INVESTIGATION OF PNICTOGEN-ASSISTED SELF-ASSEMBLY AND SELF- SORTING DESIGN PRINCIPLES TOWARDS PREORGANIZED MACROCYCLES
Datum
2024-08-07
Autor:innen
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Verlag
University of Oregon
Zusammenfassung
Shape-persistent molecules have abundant chemical potential as organic functional materials. Access to these molecular cages and macrocycles, however, is nontrivial and often require long or low-yielding synthetic pathways that bottleneck their potential applications. To ameliorate this, dynamic covalent chemistry has shown to be promising in the formation of shape-persistent molecules as it marries the error-correction of self-assembly with thermodynamic control while giving the robustness of a covalent bond. The DWJ lab focuses on utilizing dynamic covalent reactions towards the facile preorganization of macrocyclic ensembles through the pnictogen-assisted self-assembly of oligothiols. This dissertation expands upon disulfide self-assembly design principles for a holistic understanding of the method’s boundaries.Chapter I introduces supramolecular concepts that are the cornerstone of this project. Specifically, self-assembly and dynamic covalent chemistry is introduced, with background information on the project’s beginnings provided as well. In Chapter II, the synthetic scope of disulfide self-assembly is explored. Following, Chapter III utilizes our newfound understanding to explore efficient pathways into material formation.
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Specifically, Perylene Diimide-containing macrocycles are generated in an efficient and high throughput dynamic pathway with implication on tailored organic materials. Chapter IV investigates the self-assembly of multicomponent oligothiol systems (self-sorting) towards the predictive assembly of three-dimensional architectures. Chapter V concludes the dissertation and provides potential future directions for this project.
This dissertation includes co-authored and previously published results.
Beschreibung
Schlagwörter
Dynamic Covalent Chemistry, Macrocycles, Organic Chemistry, Physical Organic Chemistry, Self-assembly, Supramolecular Chemistry