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Cucurbituril chemistry: a tale of supramolecular success

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TLDR
Cucurbit[n]urils have become key units in various self-organizing and stimulus-controlled assemblies, as well as in advanced materials and drug carriers.
Abstract
This review highlights the past six year advances in the blossoming field of cucurbit[n]uril chemistry. Because of their exceptional recognition properties in aqueous medium, these pumpkin-shaped macrocycles have been generating some tremendous interest in the supramolecular community. They have also become key units in various self-organizing and stimulus-controlled assemblies, as well as in advanced materials and drug carriers. The scope of this review is limited to the main family of cucurbit[n]urils (n = 5, 6, 7, 8, 10). The reader will find an overview of their preparation, their physicochemical and biological properties, as well as their recognition abilities towards various organic and inorganic guests. Detailed thermodynamic and kinetic considerations, as well as multiple applications including supramolecular catalysis are also discussed.

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Citations
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Journal ArticleDOI

Cucurbiturils: from synthesis to high-affinity binding and catalysis

TL;DR: The fundamental properties of CBn homologues and their cyclic derivatives are discussed with a focus on their synthesis and their applications in catalysis.
Journal ArticleDOI

Supramolecular polymeric hydrogels

TL;DR: A critical review summarising the formation of dynamic polymeric networks through specific non-covalent interactions, with a particular emphasis on those systems based on host-guest complex formation, as well as the characterisation of their physical characteristics.
References
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Journal ArticleDOI

Reconfigurable four-component molecular switch based on pH-controlled guest swapping.

TL;DR: The four-component ensemble comprising CB[6], beta-CD, and guests 1 and 2 forms complexes CB[ 6].1H+ and beta- CD but swaps partners forming complexes CB,[6].2 and Beta-CD at pH > 13.1 and suggests application as a basis for stimuli-responsive reconfigurable systems.
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Controlling the extent of spin exchange coupling in 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) biradicals via molecular recognition with cucurbit[n]uril hosts.

TL;DR: In the final 2:1 complex, no spin exchange coupling was observed, but the initial levels ofspin exchange coupling could be regenerated in a reversible fashion by adding a competing guest, adamantyltrimethylammonium (AdTMA), to the solution.
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Inclusion complexes of the antitumour metallocenes Cp2MCl2 (M = Mo, Ti) with cucurbit[n]urils

TL;DR: Encapsulation of Cp(2)TiCl(2(aq)) by Q[7] greatly slowed the protonolysis of the cyclopentadienyl ligands in aqueous phosphate buffer (pD 7), while encapsulation in Q[8] only slightly retarded the hydrolytic degradation of the metallocene.
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One ring to bind them all: shape-selective complexation of phenylenediamine isomers with cucurbit[6]uril in the gas phase.

TL;DR: Computational methods, Fourier transform ion cyclotron resonance mass spectrometry, and ion mobility studies show that the lowest energy binding sites for ortho- and meta-phenylenediamine are on the exterior of cucurbit[6]uril, whereas para- Phenylenedienine preferentially binds in the interior, in a pseudorotaxane fashion.
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U-shaped conformation of alkyl chains bound to a synthetic receptor cucurbit[8]uril.

TL;DR: The enthalpy-entropy compensation plot for the complexation suggests large conformational changes of the long alkyl chains and extensive dehydration associated with the inclusion complex formation.
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