Fluorous Phase-Enhanced Fluorescent Sensitivity for Enantioselective Recognition of Lysine

A novel fluorinated chiral dialdehyde (S,S)-1, prepared from (S,S)- or (R,R)-2,6-bis(1-hydroxyethyl)pyridine and 2-naphthol containing a highly fluorinated alkyl group, is found to show enantioselective and chemoselective fluorescent recognition of lysine in the fluorous phase. We discovered that the fluorous phase greatly enhances the fluorescent sensitivity and selectivity of the probe. Thus, the fluorous phase not only can allow the fluorescence measurement to be conducted away from common organic and aqueous media to minimize undesirable interference but also can provide a unique environment to greatly improve the selective fluorescent response.