Abstract: Chiral indanyl substituted tetra-armed cyclens (TAC) formed octadentate complexes with Na+. Since their four side arms stand up and are bundled to form quadruplicated helical structures, they can have Delta- or Lambda-types enantiomers based on complex helicity. In this study, TAC-imprinted polymers were prepared using an ion-pair complex of the sodium salt of (S)-indanyl substituted TAC (TAC(S)) and 2-sulfoethyl methacrylate as a template, and ethylene glycol dimethacrylate as a cross-linker. Affinity of the obtained polymers for the TAC Na+ complexes was evaluated chromatographically and the imprinted polymer gave longer retention time for the template than that for its antipode where the separation factor was given to be 1.29-1.45 under the NaOH concentrations of 10-25 mM in the eluent. These results indicate that the imprinted polymer could discriminate helix structures of TAC Na+ complexes. (C) 2003 Elsevier B.V. All rights reserved