Nature is truly amazing in the selectivity it exhibits for the stereospecific recognition of a vast diversity of compounds through assembly of supramolecular hosts. There have been many synthetic attempts to mimic this in a variety of fields using macrocyclic hosts due to the high affinity, analyte-selective binding of the hosts. However, the covalent modification of the synthetic hosts is costly in resources and time, and few stereoselective examples have been shown. Here is presented a modular, hierarchical approach to stereospecific recognition using Cucurbit(8)uril (Q8) for operating in aqueous environments in supramolecular chemistry. Q8 is used for its ability for selective, sequential binding to two different guests, an auxiliary guest (AG) and an analyte (N). Recently we have shown through 1H NMR that an assembled Q8 and chiral AG complex is selective for an N of the same handedness. Through simple synthetic modifications, the AG can be designed to define and tune the selectivity for stereospecific binding to N, and the AG can later be easily exchanged to form a new modular system for selective chiral recognition of N’. Here we present ongoing research into demonstrating the high-affinity selective chiral recognition of analytes by a modular supramolecular chiral complex composed of Q8 and an exchangeable chiral AG.

Selective chiral recognition by modular supramolecular cucurbit[8]url complexes

2019 Spring National Meeting

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