Skip to main content
SpringerLink
Log in

EPR Characterization of the Light-Induced Negative Polaron in a Functionalized Dithienylthiazolo[5,4-d]thiazole Acceptor for Organic Photovoltaics

  • Original Paper
  • Published:
Applied Magnetic Resonance Aims and scope Submit manuscript

Abstract

Functionalized 2,5-dithienylthiazolo[5,4-d]thiazole (DTTzTz) derivatives have attracted interest towards application as non-fullerene acceptors in solution-processed organic solar cells. Here, we present a combined high-field electron paramagnetic resonance and density functional theory study of the light-induced negative polaron on the novel acceptor 2,4-diCN-Ph-DTTzTz formed after charge transfer in bulk heterojunction blends with a donor polymer. Despite spectral overlap with the polymer cation, the g-anisotropy of the acceptor radical could be directly confirmed through detection of its unique 14N hyperfine couplings using electron–electron double resonance (ELDOR)-detected nuclear magnetic resonance (EDNMR) for spectral filtering. The spectral assignment is further underpinned by quantum-chemical calculations, which also provide detailed information about the spin density and charge distribution of the polaron in the DTTzTz acceptor.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. J. Yuan, Y. Zhang, L. Zhou, G. Zhang, H.-L. Yip, T.-K. Lau, X. Lu, C. Zhu, H. Peng, P. A. Johnson, M. Leclerc, Y. Cao, J. Ulanski, Y. Li, Y. Zou, Joule 3, 1140 (2019)

    Article  Google Scholar 

  2. J. Hou, O. Inganäs, R.H. Friend, F. Gao, Nat. Mater. 17, 119 (2018)

    Article  ADS  Google Scholar 

  3. W. Zhao, D. Qian, S. Zhang, S. Li, O. Inganäs, F. Gao, J. Hou, Adv. Mater. 28, 4734 (2016)

    Article  Google Scholar 

  4. I. Osaka, R. Zhang, J. Liu, D.-M. Smilgies, T. Kowalewski, R.D. McCullough, Chem. Mater. 22, 4191 (2010)

    Article  Google Scholar 

  5. I. Osaka, R. Zhang, G. Sauvè, D.M. Smilgies, T. Kowalewski, R.D. McCullough, J. Am. Chem. Soc. 131, 2521 (2009)

    Article  Google Scholar 

  6. D. Naraso, F. Wudl, Macromolecules 41, 3169 (2008)

    Article  ADS  Google Scholar 

  7. S. Ando, D. Kumaki, J.I. Nishida, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita, J. Mater. Chem. 17, 553 (2007)

    Article  Google Scholar 

  8. J. Kudrjasova, R. Herckens, H. Penxten, P. Adriaensens, L. Lutsen, D. Vanderzande, W. Maes, Org. Biomol. Chem. 12, 4663 (2014)

    Article  Google Scholar 

  9. J. Kudrjasova, M. Van Landeghem, T. Vangerven, J. Kesters, G.H.L. Heintges, I. Cardinaletti, R. Lenaerts, H. Penxten, P. Adriaensens, L. Lutsen, D. Vanderzande, J. Manca, E. Goovaerts, W. Maes, ChemistrySelect 2, 1253 (2017)

    Article  Google Scholar 

  10. N. Nevil, Y. Ling, S. Van Mierloo, J. Kesters, F. Piersimoni, P. Adriaensens, L. Lutsen, D. Vanderzande, J. Manca, W. Maes, S. Van Doorslaer, E. Goovaerts, Phys. Chem. Chem. Phys. 14, 15774 (2012)

    Article  Google Scholar 

  11. M. Van Landeghem, R. Lenaerts, J. Kesters, W. Maes, E. Goovaerts, unpubl. results

  12. J. Niklas, O. G. Poluektov, Adv. Energy Mater. 1602226 (2017)

    Article  Google Scholar 

  13. Y. Ling, S. Van Mierloo, A. Schnegg, M. Fehr, P. Adriaensens, L. Lutsen, D. Vanderzande, W. Maes, E. Goovaerts, S. Van Doorslaer, Phys. Chem. Chem. Phys. 16, 10032 (2014)

    Article  Google Scholar 

  14. J. Niklas, K.L. Mardis, B.P. Banks, G.M. Grooms, A. Sperlich, V. Dyakonov, S. Beaupré, M. Leclerc, T. Xu, L. Yu, O.G. Poluektov, Phys. Chem. Chem. Phys. 15, 9562 (2013)

    Article  Google Scholar 

  15. S. Stoll, A. Schweiger, J. Magn. Reson. 178, 42 (2006)

    Article  ADS  Google Scholar 

  16. F. Neese, Wiley Interdiscip. Rev. Comput. Mol. Sci. 2, 73 (2012)

    Article  Google Scholar 

  17. F. Neese, J. Chem. Phys. 115, 11080 (2001)

    Article  ADS  Google Scholar 

  18. F. Neese, J. Chem. Phys. 122, 044110 (2005)

    Article  ADS  Google Scholar 

  19. A.D. Becke, Phys. Rev. A 38, 3098 (1988)

    Article  ADS  Google Scholar 

  20. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 97, 2571 (1992)

    Article  ADS  Google Scholar 

  21. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988)

    Article  ADS  Google Scholar 

  22. V. Barone, in Recent Advances in Density Functional Methods, ed. by D. P. Chong (World Scientific, Singapore, 1995), Part 1, pp. 287–334

  23. A. Aguirre, P. Gast, S. Orlinskii, I. Akimoto, E.J.J. Groenen, H. El-Mkami, E. Goovaerts, S. Van Doorslaer, Phys. Chem. Chem. Phys. 10, 7129 (2008)

    Article  Google Scholar 

  24. A. Nalepa, K. Möbius, W. Lubitz, A. Savitsky, J. Magn. Reson. 242, 203 (2014)

    Article  ADS  Google Scholar 

  25. M. Van Landeghem, W. Maes, E. Goovaerts, S. Van Doorslaer, J. Magn. Reson. 288, 1 (2018)

    Article  ADS  Google Scholar 

Download references

Acknowledgements

The authors want to acknowledge the Research Foundation Flanders (FWO-Vlaanderen) for support of this work through the project G0B6715 N and the PhD fellowship of M. Van Landeghem.

Author information

Authors and Affiliations

  1. Experimental Condensed Matter Physics, University of Antwerp, Universiteitsplein 1, 2610, Antwerp, Belgium

    Melissa Van Landeghem & Etienne Goovaerts

  2. Design and Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University, Agoralaan 1, 3590, Diepenbeek, Belgium

    Julija Kudrjasova & Wouter Maes

  3. Imec, Associated Laboratory IMOMEC, Wetenschapspark 1, 3590, Diepenbeek, Belgium

    Julija Kudrjasova & Wouter Maes

  4. Laboratory of Biophysics and Biomedical Physics, University of Antwerp, Universiteitsplein 1, 2610, Antwerp, Belgium

    Sabine Van Doorslaer

Authors
  1. Melissa Van Landeghem
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Julija Kudrjasova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wouter Maes
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Etienne Goovaerts
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sabine Van Doorslaer
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sabine Van Doorslaer.

Additional information

Publisher's Note

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

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1011 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Van Landeghem, M., Kudrjasova, J., Maes, W. et al. EPR Characterization of the Light-Induced Negative Polaron in a Functionalized Dithienylthiazolo[5,4-d]thiazole Acceptor for Organic Photovoltaics. Appl Magn Reson 50, 1253–1265 (2019). https://doi.org/10.1007/s00723-019-01146-4

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00723-019-01146-4

Search

Navigation