C–H activation-enabled synthesis of a piperazine-embedded azadibenzo[a,g]corannulene analogue

Abstract

A novel piperazine-embedded azadibenzo[a,g]corannulene analogue was synthesized by a four-step bottom-up synthesis, including a nucleophilic aromatic substitution (S_NAr) and a palladium-catalyzed intramolecular C–H activation arylation as key steps. This intriguing molecule represents the first example of an azacorannulene analogue bearing a piperazine ring on its polycyclic skeleton. X-ray diffraction analysis reveals a C_s-symmetric deformed bowl-shaped structure and one-dimensional columnar packing through π–π interactions with slightly offset centres, attributed to the presence of two sp³ carbons on its polycyclic core.