Water‐Soluble Triazabutadienes that Release Diazonium Species upon Protonation under Physiologically Relevant Conditions

Triazabutadienes are an understudied structural motif that have remarkable reactivity once rendered water‐soluble. It is shown that these molecules readily release diazonium species in a pH‐dependent manner in a series of buffer solutions with pH ranges similar to those found in cells. Upon further development, we expect that this process will be well suited to cargo‐release strategies and organelle‐specific bioconjugation reactions. These compounds offer one of the mildest ways of generating diazonium species in aqueous solutions.