Resorcin[4]arenes: A Convenient Scaffold To Study Supramolecular Self-Assembly and Host:Guest Interactions for the Undergraduate Curriculum

• Michael C. Young ^[1] ; Katherine E. Djernes ^[2] ; John L. Payton ^[1] ; Daniel Liu ^[1] ; Richard J. Hooley ^[2]
  1. [1] University of Toledo

     University of Toledo

     City of Toledo, Estados Unidos

     
  2. [2] University of California, Riverside

     University of California, Riverside

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 96, Nº 4, 2019, págs. 781-785
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • 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.