Poly(alpha-hydroxy acids) via Ring-Opening Polymerization of O-Carboxyanhydrides

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In this project funded by the Macromolecular, Supramolecular and Nanochemistry Program of the Chemistry Division of the National Science Foundation, Jianjun Cheng at the University of Illinois at Urbana-Champaign aims to develop methods for facile preparation of poly(alpha-hydroxy acids) bearing pendant functionalities. The project will first focus on the design and synthesis of various O-carboxyanhydride monomers containing natural or unnatural amino acid side chains. These monomers will then be used in the development of organo- and metal-catalyzed, living ring-opening polymerization of O-carboxyanhydrides to yield well-defined poly(alpha-hydroxy acids) with functionalized side chains. Finally, some applications of poly(alpha-hydroxy acids), such as their uses in encapsulation, conjugation and membrane penetration, will be explored. The broader impacts and proposed education and outreach activities include mentoring academically underperforming undergraduate students and leading summer education and outreach programs designed for stimulating interest of high school and college students in science and engineering. Polyesters are useful materials encountered in many aspects of everyday life: clothing fiber, plastic bottles, plastic shopping bags, etc. One drawback of many commercial polyesters is that they are not easily modified to form new materials with new properties. In this research project, new classes of polyesters that incorporate different types of chemical groups are developed. Such materials could impact a range of technologies in which plastics are used, such as new technologies for recycling of polyester plastics, the generation of renewable plastics and new functional materials for biomedical applications.