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

Zhang Y, Hu F, Wang B, Zhang X, Liu C - Sensors (Basel) (2015)

Bottom Line: Notably, the optically active β-amino acids were obtained by a Lewis base catalyzed hydrosilylation of β-enamino esters according to our former work.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 Article: PubMed Central - PubMed

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.

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.

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Stern–Völmer plot of S-G1 (8 × 10−5 mol·L−1) in EtOH in the presence of d-proline and l-proline (λex = 330 nm).
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sensors-15-10723-f005: Stern–Völmer plot of S-G1 (8 × 10−5 mol·L−1) in EtOH in the presence of d-proline and l-proline (λex = 330 nm).

Mentions: The Stern–Völmer constants of S-G1 in the presence d- and l-Proline (Figure 5) were found to be 63.7 and 113.4 M−1, respectively, under the same conditions as the use of d- and l-Tartaric acid. The ratio KSVS,D/KSVS,L is 0.56. Similar to enantiomers of tartaric acids, the fluorescence response of S-G1 toward l-Proline acid is more significant than that with d-Proline.


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

Zhang Y, Hu F, Wang B, Zhang X, Liu C - Sensors (Basel) (2015)

Stern–Völmer plot of S-G1 (8 × 10−5 mol·L−1) in EtOH in the presence of d-proline and l-proline (λex = 330 nm).
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4481974&req=5

sensors-15-10723-f005: Stern–Völmer plot of S-G1 (8 × 10−5 mol·L−1) in EtOH in the presence of d-proline and l-proline (λex = 330 nm).
Mentions: The Stern–Völmer constants of S-G1 in the presence d- and l-Proline (Figure 5) were found to be 63.7 and 113.4 M−1, respectively, under the same conditions as the use of d- and l-Tartaric acid. The ratio KSVS,D/KSVS,L is 0.56. Similar to enantiomers of tartaric acids, the fluorescence response of S-G1 toward l-Proline acid is more significant than that with d-Proline.

Bottom Line: Notably, the optically active β-amino acids were obtained by a Lewis base catalyzed hydrosilylation of β-enamino esters according to our former work.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 Article: PubMed Central - PubMed

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.

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.

Show MeSH