In conclusion, we present here a novel hybrid photochromic dyad composed of two dimethyldihydropyrene (DHP) photochromic units attached at the axial positions of an NDI core. Upon exposure to 370 nm irradiation, the dyad having the photoswitchable units in the closed form, generates a stable NDIcentered radical in dimethylformamide (DMF), as demonstrated by electron paramagnetic resonance (EPR) spectroscopy. The amine impurities present in the solvent acts as the electron donor. This has been shown by additional experiments with added amine sources or conducting the experiment in amine as the solvent. This was further substantiated by the fact that the radical-species cannot be generated in solvents such as acetonitrile, chloroform and tetrahydrofuran. Variable-temperature EPR studies reveal an enhancement of the EPR signals with rising temperature, indicative of the disaggregation of stacked units, consistent with observations from UV-visible spectroscopy. Upon irradiation with 525 nm light, the DHP-photoswitch undergoes isomerization to the non-planar, less conjugated, and hence less electron-rich cyclophanediene (CPD) form where the radical-anion cannot be generated. The same radical-anion can also be generated through chemical reduction. Our successful demonstration of repeated cycles of radical formation and quenching under various light sources underscores the potential of the DHP-NDI-DHP dyad in light-induced reversible radical generation, holding promise for advancements in materials science.