A series of surfactant monomers and polymers bearing different redox-active moieties were synthesized. Solubility, surface activity, aggregation behavior, and electrochemical properties of the compounds were investigated. Changes in the hydrophilic-hydrophobic balance were achieved by controlling the number of charges on the surfactants via the redox moiety. Redox reactions of surfactants bearing N-alkylated nicotinic acid or (ferrocenylmethyl)ammonium structures were not reversible in water. However, other ferrocene and viologen surfactants showed good reversibility of the redox reactions, and drastic changes in their solubility were observed. These surfactants are considered as promising systems to trigger reversible changes in self-organization.