Skip to main content
SpringerLink
Log in

Structures and photo- and thermochromic properties of spiropyrans of the 2-oxaindan series with polycondensed chromene fragments

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

Spiropyrans of the 2-oxaindan series with 2H-chromene fragments benzo- and 2,3-naphthoannelated at the 7–8 bond were synthesized. The molecular structures of four of the spiropyrans obtained were determined by x-ray diffraction studies, and their photo- and thermochromic properties were studied. Annelation of arene rings significantly increases the relative stabilities fo the photocolored forms of the spiropyrans. A correlation between the length of the Cspiro-O bond and the capacity of spiropyrans for photocoloration was discovered. In addition, the free energies of activation of the thermochromic transformations of spiropyrans determined by dynamic NMR spectroscopy are insensitive to variations in the length of the indicated bond.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /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.

Institutional subscriptions

Similar content being viewed by others

Explore related subjects

Discover the latest articles, news and stories from top researchers in related subjects.

Literature Cited

  1. A. V. Metelitsa, O. T. Lyashik, N. V. Volbushko, M. I. Knyazhanskii, E. A. Medyantseva, and V. I. Minkin, Zh. Org. Khim. (in press).

  2. R. C. Bertelson, in: Photochromism, G. H. Brown (ed.), Wiley-Interscience, New York (1971), Chap. 3, p. 45.

    Google Scholar 

  3. G. D. Platonova, I. A. Belaits, and V. A. Barachevskii, Zh. Fiz. Khim., 54, 799 (1980).

    Google Scholar 

  4. D. Gaude, M. Le Baccon, R. Guglielmetti, and R. Gautron, Bull. Soc. Chim. Fr., No. 10, 489 (1979).

    Google Scholar 

  5. V. A. Barachevskii, V. M. Kozenkov, and E. D. Kvasnikov, Usp. Nauchn. Fotogr., 19, 108 (1978).

    Google Scholar 

  6. N. A. Voloshin, N. E. Shelepin, and V. I. Minkin, USSR Inventor's Certificate No. 518491; Byull. Izobret., No. 23, 75 (1976).

    Google Scholar 

  7. B. Ya. Simkin, S. P. Makrov, N. G. Furmanova, K. Sh. Karaev, and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 6, 747 (1984).

    Google Scholar 

  8. S. M. Aldoshin and L. O. Atovmyan, Problems in Crystal Chemistry [in Russian], Nauka, Moscow (1984).

    Google Scholar 

  9. S. M. Aldoshin and L. O. Atovmyan, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2009 (1985).

    Google Scholar 

  10. B. P. Biryukov and B. V. Unkovskii, in: Crystal Chemistry. Advances in Science [in Russian], Vol. 9, All-Union Institute of Scientific and Technical Information (1974), p. 110; Vol. 11 (1976), p. 132.

  11. Tables of Interatomic Distances and Configurations in Molecules and Ions, Vol. 1, The Chem. Soc., Burlington House, London (1965).

  12. G. A. Jeffrey, J. A. Pople, J. S. Binkley, and S. Vishveshwara, J. Am. Chem. Soc., 100, 373 (1978).

    Google Scholar 

  13. B. Robinson and A. Hargreaves, Acta Crystallogr., 17, 944 (1964).

    Google Scholar 

  14. K. Sh. Karaev, N. G. Furmanova, and N. V. Belov, Kristallografiya, 26, 199 (1981); Dokl. Acad. Nauk SSSR, 262, 609 (1982).

    Google Scholar 

  15. K. Sh. Karaev, N. G. Furmanova, and N. V. Belov, Dokl. Akad. Nauk SSSR, 260, 1121 (1981).

    Google Scholar 

  16. J. R. Holden and S. Dickinson, J. Phys. Chem., 81, 1505 (1977).

    Google Scholar 

  17. B. Ya. Simkin, S. P. Makarov, and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 8, 1028 (1982).

    Google Scholar 

  18. V. A. Lokshin, N. A. Voloshin, N. S. Trofimov, N. E. Shelepin, and V. I. Minkin, Izv. Severokavkaz. Nauchn. Tsentr Vyssh. Shkol. Estestv. Nauki, No. 1, 68 (1983).

    Google Scholar 

  19. S. Toppet, W. Quintens, and G. Smets, Tetrahedron, 31, 1957 (1975).

    Google Scholar 

  20. B. Ya. Simkin, S. P. Makarov, and V. I. Minkin, Khim. Geterotsikl. Soedin. (in press).

  21. A. Samat, J. Kister, F. Garnier, J. Metzger, and R. Guglielmetti, Bull. Soc. Chim. Fr., Nos. 11–12, 2627 (1975).

    Google Scholar 

  22. V. A. Murin, V. A. Barachevskii, N. A. Voloshin, N. E. Shelepin, and V. I. Minkin, Opt. Spektrosk., 46, 1027 (1979).

    Google Scholar 

  23. S. M. Aldoshin and L. O. Atovmyan, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2016 (1985).

    Google Scholar 

  24. S. M. Aldoshin and L. O. Atovmyan, Mol. Cryst. Liq. Cryst. (in press).

  25. O. Chaudé, Cah. Phys. (France), 50, 17 (1954); 51, 6.

    Google Scholar 

  26. V. A. Lokshin, N. S. Trofimova, N. E. Shelepin, and V. I. Minkin, USSR Inventor's Certificate No. 941346; Byull. Izobret., No. 25, 108 (1982).

    Google Scholar 

  27. I. M. Andreeva, E. A. Bondarenko, N. V. Volbushko, M. I. Knyazhanskii, E. A. Medyantseva, A. V. Metelitsa, V. I. Minkin, and B. Ya. Simkin, Khim. Geterotsikl. Soedin., No. 8, 1035 (1980).

    Google Scholar 

  28. V. I. Andrianov, Z. Sh. Safina, and B. L. Tarnopol'skii, Rentgen-75. Automated System of Programs for Decoding Crystals [in Russian], Chernogolovka (1975).

Download references

Author information

Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, M. A. Suslov Rostov State University, 334077, Rostov-on-Don

    S. M. Aldoshin, V. A. Lokshin, A. N. Rezonov, N. V. Volbushko, N. E. Shelepin, M. I. Knyazhanskii, L. O. Atovmyan & V. I. Minkin

Authors
  1. S. M. Aldoshin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Lokshin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. N. Rezonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. V. Volbushko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. E. Shelepin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. M. I. Knyazhanskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. L. O. Atovmyan
    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

Additional information

Communication XIX from the series “Photo- and thermochromic spirans.” See [1] for Communication XVIII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 744–755, June, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Aldoshin, S.M., Lokshin, V.A., Rezonov, A.N. et al. Structures and photo- and thermochromic properties of spiropyrans of the 2-oxaindan series with polycondensed chromene fragments. Chem Heterocycl Compd 23, 614–624 (1987). https://doi.org/10.1007/BF00486903

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00486903

Keywords

Search

Navigation