Synthesis of cyanated tetracenes as the organic semiconductors

Two novel and air-stable cyanated tetracene derivatives, 5-cyanotetracene (1CT) and 5,11-dicyanotetracene (2CT), were synthesized as high-performance organic semiconductors. The stability of 2CT was evaluated by NMR and the electrochemical property was investigated by cyclic voltammetry (CV) and UV-vis spectrum. The reorganization energy of 2CT predicted by UB3LYP/6-311g(d,p) is 0.0881 eV, which is the lowest among existing compounds. The X-ray crystallographic analysis revealed that the 2CT single crystal has a promising face-to-face packing with a relative short intermolecular distance of 3.403 angstrom. Based on the theoretical model we previously developed, the calculated hole mobilities of these air-stable cyanated tetracene derivatives in a-b plane are 2.9 cm(2) V-1 s(-1) for 1CT and 2.2 cm(2) V-1 s(-1) for 2CT, respectively. These oxygen-resisted organics may offer potential to fabricate the flexible electronics under air conditions. Crown Copyright (C) 2009 Published by Elsevier B.V. All rights reserved