A series of benzothiazole-derived Schiff bases was synthesized, and its interfacial behavior was investigated. Although these Schiff bases with no alkyl chains could not be spread on water surface, addition of metal ions such as Ag(I) or Cu(II) in the subphases caused an in situ coordination and led to the film formation. It was interesting to find that some of the Langmuir-Schaefer (LS) films of the Cu(II) complexes showed CD signals, although the Schiff bases were achiral. It was suggested that the stereoregular stacking of the coordinated complexes in a helical sense was responsible for the supramolecular chirality.