56777-03-8Relevant academic research and scientific papers
9,10-Dichlorooctafluoroanthracene as a building block for n-type organic semiconductors
Tannaci, John F.,Noji, Masahiro,McBee, Jennifer,Tilley, T. Don
, p. 5567 - 5573 (2007)
(Chemical Equation Presented) 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.
