Development of novel synthetic routes to bis(perfluoroalkyl)-substituted anthracene derivatives

Commercially available anthraquinones were smoothly converted to either symmetrically or unsymmetrically substituted 9,10-bis(perfluoroalkyl)anthracene-9,10-diols by way of bistrifluoromethylation or successive trifluoromethylation-nucleophilic perfluoroalkylation, respectively, and these diols can be easily aromatized to form bis(perfluoroalkyl) anthracene derivatives in good yields by treatment with a mixture of CBr4 and PPh3. Further cross-coupling reactions using halogen-containing anthracene derivatives realized a successful extension of the original pi-conjugation systems.