Synthesis of Heterocyclic Core-Expanded Bis-Naphthalene Tetracarboxylic Diimides

A highly reactive bis-naphthalene tetracarboxylic diimide (bis-NDI) intermediate, TBrDNDI, was designed and synthesized for core-expanded NDIs. Based on this intermediate, we achieved 9- and 11-membered core-expanded bis-NDI derivatives. Through expanding the NDI core and introducing electron-donor or electron-acceptor groups, the frontier energy orbitals, optical and electrical properties of these bis-NDIs can be finely tuned to obtain air-stable ambipolar or n-type materials.