Bis-EDOT end capped by n-hexyl or n-hexylsulfanyl groups: the effect of the substituents on the stability of the oxidized states†
Abstract
Three bis-EDOT derivatives end capped with n-hexyl or n-hexylsulfanyl groups have been synthesized. The oxidation processes of these compounds have been studied using cyclic voltammetry and UV-Vis-NIR spectroscopy. The strong influence of the sulfur atoms of the hexylsulfanyl chains for stabilizing the oxidation states is evidenced. Thus, it is shown that the two compounds grafted with one or two hexylsulfanyl groups are reversibly oxidized into cation radical and dication states. By contrast, compounds end capped with hexyl groups present a fast σ-dimerization of the radical cation. The reduction of the σ-dimer to give the neutral bis-EDOT derivative is slow.
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