Synthesis of a non-aggregating bay-unsubstituted perylene bisimide dye with latent bromo groups for C-C cross coupling

Article abstract of DOI:10.1021/ol401946g

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 CHCl ₃, 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.