Hierarchical study of mono- and multicharged imidazolium encapsulation in p-sulfonatocalix[4]arene molecular capsules

Irene Ling, Cameron L. Cambell, Alexandre N. Sobolev, Scott Dalgarno

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Abstract

Four ternary multi-component crystal structures comprising water-soluble p-sulfonatocalix[4]arene anion as the cavitand in the presence of different types of positively charged guest molecules comprising 1-butylimidazolium, 3,3′-(1,4-phenylenebis(methylene))bis(1-methylimidazolium), 3,3′,3′′-(benzene-1,3,5-triyltris(methylene))tris(1-methylimidazolium), or 3,3′,3′′,3′′′-(benzene-1,2,4,5-tetrayltetrakis(methylene))tetrakis(1-methylimidazolium) and aquated lanthanide(iii) ions (Gd(iii) or Ce(iii)) are reported. Careful crystallographic analysis shows that all positively charged imidazole rings are encapsulated by p-sulfonatocalix[4]arene for 1-butylimidazolium and 3,3′-(1,4-phenylenebis(methylene))bis(1-methylimidazolium), however, partial encapsulation was observed for 3,3′,3′′-(benzene-1,3,5-triyltris(methylene))tris(1-methylimidazolium) and 3,3′,3′′,3′′′-(benzene-1,2,4,5-tetrayltetrakis(methylene))tetrakis(1-methylimidazolium). The formation of a molecular capsule prevails in all structures regardless of the type of guest species. Supermolecules in three of the complexes self-assemble into a bilayer arrangement in the extended structure, whilst those involving p-sulfonatocalix[4]arene and 1-butylimidazolium form hydrated channels through alternative packing.

Original languageEnglish
Pages (from-to)4201-4207
Number of pages7
JournalCrystEngComm
Volume24
Issue number23
Early online date13 May 2022
DOIs
Publication statusPublished - 21 Jun 2022

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