Water-Soluble Cavitands ☆

Jordan, Jacobs H.; Gibb, Bruce C.

doi:10.1016/b978-0-12-409547-2.10789-9

Cited by 1 publication

(1 citation statement)

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“…A major advantage of the macrocyclic scaffold is the ability to tune the solubility properties by varying the leg groups (Figure ), which are typically introduced by the selection of the corresponding aldehyde in the octol synthesis. , Long alkyl chains, such as undecyl, render the resorcinarenes soluble in low-polarity solvents, such as hexane and benzene, whereas shorter alkyl chains aid solubility in more polar organic solvents and also facilitate crystallization . Incorporation of charged or polar groups provide solubility in aqueous environments; terminal ester groups have been used to create amphiphilic molecules that form ordered Langmuir monolayers at the air–water interface . Additionally, through the incorporation of binding groups at the leg termini, resorcin[4]arene cavitands can be deposited on various surfaces, including metals and organic supports …”

Section: Key Properties Of Resorcin[4]arene Cavitandsmentioning

confidence: 99%

Molecular Recognition with Resorcin[4]arene Cavitands: Switching, Halogen-Bonded Capsules, and Enantioselective Complexation

2018

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The development of synthetic host-guest chemistry to investigate and quantify weak, non-covalent interactions has been key to unraveling the complexity of molecular recognition in chemical and biological systems. Macrocycles have shown great utility in the design of receptors, enabling the development of highly preorganized structures. Among macrocycles, resorcin[4]arene-based cavitands have become privileged scaffolds due to their synthetic tunability, which allows access to structures with precisely defined geometries, as well as receptors that display conformational switching between two distinct states with a large difference in guest-binding properties. Here, we highlight three case studies demonstrating redox- and photoredox-controlled switching of molecular recognition properties, the formation of guest-binding supramolecular capsules based solely on halogen-bonding interactions, and enantioselective encapsulation of chiral, substituted cyclohexanes by enantiopure cage compounds as a result of perfect shape complementarity, dispersion interactions, and halogen bonding. The high geometrical and conformational control that can be achieved with resorcin[4]arene-derived host systems will continue to be a powerful resource in future molecular recognition studies.

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