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Issue 17, 2011
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Enantioselective fluorescent recognition of mandelic acid by unsymmetrical salalen and salan sensors

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Abstract

As sensors with multiple chiral centers, salalen 1 and salan 2 composed of trans-cyclohexane-1,2-diamine (trans-DACH) and 1,1′-bi-2-naphthol (BINOL) units were designed and synthesized. Fluorescent recognition studies of resulting sensors towards mandelic acid (MA) reveal that salan 2a containing (R)-BINOL and (R,R)-DACH exhibits highly sensitive and enantioselective response towards MA. The relationship between the chirality combination and the enantioselectivity is discussed. Based on the studies of concentration and solvent effect on the recognition process of 2a, it was found that the sensitivity and enantioselectivity could be enhanced via changing the concentration of sensors or altering the polarity of solvents. To explain why higher enantioselectivity can be achieved in moderate polar solvent other than in nonpolar or polar solvent, a solvent-guest competition mechanism, which may shed a light on the enhancement of the enantioselectivity of chiral recognition and noncovalent asymmetric catalysis, has been proposed and validated.

Graphical abstract: Enantioselective fluorescent recognition of mandelic acid by unsymmetrical salalen and salan sensors

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Article information


Submitted
08 Mar 2011
Accepted
17 May 2011
First published
18 May 2011

Org. Biomol. Chem., 2011,9, 6011-6021
Article type
Paper

Enantioselective fluorescent recognition of mandelic acid by unsymmetrical salalen and salan sensors

X. Yang, X. Liu, K. Shen, Y. Fu, M. Zhang, C. Zhu and Y. Cheng, Org. Biomol. Chem., 2011, 9, 6011
DOI: 10.1039/C1OB05361B

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