Isoacenofuran: A novel quinoidal building block for efficient access to high-ordered polyacene derivatives

Kei Kitamura, Ryoji Kudo, Haruki Sugiyama, Hidehiro Uekusa, Toshiyuki Hamura

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Herein, a simple and practical method for generating isoacenofuran, a new π-extended quinoidal building block, was developed. A three-step protocol involving double nucleophilic additions of alkynyllithiums to acene-2,3-dicarbaldehyde, mono-oxidation, and acid-promoted cyclization enables the generation of the target molecule, which is trapped by a dienophile to produce highly condensed acenequinones. Further transformations by double nucleophilic additions of alkynyllithium to hexacenequinone, followed by reductive aromatization, produce tetraalkynylhexacenes with a remarkably higher stability than that of the previously reported substituted hexacenes.

Original languageEnglish
Pages (from-to)14988-14991
Number of pages4
JournalChemical Communications
Volume56
Issue number95
DOIs
Publication statusPublished - 2020 Dec 11
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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