GOALI: CAS: Organocatalytic Reactions and Processes for Polymer Chemistry

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With this award, the Macromolecular, Supramolecular, and Nanochemistry Program in the Division of Chemistry is funding Professor Robert Waymouth of the Department of Chemistry at Stanford University and Dr. James Hedrick of IBM Almaden Laboratories to develop and explore new catalysts and catalytic methods for the generation of biodegradable, functional, and responsive polymers. These polymers (large molecules containing many monomer units linked together with chemical bonds) are targeted as alternatives to petrochemically-derived plastics and as new families of biodegradable materials for biomedical applications. The central focus is on the design and characterization of environmentally-benign, metal-free catalysts that enable optimum polymer production under large scale industrial conditions. Functional properties such as degradability and biocompatibility of the polymers generated using these methods are also investigated. The project effectively fosters academic and industrial collaboration on both scientific research and training of students. The collaboration improves academic-industrial interactions, which can have a very positive educational impact on students and young researchers who are rarely educated about the ways to efficiently transfer laboratory-generated knowledge into the industrial realm. This project has the potential to advance new strategies in polymer synthesis and create new technologies for the next generation of renewable plastics. The academic-industrial team of Waymouth and Hedrick develops new automated continuous flow reactors designed to function optimally under a variety of polymerization conditions. They design new catalyst families based on squaramides and indole carboxamides and related structures. The team invents “catalyst switch” strategies relying on rate differences associated with proton transfer to enable the scalable and reproducible generation of block copolymer libraries in ring-opening polymerization of polyesters and polycarbonates. They also integrate catalytic strategies for both the synthesis of functional monomers and the macromolecules resulting from their enchainment. Emphasis is placed on detailed mechanistic and theoretical investigations to illuminate the mechanistic details of organocatalytic polymerization reactions. Degradation pathways associated with bio-mimicking poly(alpha-amino esters) in aqueous media are also investigated. The organocatalytic platform associated with this award is spawning innovative technologies for the generation of bio-active polymers and oligomers that can be applied as anti-microbial agents, cell-transfection agents for the delivery of drugs, fluorescent and luminescent probes and genetic agents.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.