title: Syntheses and highly enantioselective fluorescent recognition of α-aminocarboxylic acid anions using chiral oxacalix[2]arene[2]bisbinaphthes.
abstract: The triazine-based bisbinaphthyl crown ethers oxacalix[2]arene[2]bisbinaphthes R-1, R-2, R-3 and S-1, S-2, S-3 were synthesized. The interactions of these compounds with various α-aminocarboxylic acid anions were studied. The crown ethers were found to carry out highly enantioselective fluorescent recognition of α-aminocarboxylic acid anions. It is observed that within a certain concentration range, one enantiomer of the chiral α-aminocarboxylic acid anions can increase the fluorescence intensity of the crown ethers by fivefold to sixfold, whereas the other enantiomer scarcely enhances the fluorescence. Such unusually high enantioselective responses make these crown ethers very attractive as fluorescent sensors in determining the enantiomeric composition of α-aminocarboxylic acid anions.
authors.affiliation: Institute of Fine Chemistry and Chemical Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, China. xukx@henu.edu.cn
authors.forename: Kuoxi
authors.initials: K
authors.lastname: Xu
authors.forename: Shuyan
authors.initials: S
authors.lastname: Jiao
authors.forename: Wenyong
authors.initials: W
authors.lastname: Yao
authors.forename: En
authors.initials: E
authors.lastname: Xie
authors.forename: Baowei
authors.initials: B
authors.lastname: Tang
authors.forename: Chaojie
authors.initials: C
authors.lastname: Wang
mesh_terms: D000409:Alanine / Q000138:chemical synthesis* / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D043844:Crown Ethers / Q000138:chemical synthesis* / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000032:analysis / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010649:Phenylalanine / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D002264:Carboxylic Acids; D043844:Crown Ethers; D005456:Fluorescent Dyes; D047250:Calixarenes; D010649:Phenylalanine; C008852:2-phenylglycine; D000409:Alanine; D005998:Glycine