Post-Functionalization of Pyridine-Modified Electrodes via Anodic C–N Coupling

The oxidation of 2,7,12,17-tetra-tert-butylporphyrin Zn(II) (Zn-1) on a phenyl-pyridinyl-modified glassy carbon (GC) or Indium Tin Oxide (ITO) electrode resulted in the formation of a new C–N bond linking the porphyrin and pyridine units. This innovative post-functionalization grafting strategy was investigated using electrochemical, photophysical, structural, and surface characterizations, validating the expected structure and the involved mechanism. Additionally, a reference pyridinium-porphyrin compound was electrosynthesized by oxidizing Zn-1 in the presence of a slight excess of the corresponding phenyl-4-pyridinyl nucleophile. The physicochemical properties of this reference compound matched those of the functionalized porphyrin material.