Issue 46, 2007

New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

Abstract

Donor-substituted 1,1,2,4,4-pentacyanobuta-1,3-dienes and a cyclohexa-2,5-diene-1,4-diylidene-expanded derivative were prepared by a [2 + 2] cycloaddition of tetracyanoethene (TCNE) or 7,7,8,8-tetracyanoquinodimethane (TCNQ) to anilino-substituted cyanoalkynes, followed by retro-electrocyclisation; they feature intense bathochromically-shifted intramolecular charge-transfer bands and undergo their first one-electron reductions at potentials similar to those reported for TCNE and TCNQ.

Graphical abstract: New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

Supplementary files

Article information

Article type
Communication
Submitted
25 Sep 2007
Accepted
22 Oct 2007
First published
31 Oct 2007

Chem. Commun., 2007, 4898-4900

New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes

P. Reutenauer, M. Kivala, P. D. Jarowski, C. Boudon, J. Gisselbrecht, M. Gross and F. Diederich, Chem. Commun., 2007, 4898 DOI: 10.1039/B714731G

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