Synthesis and Characterization of Polysubstituted Dibenzopyrenes as Charge-Transporting Materials

A new class of benzopyrene-based semiconducting molecules is prepared and characterized. A four-step protocol involving Suzuki coupling and aromatic dehydrogenation reactions renders the new unsymmetrical framework. Introduction of various substituents at the dibenzopyrene framework modulates mainly the optoelectronic properties rather than the packing motif. Single-crystal field-effect transistors fabricated from these materials show a mobility ranging from 0.7 to 3.2 cm(2)/(V s). The highest mobility, 3.2 cm(2)/(V s), with an on/off ratio of 10(4)-10(5) was achieved for 11-methoxy-8-(4-methoxyphenyl)dibenzo-[a,e]pyrene.