# Using Triazabutadienes as a Protected Source of Diazonium Cations to Facilitate Electrografting to a Variety of Conductive Surfaces

## TL;DR

This paper introduces a new method using triazabutadienes to create stable aryl diazonium cations for easier and more controlled electrode surface modification.

## Contribution

A stable triazabutadiene scaffold is developed for generating aryl diazonium cations under mild conditions.

## Key findings

- Triazabutadienes can be synthesized and stored for multiple-step reactions.
- UV exposure releases aryl diazonium cations in mild aqueous conditions.
- The method enables derivatization of electrode surfaces with organic moieties.

## Abstract

Aryl diazonium electrografting
is a versatile methodology for the
functionalization of electrode surfaces, yet its usage has been hampered
by both the short lifespan of aryl diazonium cations in aqueous solution
and the harsh conditions required to generate them in situ. This can make accessing complicated aryl diazonium cations and
derivatized surfaces thereof difficult. The usage of triazabutadienes
has the potential to address many of these issues as triazabutadienes
are stable enough to endure multiple-step chemical syntheses and can
persist for several hours in aqueous solution, yet upon UV exposure
rapidly release aryl diazonium cations under mild conditions (i.e.,
0 °C, pH 7 aqueous solution). Herein is described the synthesis
and utilization of a versatile, highly water-soluble triazabutadiene
scaffold which can be used to access complicated aryl diazonium cations
(via photochemical decaging with a commercially available 365 nm UV
irradiation source), which themselves can be used to directly derivatize
electrode surfaces with desired organic moieties.