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Synfacts 2010(11): 1242-1242
DOI: 10.1055/s-0030-1258729
DOI: 10.1055/s-0030-1258729
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
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
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Oktober 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201011/lookinside/thumbnails/10.1055-s-0030-1258729-1.jpg)
Significance
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.