The interfacial-dependent self-organization of a chiral amino acid amphiphile was observed on various substrates with different surface hydrophobicity. Three kinds of organizations are induced at different substrates, which appear as helical aggregates on hydrophobic surface (e.g. highly oriented pyrolytic graphite), molecular flat layer on hydrophilic surface, (e.g. mica) and a transition state between them on silicon wafer. The strength of the interactions between the helical aggregates formed in solution and the substrate is the key factor to the self-organization of the chiral molecule. The results reported here provide insight into how the surface hydrophobicity of substrates affects the self-organization of chiral molecules. (C) 2003 Elsevier Science B.V. All rights reserved.