Ortho O-Annulated Azabenzannulated Perylenediimide and Bisazacoronenediimide

The development of new n-type organic semiconductors is crucial to the development of organic electronics. The introduction of heteroatoms into polycyclic aromatic hydrocarbons (PAHs) or nanographenes has been demonstrated to be a compelling strategy to tune their optoelectronic, coordination, magnetic and self-assembly properties, in order to adapt them to specific organic electronic devices. Perylenediimide (PDI) derivatives have been an interesting hetero-doping platform for the design of new functional electron-deficient structures, but rarely has oxygen been introduced into their pi-conjugated scaffold. In this study, we present the preparation of Bisazacoronenediimide (BACD) derivatives annulated by the insertion of oxygen in their ortho position. These compounds exhibit high planarity and their properties are highly sensitive to the extension of their pi-system. Their optoelectronic properties and performance in preliminary organic electronics studies are reported. This work shows that the ortho O-annulation of BACDs is a promising route to explore for the discovery of future new high-performance rylene diimide dyes.