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Controlling the handedness of dynamic helical nanostructures of supramolecular assemblies by external stimuli is of great fundamental significance with appealing morphology-dependent applications. Significantly, access to in situchirality transformation of dynamic multistimuli-responsive systems can provide channels for real-time monitoring of the transfer processes in biological systems. However, efforts to achieve helix inversion in an all-gel-state and to comprehend the phenomena at a molecular scale are scarce. Herein, we introduce an example of supramolecular hydrogel in which graphene oxide (GO) incorporation leads to opposite helicity of the l-phenylalanine derivative (LPFEG) upon UV irradiation. The gelator modulates different degrees of packing that are responsible for the initial construction of right-handed nanofibers in GO surfaces and for the change in helix to preferred left-handedness in RGO surfaces caused by GO reduction. Specifically, LPFEG shows a mixture of right- and left-handed nanofibers with an appropriate exposure to UV light. A thermal-reversible transformation of chirality is also discovered in the supramolecular assemblies, allowing a dynamic and invertible flip of helicity upon heating and cooling. The morphology transformation makes the hybrid an ideal candidate for application in a precisely controlled drug delivery process. It can unexpectedly serve as a photosensitizer and a carrier for enantioselective absorption of specific chiral drugs enantiomer (l-dopa and S-naproxen sodium) and also exhibit on-demand drug release due to the helix reversal induced by light irradiation. Our results illustrate how the surface reactivity can direct the helical organization of adsorbed fibers, which in turn provide control over enantioselective absorption of chiral drug enantiomers, further giving rise to on-demand drug release due to handedness inversion upon UV irradiation.