9,10-Dichlorooctafluoroanthracene as a Building Block for n-Type Organic Semiconductors

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 π 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.