Log in

Chromogenic and Fluorescent Properties of 2-(2-Carboethoxy-3,4-Dichloro-6-Hydroxyphenyl)Benzoxazole

  • Published:
High Energy Chemistry Aims and scope Submit manuscript

Abstract

2-(2-Carboethoxy-3,4-dichloro-6-hydroxyphenyl)benzoxazole exhibits a number of chromogenic properties including solvatochromism and photochromism. Solvatochromic properties are due to the existence of keto–enol equilibrium and dissociation equilibrium. T-type negative photochromism is a two-step process of Z–E photoisomerization and the subsequent intramolecular proton transfer in the ground state to form the enol form. The multiemission profile is created by a number of isomeric forms, among which the enol form exhibits the most intense fluorescence with an anomalous Stokes shift due to intramolecular proton transfer in the excited state.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.

REFERENCES

  1. Qin, M., Huang, Y., Li, F., and Song, Y., J. Mater. Chem. C, 2015, vol. 3, p. 9265.

    Article  CAS  Google Scholar 

  2. Verbitskiy, E.V., Cheprakova, E.M., Subbotina, J.O., Schepochkin, A.V., Slepukhin, P.A., Rusinov, G.L., Charushin, V.N., Chupakhin, O.N., Makarova, N.I., Metelitsa, A.V., and Minkin, V.I., Dyes Pigm., 2014, vol. 100, no. 1, p. 201.

    Article  CAS  Google Scholar 

  3. Verbitskiy, E.V., Dinastiya, E.M., Baranova, A.A., Khokhlov, K.O., Chuvashov, R.D., Makarova, N.I., Vetrova, E.V., Metelitsa, A.V., Slepukhin, P.A., Rusinov, G.L., Chupakhin, O.N., and Charushin, V.N., Dyes Pigm., 2018, vol. 159, p. 35.

    Article  CAS  Google Scholar 

  4. Li, X., Gao, X., Shi, W., and Ma, H., Chem. Rev., 2014, vol. 114, p. 590.

    Article  CAS  PubMed  Google Scholar 

  5. Tian, M., Ma, Y., and Lin, W., Acc. Chem. Res., 2019, vol. 52, no. 8, p. 2147.

    Article  CAS  PubMed  Google Scholar 

  6. Molecular Switches, Feringa, B.L. and Browne, W.R., Eds., Weinheim: Wiley–VCH, 2011.

    Google Scholar 

  7. Delaire, J.A. and Nakatani, K., Chem. Rev., 2000, vol. 100, p. 1817.

    Article  CAS  PubMed  Google Scholar 

  8. Kawata, S. and Kawata, Y., Chem. Rev., 2000, vol. 100, p. 1777.

    Article  CAS  PubMed  Google Scholar 

  9. Jeong, H., Kim, D., **ang, D., and Lee, T., ACS Nano, 2017, vol. 11, p. 6511.

    Article  CAS  PubMed  Google Scholar 

  10. Meisner, Q.J., Hurley, J.J.M., Guo, P., Blood, A.R., Schaller, R.D., Gosztola, D.J., Wiederrecht, G.P., and Zhu, L., J. Phys. Chem. A, 2022, vol. 126, no. 7, p. 979.

    Article  Google Scholar 

  11. Vetrova, E.V., Tupaeva, I.O., Demidov, O.P., Sayapin, Yu.A., Gusakov, E.A., Minkin, V.I., and Metelitsa, A.V., J. Lumin., 2023, vol. 263, p. 120111.

    Article  CAS  Google Scholar 

  12. Abou-Zied, O.K., Jimenez, R., Thompson, E.H.Z., Millar, D.P., and Romesberg, F.E., J. Phys. Chem. A, 2002, vol. 106, p. 3665.

    Article  CAS  Google Scholar 

  13. Vetrova, E.V., Tupaeva, I.O., Sayapin, Y.A., Gusakov, E.A., Nikolaevskii, S.A., Demidov, O.P., Minkin, V.I., and Metelitsa, A.V., Dyes Pigm., 2020, vol. 180, p. 108417.

    Article  CAS  Google Scholar 

  14. Hurley, J.J.M., Meisner, Q.J., Guo, P., Schaller, R.D., Gosztola, D.J., Wiederrecht, G.P., and Zhu, L., J. Phys. Chem. A, 2022, vol. 126, no. 7, p. 979.

    Article  Google Scholar 

  15. Vetrova, E.V., Metelitsa, A.V., Tupaeva, I.O., Chernishev, A.V., Sayapin, Y.A., Minkin, V.I., and Dorogan, I.V., J. Photochem. Photobiol., A, 2023, vol. 442, p. 114769.

    Article  CAS  Google Scholar 

  16. Sayapin, Y.A., Nikolaevskii, S.A., Makarova, N.I., Gusakov, E.A., Tupaeva, I.O., Dorogan, I.V., Metelitsa, A.V., and Minkin, V.I., Russ. J. Org. Chem., 2016, vol. 52, p. 1018.

    Article  CAS  Google Scholar 

  17. Enderlein, J. and Erdmann, R., Opt. Commun., 1997, vol. 134, p. 371.

    Article  ADS  CAS  Google Scholar 

Download references

Funding

This work was carried out with the support of the Ministry of Science and Higher Education of the Russian Federation (state assignment for 2023, project no. FENW_2023-0020).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. V. Metelitsa.

Ethics declarations

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

Additional information

Translated by V. Makhlyarchuk

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

Vetrova, E.V., Tupaeva, I.O., Minkin, V.I. et al. Chromogenic and Fluorescent Properties of 2-(2-Carboethoxy-3,4-Dichloro-6-Hydroxyphenyl)Benzoxazole. High Energy Chem 57 (Suppl 3), S488–S493 (2023). https://doi.org/10.1134/S0018143923090199

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0018143923090199

Navigation