LEAPS-MPS: Development of New Photoacid Catalyzed Reactions for Organic Synthesis

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This award is funded in whole or in part under the American Rescue Plan Act of 2021 (Public Law 117-2). In this project, funded by the Mathematical and Physical Sciences Directorate and housed in the Chemistry Division, Professor Joseph Badillo and his students at Seton Hall University will study photoacids and photoacid catalysis to help design new chemical reactions that will be important in synthesizing new organic (carbon-based) molecules. A photoacid is a weak acid in its normal state, and only upon irradiation with light does it become a strong acid, and thus catalytically active (able to speed up reactions). This dependence on light-activation offers temporal- and spatial-control not possible with traditional acid catalysis. Despite the unique possibilities of photoacid catalysis, the synthesis and characterization of new photoacids and the development of new photoacid catalyzed reactions remains relatively unexplored. Prof. Badillo also proposes a broadening participation plan that includes having his students present their research at URM-serving conferences such as NOBCChE, working with ACS Project SEED to provide research experiences for URM high school students, and working with several Seton Hall University student organizations to bring science outreach to local minority-serving high schools.Professor Badillo will perform experiments leading to improved understanding of common photoacid catalysts’ photophysical properties by measuring excited state lifetimes (t) and acidities (pKa*). A series of non-photoracemizable chiral photoacids will be designed, synthesized and characterized, and the use of photoacid catalysis will be explored in the context of C–X (X = H, O, C) bond-forming reactions, including asymmetric excited-state proton transfer, glycosylation, and acetalization reactions. The use of photoacid generators such as halonium and sulfonium ions in the context of catalysis will also be investigated. Prof. Badillo’s plan for integrating research and broadening participation-oriented outreach activities will both bring underrepresented minority high school students to Seton Hall University for research experiences, and send Seton Hall students into local schools for science outreach activities.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.