Pentagon-Fused Sumanenes on the Aromatic Peripheries en Route to the Bottom-Up Synthesis of Fullerenes.

Bowl-shaped π-conjugated sumanenyltriamines were successfully synthesized in a one-step reaction from bromomethylsumanene. This molecule represents an example of hemiazafullerene (C54 N6 fragment) with six isolated pentagons. Its single-crystal X-ray structural analysis showed the formation of one-dimensional columnar structures incorporating chloroform. The hemifullerene (C30 fragment) was also synthesized when the nucleophile was changed to dimethylmalonate. [ABSTRACT FROM AUTHOR]