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20200925_ZW_Nicotine_paper.pdf (3.84 MB)

Calix[4]arene Sulfonate Hosts Selectively Modified on the Upper Rim: A Study of Nicotine Binding Strength and Geometry

preprint
submitted on 07.01.2021, 23:48 and posted on 08.01.2021, 13:23 by Zoey Warmerdam, Bianca Kamba, Alok Shaurya, XuXin Sun, Mary Maguire, Fraser Hof
Preprint manuscript, including synthesis of new compounds and fluorescence/NMR-based binding data.

We present the synthesis and structure-activity relationships of sulfonatocalix[4]arene hosts bearing novel substitutions. The calix[4]arenes are modified on the upper rim at either one or two of the phenolic units, where the dual modifications are introduced selectively on neighboring or opposing phenols. The calix[4]arenes are mono- or di-functionalized with nitro or formyl groups, with the remaining upper-rim sites in all cases occupied by sulfonates. Equilibrium association constants were determined between each host and the guests nicotine, nornicotine, and cotinine. Indicator displacement-based binding studies show that nicotine binds most strongly to the different members of the library followed by nornicotine, whereas cotinine displays weak to no binding. NMR titrations were carried out with nicotine and show different host-guest interaction geometries for the formyl-calix[4]arenes versus the nitro-calix[4]arenes.

Funding

NSERC Discovery Grant RGPIN 2019-04806

Deutsche Forschungsgemeinschaft (BA1624/15-1)

History

Email Address of Submitting Author

fhof@uvic.ca

Institution

University of Victoria

Country

Canada

ORCID For Submitting Author

0000-0003-4658-9132

Declaration of Conflict of Interest

No conflict of interest to declare.

Version Notes

Author manuscript, preprint to be submitted for peer review elsewhere.

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