Publications by Year: 2010

The concept of self-assembling container molecules as yocto-litre reaction flasks is gaining prominence. However, the idea of using such containers as a means of protection is not well developed. Here, we illustrate this idea in the context of kinetic resolutions. Specifically, we report on the use of a water-soluble, deep-cavity cavitand to bring about kinetic resolutions within pairs of esters that otherwise cannot be resolved because they react at very similar rates. Resolution occurs because the presence of the cavitand leads to a competitive binding equilibrium in which the stronger binder primarily resides inside the host and the weaker binding ester primarily resides in the bulk hydrolytic medium. For the two families of ester examined, the observed kinetic resolutions were highest within the optimally fitting smaller esters.

Dendronized cavitands represent unique macromolecular hosts for encapsulation of biologically relevant guests. They combine the highly specific guest binding exhibited by deep-cavity cavitands, with the modular yet monodisperse macromolecular structure provided by dendrimers. Because these structures retain the ability to assemble into dimeric capsules, they resemble a simplified synthetic analog of viral capsids, displaying a modular, functionalizable outer coating while providing a protective cavity for a range of small-molecule payloads. This article highlights their preparation, their characterization, and their unique potential for probing in vivo drug delivery.