Regioselective functionalization of core-persubstituted perylene diimides

Article abstract of DOI:10.1002/chem.201400397

Regioselective functionalization of core per-substituted perylene diimides has been achieved efficiently based on a new versatile building block, named tetrabromotetrachloro-perylene-3,4:9,10-tetracarboxylic acid dianhydride (Br₄Cl₄-PTCDA), which affords a series of novel chromophores with impressive optoelectronic properties. Direct palladium-catalyzed fourfold intramolecular ring fusion affords successfully unique propeller-shaped biscarbazole[2,3-b]carbazole diimides with six annulated rings. Organic electronics: A series of novel chromophores were afforded by regioselective functionalization of core per-substituted perylene diimides (PDIs) (see scheme). Furthermore, new carbazole diimide derivatives with an extended π-conjugated system were synthesized by direct palladium-catalyzed intramolecular ring fusion.