Issue 95, 2020

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

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.

Graphical abstract: Isoacenofuran: a novel quinoidal building block for efficient access to high-ordered polyacene derivatives

Supplementary files

Article information

Article type
Communication
Submitted
03 Oct 2020
Accepted
03 Nov 2020
First published
04 Nov 2020

Chem. Commun., 2020,56, 14988-14991

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

K. Kitamura, R. Kudo, H. Sugiyama, H. Uekusa and T. Hamura, Chem. Commun., 2020, 56, 14988 DOI: 10.1039/D0CC06620F

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