Bioinspired synthesis of pentalene-based chromophores from an oligoketone chain. Issue 50 (24th April 2018)

• Record Type: Journal Article
• Authors: Saito, Yuki; Higuchi, Masayuki; Yoshioka, Shota; Senboku, Hisanori; Inokuma, Yasuhide
• Is Part Of: Chemical communications. Volume 54:Issue 50(2018)
• Page Start: 6788
• Page End: 6791
• Publication Date: 2018-04-24
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc02379d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Inspired by natural polyketide synthesis, pentalene-based, cross-conjugated chromophores were synthesized from an aliphatic oligoketone chain. 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 π-system with low-lying LUMO levels. Furthermore, pentalenes obtained from a non-conjugated aliphatic chain exhibited visible absorption and solid-state fluorescence.