About the event
Presenter: Tanner Hanson
Title: BODIPY-Appended Bases for Influencing Hydrogen Atom Transfer
Abstract: Hydrogen atom transfer (HAT) is the concerted transfer of a proton and an electron from a single donor to a single acceptor. Influencing the Bond Dissociation Free Energy (BDFE), or homolytic bondstrength, of an X—H bond is frustrated by the connected and inversely correlated properties of reducing ability and acidity. We envision that HAT can be influenced by molecules capable of storing and deliveringprotons and electrons in separate fragments of the complex. Complexes consisting of connected electron and proton reservoirs should allow electron and proton donating abilities to be separately influenced. Fluorescent dyes are a class of main group element structures capable of redox chemistry that areunexplored for control over HAT. The fluorescent dye, 4,4-difluoro-4-bora-3a,4a-diaza-s- indacene (BODIPY) was chosen for the role of electron reservoir due to its reversible and tunable electrochemistry.. Organic Brønsted bases, being proton acceptors, were selected to fill the role of proton reservoir. Based on the previous description a prototype complex. 8-tetramethylguanidino-BODIPY (BoTMG), was developed. BoTMG was found to be unreactive toward sources of H2 equivalents, tBuNH2BH3, formic acid, Bu3SnH, and H2 . The product of BoTMG and hydrazine was investigated, but not ultimately identified. The synthesis and characterization of hydrazine-, amine-, azide-, and phosphazene-appended BODIPY complexes is described. The synthesis of these complexes is aimed understanding the influence of BODIPY-based redox events on the transfer of hydrogen atoms.
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Meeting ID: 943 4098 6087
Date & Time: Apr 9, 2021 03:00 PM Pacific Time (US and Canada)
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