Facile Azabenz-Annulations through UV-induced Photocyclization: A Promising Method for Perylenediimide-Based Organic Semiconductors

作者：Sun, Hua; Mu, Zifeng; Yang, Canglei; Zhang, Kai; Ji, Xingyu; Zhang, Tianshu; Ding, Huanda; Wang, Shifan^*; Dong, Liming; Zhang, Jing^*; Zhang, Qichun^*

来源：Chemistry - An Asian Journal, 2022, 17(3): e202101323.

DOI：10.1002/asia.202101323

• azabenz-annulations
• perylenediimides
• photocyclization
• semiconductors
• ultraviolet-induced

The derivatization of perylenediimides (PDIs) by bay decoration is essential for the development of PDI-based semiconductors owing to their excellent photoelectric properties. Herein, four bis-azabenz-annulated PDIs (bis-AzaBPDIs) are concisely synthesized in high yields through ultraviolet-induced photocyclization, where the reaction processes including aldimine condensation, cyclization, and oxidative re-aromatization are investigated. The optical characterizations and theoretical simulation reveal that the unique properties of the four bis-AzaBPDIs are comparable to their parent PDI. Organic field effect transistors with compounds 2, 3, or 4 as active layers indicated that all compounds showed unipolar electron transport properties with the mobilities of 1.1x10(-3), 5.8x10(-4), and 8.5x10(-6) cm(2) V-1 s(-1), respectively. These results suggest the great potential of bis-AzaBPDIs as organic semiconductors. The easy preparation approach reported in this work would renew research interest in developing bis-AzaBPDI-based optoelectronic molecules.

• 单位
  南京邮电大学; 西北工业大学