Issue 1, 2014

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

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
18 Sep 2013
Accepted
07 Oct 2013
First published
07 Oct 2013

Chem. Sci., 2014,5, 163-168

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

H. Miyoshi, S. Nobusue, A. Shimizu, I. Hisaki, M. Miyata and Y. Tobe, Chem. Sci., 2014, 5, 163 DOI: 10.1039/C3SC52622D

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