Triple Regioselective Functionalization of Cationic [4]Helicenes via Iridium-Catalyzed Borylation and Suzuki Cross-Coupling Reactivity

In essentially one-pot, using Ir- and Pd-catalysis, tris(arene)-functionalized cationic [4]helicenes are synthesized with full regioselectivity and enantiospecificity starting from a trivial precursor (17 examples). This poly-addition of aryl groups improves key optical properties, that is, fluorescence quantum yields and lifetimes. Electronic circular dichroism and circularly polarized luminescence signatures are observed up to the far-red domain, in particular with additional arenes prone to aggregation.

Automated summary

In this study, tris(arene)-functionalized cationic [4]helicenes are synthesized with full regioselectivity and enantiospecificity using Ir- and Pd-catalysis in essentially one-pot, starting from a trivial precursor (17 examples). The poly-addition of aryl groups improves key optical properties, such as fluorescence quantum yields and lifetimes. Electronic circular dichroism and circularly polarized luminescence signatures are observed up to the far-red domain, particularly with additional arenes prone to aggregation.