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A Proof of Concept for Proaromaticity
Y.-L. Wu, F. Bureš, P. D. Jarowski, W. B. Schweizer, C. Boudon, J.-P. Gisselbrecht, F. Diederich*
ETH Zürich, Switzerland; University of Pardubice, Czech Republic; Université de Strasbourg, France
21 October 2010 (online)
Donor- and acceptor-substituted quinoids were synthesized and used as model compounds to study the role of proaromaticity in reducing the HOMO-LUMO gap. These quinoid derivatives are represented by neutral and zwitterionic canonical structures, and feature near-infrared (NIR) absorption. The macrocycle 6 is the first example in the radiaannulene family to show evidence of aromatization.