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

Abstract

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 <i>N</i>,<i>N</i>′-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