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.
Developing novel high-performance n-type semiconductors is of great importance for the future organic electronics. The complicated synthesizing procedures of new electron deficient backbones or chemical modification to control the energy...
High performance solution processable n-type organic semiconductor is an essential element to realize lowcost, all organic and flexible composite logic circuits. In the design of n-type semiconducting materials, tuning the LUMO level of compounds is a key point. As a strong electron withdrawing unit, the introduction of chlorine atom into the chemical structure can increase the electron affinity of the material and reduce the LUMO energy level. Here, a series chlorine substituted N-heteroacene analogues of 6,7,8,9tetrachloro-4,11-bis(4-((2-ethylhexyl) ,2,3,4,8,9,10,11-octachloro-6,13-bis(4-((2ethylhexyl)oxy)phenyl)quinoxalino[2,3-b]phenazine (8Cl) and 12Cl have been synthesized and characterized. Solutionprocessed organic field-effect transistors (OFETs) based on these four compounds exhibit good electron mobilities of 0.04 cm 2 V À 1 s À 1 , 0.01 cm 2 V À 1 s À 1 , 2 × 10 À 3 cm 2 V À 1 s À 1 and 3 × 10 À 3 cm 2 V À 1 s À 1 , respectively, under ambient conditions. The results suggest that these chlorine substituted π-conjugated N-heteroacene analogues are promising n-type semiconductors in OFET applications.
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