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Charge‐Transfer Chromophores by Cycloaddition–Retro‐electrocyclization: Multivalent Systems and Cascade Reactions
Author(s) -
Kivala Milan,
Boudon Corinne,
Gisselbrecht JeanPaul,
Seiler Paul,
Gross Maurice,
Diederich François
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701733
Subject(s) - tetracyanoethylene , cycloaddition , chromophore , cascade , charge (physics) , chemistry , photochemistry , conjugated system , tetrathiafulvalene , electron transfer , acceptor , combinatorial chemistry , electron , organic chemistry , molecule , catalysis , physics , polymer , chromatography , quantum mechanics , condensed matter physics
It all clicks into place : The cycloaddition of tetracyanoethylene (TCNE) to electron‐rich alkynes (“click” reaction) followed by retro‐electrocyclization affords multivalent charge‐transfer chromophores that accept up to 24 electrons. The cascade additions of TCNE and tetrathiafulvalene (TTF) to polyynes provides access to conjugated donor–acceptor‐substituted [AB] oligomers with promising optoelectronic properties (see scheme).