An electroactive tetrathiafulvalene (TTF)-functionalized amphiphile 1 was designed and synthesized to investigate its self-assembling behavior in water, Dynamic light scattering (DLS), H-1 NMR, fluorescence spectrum, and cryogenic transmission electron microscopy (cryo-TEM) studies revealed that amphiphile 1 can form micelle-like aggregates via direct dissolution into water, and the micellar architectures could be disrupted either by addition of chemical oxidant Fe(ClO4)(3) or by complexation with electron-deficient cyclobis(paraquat-p-phenylene) tetracation. cyclophane (CBPQT(4+)) to release encapsulated hydrophobic dye Nile Red from the interior of micelles.