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

TY - JOUR

T1 - Using Triazabutadienes as a Protected Source of Diazonium Cations to Facilitate Electrografting to a Variety of Conductive Surfaces

AU - Yates, Nicholas D J

AU - Hudson, Lucy

AU - Schwabe, Oscar

AU - Parkin, Alison

N1 - © 2025 The Authors

PY - 2025/3/25

Y1 - 2025/3/25

N2 - 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.

AB - 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.

U2 - 10.1021/acs.langmuir.4c04848

DO - 10.1021/acs.langmuir.4c04848

M3 - Article

C2 - 40073388

SN - 0743-7463

VL - 41

SP - 7386

EP - 7395

JO - Langmuir

JF - Langmuir

IS - 11

ER -