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Journal of Electrochemistry ›› 2017, Vol. 23 ›› Issue (2): 130-140.doi: 10.13208/j.electrochem.161241

• Special Issue in Honor of Professor Zhaowu Tian on His 90th Birthday • Previous Articles     Next Articles

Electrografting of Mono-N-Boc-Ethylenediamine from an Acetonitrile/Aqueous NaHCO3 Mixture

Hisham Hamzah 1, Guy Denuault 1, Philip Bartlett 1*, Aleksandra Pinczewska 2, Jeremy Kilburn 3   

  1. 1. Chemistry, University of Southampton, Southampton, SO171AL, UK; 2. School of Biological and Chemical Sciences Queen Mary University of London, Mile End Road, London, E1 4NS, UK; 3. King’s College, The University of Aberdeen, Aberdeen, AB24 3FX, UK
  • Received:2016-12-01 Revised:2017-01-21 Online:2017-04-28 Published:2017-01-29
  • Contact: Philip Bartlett E-mail:p.n.bartlett@soton.ac.uk
  • Supported by:

    H. Hamzah would like to thank the Majlis Amanah Rakyat Malaysia (MARA) for the PhD scholarship. P. Bartlett gratefully acknowledges receipt of a Wolfson Research Merit award.

Abstract:

The electrografting of primary amines to carbon electrodes is now widely employed for electrode modification. Using a mixture of acetonitrile and 0.1 mol•L-1 aqueous sodium hydrogen carborate (NaHCO3) in the ratio of 4:1, the efficiency for coupling of mono-N-Boc-ethylenediamine (EDA-Boc) on the surface of glassy carbon was significantly improved as compared with that obtained using acetonitrile alone. In the presence of NaHCO3 the initial current determined in the cyclic voltammogram became higher, and the layer of attached amine was formed more rapidly, accordingly, the electrode was passivated more rapidly. The resulting film of EDA-Boc was shown to be more severely blocking toward the electrochemical reaction of [Fe(CN)6]3-. Following removal of the Boc protecting group and coupling of the free amine to anthraquinone-2-carboxylic acid, a higher surface coverage of the anthraquinone was obtained. Modelling for the electrograftng reaction using a simple kinetic scheme, it was demonstrated that the simulated voltammograms agreed well with the experimentally measured voltammograms . Comparison between the model fitting parameters obtained from the acetonitrile alone and the acetonitrile/NaHCO3 mixture showed that the competition between reaction of the amine radicals with the carbon surface and reaction in the homogeneous solution became more favourable for the surface reaction in the acetonitrile/NaHCO3 mixture.

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