Issue 45, 2007
From the journal:

Chemical Communications

A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2 + 2] cycloaddition with alkynes†

Milan Kivala,a   Corinne Boudon,b   Jean-Paul Gisselbrecht,b   Paul Seiler,a   Maurice Grossb  and  François Diederich*a  

* Corresponding authors

a Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, CH-8093 Zürich, Switzerland
E-mail: diederich@org.chem.ethz.ch
Fax: (+41) 44 632 1109

b Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie – LC3 – UMR 7177, C.N.R.S., Université Louis Pasteur, 4, rue Blaise Pascal, F-67000 Strasbourg, France

Abstract

A series of donor–acceptor molecules, featuring intense low-energy intramolecular charge-transfer bands, was prepared by regioselective [2 + 2] cycloaddition between 7,7,8,8-tetracyanoquinodimethane (TCNQ) and N,N-dialkylanilino-substituted (DAA-substituted) alkynes, followed by ring opening of the initially formed cyclobutenes.

Graphical abstract: A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2 + 2] cycloaddition with alkynes

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Article information

DOI
https://doi.org/10.1039/B713683H
Article type
Communication
Submitted
06 Sep 2007
Accepted
15 Oct 2007
First published
24 Oct 2007

Chem. Commun., 2007, 4731-4733

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A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2 + 2] cycloaddition with alkynes

M. Kivala, C. Boudon, J. Gisselbrecht, P. Seiler, M. Gross and F. Diederich, Chem. Commun., 2007, 4731 DOI: 10.1039/B713683H

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