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This aromatic regioisomer-driven method has been utilized with a cholesterol-based gelator to get ready hollow self-assembled organic nanotubes (S-ONTs) with inside and outside diameters of ca. 35 and 140 nm, respectively. Electron microscopy imaging and theoretical computations had been employed to rationalize the development system among these S-ONTs. From the three possible regioisomers, only the ortho-disubstituted cholesteryl-based gelator showed the perfect direction and distance between subs