title: Amine-terminated monolayers on carbon: preparation, characterization, and coupling reactions.
abstract: Aminophenyl and aminomethylphenyl monolayers have been electrografted to glassy carbon and pyrolyzed photoresist film from the corresponding diazonium ions using a protection-deprotection strategy based on Boc (tert-butyloxycarbonyl) and Fmoc (fluorenylmethyloxycarbonyl) groups. After grafting and then deprotecting films of Boc-NH-Ar, Fmoc-NH-Ar, and Fmoc-NH-CH2-Ar, depth profiling by atomic force microscopy confirmed that the resulting amine-terminated films were monolayers. In contrast, after deprotection, Boc-NH-CH2-Ar gave a multilayer film. Electroactive carboxylic acid derivatives were coupled to the monolayers through amide linkages. Electrochemical measurements revealed that the deprotected Fmoc-NH-CH2-Ar monolayer gave the highest surface concentration of coupled nitrophenyl and ferrocenyl groups and DFT calculations established that this monolayer has the highest theoretical surface concentration of those examined.
authors: †MacDiarmid Institute for Advanced Materials and Nanotechnology, Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
authors: Lita
authors: L
authors: Lee
authors: ‡Institut des Sciences Chimiques de Rennes (Equipe MaCSE), CNRS, UMR 6226, Université de Rennes 1, Campus de Beaulieu, Bat 10C, 35042 Rennes Cedex, France.
authors: Yann R
authors: YR
authors: Leroux
authors: ‡Institut des Sciences Chimiques de Rennes (Equipe MaCSE), CNRS, UMR 6226, Université de Rennes 1, Campus de Beaulieu, Bat 10C, 35042 Rennes Cedex, France.
authors: Philippe
authors: P
authors: Hapiot
authors: †MacDiarmid Institute for Advanced Materials and Nanotechnology, Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
authors: Alison J
authors: AJ
authors: Downard