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Synthesis of 6,13-difluoropentacene
Matthias W Tripp1, Ulrich Koert1
1Department of Chemistry, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35034 Marburg, Germany.
Abstract:
6,13-Difluoropentacene was synthesized from 1,4-difluorobenzene. Friedel-Crafts annulation of the latter with phthalic anhydride and subsequent reduction of the anthraquinone gave 1,4-difluoroanthracene. After ortho-lithiation and reaction with phthalic anhydride a carboxylic acid was obtained whose Friedel-Crafts acylation and subsequent reductive removal of the oxygen-functionalities resulted in the formation of the target compound. The HOMO-LUMO gap of 6,13-difluoropentacene was determined via UV-vis spectroscopy and compared to other fluorinated pentacenes.
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