Skip to main content
SpringerLink
Log in

Effect of Conformational States on the Photophysical Properties of Di-para-biphenyl-benzothiadiazole and a Dimethyl Derivative of It

  • STRUCTURE OF MATTER AND QUANTUM CHEMISTRY
  • Published:
Russian Journal of Physical Chemistry A Aims and scope Submit manuscript

Abstract

The authors discuss results from studying the photophysical properties of linear molecules based on 2,1,3-benzothiadiazole, specifically 4,7-di([para-biphenyl]-4-yl)benzothiadiazole (Ph-Ph-BTD) and 4,7-bis(2,5-dimethyl-[1,1'-biphenyl]-4-yl)benzothiadiazole (Ph-Xy-BTD). The synthesis of a new phenylxylene derivative of benzothiadiazole—Ph-Xy-BTD—is described. The thermal stability of the Ph-Ph-BTD and Ph-Xy-BTD compounds is studied. Their parameters of melting and solubility are determined, and the absorption spectra of solutions in n-hexane and THF are recorded. It is shown that having pendant methyl substituents in Ph-Xy-BTD lowers its melting point, increases its solubility, reduces the probability of a transition between the ground and excited state orbitals, and raises the energy of transition. The effect solvation has on the spectra, fluorescence quantum yield, and lifetime of the fluorescence of compounds in THF and n-hexane is studied. Static dipole moments in the ground (HOMO) and excited states (LUMO) of Ph-Ph-BTD and Ph-Xy-BTD molecules are determined. It is shown that the conformation of the excited state (LUMO) changes during the relaxation of the solvate and becomes more planar than that of the ground state (HOMO). A relationship is revealed between the conformation of the excited state of the studied compounds and the polarity of the solvent.

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.

Similar content being viewed by others

REFERENCES

  1. M. S. Skorotetcky, E. D. Krivtsova, O. V. Borshchev, et al., Dyes Pigm. 155, 284 (2018). https://doi.org/10.1016/j.dyepig.2018.03.043

    Article  CAS  Google Scholar 

  2. V. A. Postnikov, N. I. Sorokina, A. A. Kulishov, et al., Acta Crystallogr., B 78, 261 (2022). https://doi.org/10.1107/S2052520622001846

    Article  CAS  Google Scholar 

  3. V. A. Postnikov, N. I. Sorokina, A. A. Kulishov, et al., Acta Crystallogr., B 75, 1076 (2019). https://doi.org/10.1107/S2052520619012484

    Article  CAS  Google Scholar 

  4. S. A. Ponomarenko, N. M. Surin, O. V. Borshchev, et al., Sci. Rep. 4, 6549 (2014). https://doi.org/10.1038/srep06549

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. A. Bravar and Y. Demets, J. Instrum. 17, P12020 (2022). https://doi.org/10.1088/1748-0221/17/12/P12020

    Article  CAS  Google Scholar 

  6. H. Aihara, O. V. Borshchev, D. A. Epifanov, et al., in Proceedings of the International Conference on New Photodetectors, 2015, Moscow, Troitsk, Russia. https://pos.sissa.it/252/052/pdf.

  7. A. Sidorenkov, O. Borshchev, A. Fazliakhmetov, et al., Eur. Phys. J. C 82, 1038 (2022). https://doi.org/10.1140/epjc/s10052-022-11017-1

    Article  CAS  Google Scholar 

  8. B. H. Sohn and K. Y. Lee, US Patent US20020061420A1 (2002).

  9. U. Schlickum, R. Decker, F. Klappenberger, et al., J. Am. Chem. Soc. 130, 11778 (2008). https://doi.org/10.1021/ja8028119

    Article  CAS  PubMed  Google Scholar 

  10. J. N. Demas and G. A. Crosby, J. Phys. Chem. 75, 991 (1971). https://doi.org/10.1021/j100678a001

    Article  Google Scholar 

  11. I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd ed. (Academic, New York, 1971).

    Google Scholar 

  12. L. Pauling and R. B. Corey, J. Am. Chem. Soc. 74, 3964 (1952). https://doi.org/10.1021/ja01135a531

    Article  CAS  Google Scholar 

  13. M. J. S. Dewar, J. Am. Chem. Soc. 74, 3341 (1952). https://doi.org/10.1021/ja01133a038

    Article  CAS  Google Scholar 

  14. A. I. Kiprianov, G. G. Dyadyusha, and F. A. Mikhailenko, Russ. Chem. Rev. 35, 361 (1966). https://doi.org/10.1070/RC1966v035n05ABEH001477

    Article  Google Scholar 

  15. Solvatochromia: Problems and Methods, Ed. by N. G. Bakhshieva (Leningr. Gos. Univ., Leningrad, 1989) [in Russian].

    Google Scholar 

  16. W. Liptay, in Excited States, Ed. by E. C. Lim (Academic Press, New York, 1974), Vols. 1, 2.

    Google Scholar 

  17. E. Lippert, Zeitschr. Elektrochem. Ber. Bunsenges. Phys. Chem. 61, 962 (1957). https://doi.org/10.1002/bbpc.19570610819

    Article  CAS  Google Scholar 

  18. E. G. McRae, J. Phys. Chem. 61, 562 (1957). https://doi.org/10.1021/j150551a012

    Article  CAS  Google Scholar 

  19. N. Mataga, Y. Kaifu, and M. Koizumi, Bull. Chem. Soc. Jpn. 29, 465 (1956). https://doi.org/10.1246/bcsj.29.465

    Article  CAS  Google Scholar 

  20. J. B. Birks and D. J. Dyson, Proc. R. Soc. London, Ser. A 275 (1360) (1963). https://doi.org/10.1098/rspa.1963.0159

  21. S. J. Strickler and R. A. Berg, J. Chem. Phys. 37, 814 (1962). https://doi.org/10.1063/1.1733166

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

This work was performed on scientific equipment at the shared resource centers Structural Diagnostics of Materials and Polymer Research of the Federal Research Center of Crystallography and Photonics and the Enikolopov Institute of Synthetic Polymer Materials, respectively.

Funding

This work was supported by the Russian Science Foundation, grant no. 22-13-00255.

Author information

Authors and Affiliations

  1. Enikolopov Institute of Synthetic Polymer Materials, Russian Academy of Sciences, 117393, Moscow, Russia

    N. M. Surin, E. A. Svidchenko, M. S. Skorotetskii, V. V. Popova, V. A. Postnikov, G. A. Yurasik & O. V. Borschev

  2. Federal Research Center of Crystallography and Photonics, Russian Academy of Sciences, 119333, Moscow, Russia

    M. S. Lyasnikova, V. A. Postnikov & G. A. Yurasik

Authors
  1. N. M. Surin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. A. Svidchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. S. Skorotetskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. V. Popova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. S. Lyasnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. A. Postnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. G. A. Yurasik
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. O. V. Borschev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to E. A. Svidchenko or O. V. Borschev.

Ethics declarations

The authors of this work declare that they have no conflicts of interest.

Additional information

Translated by M. Timoshinina

Publisher’s Note.

Pleiades Publishing 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

Surin, N.M., Svidchenko, E.A., Skorotetskii, M.S. et al. Effect of Conformational States on the Photophysical Properties of Di-para-biphenyl-benzothiadiazole and a Dimethyl Derivative of It. Russ. J. Phys. Chem. (2024). https://doi.org/10.1134/S0036024424030294

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1134/S0036024424030294

Keywords:

Search

Navigation