Enantioselective fluorescent sensor for dibenzoyl tartrate anion based on chiral binaphthyl derivatives bearing an amino acid unit

The fluorescent photoinduced electron transfer (PET) chemosensors 1–3 based on (S)-1,1′-bi-2-naphthol were designed for their recognition of dibenzoyl tartrate anions. The binding properties for hydroxy acid anions were examined by the fluorescence and 1H NMR spectra. The results indicated that receptor 1 exhibit excellent enantioselectivity toward the enantiomers of dibenzoyl tartrate anion.

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(S)-2-(2-{2′-[((S)-1-Methoxycarbonyl-ethylcarbamoyl)-methoxy]-(S)-[1,1′]-binaphthalenyl-2-yloxy}-acetylamino)-propionic acid methyl esterC32H32N2O8[α]D20=-77.0 (c 0.05, CHCl3)Source of chirality: staring materialAbsolute configuration, (Sa,S,S)

(S)-2-(2-{2′-[((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-methoxy]-(S)-[1,1′]binaphthalenyl-2-yloxy}-acetylamino)-3-phenyl-propionic acid methyl esterC44H40N2O8[α]D20=-37.6 (c 0.05, CHCl3)Source of chirality: staring materialAbsolute configuration, (Sa,S,S)

(S)-3-(1H-Indol-3-yl)-2-[2-(2′-{[(S)-2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylcarbamoyl]-methoxy}-(S)-[1,1′]binaphthalenyl-2- yloxy)-acetylamino]-propionic acid methyl esterC48H42N4O8[α]D20=+24.4 (c 0.05, CHCl3)Source of chirality: staring materialAbsolute configuration, (Sa,S,S)