Skip to main content
SpringerLink
Log in

Sequential anodic oxidations of aliphatic amines in aqueous medium on pyrolyzed photoresist film surfaces for the covalent immobilization of cyclam derivatives

  • Original Paper
  • Published:
Journal of Solid State Electrochemistry Aims and scope Submit manuscript

Abstract

We investigate here the derivatization of pyrolyzed photoresist film (PPF) surface by anodic oxidations of amino-containing linkers in aqueous medium. As an example of application, nitrogen macrocycles are then covalently immobilized by chemical reactions with the modified surface. The surface coverage is estimated by X-ray photoelectron spectroscopic analyses and cyclic voltammetry using redox probes, and the thickness of the film is measured by atomic force microscopy from scratching experiments. The surface coverage increases when two successive grafting processes are carried out and stops after the third electrolysis. The influence of the electrolyte medium on the thickness of the film is also highlighted.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

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

Similar content being viewed by others

Notes

  1. We could not obtain well-defined images of surfaces modified with amino acid 1, probably because of the presence of charges (COO− groups).

  2. To our knowledge, ellipsometry measurements on PPF surfaces have never been reported. The different experiments we performed were not successful because of the difficulty to model such surfaces.

References

  1. Downard AJ (2000) Electroanalysis 12:1085

    Article  CAS  Google Scholar 

  2. Pinson J, Podvorica F (2005) Chem Soc Rev 34:429

    Article  CAS  Google Scholar 

  3. Delamar M, Hitmi R, Pinson J, Saveant JM (1992) J Am Chem Soc 114:5883

    Article  CAS  Google Scholar 

  4. Allongue P, Delamar M, Desbat B, Fagebaume O, Hitmi R, Pinson J, Saveant J-M (1997) J Am Chem Soc 119:201

    Article  CAS  Google Scholar 

  5. Andrieux CP, Gonzalez F, Saveant JM (1997) J Am Chem Soc 119:4292

    Article  CAS  Google Scholar 

  6. Barbier B, Pinson J, Desarmot G, Sanchez M (1990) J Electrochem Soc 137:1757

    Article  CAS  Google Scholar 

  7. Deinhammer RS, Ho M, Anderegg JW, Porter MD (1994) Langmuir 10:1306

    Article  CAS  Google Scholar 

  8. Geneste F, Moinet C (2005) New J Chem 29:269

    Article  CAS  Google Scholar 

  9. Adenier A, Chehimi MM, Gallardo I, Pinson J, Vila N (2004) Langmuir 20:8243

    Article  CAS  Google Scholar 

  10. Allongue P, De Villeneuve CH, Pinson J, Ozanam F, Chazalviel JN, Wallart X (1998) Electrochim Acta 43:2791

    Article  CAS  Google Scholar 

  11. Anariba F, DuVall SH, McCreery RL (2003) Anal Chem 75:3837

    Article  CAS  Google Scholar 

  12. Combellas C, Kanoufi F, Pinson J, Podvorica FI (2008) J Am Chem Soc 130:8576

    Article  CAS  Google Scholar 

  13. Adenier A, Combellas C, Kanoufi F, Pinson J, Podvorica FI (2006) Chem Mater 18:2021

    Article  CAS  Google Scholar 

  14. Cruickshank AC, Tan ESQ, Brooksby PA, Downard AJ (2007) Electrochem Commun 9:1456

    Article  CAS  Google Scholar 

  15. Lakard B, Herlem G, Fahys B (2001) J Chem Phys 115:7219

    Article  CAS  Google Scholar 

  16. Ranganathan S, McCreery RL (2001) Anal Chem 73:893

    Article  CAS  Google Scholar 

  17. Ranganathan S, McCreery R, Majji SM, Madou M (2000) J Electrochem Soc 147:277

    Article  CAS  Google Scholar 

  18. Downard AJ, Garrett DJ, Tan ESQ (2006) Langmuir 22:10739

    Article  CAS  Google Scholar 

  19. Garrett DJ, Lehr J, Miskelly GM, Downard AJ (2007) J Am Chem Soc 129:15456

    Article  CAS  Google Scholar 

  20. Brooksby PA, Downard AJ (2005) Langmuir 21:1672

    Article  CAS  Google Scholar 

  21. Kashiwagi Y, Kikuchi C, Anzai J (2002) J Electroanal Chem 518:51

    Article  CAS  Google Scholar 

  22. Manriquez J, Bravo JL, Gutierrez-Granados S, Succar SS, Bied-Charreton C, Ordaz AA, Bedioui F (1999) Anal Chim Acta 378:159

    Article  CAS  Google Scholar 

  23. Roslonek G, Taraszewska J (1992) J Electroanal Chem 325:285

    Article  CAS  Google Scholar 

  24. Jarzebinska A, Rowinski P, Zawisza I, Bilewicz R, Siegfried L, Kaden T (1999) Anal Chim Acta 396:1

    Article  CAS  Google Scholar 

  25. Taraszewska J, Roslonek G, Darlewski W (1994) J Electroanal Chem 371:223

    Article  CAS  Google Scholar 

  26. Ferrer SJ, Granados SG, Bedioui F, Ordaz AA (2003) Electroanalysis 15:70

    Article  CAS  Google Scholar 

  27. Taniguchi I, Matsushita K, Okamoto M, Collin JP, Sauvage JP (1990) J Electroanal Chem 280:221

    Article  CAS  Google Scholar 

  28. Brooksby PA, Downard AJ (2004) Langmuir 20:5038

    Article  CAS  Google Scholar 

  29. Yang W, Giandomenico CM, Sartori M, Moore DA (2003) Tetrahedron Lett 44:2481

    Article  CAS  Google Scholar 

  30. Nave C, Truter MR (1974) J Chem Soc Dalton Trans, p 2351

  31. Gallardo I, Pinson J, Vila N (2006) J Phys Chem B 110:19521

    Article  CAS  Google Scholar 

  32. Ghanem MA, Chretien JM, Pinczewska A, Kilburn JD, Bartlett PN (2008) J Mater Chem 18:4917

    Article  CAS  Google Scholar 

  33. Lund H, Hammerich O (2001) Organic electrochemistry. Marcel Dekker, New York

    Google Scholar 

  34. Barnes KK, Mann CK (1967) J Org Chem 32:1474

    Article  CAS  Google Scholar 

  35. Luczak T (2007) J Appl Electrochem 37:269

    Article  CAS  Google Scholar 

  36. Buttry DA, Peng JCM, Donnet JB, Rebouillat S (1999) Carbon 37:1929

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank Thomas Delhaye for NanoSIMS analyses (Université de Rennes 1, Plateforme d’imagerie analytique ONIS (GIS Europia), Campus de Beaulieu, 35042 Rennes cedex, France).

Author information

Authors and Affiliations

  1. Laboratoire des Sciences Chimiques de Rennes, Université de Rennes 1, UMR-CNRS 6226, Equipe catalyse et organométalliques, Campus de Beaulieu, 35042, Rennes Cedex, France

    Rihab Nasraoui & Florence Geneste

  2. Laboratoire des Sciences Chimiques de Rennes, Université de Rennes 1, UMR-CNRS 6226, Equipe Matière Condensée et Systèmes Electroactifs, Campus de Beaulieu, 35042, Rennes Cedex, France

    Jean-François Bergamini

  3. Institut de Physique de Rennes, Université de Rennes 1, UMR 6627, Equipe Physique des Surfaces et Interfaces, Campus de Beaulieu, 35042, Rennes Cedex, France

    Soraya Ababou-Girard

Authors
  1. Rihab Nasraoui
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jean-François Bergamini
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Soraya Ababou-Girard
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Florence Geneste
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Florence Geneste.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nasraoui, R., Bergamini, JF., Ababou-Girard, S. et al. Sequential anodic oxidations of aliphatic amines in aqueous medium on pyrolyzed photoresist film surfaces for the covalent immobilization of cyclam derivatives. J Solid State Electrochem 15, 139–146 (2011). https://doi.org/10.1007/s10008-010-1075-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10008-010-1075-z

Keywords

Search

Navigation