Resumen de Resorcin[4]arenes: A Convenient Scaffold To Study Supramolecular Self-Assembly and Host:Guest Interactions for the Undergraduate Curriculum
Michael C. Young, Katherine E. Djernes, John L. Payton, Daniel Liu, Richard J. J.
In response to the call for an increased emphasis from the American Chemical Society on including macromolecular studies in the undergraduate curriculum, a supramolecular-themed experiment was designed for undergraduate-level organic laboratory courses that provides a convenient platform to study physical behaviors of supramolecular assemblies. Students synthesize an easily purified resorcin[4]arene and characterize the product of its self-assembly via 1H NMR spectroscopy. These bowl-shaped molecules are noteworthy because of their propensity to self-assemble in organic solution in the presence of trace water or alcohol solvents. Upon self-assembly, the resulting hexamer adopts a well-defined molecular cage structure with a large internal cavity that can be used to explore host:guest chemistry. After completing the experiment, students are expected to gain a better understanding of electrophilic aromatic substitution, 1H NMR spectroscopy, supramolecular chemistry and self-assembly, and molecular recognition.
