Direct synthesis of gold(iii)-annulated perylene diimides via multiple C–H aurations†

Abstract

GA1We present a direct synthesis of novel gold(III)-annulated perylene diimides (Au-PDIs and Au₂-PDIs) from ortho-pyridyl-substituted PDIs, achieving facile auration of two or four C–H bonds in one pot. Au₂-PDI 12 (λ_max = 635 nm) emerged as the most red-shifted compound among all reported heteroannulated PDIs. Cyclic voltammetry and density functional theory calculations indicate degenerated LUMO levels and substantial narrowing of the HOMO–LUMO energy gaps. This synthetic strategy is expected to unlock the potential of diverse transition metal-annulated PDIs.