Skip to main content
Log in

Ultrafast time-resolved spectroscopy elucidating photo-driven electron and energy transfer processes in a broadband light-absorbing BODIPY-C60-distyryl BODIPY triad

  • Regular Article
  • Published:
The European Physical Journal Special Topics Aims and scope Submit manuscript

Abstract

Photoinduced electron and energy transfer pathways are elucidated in a panchromatic light-absorbing, covalently linked triad (BODIPY-C60-distyryl BODIPY, noted as BDP-C60-DSBDP) along with the two reference dyads: BODIPY-C60 (BDP-C60) and distyryl-BODIPY-C60 (DSBDP-C60). The flexible linker between the BODIPY and C60 units leads to different possible conformations with varying donor–acceptor distances. Ultrafast transient absorption along with the time-resolved emission spectroscopies revealed the occurrence of different photoinduced electron/energy transfer processes in these conformers. Photoexcitation of the BODIPY units in the two reference dyads leads to one electron and two energy transfer steps from BODIPY to C60. However, in the BDP-C60-DSBDP triad, additional energy transfer processes from BDP to DSBDP were evidenced upon photoexcitation of the BDP unit. The singlet excited state of DSBDP in the triad then follows the same relaxation route as that of the DSBDP-C60 dyad. The intricate photophysics, particularly the formation of radical ion pairs in these flexible covalently linked donor–acceptor systems contribute to our fundamental understanding of electron and energy transfer mechanisms, which is important to build donor–acceptor assemblies for energy applications.

Graphical abstract

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1.
Fig.1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

Data availability statement

This manuscript has data included as electronic supplementary material.

References

  1. V. Balzani, A. Credi, M. Venturi, Chemsuschem 1, 26–58 (2008)

    Article  Google Scholar 

  2. D. Gust, T.A. Moore, A.L. Moore, Acc. Chem. Res. 42, 1890–1898 (2009)

    Article  Google Scholar 

  3. F. D’Souza, O. Ito, Chem. Comm. 2, 4913–4928 (2009)

    Article  Google Scholar 

  4. D.M. Guldi, B.M. Illescas, C.M. Atienza, M. Wielopolski, N.M. Martın, Chem. Soc. Rev. 38, 1587–1597 (2009)

    Article  Google Scholar 

  5. M.E. El-Khouly, S. Fukuzumi, F. D’Souza, ChemPhysChem 15, 30–47 (2014)

    Article  Google Scholar 

  6. F. D’Souza, O. Ito, Coord. Chem. Rev. 249, 1410–1422 (2005)

    Article  Google Scholar 

  7. G. Kodis, Y. Terazono, A. Liddell, J. Paul, V. Andre, M. Garg, T.A. Hambourger, A.L. Moore, J. Am. Chem. Soc. 128, 1818–1827 (2006)

    Article  Google Scholar 

  8. C. Luo, D.M. Guldi, H. Imahori, K. Tamaki, Y. Sakata, J. Am. Chem. Soc. 122, 6535–6551 (2000)

    Article  Google Scholar 

  9. F. D’Souza, P. Smith, M. Zandler, A. McCarty, M. Itou, Y. Araki, O. Ito, J. Am. Chem. Soc. 126, 7898–7907 (2004)

    Article  Google Scholar 

  10. T. Lazarides, G. Charalambidis, A. Vuillamy, M. Réglier, E. Klontzas, G. Froudakis, S. Kuhri, D.M. Guldi, A. Coutsolelos, Inorg. Chem. 50, 8926–8936 (2011)

    Article  Google Scholar 

  11. M.E. El-Khouly, C.A. Wijesinghe, V.N. Nesterov, M.E. Zandler, S. Fukuzumi, F. D’Souza, Chem. A Eur. J. 18, 13844–13853 (2012)

    Article  Google Scholar 

  12. Y. Rio, S. Wolfgang, A. Gouloumis, P. Vázquez, J.L. Sessler, D.M. Guldi, T. Tomás, Chem. A Eur. J. 16, 1929–1940 (2010)

    Article  Google Scholar 

  13. A. Loudet, K. Burgess, Chem. Rev. 107, 4891–4932 (2007)

    Article  Google Scholar 

  14. G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. Int. Ed. Engl. 47, 1184–1201 (2008)

    Article  Google Scholar 

  15. C.O. Obondi, G.N. Lim, P.A. Karr, V.N. Nesterov, F. D’Souza, Phys. Chem. Chem. Phys. 18, 18187–18200 (2016)

    Article  Google Scholar 

  16. J.Y. Liu, H.S. Yeung, W. Xu, X. Li, D.K.P. Ng, Org. Lett. 10, 5421–5424 (2008)

    Article  Google Scholar 

  17. M. Rudolf, S.V. Kirner, D.M. Guldi, Chem. Soc. Rev. 45, 612–630 (2016)

    Article  Google Scholar 

  18. D.M. Guldi, M. Prato, Acc. Chem. Res. 33, 695–703 (2000)

    Article  Google Scholar 

  19. A.N. Amin, M. El-Khouly, N. Subbaiyan, M.E. Zandler, S. Fukuzumi, Chem. Commun. 48, 206–208 (2012)

    Article  Google Scholar 

  20. A. Iagatti, L. Cupellini, G. Biagiotti, S. Caprasecca, S. Fedeli, A. Lapini, E. Ussano, S. Cicchi, P. Foggi, M. Marcaccio, B. Mennucci, M. Di Donato, J. Phys. Chem. C 120, 16526–16536 (2016)

    Article  Google Scholar 

  21. J.Y. Liu, M.E. El-Khouly, S. Fukuzumi, D.K. Ng, Chem. An Asian J. 6, 174–179 (2011)

    Article  Google Scholar 

  22. C.A. Wijesinghe, M. El-Khouly, J. Blakemore, M. Zandler, S. Fukuzumi, F. D’Souza, Chem. Commun. 46, 3301 (2010)

    Article  Google Scholar 

  23. V. Bandi, H.B. Gobeze, F. D’Souza, Chem. A Eur. J. 21, 11483–11494 (2015)

    Article  Google Scholar 

  24. T.-T. Tran, J. Rabah, M.H. Ha-Thi, E. Allard, S. Nizinski, G. Burdzinski, S. Aloïse, H. Fensterbank, K. Baczko, H. Nasrallah, A. Valée, G. Clavier, F. Miomandre, T. Pino, R. Méallet-Renault, J. Phys. Chem. B 124, 9396–9410 (2020)

    Article  Google Scholar 

  25. V. Bandi, F.P. D’Souza, H.B. Gobeze, F. D’Souza, Chem. Commun. 52, 579–581 (2015)

    Article  Google Scholar 

  26. C.O. Obondi, G.N. Lim, P. Martinez, V. Swamy, F. D’Souza, Nanoscale 9, 18054–18065 (2017)

    Article  Google Scholar 

  27. N. Zarrabi, C.O. Obondi, G.N. Lim, S. Seetharaman, B.J. Boe, F. D’Souza, P.K. Poddutoori, Nanoscale 10, 20723–20739 (2018)

    Article  Google Scholar 

  28. S. Shao, M.B. Thomas, K.H. Park, Z. Mahaffey, D. Kim, F. D’Souza, Chem. Commun. 54, 54–57 (2018)

    Article  Google Scholar 

  29. V. Bandi, F.P. D’Souza, H.B. Gobeze, F. D’Souza, Chem. A Eur. J. 21, 2669–2679 (2015)

    Article  Google Scholar 

  30. J. Rabah, L. Yonkeu, K. Wright, A. Vallée, R. Méallet-Renault, M.H. Ha-Thi, A. Fatima, G. Clavier, H. Fensterbank, E. Allard, Tetrahedron 2, 132467 (2021)

    Article  Google Scholar 

  31. A. Fatima, J. Rabah, E. Allard, H. Fensterbank, K. Wright, G. Burdzinski, G. Clavier, M. Sliwa, T. Pino, R. Méallet-Renault, K. Steenkeste, M. H. Ha-Thi, Photochem. Photo Biol. Sci. 21, 1573–1584 (2022)

    Article  Google Scholar 

  32. A. Ghose, M. Rebarz, O. Maltsev, L. Hintermann, C. Ruckebusch, E. Fron, J. Hofkens, Y. Mély, P. Naumov, M. Sliwa, P. Didier, J. Phys. Chem. B 119, 2638–2649 (2015)

    Article  Google Scholar 

  33. M. Wendel, S. Nizinski, D. Tuwalska, K. Starzak, D. Szot, D. Prukala, M. Sikorski, S. Wybraniec, G. Burdzinski, Phys. Chem. Chem. Phys. 17, 18152–18158 (2015)

    Article  Google Scholar 

  34. T. Chaudhuri, S. Mula, S. Chattopadhyay, M. Banerjee, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 75, 739–744 (2010)

    Article  ADS  Google Scholar 

  35. T.D.M. Bell, K.P. Ghiggino, A. Haynes, S.J. Langford, C.P. Woodward, J. Porphyr, Phthalocyanines 11, 455–462 (2007)

    Article  Google Scholar 

  36. V. Bandi, H.B. Gobeze, V. Lakshmi, M. Ravikanth, F. D’Souza, J. Phys. Chem. C 119, 8095–8102 (2015)

    Article  Google Scholar 

  37. L. Huang, X. Yu, W. Wu, J. Zhao, Org. Lett. 14, 2594–2597 (2012)

    Article  Google Scholar 

Download references

Acknowledgements

This work was supported by the CNRS (International Emerging Action, PICS project n° 08198), the LabEx PALM ANR-10LABX-0039-PALM and CHARMMMAT ANR-11-LABX-0039, Région Ile-de-France DIM Nano-K. Anam Fatima is grateful for the MESRI Grant (2019-2022). Jad Rabah thanks the MESRI for a PhD fellowship (2017-2020).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to G. Burdzinski, R. Méallet-Renault, K. Steenkeste or M. H. Ha-Thi.

Ethics declarations

Conflict of interest

On behalf of all authors, the corresponding authors state that there is no conflict of interest.

Additional information

Ultrafast Phenomena from attosecond to picosecond timescales: theory and experiments. Guest editors: Franck Lépine, Lionel Poisson.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 4213 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fatima, A., Rabah, J., Allard, E. et al. Ultrafast time-resolved spectroscopy elucidating photo-driven electron and energy transfer processes in a broadband light-absorbing BODIPY-C60-distyryl BODIPY triad. Eur. Phys. J. Spec. Top. 232, 2131–2144 (2023). https://doi.org/10.1140/epjs/s11734-022-00670-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1140/epjs/s11734-022-00670-y

Navigation