Benz[c]indeno[2,1-a]fluorene: A 2,3-naphthoquinodimethane incorporated into an indenofluorene frame

Hirokazu Miyoshi, Shunpei Nobusue, Akihiro Shimizu, Ichiro Hisaki, Mikiji Miyata, Yoshito Tobe*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

Synthesis of 13,14-dimesitylbenz[c]indeno[2,1-a]fluorene (9b), a 2,3-naphthoquinodimethane derivative isolated for the first time, was achieved. The X-ray crystallographic structure and spectroscopic and electrochemical properties of 9b indicate substantial singlet biradical character which is higher than that of 11,12-dimesitylindeno[2,1-a]fluorene (8b), in accord with the quantum chemical study. Cycloadditions with oxygen and dichlorodicyano-p- benzoquinone took place at the inner naphthalene carbons rather than the most reactive exocyclic carbons because of the effective steric protection by the mesityl groups at the latter positions. [4 + 2] Cyclodimerization also took place at the inner naphthalene position as a 4π component and at the outer naphthalene ring as a 2π component.

Original languageEnglish
Pages (from-to)163-168
Number of pages6
JournalChemical Science
Volume5
Issue number1
DOIs
StatePublished - 1 Jan 2014

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