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

Hirokazu Miyoshi, Shunpei Nobusue, Akihiro Shimizu, Tobe Yoshito*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

58 Scopus citations

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.

Original languageEnglish
Pages (from-to)6560-6577
Number of pages18
JournalChemical Society Reviews
Volume44
Issue number18
DOIs
StatePublished - 21 Sep 2015

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