title: 9,10-Dichlorooctafluoroanthracene as a building block for n-type organic semiconductors.
abstract: 9,10-Dichlorooctafluoroanthracene (1) was synthesized from commercially available tetrafluorophthalic acid by an optimized solution-phase route. To establish 1 as a synthon for n-type organic semiconductors, the compound was reacted with phenylboronic acid under modified Suzuki-Miyaura coupling conditions to generate octafluoro-9,10-diphenylanthracene (7) in high yield. Cyclic voltammetry and X-ray crystallography indicate that 7 has a stabilized LUMO energy level and exhibits extended pi stacking, which should lead to efficient electron transport in solid-state devices. 1,2,3,4,5,6,7,8-Octafluoroanthracene (2) was also synthesized as a potential n-type building block, but suitable C-C coupling conditions for this compound were not found, and 2 could not be converted into 9,10-dibromooctafluoroanthracene or octafluoro-9,10-diiodoanthracene.
authors.affiliation: Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720, USA.
authors.forename: John F
authors.initials: JF
authors.lastname: Tannaci
authors.forename: Masahiro
authors.initials: M
authors.lastname: Noji
authors.forename: Jennifer
authors.initials: J
authors.lastname: McBee
authors.forename: T Don
authors.initials: TD
authors.lastname: Tilley