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Synfacts 2010(11): 1242-1242  
DOI: 10.1055/s-0030-1258729
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

A Proof of Concept for Proaromaticity

Contributor(s): Timothy M. Swager, Shuang Liu
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
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Publication History

Publication Date:
21 October 2010 (online)

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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.