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Peer-reviewedCC BY 4.0Journal of Peptide Science

Self‐Assembled Monolayers on Gold Surfaces of Ferrocene‐BODIPY‐Fullerene‐Helical Peptide Conjugates: Studies of Electron Transfer Processes by Ultra‐Fast Electrochemistry

  • Jad Rabah1
  • Anne Vallée1,2
  • Hélène Fensterbank1
  • Minh‐Huong Ha‐Thi3
  • Rachel Méallet3
  • Souhir Boujday2
  • Emmanuel Maisonhaute4
  • Karen Wright1
  • Emmanuel Allard1
4 affiliations
  1. 1Université Paris‐Saclay, UVSQ, CNRS, Institut Lavoisier de Versailles Versailles France
  2. 2Laboratoire de Réactivité de Surface Sorbonne Université Paris France
  3. 3Université Paris‐Saclay, CNRS, Institut Des Sciences Moléculaires d'Orsay Orsay France
  4. 4Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, IPCM Paris France
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Abstract

Three complex ferrocene‐BODIPY‐fullerene‐peptide conjugates were synthesized by successive CuAAC reactions between firstly ferrocene‐BODIPY azides, then a lipoyl peptide azide, with a dual‐clickable fullerene platform. These conjugates displayed broad absorption in the visible region due to their extended π‐conjugation and the presence of an intramolecular charge transfer band from ferrocene to BODIPY, particularly in the case of BODIPY derivatives functionalized at the beta and alpha positions with ethynylFc and vinylFc groups, respectively. The terminal lipoyl peptide allowed grafting of the conjugates on gold surfaces, to form self‐assembled monolayers that were characterized by PM‐IRRAS and ultrafast electrochemical techniques. Estimation of the heterogeneous electron transfer rate constants for these monolayers revealed higher values for electron transfer from the BDP or C60 entities to the metal surface compared with conjugates without ferrocene units. This could be attributed to a reduced distance between the (Fc)2‐BODIPY‐C60 part and the metal surface, due to folding of the conjugates within the monolayer.

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Cite

BibTeXRIS
BibTeX
@article{rabah2026selfassembled,
  title = {{Self‐Assembled Monolayers on Gold Surfaces of Ferrocene‐BODIPY‐Fullerene‐Helical Peptide Conjugates: Studies of Electron Transfer Processes by Ultra‐Fast Electrochemistry}},
  author = {Jad Rabah and Anne Vallée and Hélène Fensterbank and Minh‐Huong Ha‐Thi and Rachel Méallet and Souhir Boujday and Emmanuel Maisonhaute and Karen Wright and Emmanuel Allard},
  journal = {Journal of Peptide Science},
  year = {2026},
  month = oct,
  doi = {10.1002/psc.70142},
  url = {https://doi.org/10.1002/psc.70142},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Self‐Assembled Monolayers on Gold Surfaces of Ferrocene‐BODIPY‐Fullerene‐Helical Peptide Conjugates: Studies of Electron Transfer Processes by Ultra‐Fast Electrochemistry
AU  - Jad Rabah
AU  - Anne Vallée
AU  - Hélène Fensterbank
AU  - Minh‐Huong Ha‐Thi
AU  - Rachel Méallet
AU  - Souhir Boujday
AU  - Emmanuel Maisonhaute
AU  - Karen Wright
AU  - Emmanuel Allard
PY  - 2026
DA  - 2026/10/27
JO  - Journal of Peptide Science
DO  - 10.1002/psc.70142
UR  - https://doi.org/10.1002/psc.70142
AB  - Three complex ferrocene‐BODIPY‐fullerene‐peptide conjugates were synthesized by successive CuAAC reactions between firstly ferrocene‐BODIPY azides, then a lipoyl peptide azide, with a dual‐clickable fullerene platform. These conjugates displayed broad absorption in the visible region due to their extended π‐conjugation and the presence of an intramolecular charge transfer band from ferrocene to BODIPY, particularly in the case of BODIPY derivatives functionalized at the beta and alpha positions with ethynylFc and vinylFc groups, respectively. The terminal lipoyl peptide allowed grafting of the conjugates on gold surfaces, to form self‐assembled monolayers that were characterized by PM‐IRRAS and ultrafast electrochemical techniques. Estimation of the heterogeneous electron transfer rate constants for these monolayers revealed higher values for electron transfer from the BDP or C60 entities to the metal surface compared with conjugates without ferrocene units. This could be attributed to a reduced distance between the (Fc)2‐BODIPY‐C60 part and the metal surface, due to folding of the conjugates within the monolayer.
SN  - 1075-2617
SN  - 1099-1387
ER  -