Iodine-doped sumanene and its application for the synthesis of chalcogenasumanenes and silasumanenes

The synthesis of an iodine-doped sumanene, which represents the first example of halogen-doped buckybowls, is described. Pristine trithiasumanene, trisilasumanene and the hitherto unknown parent triselenasumanene, three interesting heterobuckybowls with significant synthetic challenges, were efficiently prepared from the iodine-doped sumanene through non-pyrolytic conditions. This work demonstrates the high potential of hypervalent iodines embedded in extended π-conjugated systems for the synthesis of novel curved and planar polycyclic aromatic hydrocarbons.