Issue 18, 2015

Non-alternant non-benzenoid kekulenes: the birth of a new kekulene family

Abstract

“Kekulene” is a doughnut-like shaped polycyclic aromatic hydrocarbon consisting of cyclically arrayed benzene rings. It has attracted a great deal of theoretical interest because it is regarded as an ideal model to study conjugation circuits of π electrons, i.e. whether they delocalize locally in benzene rings or globally throughout the molecule. Though kekulene was synthesized in 1978, it was the only known compound of this class of compounds for a long time. Recently, new kekulene-related molecules, septulene, which is a non-alternant benzenoid hydrocarbon, and a tetracyclopentatetraphenylene (TCPTP) derivative belonging to non-alternant non-benzenoid hydrocarbons, were synthesized. This article presents theoretical and experimental aspects of kekulene-related molecules focusing on the viewpoint of conjugation circuits by classifying them into three types: benzenoid kekulenes including kekulene itself and septulene, yet unknown anti-kekulene and non-alternant non-benzenoid kekulenes represented by TCPTP.

Graphical abstract: Non-alternant non-benzenoid kekulenes: the birth of a new kekulene family

Article information

Article type
Review Article
Submitted
01 mars 2015
First published
30 avr. 2015

Chem. Soc. Rev., 2015,44, 6560-6577

Non-alternant non-benzenoid kekulenes: the birth of a new kekulene family

H. Miyoshi, S. Nobusue, A. Shimizu and Y. Tobe, Chem. Soc. Rev., 2015, 44, 6560 DOI: 10.1039/C5CS00185D

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