Issue 18, 2015

Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals

Abstract

Aromaticity is an important concept to understand the stability and physical properties of π-conjugated molecules. Recent studies on pro-aromatic and anti-aromatic molecules revealed their irresistible tendency to become diradicals in the ground state. Diradical character thus becomes another very important concept and it is fundamentally correlated to the physical (optical, electronic and magnetic) properties and chemical reactivity of most of the organic optoelectronic materials. Molecules with distinctive diradical character show unique properties which are very different from those of traditional closed-shell π-conjugated systems, and thus they have many potential applications in organic electronics, spintronics, non-linear optics and energy storage. This critical review first introduces the fundamental electronic structure of Kekulé diradicals within the concepts of anti-aromaticity and pro-aromaticity in the context of Hückel aromaticity and diradical character. Then recent research studies on various stable/persistent diradicaloids based on pro-aromatic and anti-aromatic compounds are summarized and discussed with regard to their synthetic chemistry, physical properties, structure–property relationships and potential material applications. A summary and personal perspective is given at the end.

Graphical abstract: Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals

Article information

Article type
Review Article
Submitted
21 1月 2015
First published
21 5月 2015

Chem. Soc. Rev., 2015,44, 6578-6596

Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals

Z. Zeng, X. Shi, C. Chi, J. T. López Navarrete, J. Casado and J. Wu, Chem. Soc. Rev., 2015, 44, 6578 DOI: 10.1039/C5CS00051C

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