Design Rules for Dynamic Macrocyclization

University Of Illinois At Urbana-Champaign, Urbana IL

Investigators

Abstract

With this award, the Chemical Synthesis Program is supporting the research of Professor Jeffrey S. Moore of the Department of Chemistry at the University of Illinois, Urbana-Champaign. Professor Moore's research efforts revolve around the rational design of functional macromolecular architectures. This project will continue work on the development of efficient methods for shape-persistent macrocycle synthesis by dynamic alkyne metathesis. While the preparation of shape-persistent macrocycles via dynamic covalent chemistry is an established process, product distribution is not always intuitive, and a general set of design criteria for monomers is needed. Detailed structure-property relationship studies will be undertaken to develop a deeper understanding of the role of the monomer identity on the dynamic formation of macrocycles. From these studies, a set of design rules will be developed that will generalize the conditional requirements for the efficient preparation of macrocycles under thermodynamic control. The preparation of novel arylene ethynylene macrocycles with potentially novel functionality will be a direct result of this study. Successful development of the methodology will have an impact on the development of sensors for battlegrounds, as these macrocycles are highly sensitive to explosives and their precursors. In addition, this project will provide excellent training in advanced chemistry research to graduate students. Scientific outreach activities involving high school students, summer camps, science clubs, and unpaid scientific consulting for TV stations are also integrative parts of this project.