Triazabutadienes have been shown to trigger the release of highly reactive diazonium species in a pH dependent fashion when placed in acidic conditions. Applying the use of click chemistry in late stage modification of triazabutadienes, grants access to various applications, both biological and material based. 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. This allows for target specificity and mild cleavage of the linker, leading to liberation of the diazonium near sites of interest. Incorporation of alkyne handles onto these molecules will allow chemical functionalization and cross-linking properties. The 1,2,3-triazole triazabutadiene derivatives were synthesized via Huisgen 1,3-dipolar cycloaddition from mono- or di-substituted alkynyl modifications on the triazabutadiene and reacted with various azides to show substrate diversity.

Development of clickable triazabutadienes as cleavable cross-linkers

251st National Meeting (2016)

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