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Issue 12, 2013
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Chirality sensing using stereodynamic probes with distinct electronic circular dichroism output

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Abstract

Circular dichroism (CD) spectroscopy is one of the most useful techniques for the stereochemical analysis of chiral biopolymers and fine chemicals. It has become invaluable for the assignment of the absolute configuration, the study of conformational isomers, and the determination of racemization kinetics of CD active chiral compounds. Molecular interactions between a nonracemic chiral substrate and a chromophoric, CD-silent probe that is achiral or exists as a racemic mixture of rapidly interconverting enantiomeric conformations or configurations can induce a strong, characteristic chiroptical readout. A covalent or noncovalent binding event that coincides with a well-defined asymmetric induction process can effectively imprint the chiral information of the substrate on the stereodynamic sensor and thus generate intense Cotton effects in the UV region of the latter. The probe can thus function as a stereochemical reporter unit and analysis of the CD spectrum often provides accurate information about the absolute configuration and enantiomeric composition of the substrate used. In this review, recent developments in circular dichroism analysis of chiral compounds with stereodynamic probes are described and particular emphasis is given to sensor design, chiral induction processes and applications scope.

Graphical abstract: Chirality sensing using stereodynamic probes with distinct electronic circular dichroism output

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Publication details

The article was received on 03 Dec 2012 and first published on 13 Mar 2013


Article type: Review Article
DOI: 10.1039/C3CS35498A
Citation: Chem. Soc. Rev., 2013,42, 5408-5424
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    Chirality sensing using stereodynamic probes with distinct electronic circular dichroism output

    C. Wolf and K. W. Bentley, Chem. Soc. Rev., 2013, 42, 5408
    DOI: 10.1039/C3CS35498A

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