Influence of π-Stacking on the Redox Properties of Oligothiophenes: (α-Alkyloligo-thienyl)para[2.2]cyclophanes

Oligothienyl-substituted paracyclophanes bearing α-thienyl substituents, which block polymerization at these sites, undergo oxidation to form stable radical cations and dications. Splitting of the first voltammetric oxidation wave of stacked dimers into two single-electron processes corresponding to formation of the stacked mono(radical cation) and the stacked bis(radical cation) illustrates the influence of π-stacking on the behavior of conjugated chains, which serve as models for stacked polarons in conjugated polymers.

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