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Updated: May 17, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Jahn-Teller effect in circulenes: X-ray diffraction study of coronene and corannulene radical anions
Alexander S Filatov1, Natalie J Sumner, Sarah N Spisak
1Department of Chemistry, University at Albany, State University of New York, 12222, USA.
Abstract:
Single-crystal X-ray diffraction studies of two polyaromatic radical anions crystallized as sodium salts, namely [Na(DME)(3) ](+)[C(20) H(10)(-)] (1) and [Na(DME)(3)](+)[C(24)H(12)(-)] (2) are reported. This allowed the first structural evaluation of Jahn-Teller (JT) effects for monoreduced circulenes and a comparison between bowl-shaped corannulene and planar coronene. The C(s) and D(2h) symmetrical distortions are found to fit the experimental data for C(20)H(10)(·-) and C(24)H(12)(·-), respectively. The continuous symmetry measure (CSM) analysis was carried out to provide a quantitative measure of the JT distortions in 1 and 2. In addition, the X-ray crystallographic results were fully supported by DFT calculations.
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