Synthesis of a Non-aggregating Bay-Unsubstituted Perylene Bisimide Dye with Latent Bromo Groups for C–C Cross Coupling

To address the absence of synthetic routes to access easily functionalizable, non-aggregating, and soluble bay-unsubstituted perylene bisimide dyes, an efficient, three-step, multigram-scale synthesis of the divergent building block N,N′-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarbo...

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Veröffentlicht in:Organic letters 2013-09, Vol.15 (18), p.4674-4677
Hauptverfasser: Frischmann, Peter D, Würthner, Frank
Format: Artikel
Sprache:eng
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Zusammenfassung:To address the absence of synthetic routes to access easily functionalizable, non-aggregating, and soluble bay-unsubstituted perylene bisimide dyes, an efficient, three-step, multigram-scale synthesis of the divergent building block N,N′-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic bisimide is reported. Suzuki coupling yields new dyes that maintain excellent solubility and exhibit unity quantum yields in CHCl3, THF, toluene, and CH3CN. The methodology reported here enables access to dyes with sensitive functional groups such as aldehydes that are not accessible by traditional imidization routes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401946g