Jahn-Teller effect in circulenes: X-ray diffraction study of coronene and corannulene radical anions

Alexander S Filatov; Natalie J Sumner; Sarah N Spisak; Alexander V Zabula; Andrey Yu Rogachev; Marina A Petrukhina

doi:10.1002/chem.201202026

Jahn-Teller effect in circulenes: X-ray diffraction study of coronene and corannulene radical anions

Chemistry. 2012 Dec 3;18(49):15753-60. doi: 10.1002/chem.201202026. Epub 2012 Oct 15.

Authors

Alexander S Filatov¹, Natalie J Sumner, Sarah N Spisak, Alexander V Zabula, Andrey Yu Rogachev, Marina A Petrukhina

Affiliation

¹ Department of Chemistry, University at Albany, State University of New York, 12222, USA.

PMID: 23070781
DOI: 10.1002/chem.201202026

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.