Enantioselective Recognition of Chiral Carboxylic Acids by a β-Amino Acid and 1,10-Phenanthroline Based Chiral Fluorescent Sensor

Sensors

Yonghong Zhang¹  Fangzhi Hu²  Bin Wang³  Xiaomei Zhang²  Chenjiang Liu¹ 

[1] Key Laboratory of Petroleum and Gas Fine Chemicals of Ministry of Education, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China; E-Mail:;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China; E-Mails:;Physics and Chemistry Detecting Center, Xinjiang University, Urumqi 830046, China; E-Mail:

关键词: enantioselective recognition;    fluorescent sensor;    carboxylic acids;    10-phenanthroline;    β-amino acid;   

DOI  :  10.3390/s150510723

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.