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

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 1.1×10−3, 5.8×10−4, and 8.5×10−6 cm2 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. [ABSTRACT FROM AUTHOR]