Systematic Synthesis and Characterization of the 2-λ5-Phosphaquinolin-2-One Scaffold Towards their Optimization and Application
| dc.contributor.advisor | Haley, Michael | |
| dc.contributor.author | Bard, Jeremy | |
| dc.date.accessioned | 2021-11-23T15:10:27Z | |
| dc.date.available | 2021-11-23T15:10:27Z | |
| dc.date.issued | 2021-11-23 | |
| dc.description.abstract | The recently discovered phosphaquinolinone scaffold combines photophysical activity and supramolecular functionality to serve as a promising new class of compounds for a variety of different applications. The first part of this dissertation focuses on our work in developing a deep, fundamental understanding of many different aspects of the structure, including the photophysical properties, the solution-state dimerization, and the solid-state crystal packing structures. This was performed through a series of systematic syntheses focuses on backbone composition, substituent group placement, and phosphorus center modification. Through a combination of experimental and computational approaches, a series of relationships and trends have been drawn to allow for prediction of both emission energy and dimerization strength of previously not prepared heterocycles based solely upon computed values. These trends open the door for guided design of future heterocycles.The second part of this dissertation focuses on building off of the fundamental knowledge gained in the initial structure-property relationship studies and applying those findings to application-driven projects. The first of these involves preparing a series of conjugated host molecules that contain the phosphaquinolinone moiety. These hosts are capable of binding HSO4- both strongly and selectively and are able to extract it from aqueous solutions. These hosts can potentially be utilized in high-level nuclear waste remediation processes, as the removal of HSO4- is crucial to improving the currently used vitrification methods. The second of these studies involves the development of the PN scaffold as a live cell imaging reagent. Initial results indicate that this scaffold indeed holds promise as a useful cell imaging reagent as it is non-cytotoxic, relatively pH-insensitive, and cell-permeable. This dissertation contains both previously published and unpublished co-authored materials. | en_US |
| dc.identifier.uri | https://hdl.handle.net/1794/26866 | |
| dc.language.iso | en_US | |
| dc.publisher | University of Oregon | |
| dc.rights | All Rights Reserved. | |
| dc.subject | Dimerization | en_US |
| dc.subject | Fluorescent | en_US |
| dc.subject | Heterocycle | en_US |
| dc.subject | Nitrogen | en_US |
| dc.subject | Phosphorus | en_US |
| dc.subject | Supramolecular | en_US |
| dc.title | Systematic Synthesis and Characterization of the 2-λ5-Phosphaquinolin-2-One Scaffold Towards their Optimization and Application | |
| dc.type | Electronic Thesis or Dissertation | |
| thesis.degree.discipline | Department of Chemistry and Biochemistry | |
| thesis.degree.grantor | University of Oregon | |
| thesis.degree.level | doctoral | |
| thesis.degree.name | Ph.D. |
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