The Design, Synthesis, and Properties of Strained Alkyne Cycloparaphenylenes.
| dc.contributor.advisor | Jasti, Ramesh | |
| dc.contributor.author | Fehr, Julia | |
| dc.date.accessioned | 2024-03-25T17:34:55Z | |
| dc.date.available | 2024-03-25T17:34:55Z | |
| dc.date.issued | 2024-03-25 | |
| dc.description.abstract | Strained molecules possess the potential energy required to do work in the form of further chemical transformations. Strained alkynes in particular are an attractive handle for such applications as they can undergo the metal-free strain-promoted azide-alkyne cycloaddition (SPAAC). Beyond heightening reactivity, imparting strain also affects other properties, as has been shown in the study of strained conjugated molecules. In this context, strain modulates the electronics of the molecules and typically heightens their conductivity and solubility. These ideas are described in detail in Chapter 1. This work includes published and unpublished coauthored material that highlights both of these applications by focusing on the design and study of strained alkyne-containing carbon nanohoops (also known as [n+1] cycloparaphenylenes or [n+1]CPPs). Carbon nanohoops are highly strained conjugated macrocycles composed primarily of para-substituted phenylene units. Incorporation of an alkyne into the backbone of these molecules provides a handle for controlled strain-promoted reactivity. Modulating the topology and electronics of [n+1]CPPs to in turn alter reactivity towards the SPAAC reaction is the focus of Chapter 2 of this work. Chapter 3 focuses on exploring other types of strain-promoted reactivity, in particular alkyne cyclotrimerization resulting in the formation of pinwheel-shaped large molecules. Finally, early efforts to modulate the emission color of a [n+1]CPP, to synthesize a thermally-activated delayed fluorescence nanohoop, and to synthesize a di-alkyne carbon nanohoop are described in Chapter 4. | en_US |
| dc.identifier.uri | https://hdl.handle.net/1794/29290 | |
| dc.language.iso | en_US | |
| dc.publisher | University of Oregon | |
| dc.rights | All Rights Reserved. | |
| dc.subject | alkyne | en_US |
| dc.subject | aromatic | en_US |
| dc.subject | fluorophore | en_US |
| dc.subject | nanomaterial | en_US |
| dc.subject | strain | en_US |
| dc.title | The Design, Synthesis, and Properties of Strained Alkyne Cycloparaphenylenes. | |
| 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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