Synthesis and Application of Cucurbit[n]uril Type Receptors

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Containers are ubiquitous in everyday life with uses including the preservation of foods and beverages and to protect products against damage. Molecules need containers for the same reasons. For example, molecular containers are currently used in everyday life to formulate insoluble drugs. The research group of Professor Lyle Isaacs at the University of Maryland, College Park studies the preparation and application of a new advanced class of molecular containers called cucurbiturils. The work has the potential to impact both academic and industrial science by providing a series of container compounds bearing reactive functional groups that allow their incorporation into advanced functional systems for real world applications. Additional broader impacts of the research include education and training of undergraduate and graduate students as interdisciplinary scientists, which is accomplished in part through international collaborations and by the development of a series of videos to attract students to molecular container chemistry via a flipped classroom approach.The Macromolecular, Supramolecular and Nanochemistry (MSN) program of the Chemistry Division supports the work of Professor Isaacs, which focuses on the development of the synthetic and supramolecular chemistry of the cucurbit[n]uril (CB[n]) family of molecular container compounds. The work aims to understand the anomalously tight binding CB[7]-diamantane(NMe3)2 complex via the synthesis and Ka determination of structural analogues. These tight binding CB[n]-guest pairs can be used in concert with monofunctionalized CB[n] derivatives prepared by the the Isaacs group to enable new application areas including those that currently benefit from biotin-avidin technology like bioassays. Finally, the work addresses the scope and nature of selective interactions between acyclic CB[n] containers and peptides and proteins.