Synthesis of flake-shaped [3]cyclo-4,6-dibenzofuranylene

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4 Citations (Scopus)

Abstract

The cyclic trimer of dibenzofuran linked at the 4,6-positions, named [3]cyclo-4,6-dibenzofuranylene, was synthesized by Ni(0)-mediated reductive coupling of 4,6-dibromodibenzofuran. DFT calculation indicated that the flake-shaped C2 symmetric structure is the most stable conformer and the propeller-shaped D3 symmetric structure is the minor conformer with a higher energy (+19.1 kcal mol-1). The calculated inversion energy of the C2 conformer through a Cs symmetric transition state was +4.1 kcal mol-1, showing rapid fluctuation, which is consistent with the observation of only one set of 1HNMR signals of dibenzofuran of [3]cyclo-4,6-dibenzofuranylene.

Original languageEnglish
Pages (from-to)95-96
Number of pages2
JournalChemistry Letters
Volume47
Issue number1
DOIs
Publication statusPublished - 2018 Jan 1
Externally publishedYes

Keywords

  • Cyclic trimer
  • Dibenzofuran
  • Flake-shape

ASJC Scopus subject areas

  • Chemistry(all)

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