Short Synthesis of [5]- and [7]Phenacenes with Silyl Groups at the Axis Positions

David Roy, Hiroyuki Maekawa, Masahito Murai, Kazuhiko Takai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

[5]Phenacene with trimethylsilyl groups at the axis positions was synthesized by the ruthenium-catalyzed direct C-H arylation of a 1-formyl-7-phenanthrene-derived aldimine, followed by sequential Wittig olefination and bismuth-catalyzed cyclization of the resulting vinyl ethers. By using the same synthetic building blocks and sequential Wittig olefination and photocyclization, the number of fused benzene rings was readily increased to seven to afford 3,12-disilyl[7]phenacene. The introduction of silyl groups endowed the [n]phenacene frameworks with good solubility, as well as enabling further functionalization. The electronic structure of these new [n]phenacenes was determined by photophysical measurements and by density functional theory calculations, which clearly implied effective conjugation throughout the entire πframework. End game: [5]- and [7]Phenacenes with two silyl groups at the axis positions were synthesized through repeated ruthenium-catalyzed direct C-H arylation/Wittig olefination/bismuth-catalyzed cyclization steps. The incorporation of silyl functionalities endowed these polycyclic aromatic hydrocarbons with solubility without significantly affecting their photophysical properties.

Original languageEnglish
Pages (from-to)2518-2524
Number of pages7
JournalChemistry - An Asian Journal
Volume10
Issue number11
DOIs
Publication statusPublished - Nov 1 2015

Keywords

  • bismuth
  • cyclization
  • organic field-effect transistors
  • phenacenes
  • polycycles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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