Spontaneous adsorption of 3,5-bis(3,5-dinitrobenzoylamino) benzoic acid onto carbon

Dendritic molecules contain multifunctional groups that can be used to efficiently control the properties of an electrode surface. We are developing strategies to generate a highly functionalized surface using multifunctional and rigid dendrons immobilized onto different substrates. In the present work, we explore the immobilization of a dendritic molecule: 3,5-bis(3,5-dinitrobenzoylamino) benzoic acid (D-NO2) onto carbon surfaces showing a simple and rapid way to produce conductive surfaces with electroactive chemical functions. The immobilized D-NO2 layer has been characterized using atomic force microscopy and cyclic voltammetry. D-NO2 adsorbs onto carbon surfaces spontaneously by dipping the electrode in dendron solutions. Reduction of this layer generates the hydroxylamine product. The resulting redox-active layer exhibits a well-behaved redox response for the adsorbed nitroso/hydroxylamine couple. The film permeability of the derivatized surface has been analyzed employing the electrochemical response of redox probes: Ru(NH3)(6)(3+)/Ru(NH3)(6)(2+) and Fe(CN)(6)(3-)/Fe(CN)(6)(4-). Electrocatalytic oxidation of nicotinamide adenine dinucleotide onto a modified carbon surface was also observed. (C) 2009 Elsevier Ltd. All rights reserved.