Photoactivation Properties of Self-n-Doped Perylene Diimides: Concentration-dependent Radical Anion and Dianion Formation.

ABSTRACT: Perylene diimides (PDIs) have garnered attention as organic photocatalysts in recent years for their ability to drive challenging synthetic transformations, such as aryl halide reduction and olefin iodoperfluoroalkylation. Previous work in this area employs spectator pendant groups attached to the imide nitrogen positions of PDIs that are only added to impart solubility. In this work, we employ electron-rich ammonium iodide or ammonium hydroxide pendant groups capable of self-n-doping the PDI core to form radical anions (R ^•- ) and dianions (D ^••2- ). We observe R ^•- formation is favored at low concentrations where aliphatic linkers are able to freely rotate, while D ^••2- formation is favore

SUBMITTER: Powell D 

PROVIDER: S-EPMC9284616 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature