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Open Access Dissertation
Doctor of Philosophy (PhD)
Year Degree Awarded
Month Degree Awarded
E. Bryan Coughlin
Molecular Biology | Organic Chemistry
Copper catalyzed cycloaddition of terminal alkynes and azides has revolutionized the field of bioconjugate chemistry. Unfortunately, typical copper catalysts are known to disrupt relevant biological systems, so it has become necessary to develop new, copper-free methods that are less cytotoxic. particular interest are "click" probes which can be activated with an outside light source, giving the user spatial and temporal control over the system being investigated. We have developed a method in which an aryl diazonium salt is rapidly generated using photolysis of the triazene functional group, and subsequently coupled with an electron rich aromatic nucleophile to yield an azobenzene. Benefits of this method over current photo-click methods include the fast rate of photolysis and almost instantaneous reaction times with subsequent reaction partners, allowing for minimal exposure to a UV light source and little to no incubation time with reactive partners, respectively
Gann, Adam, "Photolysis of Triazenylbenzoic Acids for Click Chemistry" (2016). Doctoral Dissertations. 661.