Substitution and Analysis of Additional Heteroatoms in 1,2λ5-Azaphosphinines

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dc.contributor.advisorHaley, Michael
dc.contributor.authorMcNeill, John
dc.date.accessioned2024-12-19T20:05:35Z
dc.date.available2024-12-19T20:05:35Z
dc.date.issued2024-12-19
dc.description.abstractAzaphosphinines are, simply put, six-membered heterocycles containing one nitrogen and one phosphorus atom. While garnering more attention in the last couple decades, they are still decidedly understudied. This lack of research is primarily due to the difficult and often intense reaction conditions required to synthesize them. This is especially true for the azaphosphinine moiety’s early iterations. In the Haley and Johnson groups we have found a facile synthetic pathway that allows us to circumvent these issues. In this dissertation I will discuss not only a history of the azaphosphinine functional group but also the results of my independent research. The main body of my Ph.D. work is concerned with the substitution of additional heteroatoms into our thoroughly studied azaphosphinines. These substitutions result in dramatic changes to both the supramolecular and photophysical properties of the heterocycles. While most of the work I will discuss is related to different orientations of pyrido-fused azaphosphinines, I also include a study on the thionation of the ubiquitous phosphoryl group. Chapter I is a holistic review of azaphosphinines. I begin by discussing the nomenclature and unusual electronic properties of these heterocycles before detailing a chronological progression of the literature concerning the three isomers and both valencies of the azaphosphinine functional group. In Chapter II I describe the synthesis and unexpected tautomerization effects observed in pyrido[2,3-e]-1,2λ5- azaphosphinines. Chapter III continues to explore the electronic effects of a pyrido fusion, but in this case, we are now considering the internal charge transfer present in pyrido[3,4-e]-1,2λ5-azaphosphinines. And lastly Chapter IV examines the thionating effect of Lawesson’s Reagent on our heterocycles and the dramatic impacts this transformation has on their photophysical properties. This dissertation includes previously published co-authored material.en_US
dc.identifier.urihttps://hdl.handle.net/1794/30290
dc.language.isoen_US
dc.publisherUniversity of Oregon
dc.rightsAll Rights Reserved.
dc.subjectHeteroatomen_US
dc.subjectHeterocyclesen_US
dc.subjectNitrogenen_US
dc.subjectPhosphorusen_US
dc.subjectPyridineen_US
dc.subjectSupramolecularen_US
dc.titleSubstitution and Analysis of Additional Heteroatoms in 1,2λ5-Azaphosphinines
dc.typeElectronic Thesis or Dissertation
thesis.degree.disciplineDepartment of Chemistry and Biochemistry
thesis.degree.grantorUniversity of Oregon
thesis.degree.leveldoctoral
thesis.degree.namePh.D.

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