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Sensors 2015, 15(5), 10723-10733; doi:10.3390/s150510723

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

1
Key Laboratory of Petroleum and Gas Fine Chemicals of Ministry of Education, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China
2
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
3
Physics and Chemistry Detecting Center, Xinjiang University, Urumqi 830046, China
*
Author to whom correspondence should be addressed.
Academic Editor: W. Rudolf Seitz
Received: 2 April 2015 / Revised: 24 April 2015 / Accepted: 24 April 2015 / Published: 6 May 2015
(This article belongs to the Section Chemical Sensors)
View Full-Text   |   Download PDF [885 KB, uploaded 6 May 2015]   |  

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. View Full-Text
Keywords: enantioselective recognition; fluorescent sensor; carboxylic acids; 10-phenanthroline; β-amino acid enantioselective recognition; fluorescent sensor; carboxylic acids; 10-phenanthroline; β-amino acid
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Zhang, Y.; Hu, F.; Wang, B.; Zhang, X.; Liu, C. Enantioselective Recognition of Chiral Carboxylic Acids by a β-Amino Acid and 1,10-Phenanthroline Based Chiral Fluorescent Sensor. Sensors 2015, 15, 10723-10733.

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