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Issue 7, 2016
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From substituent effects to applications: enhancing the optical response of a four-component assembly for reporting ee values

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Abstract

High-throughput screening for asymmetric catalysts has stimulated an interest in optically-based enantiomeric-excess (ee) sensors, primarily for their improved time and cost efficiency when compared to the standard HPLC analysis. We present herein substituent-effect studies on a recently reported Zn(II) multicomponent assembly that is used for chiral, secondary alcohol ee determination. The systematic altering of assemblies formed from select substituted pyridyl ligands pointed to the conclusion that steric effects dominate the mode of interaction at the pyridyl 3- and 6-positions. From these results we identified a new Zn(II)-centered multicomponent assembly with a higher dynamic range than previously reported. Calibration curves of the CD signals resulting from the new assembly led to an ee assay with a 1.7% error. To further the utility of the new assembly, a correlation was developed between alcohol substituent size to the respective enantiopure CD value.

Graphical abstract: From substituent effects to applications: enhancing the optical response of a four-component assembly for reporting ee values

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Publication details

The article was received on 01 Dec 2015, accepted on 07 Mar 2016 and first published on 07 Mar 2016


Article type: Edge Article
DOI: 10.1039/C5SC04629G
Citation: Chem. Sci., 2016,7, 4085-4090
  • Open access: Creative Commons BY license
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    From substituent effects to applications: enhancing the optical response of a four-component assembly for reporting ee values

    C. Lin, M. W. Giuliano, B. D. Ellis, S. J. Miller and E. V. Anslyn, Chem. Sci., 2016, 7, 4085
    DOI: 10.1039/C5SC04629G

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