This study reports the synthesis and solution self-assembly of a bis(urea) derivative decorated with a poly(ethylene oxide) chain and an electroactive tetrathiafulvalene (TTF) unit, into oxidationsensitive supramolecular nanocylinders. As evidenced by cryo-transmission electron microscopy and light scattering experiments, the preparation pathway has a strong influence on the morphology and characteristics of the self-assembled structures, proving their frozen (out-of-2 equilibrium) nature. The targeted supramolecular nanocylinders could be obtained both in aqueous medium and acetonitrile. In water, TTF can be chemically oxidized to TTF •+ by Fe(III), resulting in a very moderate disassembly of the supramolecular nanocylinders. On the contrary, TTF can be oxidized up to TTF 2+ with the same oxidant in acetonitrile, leading to an almost complete disassembly of the nanocylinders. Oxidation of TTF eventually leads to its degradation in both solvents, even in the absence of oxygen and light. This paper shows that oxidation-sensitive supramolecular nanocylinders can be prepared in acetonitrile by combining bis(urea) and TTF units to a polymer.