Stable π-conjugated anions are formed in the reaction of π-conjugated systems with alkali metals. Reactivity, aromatic properties and aggregation of the anions are described.

Chemical reduction of polyaromatic hydrocarbons yielded solutions of long‐lived polyanionic species. Reduction of a sulfur heterocycle afforded a stable sulfur‐containing dianion. Sulfur extrusion from this dianion proceeded upon further contact with the reducing metal. NMR and UV studies indicate a sulfur extrusion mechanism different than that previously observed in THF. Electron transfer to the already reduced hydrocarbon skeleton results in the stepwise cleavage of the two C–S bonds and the extrusion of a sulfur atom. Dimers of aromatic hydrocarbons such as pyrene and phenanthrene have been reduced as well. The interplay between coulombic repulsions and resonance energies is described.

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