Synthesis and properties of new stable thienoacenes for organic electronics

ORGN 353

Jaclyn L. Brusso, Oliver D. Hirst, Ganesan Srinivasan, and Dmitrii F. Perepichka, dmitrii.perepichka@mcgill.ca. Department of Chemistry, McGill University, 801 Sherbrooke St West, Montreal, QC H3A 2K6, Canada
π-Conjugated organic molecules have attracted considerable attention over the past decade as materials for organic electronics. Tunable electronic/optical characteristics and inexpensive device fabrication options, which are not easily achieved in established inorganic materials, provide the drive for the development of new and modified π-conjugated systems. Extending the π-conjugation is one of the main approaches to achieve high charge mobility in molecular materials. However, the same structural modification also leads to increased energy of the HOMO and associated low stability of the material, particularly in device operation. Oligo-acene and thiophenes are two main classes of organic materials with demonstrated high charge mobility. Several linearly conjugated thienoanthracenes and thienopentacenes are known, although they suffer from the same environmental instability known for pentacene. In this presentation we will describe synthesis of a new aromatic system comprised of thiophene moieties annealed to an anthracene backbone. The compounds are very stable and can be easily processed in thin films via sublimation (R-H) or spin-coating (R=Alk). The comparative optical, electrochemical and device studies of compounds I and II will be reported.