Bioinspired synthesis of pentalene-based chromophores from an oligoketone chain

• Saito, Yuki

• Higuchi, Masayuki

• Yoshioka, Shota

• Senboku, Hisanori

• Inokuma, Yasuhide

Abstract

We report a bioinspired synthesis of 2,5-dihydropentalene-based chromophores from an aliphatic oligoketone bearing 1,3- and 1,4-diketone subunits. Unlike the natural polyketone sequence, fused five-membered rings were formed via an intramolecular aldol condensation. A subsequent Knoevenagel condensation reaction with malononitrile furnished a multiply cross-conjugated -system with low-lying LUMO levels. Furthermore, pentalenes obtained from a non-conjugated aliphatic chain exhibited visible absorption and solid-state fluorescence.

Journal

• Chemical communications

  Chemical communications 54 (50), 6788-6791, 2018-06-25

  Royal Society of Chemistry

Keywords

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

Details

• CRID: 1050001202679069056
• NII Article ID: 120006648348
• DOI: 10.1039/c8cc02379d
• ISSN: 1364548X
• ISSN: 13597345
• HANDLE: 2115/74766
• Web Site: http://pubs.rsc.org/en/content/articlepdf/2018/CC/C8CC02379D
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN