Short synthesis of alkyl-substituted acenes using carbonyl-directed C-H and C-O functionalization

Daiki Matsumura, Kentaroh Kitazawa, Seiya Terai, Takuya Kochi, Yutaka Ie, Masashi Nitani, Yoshio Aso, Fumitoshi Kakiuchi

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

A convenient method for the synthesis of tetraalkylanthracenes and -pentacenes by means of ruthenium-catalyzed regioselective C-H alkylation of the corresponding acenequinones was developed. Dialkyldiarylpentacene was also synthesized using chemoselective tandem C-H alkylation/C-O arylation of dimethoxypentacenequinone. It was suggested that a tetraalkylpentacene is stable under air in the dark and possesses an appropriate HOMO level as active material for p-type organic field-effect transistors (OFETs).

Original languageEnglish
Pages (from-to)3882-3885
Number of pages4
JournalOrganic Letters
Volume14
Issue number15
DOIs
Publication statusPublished - 2012 Aug 3

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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