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Significance Derivatized sterols and terpenoids represent an effective platform for introducing functionality into the surface of lipid-coated NPs and other membrane-based materials. This work demonstrates that the hydrogen-bonding network (HBN) at the lipid–water interface plays a crucial role in determining the orientation of derivatized sterols and other terpenoids in hybrid lipid membranes. A rational engineering of the interactions with the HBN provides control over the molecular orientation in the lipid coating and facilitates configurable surface properties that adjust in response to external cues. The control of the surface properties combined with the plasmonic signal enhancement through the NP core renders L-NPs bright Raman tags for the identification of biomarker overexpression at the single-cell level.

Interfacial hydration determines orientational and functional dimorphism of sterol-derived Raman tags in lipid-coated nanoparticles