Development of Clickable Triazabutadienes as Cleavable Cross-Linkers
AdvisorJewett, John C.
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PublisherThe University of Arizona.
RightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
AbstractThis study illustrates the utility of click chemistry in functionalizing triazabutadienes by allowing access to various applications both biological and material based. Triazabutadienes have been shown to trigger the release of highly reactive diazonium species in a pH dependent way when placed in acidic conditions. Electron-rich phenyl systems such as tyrosine residues have been shown to react with diazonium compounds to form stable azo bonds. Modification of these triazabutadiene motifs can functionalize them as linkers or impact solubility; which can allow for target specificity and mild cleavage of linker in order to liberate diazonium near site of interest. Incorporation of azide-alkyne cycloadditions onto these molecules will allow chemical functionalization and cross-linking properties. The 1,2,3-triazole triazabutadiene derivatives are synthesized via Huisgen 1,3-dipolar cycloaddition from alkynyl modifications on the triazabutadiene that are reacted with various azides that show substrate diversity.
Degree ProgramGraduate College