title: Enantioselective Recognition of Chiral Carboxylic Acids by a β-Amino Acid and 1,10-Phenanthroline Based Chiral Fluorescent Sensor.
abstract: A novel chiral 1,10-phenanthroline-based fluorescent sensor was designed and synthesized from optical active β-amino acids. It used 1,10-phenanthroline moiety as a fluorescent signaling site and binding site, with optically active β-amino acids as a chiral barrier site. Notably, the optically active β-amino acids were obtained by a Lewis base catalyzed hydrosilylation of β-enamino esters according to our former work. The chiral sensor has been used to conduct the enantioselective recognition of chiral mono and dicarboxylic acids derivatives. Using this fluorescent sensor, a moderate "turn-off" fluorescence-diminishment response towards enantiomer of tartaric acids, and proline was observed. It found that l-enantiomers quench the chiral fluorescence sensor more efficiently than d-enantiomers due to the absolute configuration of the β-amino acid.
authors.affiliation: Key Laboratory of Petroleum and Gas Fine Chemicals of Ministry of Education, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China. zhzhzyh@126.com.
authors.forename: Yonghong
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. ssfangzhi@126.com.
authors.forename: Fangzhi
authors.initials: F
authors.lastname: Hu
authors.affiliation: Physics and Chemistry Detecting Center, Xinjiang University, Urumqi 830046, China. wangbin.yang@163.com.
authors.forename: Bin
authors.initials: B
authors.lastname: Wang
authors.affiliation: Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. xmzhang@cioc.ac.cn.
authors.forename: Xiaomei
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Petroleum and Gas Fine Chemicals of Ministry of Education, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China. pxylcj@126.com.|Physics and Chemistry Detecting Center, Xinjiang University, Urumqi 830046, China. pxylcj@126.com.
authors.forename: Chenjiang
authors.initials: C
authors.lastname: Liu
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000032:analysis* / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D010618:Phenanthrolines / Q000737:chemistry*; D013050:Spectrometry, Fluorescence / Q000379:methods*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D005456:Fluorescent Dyes; D010618:Phenanthrolines; C025205:1,10-phenanthroline