Synthesis, Stepwise Bromination, and Functionalization of Picene Diimide.

Materials Synthesis and Processing Polycyclic aromatic hydrocarbon (PAH) diimides are indispensable candidates for n-type organic semiconductors in organic optoelectronic devices. Developing new PAH diimide building blocks are of remarkable significance for material diversity and further advance in organic semiconductors. In this contribution, 4,5,8,9-picene diimide (PiDI) was designed and synthesized. Controllable stepwise bromination of PiDI were accomplished to afford 13-monobromo-, 13,14-dibromo-, 2,13,14-tribromo- and 2,11,13,14-tetrabromo-PiDI. Moreover, cyanation of 2,11,13,14-tetrabromo-PiDI gave the corresponding tetracyanated PiDI, which can be utilized as n-type semiconductor with OFET electron mobility up 0.073 cm2 V-1 s-1 . This result demonstrates the potential of PiDI as a building block for constructing new high-performance electronic-transporting materials.