Supramolecular Design of Novel Reagents and Organo-Catalysts for Aqueous Solution

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With the support of the Macromolecular, Supramolecular and Nanochemistry Program in the Division of Chemistry, Professor Bruce C. Gibb of Tulane University seeks to gain a better understanding of the science of placing molecules within capsules. More specifically, this storage of “guest molecules” will be used to facilitate their chemical transformation into new matter. It is anticipated that understanding these transformations will lead to new efficient and environmentally friendly synthetic methods, and so contribute to the advancement of the chemical enterprise. The described work will not only help train the next generation of chemists, but will also be integrated into community outreach activities to promote STEM (science, technology, engineering and mathematics) education and positively impact the minority population of Orleans Parish and Southern Louisiana.There are two interrelated aims to the work: (a) to contribute to the state-of-the-art of supramolecular chemistry by helping bridge the gap between the field and synthetic methodology, and (b) to achieve the synthesis and exploration of new reagents and catalysts that utilize water and the hydrophobic effect to enable reactions that occur under mild and environmentally benign conditions. Specifically, the work will involve (1) a novel iodination process for aromatic rings to create a mild catalytic process of broad substrate scope; (2) studies into new yoctoliter (10^–24 L) capsules that are negatively charged at low pH and will promote or catalyze reactions involving cationic intermediates and transition states, and (3) the synthesis of new supramolecular capsules possessing endo-functionality — functional groups that are integrated into the walls of the inner-space — that will lead to better control of the bound guest. These three sub-programs aim to help create new supramolecular host-guest complexes and new platforms for organocatalysis.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.