Electron-Deficient Benzo[de]isoquinolino[1,8-gh]quinoline Diamide pi-Electron Systems

Synthetically versatile electron-deficient pi-electron systems are urgently needed for organic electronics, yet their design and synthesis are challenging due to the low reactivity from large electron affinities. In this work, we report a benzo[de]isoquinolino[1,8-gh]quinoline diamide (BQQDA) pi-electron system. The electron-rich condensed amide as opposed to the generally-employed imide provides a suitable electronic feature for chemical versatility to tailor the BQQDA pi-electron system for various electronic applications. We demonstrate an effective synthetic method to furnish the target BQQDA parent structure, and highly selective functionalization can be performed on bay positions of the pi-skeleton. In addition, thionation of BQQDA can be accomplished under mild conditions. Fine-tuning of fundamental properties and supramolecular packing motifs are achieved via chemical modifications, and the cyanated BQQDA organic semiconductor demonstrates a high air-stable electron-carrier mobility.

Automated summary

In this work, a benzo[de]isoquinolino[1,8-gh]quinoline diamide (BQQDA) pi-electron system was reported. The use of an electron-rich condensed amide instead of the usually employed imide provided suitable electronic features for chemical versatility in tailoring the BQQDA pi-electron system. Chemical modifications allowed for selective functionalization of the bay positions of the pi-skeleton. Furthermore, thionation of BQQDA was achieved under mild conditions. The resulting cyanated BQQDA organic semiconductor exhibited a high air-stable electron-carrier mobility.