Amino functionalized thin films prepared from Gabriel synthesis applied on electrografted diazonium salts

Abstract A new diazonium salt bearing an aliphatic primary amine protected with a phthalimide group has been synthesized and isolated from the reaction of the corresponding aniline derivative with NOBF 4 in acetonitrile. Electrochemical grafting of this compound in potentiodynamic conditions on vitreous carbon or on gold form thick, stable, adherent and insulating polyphenylene-like films on the electrode surface. Treatment with hydrazine of these polymers cleaves the imide functions to release amine groups prone to subsequent immobilization of molecules, biomolecules or particles via a covalent amide linkage. That primer polyphenylene-like layer establishes a good electrical communication between the surface of the electrode and the immobilized probes.