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Coumarin carbamates with cholesteryl group 1 and 2 have been designed, synthesized and characterized. The isomeric compounds show different gelation behaviors in organic solvents such as toluene and CH₃CN. Rheological studies reveal the different viscoelastic properties of the gels. Gels of the isomers differ in morphology. While an intertwined fibre‐like structure is noted for the toluene gel of 1, rod like fibres are observed for toluene gel of 2. The positional alteration of carbamate group around coumarin changes the polarity of the isomers and hence influences the packing of molecules to establish different 3D networks for gel formation as explained by DFT study. Gels of the isomers show multiple applications with different attributes. Toluene gel of 1 is found to be F⁻‐responsive and undergoes gel‐to‐sol phase transition due to the disruption of intermolecular hydrogen bonding through deprotonation …