New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes.
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.
Reutenauer
Philippe
P
Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, CH-8093 Zürich, Switzerland.
Kivala
Milan
M
Jarowski
Peter D
PD
Boudon
Corinne
C
Gisselbrecht
Jean-Paul
JP
Gross
Maurice
M
Diederich
Franćois
F