Thesis
BODIPY-appended bases for influencing hydrogen atom transfer
Washington State University
Master of Science (MS), Washington State University
05/2021
DOI:
https://doi.org/10.7273/000004256
Handle:
https://hdl.handle.net/2376/125253
Abstract
Metal-based catalysts have found widespread use in performing reactions too difficult for non-catalytic methods. The rare metals often used in these catalysts have raised concerns over their cost and toxicity. Catalysts made from more abundant metals tend to be less reactive than their precious metal counterparts. Ligand structures capable of redox activity have been used to enhance the performance of metal catalysts. The behavior of redox active ligands in metal-catalyzed reactions has been described as “metal-like”. The “metal-like” behavior of this class of ligands has prompted exploration into whether metal atoms are needed to perform catalytic reactions. A simplified view of a catalyst, consisting of an electron reservoir and substrate dock, has been put forth. 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. The simplest chemical transformation, reduction of protons, was selected for study. Organic Brønsted bases, being proton acceptors, were selected to fill the role of substrate dock. The prototype proton reduction complex developed from the previous description, 8-tetramethylguanidino-BODIPY (BoTMG), was treated with sources of H2 equivalents. 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 theses complexes is aimed at understanding the influence of BODIPY-based redox events on the transfer of hydrogen atoms. This work breaks further ground toward establishing the principles by which catalyst complexes composed solely of main group elements may be constructed.
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Details
- Title
- BODIPY-appended bases for influencing hydrogen atom transfer
- Creators
- Tanner B. Hanson
- Contributors
- ZACHARIAH M HEIDEN (Advisor) - Washington State University, Chemistry, Department of
- Awarding Institution
- Washington State University
- Academic Unit
- Chemistry, Department of
- Theses and Dissertations
- Master of Science (MS), Washington State University
- Publisher
- Washington State University
- Identifiers
- 99900896416901842
- Language
- English
- Resource Type
- Thesis