Calixarenes sulfonated at the wide rim are water-soluble and known to strongly associate with positive and dipositive organic nitrogen species such as 1-methylpyridinium and 1,1′-dimethyl-4,4′-bipyridinium ions. Octasulfonated dicalixarene species 1 exhibits a direct connection between calixarene subunits at the 2-position. The solid-state structure of species 1 has two calixarene subunits, each in the cone conformation, oriented anti to one another. NMR spectroscopy of 1 in solution is consistent with this conformation assignment. Thus, 1 is a good candidate component for supramolecular assemblies, including supramolecular polymers, because the two subunits of this di-host species present in opposite directions, and could act independently of one another when interacting with guest and di-guest species. The interactions of 1 with cationic guests and di-guests derived from pyridine, 4,4′-bipyridine, and 1,4-diazabicyclo[2.2.2]octane (DABCO) studied by NMR spectroscopy and titration calorimetry will be described.

Methylene-bridge-linked dicalixarene as component for supramolecular assemblies in aqueous media

251st National Meeting (2016)

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