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Abstract: Synthetic receptors selective for the enantiomers of Troger's base (1), a compound containing chiral nitrogen atoms, have been prepared by the molecular imprinting of 1 in methacrylic acid-ethylene glycol dimethacrylate copolymers. Spectroscopic evaluation of the self- assembly phase, prior to polymerization, demonstrated the formation of template-functional monomer adducts of K-diss 0.7 +/- 0.1 mM at 293 K in chloroform. The synthetic receptors demonstrated enantioselectivity when used as HPLC chiral stationary phases; enantioseparation factors (alpha) of up to 4.8 +/- 0.2 are reported. Baseline resolution of racemic 1 was readily achieved. Furthermore, the influence of water on polymer-ligand selectivity was examined, which yielded insights into the molecular basis for ligand selectivity in these synthetic receptors. (C) 1999 Academic Press
Template and target information: Tröger's base, Troger's base, 2,8-dimethyl-6H,12H-5,11-methanodibenzo[b, f ][1,5]diazocine