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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.
Highlights
Enantioselective recognition of the two enantiomers of chiral compounds is an important subject in the field of asymmetric catalysis systems and in the field of medicinal and biomedical applications [1,2,3,4,5,6]
To further illustrate the synthetic potential of this methodology, we describe the first general enantioselective recognition of carboxylic acids by a 1,10-phenanthroline-based fluorescent sensor, which synthesized from optical active β-amino acids derivatives
We design S-G1 utilizing 1,10-phenanthroline moiety as a fluorescence signaling unit and optically active β-amino acids as a chiral barrier site to undertake the desired push-pull type fluorescent sensor to recognition of carboxylic acids for the following reasons: (1) 1,10-Phenanthroline was used as a fluorophore core and the scaffold of the chiral sensors; (2) The nitrogen atoms of 1,10-phenanthroline as a binding site that should bind -COOH of chiral carboxylic acids well through multiple hydrogen bonds; (3) The optical active β-amino acids as the chirogenic barrier site that may lead to good chiral recognition; (4) When sensors interact with the chiral carboxylic acids, the fluorescence of
Summary
Enantioselective recognition of the two enantiomers of chiral compounds is an important subject in the field of asymmetric catalysis systems and in the field of medicinal and biomedical applications [1,2,3,4,5,6]. To further illustrate the synthetic potential of this methodology, we describe the first general enantioselective recognition of carboxylic acids by a 1,10-phenanthroline-based fluorescent sensor, which synthesized from optical active β-amino acids derivatives
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