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 মার্চ 2018
Accepted
17 এপ্রিল 2018
First published
17 এপ্রিল 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements