A Tetracene Derivative with π-stacking Structure: the Synthesis, Crystal Structure and Transistor Properties

Although it has been suggested that forming face-to-face π- stacks in organic semiconductors may give high charge-carrier mobility due to the enhanced electronic couplings, this hypothesis has not so far experimentally confirmed conclusively. Towards this end, we synthesized a tetracene derivative, tetrachlorotetracene, which crystallizes with slip π-stacks. Electrostatic potential maps of tetrachlorotetacene and the parent tetracene molecule show that the slip-stack packing structure is favored in terms of electrostatic forces in tetrachlorotetracene crystals but not in parent tetracene crystals where herringbone structure is adopted. Single crystal filed-effect transistors based on tetrachlorotetracene crystals show p-type behavior with mobilities above 1.7 cm2/Vs. This value is much higher than pentacene and tetracene crystals measured under similar conditions.