Log in

Gold modification by reduction of a diazonium salt prepared from an aliphatic diamine: a new useful means to remove hazardous substances

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

We studied the electrochemical reduction based on gold electrode of a diazonium salt prepared from ethylenediamine. This is the first time where the covalent functionalization on the gold electrode of an alkyldiazonium salt, 2-aminoethane-1-diazonium chloride, is demonstrated. This step requires the preparation beforehand by diazotization of one amine group from ethylenediamine. The resulting electrodeposited ethylamine film was confirmed by spectroscopic characterizations from gold surface modification monitored by electrochemical quartz crystal microbalance (EQCM) coupled to cyclic voltammetry (CV). The development of chemosensors based on such a covalent functionalization of a metal can reduce the chemical threats to human health along with drastically removing contaminants according to the green chemistry principles.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (France)

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  • Ameur S, Bureau C, Charlier J, Palacin S (2004) Immobilization of biomolecules on electrodes modified by electrografted films. J Phys Chem B 108:13042–13046

    Article  CAS  Google Scholar 

  • Bai Q, Huang X (2016) Using quartz crystal microbalance for field measurement of liquid viscosities. J Sensors 2016(2):1–8

    Article  CAS  Google Scholar 

  • Baranton S, Bélanger D (2005) Electrochemical derivatization of carbon surface by reduction of in-situ generated diazonium cations. J Phys Chem B 109:24401–24410

    Article  CAS  Google Scholar 

  • Benedetto A, Balog M, Viel P, Le Derf F, Sallé M, Palacin S (2008) Electro-reduction of diazonium salts on gold: why do we observe multi-peaks. Electrochim Acta 53:7117–7122

    Article  CAS  Google Scholar 

  • Boukerma K, Chehimi MM, Pinson J, Blomfield C (2003) X-ray photoelectron spectroscopy evidence for the covalent bond between an iron surface and aryl groups attached by the electrochemical reduction of diazonium salts. Langmuir 19:6333–6335

    Article  CAS  Google Scholar 

  • Buchwalter TSOaJK LP (1991) Adhesion of polyimides to ceramics: Effects of aminopropyltriethoxysilane and temperature and humidity exposure on adhesion. J Adhes Sci Technol 5:333–343

    Article  Google Scholar 

  • Chamoulaud G, Bélanger D (2007) Spontaneous derivatization of a copper electrode with in situ generated diazonium cations in aprotic and aqueous media. The Journal of Physical Chemistry. C 111(20):7501–7507

    CAS  Google Scholar 

  • Chehimi MM (2012) Aryl diazonium salts new coupling agents in polymer and surface science. John Wiley & Sons, Weinheim, Germany, 2012

  • Chehimi M, Pinson J, Charleux B, Bureau C, Tronche C, Matrab T., Perruchot, Cabet-deliry CE, Save M (2011) Modified surface material, method for preparing same and uses thereof. In: US. Pat 8053567

  • Chen J, Wu G, **ong Z, Wu H, Chua YS, Zhou W, Liu B, Ju X, Chen P (2014) Synthesis, thermal behavior, and dehydrogenation kinetics study of lithiated ethylenediamine. Chemistry 42:13636–13643

    Article  Google Scholar 

  • Combellas C, Delamar M, Kanoufi F, Pinson J, Podvorica FI (2005) Spontaneous grafting of iron surfaces by reduction of aryldiazonium salts in acidic or neutral aqueous solution. Appl Protection Iron against Corrosion Chem Mater 17:3968–3975

    CAS  Google Scholar 

  • Culler SR, Naviroj S, Ishida H, Koenig JL (1983) Analytical and spectroscopic investigation of the interaction of CO2 with amine functional silane coupling agents on glass fibers. J Colloid Interface Sci 96:69–79

    Article  CAS  Google Scholar 

  • Delamar M, Hitmi R, Pinson J, Saveant JM (1992) Covalent modification of carbon surfaces by grafting of functionalized aryl radicals produced from electrochemical reduction of diazonium salts. J Am Chem Soc 114:5883–5884

    Article  CAS  Google Scholar 

  • Douglas TEL, Haugen HJ (2008) Coating of polyurethane scaffolds with collagen: comparison of coating and cross-linking techniques. J Mater Sci Mater Med 19:2713–2719

    Article  CAS  Google Scholar 

  • Downard AJ (2000) Electrochemically assisted covalent modification of carbon electrodes. Electroanalysis 12:1085–1096

    Article  CAS  Google Scholar 

  • Downard AJ, bin Mohamed A (1999) Suppression of protein adsorption at glassy carbon electrodes covalently modified with tetraethylene glycol diamine. Electroanalysis 11:418–423

    Article  CAS  Google Scholar 

  • Edward JJ (2003) US. Pat, 6555175

  • Gabriel C, Gabriel S, Grant EH, Grant EH, Halstead BSJ, Mingos DMP (1998) Dielectric parameters relevant to microwave dielectric heating. Chem Soc Rev 27:213–224

    Article  CAS  Google Scholar 

  • Gam-Derouich S, Carbonnier B, Turmine M, Lang P, Jouini M, Ben Hassen-Chehimi D, Chehimi MM (2010) Electrografted aryl diazonium initiators for surface-confined photopolymerization: a new approach to designing functional polymer coatings. Langmuir 26:11830–11840

    Article  CAS  Google Scholar 

  • Herlem G, Goux C, Fahys B, Dominati F, Coçalves AM, Mathieu C, Sutter E, Trokourey A, Penneau F (1997) Surface modification of platinum and gold electrodes by anodic oxidation of pure ethylenediamine. J Electroanal Chem 435:259–265

    Article  CAS  Google Scholar 

  • Hetemi D, Combellas C, Kanoufi F, Pinson J, Podvorica FI (2016) Surface modification by electrochemical reduction of alkyldiazonium salts. Electrochem Commun 68:5–9

    Article  CAS  Google Scholar 

  • Itoh T, McCreery RL (2002) In-situ raman spectroelectrochemistry of electron transfer between glassy carbon and a chemisorbed nitroazobenzene monolayer. J Am Chem Soc 124:10894–10902

    Article  CAS  Google Scholar 

  • Lyskawa J, Bélanger D (2006) Direct modification of a gold electrode with aminophenyl groups by electrochemical reduction of in-situ generated aminophenyl monodiazonium cations. Chem Mater 18:4755–4763

    Article  CAS  Google Scholar 

  • Mesnage A, Esnouf S, Jégou P, Deniau G, Palacin S (2010) Understanding the redox-induced polymer grafting process: a dual surface-solution analysis. Chem Mater 22:6229–6239

    Article  CAS  Google Scholar 

  • Mirkhalaf F, Mason TJ, Morgan DJ, Saez V (2011) Frequency effects on the surface coverage of nitrophenyl films ultrasonically grafted onto indium tin oxide. Langmuir 27:1853–1858

    Article  CAS  Google Scholar 

  • Mozetic M (2019) Surface Modification to improve properties of materials. 12(3), 441; https://doi.org/10.3390/ma12030441

  • Palacin S, Bureau C, Charlier J, Deniau G, Mouanda B, Viel P (2004) Molecule-to-metal bonds: electrografting polymers on conducting surfaces. ChemphysChem 5:1468–1481

    Article  CAS  Google Scholar 

  • Pinson J, Podvorica F (2005) Attachment of organic layers to conductive or semiconductive surfaces by reduction of diazonium salts. Chem Soc Rev 34:429–439

    Article  CAS  Google Scholar 

  • Shieh YT, Liu KH (2003) The effect of carbonyl group on sorption of CO2 in glassy polymers. J Supercrit Fluids 25:261–268

    Article  CAS  Google Scholar 

  • Walczak MM, Popenoe DD, Deinhammer RS, Lamp BD, Chung C, Porter MD (1991) Reductive desorption of alkanethiolate monolayers at gold: a measure of surface coverage. Langmuir 7:2687–2693

    Article  CAS  Google Scholar 

  • Wang Z (2010) Comprehensive organic name reactions and reagents. conrr558. Wiley, 3824 pages https://doi.org/10.1002/9780470638859.

  • Wanunu M, Meller A (2007) Chemically modified solid-state nanopores. Nano Lett 7:1580–1585

    Article  CAS  Google Scholar 

  • Widrig CA, Chung C, Porter MD (1991) The electrochemical desorption of n-alkanethiol monolayers from polycrystalline Au and Ag electrodes. J Electroanal Chem Interfacial Electrochem 310:335–359

    Article  CAS  Google Scholar 

  • **n Z, Felix R, Vitali S, Guoguang S, Jekaterina R, Karsten H, Silvia J, Jörg R (2014) Influence of the para-substitutent of benzene diazonium salts and the solvent on the film growth during electrochemical reduction. Z Phys Chem 228:557–573

    Article  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge Prof. Jean Pinson (University Paris Diderot, France) for scientific discussions and comments.

Availability of data and materials

All data generated or analysed during this study are included in this published article (“Materials and methods” section) and publicly available dataset.

Funding

We gratefully acknowledge the Iraqi Ministry of Higher Education and the Scientific Research and Cultural Bureau /Embassy of the Republic of Iraq in Paris – France for financial support. This work was also supported by Campus France and the Region of Franche-Comté. We also thank the RENATECH network for SEM facilities.

Author information

Authors and Affiliations

Authors

Contributions

Ahmed Kandory, Anne-Marie Goncalves, Mathieu Frégnaux, Hélène Cattey: conceptualization, methodology, formal analysis, writing

Badr Alaoui-Sossé, Lotfi Aleya, Guillaume Herlem: writing, original draft, data curation

Corresponding author

Correspondence to Lotfi Aleya.

Ethics declarations

Ethics approval and consent to participate

Not applicable

Consent for publication

Not applicable

Competing interest

The authors declare no competing interests.

Additional information

Responsible Editor: Philippe Garrigues

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kandory, A., Goncalves, AM., Frégnaux, M. et al. Gold modification by reduction of a diazonium salt prepared from an aliphatic diamine: a new useful means to remove hazardous substances. Environ Sci Pollut Res 29, 1239–1245 (2022). https://doi.org/10.1007/s11356-021-15696-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-021-15696-3

Keywords

Navigation