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Multiple noncovalent interaction constructed polymeric supramolecular crystals: recognition of butyl viologen by para-dicyclohexanocucurbit[6]uril and α,α′,δ,δ′-tetramethylcucurbit[6]uril

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Abstract

Binding interactions of butyl viologen (BV+) with para-dicyclohexanocucurbit[6]uril (Cy2Q[6]) and α,α′,δ,δ′-tetramethyl cucurbit[6]uril (TMeQ[6]) were investigated by 1H NMR spectroscopy, isothermal titration calorimetry (ITC) and X-ray crystallography. In the solid state, the BV+ guest and both hosts form polymeric supramolecular crystals through multiple noncovalent interactions, including host–guest interaction, π–π stacking interaction, and metal–host coordination. In the aqueous solution, the butyl chain of BV+ was selectively encapsulated into the hosts Cy2Q[6] and TMeQ[6], while the bipyridinium group resides outside of the host portals, forming [2]pseudorotaxane. The ITC experiment indicates that the host–guest binding processes are exclusively enthalpy driven.

Graphical abstract: Multiple noncovalent interaction constructed polymeric supramolecular crystals: recognition of butyl viologen by para-dicyclohexanocucurbit[6]uril and α,α′,δ,δ′-tetramethylcucurbit[6]uril

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Publication details

The article was received on 11 Aug 2017, accepted on 01 Sep 2017 and first published on 05 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00708F
Citation: Org. Chem. Front., 2017, Advance Article
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    Multiple noncovalent interaction constructed polymeric supramolecular crystals: recognition of butyl viologen by para-dicyclohexanocucurbit[6]uril and α,α′,δ,δ′-tetramethylcucurbit[6]uril

    Z. Xiao, R. Lin, Z. Tao, Q. Liu, J. Liu and X. Xiao, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00708F

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