Synthesis, Characterization, and Bipolar Transporting Behavior of a New Twisted Polycyclic Aromatic Hydrocarbon: 1 ',4 '-Diphenyl-naphtho-(2 '.3 ':1.2)-pyrene-6 '-nitro-7 '-methyl Carboxylate

An asymmetric twistacene, 1',4'-diphenyl-naphtho-(2'.3':1.2)-pyrene-6'-nitro-7'-methyl carboxylate (tetracene 2), was synthesized by using benzyne-trapping chemistry. Its structure, determined by X-ray crystallography, confirmed that this material has a twisted topology with torsion angles as high as 23.8(3)degrees. Organic light-emitting devices using tetracene 2 as either charge-transporting materials or emitters have been fabricated. The results indicate that this material has bipolar transporting behavior in these devices.