Synthesis and Recognition Properties of Cucurbit[n]uril Type Receptors

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Containers have a variety of uses, such as to preserve foodstuff, to organize collections of objects, and to hold objects during their shipment to specific destinations. In the chemistry realm, molecular containers are used to isolate molecules that smell, to extend the lifetime of unstable compounds by not allowing them to react with other molecules, and to change important molecular properties like solubility. At the University of Maryland, Professor Lyle Isaacs' research group studies next generation molecular containers known as cucurbiturils. By creating a series of new cucurbituril-type containers, studying their basic container properties, and showing how they may be integrated into complex systems, the Isaacs' group enables other academic and industrial labs to adapt cucurbituril molecular containers to applications such as drug delivery and sensing of addictive over-the-counter drugs. Isaacs' research data is used to stimulate interactions with computational chemists via the program Statistical Assessment of the Modeling of Proteins and Ligands (SAMPL) Challenges. The researchers also conduct outreach activities with pre-schools, and disseminate problem sets for use in spectroscopic methods courses.The research focuses on the development of the synthetic and supramolecular chemistry of a family of molecular container compounds called cucurbit[n]uril (CB[n]). An important aim of this project is to develop structure affinity relationships that refine the understanding of the extraordinarily tight binding affinity of CB[n] toward cationic diamondoid molecules. The new acyclic cucurbituril containers have triptycene derived aromatic walls that allow tailoring of the surface to enable chiral recognition and guest selectivity. By linking the CB[n] containers to metal-organic polyhedra, the research team investigates how guests are take up inside the CB[n] containers, further promoting chemical reactivity inside the metal-organic polyhedra.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.