Fluorescent-Cavity Host: An Efficient Probe to Study Supramolecular Recognition Mechanisms

Using fluorometry to study the interactions between guests and host cavities is often challenging, especially for hosts with small cavities because the fluorophore may not be close to the binding site. Therefore, it is critical to overcome this hurdle to broaden the applicability of fluorometry in supramolecular chemistry. Herein, we designed a fluorescent-cavity host (<b>H1</b>) by conjugating the binding site of a pillar[5]­arene cavity and studied its host–guest recognition mechanism in the cavity. Distinct fluorescent responses of <b>H1</b> were observed for cyano homologues: the fluorescence was enhanced for succinonitrile but quenched for malononitrile. Such an unusual phenomenon with such subtle difference in guest structure was attributed to the different host–guest interactions induced by the subtle difference of guest locations within the <b>H1</b> cavity. Our results indicate that developing fluorescent-cavity hosts as probes will provide a powerful and insightful way to explore the exquisite detail of host–guest recognition, self-assembly, and molecular machinery