With this CAREER Award, the Chemical Synthesis program is supporting fundamental research of Professor Elisa Tomat at the University of Arizona. Professor Tomat will employ selected oligopyrrolic compounds to investigate the interplay of metal coordination and ligand-based redox chemistry in transition metal complexes. This work focuses on the synthesis and ligand properties of oligopyrroles. These new substances are inspired by naturally occurring compounds derived from bacterial biosynthesis and from the oxidative metabolism of heme. The investigation of ligand systems which act as electron sources or reservoirs offers new avenues for the engineering of reactivity pathways, thereby creating a conceptual framework for the development of versatile tunable catalysts of potentially high impact in the chemical and pharmaceutical industry. Professor Tomat will integrate the research and educational components of this project within Chemistry Discovery, a new outreach program for middle school students. Through a series of workshops aimed at highlighting the connections between everyday experience and chemistry advances, Chemistry Discovery provides middle school students with a discovery-based experience that captures the creativity of the STEM fields through experiments. Professor Tomat has established partnerships with local school districts and charter schools. Chemistry Discovery reaches an underprivileged community which is underrepresented in the sciences. In addition to the production of novel educational resources, Chemistry Discovery engages undergraduate students in the development of outreach workshops through a one-unit undergraduate course offering. The program promotes the pursuit of higher education in the STEM fields by providing an opportunity for middle-school students to discuss scientific observations while interacting with college students. In this research, new methods are to be developed for the synthesis of dipyrrolic and tripyrrolic ligands. Because the electronic structure of oligopyrroles is highly tunable by synthetic manipulations, a range of coordination and redox properties will be accessed. This research seeks to facilitate the design of complexes which enlist both the ligand platform and the metal center as sites of electron exchange. The coordination and redox chemistry of these classes of oligopyrrolic ligands will be investigated, in particular with respect to late transition metals of potential interest for catalytic applications. Trends in redox properties will be correlated with reactivity profiles involving ligand-based one-electron exchanges.