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.[on SciFinder (R)]
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Submitted on : Tuesday, May 12, 2015 - 5:22:03 PM
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Lita Lee, Alison J. Downard, Yann R. Leroux, Philippe Hapiot. Amine-Terminated Monolayers on Carbon: Preparation, Characterization, and Coupling Reactions. Langmuir, American Chemical Society, 2015, 31 (18), pp. 5071-5077. ⟨10.1021/acs.langmuir.5b00730⟩. ⟨hal-01151346⟩

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