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Workshop / Seminar

AER/I Chemistry defense practice seminar with Tanner Hanson

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About the event

Presenter: Tanner Hanson
Group: Heiden
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

Passcode: 630931

Date & Time: Apr 9, 2021 03:00 PM Pacific Time (US and Canada)

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