The coordination of metal ions with a pair of chiral tripodal ligands (R or S)-2-(2-((bis(pyridin-2-ylmethyl)amino)methyl)phenoxy)-N-(1-phenylethyl)acetamide (R- or S-L) results in the circular dichroism (CD) enhancement distinctly, giving fingerprint information among different metals. Specifically, the CD signals show more obvious magnification upon coordination with Ln 3+ compared with Zn 2+ and other metals. Structural analyses show that in Eu-complex (1), the Eu 3+ metal center is surrounded in a 10-coordinating geometry and the ligand takes fan-like configuration, while in Zn-complex (2), Zn 2+ is surrounded in a 7-coordinating geometry and the ligand takes pincer-like configuration. These differences in the coordination structure as well as intramolecular packing effects are responsible for the variation in CD signal responses of different metal-coordinated systems.