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Synthesis of 6,13-difluoropentacene

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...

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Detalles Bibliográficos
Autores principales: Tripp, Matthias W, Koert, Ulrich
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7476596/
https://www.ncbi.nlm.nih.gov/pubmed/32952730
http://dx.doi.org/10.3762/bjoc.16.181
Descripción
Sumario: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.