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

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

John F Tannaci, Masahiro Noji, Jennifer McBee, T Don Tilley

J Org Chem. 2007 Jul 20;72(15):5567-73.

PMID: 17590045

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP219724466	9,10-Dichlorooctafluoroanthracene		219724-46-6	Price

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