Enantioselective recognition by optically active chiral fluorescence sensors bearing amino acid units

Chiral fluorescence receptors 1 and 2 were synthesized and their structures characterized by IR, 1H NMR, 13C NMR, MS spectra, and elemental analysis. The chiral recognition abilities of 1 and 2 were studied by 1H NMR and fluorescence spectra. The results demonstrate that receptors 1 and 2 with bis(tetrabutylammonium) dibenzoyl tartrate formed a 1:1 complex. Receptor 2 exhibits an excellent enantioselective recognition ability toward the enantiomers of bis(tetrabutylammonium) dibenzoyl tartrate.

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(S,S)-2,7-Bis[N-(N′-tert-butoxy-tryptophy)amino-ethenecarbamoyl-oxy]naphthaleneC50H60N8O10[α]D20=-16.8 (c 0.05, CHCl3)

(S,S)-2,7-Bis[N-(N′-tert-butoxy-tryptophy)amino-propylcarbamoyl-oxy]naphthaleneC52H64N8O10[α]D20=-10.4 (c 0.05, CHCl3)