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Synfacts 2009(1): 0040-0040  
DOI: 10.1055/s-0028-1087262
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Rylene NIR Dyes

Contributor(s): Timothy M. Swager, Fei Wang
Z. Liu, C. Li, M. Wagner, Y. Avlasevich, A. Herrmann, K. Müllen*
Max Planck Institute for Polymer Research, Mainz, Germany
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

Reported is the design and synthesis of a group of novel near-infrared (NIR) dyes. These dyes are p-amino-substituted rylene ­dicarboximides. Compared with the bromides, the amino-substitution generated moderate red shifts (˜16-91 nm). More interestingly, further base treatment caused dramatic red shifts of the ­absorption maxima of these dyes (˜135-435 nm). The quinoidal structures of the deprotonated dyes were confirmed by ¹H,¹H COSY NMR spectroscopy.