Triazabutadienes degrade upon protonation to release aryl diazonium molecules in physiological-relevant conditions.1 Methods for diazonium generation have attractive biological applications, as aryl diazoniums selectively label tyrosine residues.2 Triazabutadienes could therefore be used to unmask diazoniums and modify tyrosine residues on a protein of interest, aiding fundamental understanding of protein interaction and function. In order to apply triazabutadienes to a biological context, these potential chemical probes must exhibit high stability in aqueous solutions. Considering that triazabutadiene degradation can occur at neutral pH, we seek to further stabilize these molecules by blocking the acid-reactive pathway. Here we report the design and properties of new triazabutadienes that release diazonium molecules in a controlled manner. (1) Kimani, F. W.; Jewett, J. C. Angew. Chem. Int. Ed. 2015, 54, 4051. (2) Hooker, J. M.; Kovacs, E. W.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 3718.

Fine-tuning triazabutadiene stability for controlled diazonium release

251st National Meeting (2016)

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