An octasulfonated 2,2′-linked dicalixarene (2) was prepared by ipso-sulfonation of 2,2′-linked p-tert-butyldicalixarene 1 in 74% yield. Sulfonated species 2 (“host”) is soluble in aqueous media and exhibits a strong affinity for cationic aromatic heterocycles (“guests”) such as methylpyridinium and 1,1′-dimethyl-4,4′-bipyridinium. The interaction between host and guest was studied by 1H NMR spectroscopy to determine association constants and stoichiometry of binding. The interaction of 2 with difunctional guests in an effort to generate supramolecular polymers will be described.

2,2′-Linked sulfonated dicalix[4]arene as a component in supramolecular species

249th National Meeting (2015)

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