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Synthesis of 6,13-difluoropentacene.

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.

SUBMITTER: Tripp MW

PROVIDER: S-EPMC7476596 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Synthesis of 6,13-difluoropentacene.

Tripp Matthias W MW Koert Ulrich U

Beilstein journal of organic chemistry 20200902

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 <i>ortho</i>-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 determ ...[more]

PMID: 32952730

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