Antenna Biphenols: Development of Extended Wavelength Chiroptical Reporters

Molecular hosts capable of chiroptical sensing of complexed guest molecules offer an attractive alternative to conventional methods for the analysis of the absolute configuration and enantiopurity. Sensors based on the Pfeiffer effect rely on complexation-driven asymmetric transformation of the firs...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-02, Vol.81 (3), p.1185-1191
Main Authors: Bentley, Keith W, Joyce, Leo A, Sherer, Edward C, Sheng, Huaming, Wolf, Christian, Welch, Christopher J
Format: Article
Language:English
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Summary:Molecular hosts capable of chiroptical sensing of complexed guest molecules offer an attractive alternative to conventional methods for the analysis of the absolute configuration and enantiopurity. Sensors based on the Pfeiffer effect rely on complexation-driven asymmetric transformation of the first kind and can produce a chiroptical signal against an otherwise null background. To be most effective, the wavelength of the induced chiroptical sensor readout should be free and clear of interfering signals coming from the sample under investigation. In this study, we report the introduction of stereodynamic zinc complexes of antenna biphenols, a new class of sensors bearing antenna-like appendages that can extend the wavelength of the chiroptical signal while also improving enantioselective guest recognition.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02716