title: Maleimide-activated aryl diazonium salts for electrode surface functionalization with biological and redox-active molecules.
abstract: A versatile and simple method is introduced for formation of maleimide-functionalized surfaces using maleimide-activated aryl diazonium salts. We show for the first time electrodeposition of N-(4-diazophenyl)maleimide tetrafluoroborate on gold and carbon electrodes which was characterized via voltammetry, grazing angle FTIR, and ellipsometry. Electrodeposition conditions were used to control film thickness and yielded submonolayer-to-multilayer grafting. The resulting phenylmaleimide surfaces served as effective coupling agents for electrode functionalization with ferrocene and the redox-active protein cytochrome c. The utility of phenylmaleimide diazonium toward formation of a diazonium-activated conjugate, followed by direct electrodeposition of the diazonium-modified DNA onto the electrode surface, was also demonstrated. Effective electron transfer was obtained between immobilized molecules and the electrodes. This novel application of N-phenylmaleimide diazonium may facilitate the development of bioelectronic devices including biofuel cells, biosensors, and DNA and protein microarrays.
authors.affiliation: Biosensors and Nanomaterials, Sandia National Laboratories, Albuquerque, New Mexico 87185, USA.
authors.forename: Jason C
authors.initials: JC
authors.lastname: Harper
authors.forename: Ronen
authors.initials: R
authors.lastname: Polsky
authors.forename: David R
authors.initials: DR
authors.lastname: Wheeler
authors.forename: Susan M
authors.initials: SM
authors.lastname: Brozik
mesh_terms: D001881:Borates / Q000737:chemistry*; D045304:Cytochromes c / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D004566:Electrodes; D008301:Maleimides / Q000737:chemistry*; D046228:Microarray Analysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013499:Surface Properties
chemical_list: D001881:Borates; D003979:Diazonium Compounds; D008301:Maleimides; C529073:N-(4-diazophenyl)maleimide tetrafluoroborate; C043592:maleimide; D045304:Cytochromes c