Synthesis, structural analysis, and properties of [8]circulenes

Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7791-4. doi: 10.1002/anie.201303875. Epub 2013 Jun 21.

Abstract

Polygons: [8]Circulenes were easily prepared by Pd-catalyzed annulations of tetraiodotetraphenylenes with alkynes. Their saddle-shaped structure with an [8]radialene character was identified by X-ray crystallography. Similar to 1,3,5,7-cyclooctatetraene, they have a tub-shaped eight-membered ring, but all of the bond lengths and bond angles are almost equal. Variable-temperature NMR investigations showed interesting dynamic behavior.

Keywords: [8]circulenes; alkynes; annulation; palladium; tetraphenylenes.