| Abstract: | New enantiopure dimethyl‐substituted acridino‐18‐crown‐6 and acridino‐21‐crown‐7 ethers containing a carboxyl group at position 9 of the acridine ring (S,S )‐ 8 , (S,S )‐ 9 , (R,R )‐ 10 ] were synthesized. The pK a values of the new crown ethers (S,S )‐ 8 , (S,S )‐ 9 , (R,R )‐ 10 ] and of an earlier reported macrocycle (R,R )‐ 2 ] were determined by UV‐pH titrations. Crown ether (S,S )‐ 8 was attached to silica gel by covalent bonds and the enantiomeric separation ability of the newly prepared chiral stationary phase (S,S )‐CSP‐ 12 ] was studied by high‐performance liquid chromatography (HPLC). Homochiral preference was observed and the best separation was achieved for the enantiomers of 1‐NEA. Ligands (S,S )‐ 9 and (R,R )‐ 10 are precursors of enantioselective sensor and selector molecules for the enantiomers of protonated primary amines, amino acids, and their derivatives. |
