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

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• 作者：Peter D. Frischmann ; Frank W眉rthner
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：September 20, 2013
• 年：2013
• 卷：15
• 期：18
• 页码：4674-4677
• 全文大小：250K
• 年卷期：v.15,no.18(September 20, 2013)
• ISSN：1523-7052

文摘

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鈥?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.