents. NDIs which are tri(alkylamino)-substituted at the naphthalene core exhibit high (up to 70%) fluorescence quantum yields.

Key words

dyes - fluorophores - rylenes - nucleophilic aromatic substitution - intramolecular ring closure