Perfluoropentacene and Perfluorotetracene: Syntheses, Crystal Structures, and FET Characteristics

The syntheses and FET characteristics of perfluoropentacene and perfluorotetracene are described. Both acenes are planar and crystalline materials that adopt π-stack structures with the short interpalnar distances of 3.27 Å in perfluorotetracene and 3.21 Å in perfluoropentacene. The oxidation and reduction peak potentials of the perfluorinated acenes shift positively compared with those of the corresponding acenes, suggesting that the HOMO and LUMO energies are diminished by fluorine substituents. Organic field-effect transistors (OFETs) with perfluoropentacene exhibit n-type semiconducting properties with high electron mobility of 0.22 cm2/V s. Keywords: organic field-effect transistororganic n-type semiconductorsperfluoropentaceneperfluorotetracene Acknowledgments This work was supported by Japan Society for the Promotion of Science (Grant-in-Aid for Scientific Research B14340226 and Grant-in-Aid for Young Scientists B15750161). We thank Prof. H. Kawaguchi, Dr. T. Matsuo, Prof. K. Inoue, and Dr. M. Akita for help in X-ray structural determination. Notes a OFETs were fabricated on OTS-modified SiO2/Si substrates.