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.
Keywords: azabenz-annulations; perylenediimides; photocyclization; semiconductors; ultraviolet-induced.
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