Issue 23, 2022

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
31 mar 2022
Accepted
13 may 2022
First published
13 may 2022
This article is Open Access
Creative Commons BY license

CrystEngComm, 2022,24, 4201-4207

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

I. Ling, C. L. Campbell, A. N. Sobolev and S. J. Dalgarno, CrystEngComm, 2022, 24, 4201 DOI: 10.1039/D2CE00459C

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