CAREER: Designing Hypervalent Bismuth Complexes with Reactive Perfluorinated Groups for Selective Organofluorination and Expanding Outreach in STEM Education in Hawaii.

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With the support of the Chemical Synthesis Program of the Division of Chemistry, Dr. Jakub Hyvl of the University of Hawaii–Manoa, Department of Chemistry, is studying the synthesis of bismuth compounds, which potentially can be developed into replacements for expensive metals that currently are used to facilitate important chemical transformations. Many chemical reactions require catalysts to proceed at and acceptable rate. A common characteristic of one important type of catalysts is their ability to gain and lose electrons; that is to participate in oxidative or reductive processes. Since many of these catalysts contain expensive metals such as platinum, there is great interest in discovering similar catalysts based on less expensive components. In this project, the preparation of bismuth compounds that are capable of the sort of gain/loss of electrons typical of platinum is being explored. The project focuses on bismuth because it is much cheaper and environmentally more benign than platinum. In addition to the scientific project, there is an educational component that involves close collaborations with local programs and science teachers. It will engage middle and high school students, especially Native Hawaiian, and other underrepresented students.Bismuth is inexpensive, abundant, and non-toxic. This project aims at synthesizing bismuth compounds that mimic the reactivity of noble metal transition metal complexes. In the research portion of this project, organobismuth species that are capable of performing efficient difluorocarbenation and perfluoroalkylation reactions are being synthesized. These involve hypervalent bismuth compounds with an expanded coordination number that can cycle between oxidation states Bi(III)/Bi(V) and Bi(I)/Bi(III). These attributes are to be used to facilitate a selective organofluorine transfer, a pharmaceutically relevant transformation that is often challenging. The educational portion of this project will reach out to K-12 students, collaborate with local programs and science teachers, and place an emphasis on Native Hawaiians and other traditionally underrepresented minorities.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.