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Angular tetrachloro[6]phenylene: a step toward circular phenylenes

Carbon-rich compounds and materials have garnered much attention recently due to their small band gaps and thus applications as organic conductors and ferromagnets that form monolayers in solid-phase state. One such type of materials that can form carbon monolayers are [N]phenylenes, hydrocarbons built of fused alternating aromatic benzene and anti-aromatic cyclobutadiene rings. Vollhardt’s group has developed efficient synthetic routes to this family of compounds, including helical angular phenylenes.

As a precursor for circular phenylenes, PhenyleneCl4 crystals were studied. Scheme  shows transformation of molecular material into monolayers with potential conducting properties.