Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C-O Arylation of Dimethoxyanthraquinones

Yusuke Suzuki, Kohei Yamada, Kentaro Watanabe, Takuya Kochi, Yutaka Ie, Yoshio Aso, Fumitoshi Kakiuchi

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Abstract

A convenient method for the syntheses of dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes via the ruthenium-catalyzed chemoselective C-O arylation of 1,4- and 1,5-dimethoxyanthraquinones is described. Dimethoxyanthraquinones reacted selectively with arylboronates at the ortho C-O bonds to give diarylation products. An efficient two-step procedure consisting of a Corey-Chaykofsky reaction and subsequent dehydrative aromatization afforded derivatives of dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes. Hole-transporting characteristics were observed for a device with a bottom-contact configuration that was fabricated from one of these polycyclic aromatic hydrocarbons.

Original languageEnglish
Pages (from-to)3791-3794
Number of pages4
JournalOrganic Letters
Volume19
Issue number14
DOIs
Publication statusPublished - 2017 Jul 21

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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