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 Å. 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 cm2 V−1 s−1 for 1CT and 2.2 cm2 V−1 s−1 for 2CT, respectively. These oxygen-resisted organics may offer potential to fabricate the flexible electronics under air conditions.