Issue 50, 2018

Bioinspired synthesis of pentalene-based chromophores from an 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.

Graphical abstract: Bioinspired synthesis of pentalene-based chromophores from an oligoketone chain

Supplementary files

Article information

Article type
Communication
Submitted
26 mar 2018
Accepted
17 apr 2018
First published
17 apr 2018

Chem. Commun., 2018,54, 6788-6791

Bioinspired synthesis of pentalene-based chromophores from an oligoketone chain

Y. Saito, M. Higuchi, S. Yoshioka, H. Senboku and Y. Inokuma, Chem. Commun., 2018, 54, 6788 DOI: 10.1039/C8CC02379D

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