Chiral fluorescence polyethers based on BINOL for enantioselective recognition of phenylalanine anion. (14th June 2016)

• Record Type: Journal Article
• Authors: Zhao, Chunhui; Ouyang, Kunbing; Zhang, Jin; Yang, Nianfa
• Is Part Of: Polymer. Volume 93(2016)
• Page Start: 9
• Page End: 13
• Publication Date: 2016-06-14
• Subjects: Chiral polyether -- Fluorescence enantioselective recognition -- Phenylalanine anion; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.polymer.2016.04.013
• Languages: English
• ISSNs: 0032-3861

Abstract

Abstract: 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 abstract: Series 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. Highlights: BINOL-based fluorescence sensors with two chiral moieties were reported. Enantioselective recognition was conducted in aqueous solution of THF/H2 O. Configurations of both BINOL and ECH affect the selectivity. The value of enantiomeric fluorescence difference ratio ( ef ) reached to 6.29.