Monoreduced 1,2-dihydrocorannulene versus the parent corannulene

Sarah N Spisak; Gabrielle C Hoover; Zheng Wei; Alexander V Zabula; Alexander S Filatov; Marina A Petrukhina

doi:10.1107/S2053229615013145

Monoreduced 1,2-dihydrocorannulene versus the parent corannulene

Acta Crystallogr C Struct Chem. 2015 Aug;71(Pt 8):690-4. doi: 10.1107/S2053229615013145. Epub 2015 Jul 15.

Authors

Sarah N Spisak¹, Gabrielle C Hoover¹, Zheng Wei¹, Alexander V Zabula², Alexander S Filatov¹, Marina A Petrukhina¹

Affiliations

¹ Department of Chemistry, University at Albany, Albany, NY 12222, USA.
² Department of Chemistry, University of Wisconsin, Madison, WI 53706, USA.

PMID: 26243416
DOI: 10.1107/S2053229615013145

Abstract

The monoanion of dihydrogenated corannulene isolated in the form of its potassium salt, namely tris(diglyme-κ(3)O,O',O'')potassium hexacyclo[11.5.2.0(4,17).0(7,16).0(10,15).0(14,18)]icosa-1,3,5,7(16),8,10(15),11,13,17-nonaenide, [K(C6H14O3)3](C20H12), has been structurally characterized for the first time. The X-ray study confirms the previous NMR spectroscopic prediction that the two H atoms are attached to the same six-membered ring to form 1,2-dihydrocorannulene, thus destroying the aromaticity of only one arene ring of the corannulene core. The direct comparison of (C20H12)(-) with the parent corannulene anion, (C20H10)(-), is provided to illustrate the geometry perturbations caused by rim hydrogenation.

Keywords: bowl-shaped polyarenes; corannulene; crystal structure; hydrogen adsorption; hydrogen storage; monoreduced 1,2-dihydrocorannulene; potassium salt.