Chiral fluorescence polyethers based on BINOL for enantioselective recognition of phenylalanine anion

•BINOL-based fluorescence sensors with two chiral moieties were reported.•Enantioselective recognition was conducted in aqueous solution of THF/H2O.•Configurations of both BINOL and ECH affect the selectivity.•The value of enantiomeric fluorescence difference ratio (ef) reached to 6.29.

Series of polyethers with different configurations were synthesized from chiral BINOL and optical epichlorohydrin. The optical behavior of the obtained polyethers is evaluated with specific optical rotation, UV–vis spectroscopy, circular dichroism (CD) and fluorescence spectroscopy. Thermogravimetric analysis (TGA) reveals the polyethers a good thermal stability. The fluorescence responses of the chiral polyethers on chiral phenylalanine anion were investigated. The sensors (S,S)-4 and (R,R)-4 showed high enantioselective fluorescent sensing ability to phenylalanine anion. The value of enantiomeric fluorescence difference ratio (ef) reached to 6.29.

Graphical abstractSeries of polyethers with different configurations were synthesized from chiral BINOL and optical epichlorohydrin. The sensors (S,S)-4 and (R,R)-4 showed high enantioselective fluorescent sensing ability to phenylalanine anion. The value of enantiomeric fluorescence difference ratio (ef) reached to 6.29.Figure optionsDownload full-size imageDownload high-quality image (169 K)Download as PowerPoint slide