Skip to main content
SpringerLink
Log in

Spiropyrans and spirooxazines 10. Synthesis of photochromic 5′-(1,3-benzoxazol-2-yl)-substituted spiro[indoline-naphthopyrans]

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

New photochromic 5′-(1,3-benzoxazol-2-yl)-substituted spiro[indoline-naphthopyrans] exhibiting luminescent properties in the spirocyclic form were synthesized. Their reverse thermal reaction barrier decreases with the increase in the electron-withdrawing properties of substituent in the indoline fragment.

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

Similar content being viewed by others

References

  1. A. V. Metelitsa, N. A. Voloshin, S. O. Bezuglyi, E. V. Solov’eva, K. E. Shepelenko, Yu. R. Abubikerova, V. I. Minkin, Russ. Chem. Bull., Int. Ed., 2013, 62, 529 [Izv. Akad. Nauk, Ser. Khim., 2013, 527].

    Article  CAS  Google Scholar 

  2. V. I. Minkin, Chem. Rev., 2004, 104, 2751.

    Article  CAS  Google Scholar 

  3. B. S. Luk’yanov, M. B. Luk’yanova, Chem. Heterocycl. Compd., 2005, 41, 281 [Khim. Geterotsikl. Soedin., 2005, 321].

    Article  Google Scholar 

  4. R. Klajn, Chem. Soc. Rev., 2013, DOI: 10.1039/C3CS60181A.

    Google Scholar 

  5. R. C. Bertelson, in Organic Photochromic and Thermochromic Compounds. Topics in Applied Chemistry, Eds J. C. Crano, R. J. Guglielmetti, Plenum Press, New York, 1999, p. 11.

  6. V. A. Barachevsky, J. Fluorescence, 2000, 10, 185.

    Article  CAS  Google Scholar 

  7. S. A. Ahmed, M. Tanaka, H. Ando, K. Tawa, K. Kimura, Tetrahedron, 2004, 60, 6029.

    Article  CAS  Google Scholar 

  8. J.-R. Chen, J.-B. Wong, P.-Y. Kuo, D.-Y. Yang, Org. Lett., 2008, 10, 4823.

    Article  CAS  Google Scholar 

  9. M. Tomasulo, E. Deniz, R. J. Alvarado, F. M. Raymo, J. Phys. Chem. C, 2008, 112, 8038.

    Article  CAS  Google Scholar 

  10. B. Seefeldt, R. Kasper, M. Beining, J. Mattay, J. Arden-Jacob, N. Kemnitzer, K. H. Drexhage, M. Heilemann, M. Sauer, Photochem. Photobiol. Sci., 2010, 9, 213.

    Article  CAS  Google Scholar 

  11. S. M. Aldoshin, J. Photochem. Photobiol. A: Chem., 2008, 200, 19.

    Article  CAS  Google Scholar 

  12. M. Inouye, Coord. Chem. Rev., 1996, 148, 265.

    Article  CAS  Google Scholar 

  13. S. Kum, H. Nishihara, Struct. Bond, 2007, 123, 79.

    Article  Google Scholar 

  14. S. V. Paramonov, V. Lokshin, O. A. Fedorova, J. Photochem. Photobiol. C: Photochem. Rev., 2011, 12, 209.

    Article  CAS  Google Scholar 

  15. M. I. Zakharova, C. Coudret, V. Pimienta, J. C. Micheau, S. Delbaere, G. Vermeersch, A. V. Metelitsa, N. A. Voloshin, V. I. Minkin, Photochem. Photobiol. Sci., 2010, 9, 199.

    Article  CAS  Google Scholar 

  16. J. Q. Ren, H. Tian, Sensors, 2007, 7, 3166.

    Article  CAS  Google Scholar 

  17. M. Natali, L. Soldi, S. Giordani, Tetrahedron, 2010, 66, 7612.

    Article  CAS  Google Scholar 

  18. A. V. Chernyshev, N. A. Voloshin, I. M. Raskita, A. V. Metelitsa, V. I. Minkin, J. Photochem. Photobiol. A: Chem., 2006, 184, 289.

    Article  CAS  Google Scholar 

  19. N. A. Voloshin, A. V. Chernyshev, A. V. Metelitsa, V. I. Minkin, Chem. Heterocycl. Compd., 2011, 47, 865 [Khim. Geterotsikl. Soedin., 2011, 1055].

    Article  CAS  Google Scholar 

  20. N. A. Voloshin, A. V. Chernyshev, A. V. Metelitsa, E. B. Gaeva, V. I. Minkin, Russ. Chem. Bull., Int. Ed., 2011, 60, 1921 [Izv. Akad. Nauk, Ser. Khim., 2011, 1888].

    Article  CAS  Google Scholar 

  21. J. Hobley, V. Malatest, R. Millini, L. Montanari, W. Parker, Phys. Chem. Chem. Phys., 1999, 1, 3259.

    Article  CAS  Google Scholar 

  22. C. D. Gabbut, J. D. Hepworth, B. M. Heron, Dyes and Pigments, 1999, 42, 35.

    Article  Google Scholar 

  23. J. Hobley, V. Malatesta, Phys. Chem. Chem. Phys., 2000, 2, 57.

    Article  CAS  Google Scholar 

  24. L. Shragina, F. Buchgoltz, S. Yitzchaik, V. Krongauz, Liq. Cryst., 1990, 7, 643.

    Article  CAS  Google Scholar 

  25. E. Pottier, M. Sergent, R. Phan Tan Luu, R. Guglielmetti, Bull. Soc. Chim. Belg., 1992, 101, 719.

    Article  CAS  Google Scholar 

  26. S. Murphy, X. Yang, G. B. Schuster, J. Org. Chem., 1995, 60, 2411.

    Article  CAS  Google Scholar 

  27. J. E. Kwon, S. Lee, Y. You, K.-H. Baek, K. Ohkubo, J. Cho, S. Fukuzumi, I. Shin, S. Y. Park, W. Nam, Inorg. Chem., 2012, 51, 8760.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Southern Scientific Center, Russian Academy of Sciences, 41 ul. Chekhova, 344006, Rostov on Don, Russian Federation

    N. A. Voloshin & V. I. Minkin

  2. Research Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov on Don, Russian Federation

    A. V. Chernyshev, E. V. Solov’eva, I. A. Rostovtseva, A. V. Metelitsa, G. S. Borodkin, V. A. Kogan & V. I. Minkin

Authors
  1. N. A. Voloshin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Chernyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Solov’eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. A. Rostovtseva
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Metelitsa
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. S. Borodkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. A. Kogan
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. V. I. Minkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. A. Voloshin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences O. N. Chupakhin on the occasion of his 80th birthday.

For Part 9, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1373–1377, June, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Voloshin, N.A., Chernyshev, A.V., Solov’eva, E.V. et al. Spiropyrans and spirooxazines 10. Synthesis of photochromic 5′-(1,3-benzoxazol-2-yl)-substituted spiro[indoline-naphthopyrans]. Russ Chem Bull 63, 1373–1377 (2014). https://doi.org/10.1007/s11172-014-0605-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-014-0605-8

Key words

Search

Navigation