The Topology of Molecules with Twelve Fused Phenyl Rings ([12]Circulenes): Rings, Infinitenes, and Möbius Infinitenes.

Following the recent preparation of infinitene ( , , 862-871), a computational (ωB97XD/6-311G(d)) exploration of 42 isomeric compounds with 12 fused phenyl rings identified structures with linking number of zero (ring, saddle, and ribbon shapes), two (infinitene-like shape), and one (Möbius infinitene shape) is reported. An infinitene isomer composed of two [5]helicene fragments connected to two stacked phenyl rings and a Möbius infinitene isomer are identified that are more stable than the known infinitene. The energies of the structures are examined by assessing their macrocyclization (strain) energies, π-stacking, and possible aromaticity. Examples of fused phenyl molecules with linking numbers of 3, 4, 5, and 6 are shown, indicating the potential topological range that these molecules can possess.