A mechanically interlocked and self-complexing molecular ouroboros that incorporates the pi-electron-rich monopyrrolotetrathiafulvalene (MPTTF) unit and the it-electron-poor tetracationic macrocycle cyclobis(paraquat-p-phenylene) (CBPQT(4+)) has been synthesized and characterized. The molecular ouroboros constitutes an interesting class of redox-active interlocked molecules that is structurally similar to the image of the Serpent biting its own tail, whereas, and towards advanced functionality, its mode of action resembles a wound spring. Electrochemical methods and short timescale UV-vis-NIR (NIR: near IR) chemical switching experiments verified the reversible oxidation and reduction of the molecular ouroboros akin to the build-up and release of tension in a spring. Building out from this concept, it was determined by the time evolution of the H-1 NMR and UV-vis-NIR spectra, however, that the initially interlocked molecular ouroboros is converted into a linear non-interlocked state by the employment of an appropriate oxidation-reduction cycle. The oxidation-induced dethreading process Occurs when the dicationic MPTTF2+ unit is kept within close proximity to the CBPQT(4)+ ring by the circular interlocked structure in order to maintain the electrostatic repulsive force between the MPTTF 21 unit and the CBPQT(4+) ring for longer periods of time. The resulting high-energy, and now tightly wound, interlocked conformation overcomes a steric barrier in many minutes, relaxing thermodynamically to form the lowest-energy linear state in an irreversible process that would otherwise be kinetically improbable without the oxidation.