Jump to main content
Jump to site search

Issue 1, 2014
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Sep 2013, accepted on 07 Oct 2013 and first published on 07 Oct 2013


Article type: Edge Article
DOI: 10.1039/C3SC52622D
Citation: Chem. Sci., 2014,5, 163-168
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements