Skip to main content
SpringerLink
Log in

Synthesis and fine-tuning of thermal stability of the negative nitrile-rich photochromes of hydroxytricyanopyrrole (HTCP) series

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A series of negative T-type nitrile-rich photochromes containing a hydroxytricyanopyrrole acceptor was synthesized. It was shown that thermal stability of the photoinduced form could be tuned by the replacement of a substituent in para-position to OH-group as well as by the change of a solvent. Ethanol solutions of the synthesized compounds showed significantly shorter half-lives of the reverse dark (thermal) reaction in comparison with solutions in acetonitrile.

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
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Scheme 3
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. H. Tian, J. Zhang, Photochromic Materials: Preparation, Properties and Applications (Wiley-VCH, Weinheim, 2016)

    Google Scholar 

  2. R. Klajn, Chem. Soc. Rev. 43, 148 (2014)

    Article  CAS  Google Scholar 

  3. M.M. Russew, S. Hecht, Adv. Mater. 22, 3348 (2010)

    Article  CAS  Google Scholar 

  4. M. El Gemayel, K. Bçrjesson, M. Herder, D.T. Duong, J. Hutchison, C. Ruzi, G. Schweicher, A. Salleo, Y. Geerts, S. Hecht, E. Orgiu, P. Samori, Nat. Commun. 6, 6330 (2015)

    Article  Google Scholar 

  5. R.S. Stoll, S. Hecht, Angew. Chem. Int. Ed. 49, 5054 (2010)

    Article  CAS  Google Scholar 

  6. O. Alghazwat, A. Elgattar, T. Khalil, Z. Wang, Y. Liao, Dyes Pigm. 171, 107719 (2019)

    Article  CAS  Google Scholar 

  7. J. Liu, W. Tang, L. Sheng, Z. Du, T. Zhang, X. Su, S.X.-A. Zhang, Chem. Asian J. 14, 438 (2019)

    Article  CAS  Google Scholar 

  8. M.M. Lerch, M.J. Hansen, G.M. van Dam, W. Szymanski, B.L. Feringa, Angew. Chem. Int. Ed. 55, 10978 (2016)

    Article  CAS  Google Scholar 

  9. M. Dong, A. Babalhavaeji, S. Samanta, A.A. Beharry, G.A. Woolley, Acc. Chem. Res. 48, 2662 (2015)

    Article  CAS  Google Scholar 

  10. J. Broichhagen, J.A. Frank, D. Trauner, Acc. Chem. Res. 48, 1947 (2015)

    Article  CAS  Google Scholar 

  11. W.A. Velema, W. Szymanski, B.L. Feringa, J. Am. Chem. Soc. 136, 2178 (2014)

    Article  CAS  Google Scholar 

  12. W. Szymanski, J.M. Beierle, H.A.V. Kistemaker, W.A. Velema, B.L. Feringa, Chem. Rev. 113, 6114 (2013)

    Article  CAS  Google Scholar 

  13. T. Ube, T. Ikeda, Angew. Chem. Int. Ed. 53, 10290 (2014)

    Article  CAS  Google Scholar 

  14. S. Kobatake, S. Takami, H. Muto, T. Ishikawa, M. Irie, Nature 446, 778 (2007)

    Article  CAS  Google Scholar 

  15. L. Wang, Q. Li, Chem. Soc. Rev. 47, 1044 (2018)

    Article  CAS  Google Scholar 

  16. M. Natali, S. Giordani, Chem. Soc. Rev. 41, 4010 (2012)

    Article  CAS  Google Scholar 

  17. S. Erbas-Cakmak, D.A. Leigh, C.T. McTernan, A.L. Nussbaumer, Chem. Rev. 115, 10081 (2015)

    Article  CAS  Google Scholar 

  18. K. Ayub, R.H. Mitchell, J. Org. Chem. 79, 664 (2014)

    Article  CAS  Google Scholar 

  19. M. Jacquet, F. Lafolet, S. Cobo, F. Loiseau, A. Bakkar, M. Boggio-Pasqua, E. Saint-Aman, G. Royal, Inorg. Chem. 56, 4357 (2017)

    Article  CAS  Google Scholar 

  20. T. Yamaguchi, A. Maity, V. Polshettiwar, M. Ogawa, Inorg. Chem. 57, 3671 (2018)

    Article  CAS  Google Scholar 

  21. M.J. Feeney, S.W. Thomas, Macromolecules 51, 8027 (2018)

    Article  CAS  Google Scholar 

  22. J. Alves, S. Wiedbrauk, D. Gräfe, S.L. Walden, J.P. Blinco, C. Barner-Kowollik, Chem. A Eur. J. 26, 809 (2020)

    Article  CAS  Google Scholar 

  23. B.F. Lui, N.T. Tierce, F. Tong, M.M. Sroda, H. Lu, Photochem. Photobiol. Sci. 18, 1587 (2019)

    Article  CAS  Google Scholar 

  24. A. Tokunaga, L.M. Uriarte, K. Mutoh, E. Fron, J. Hofkens, M. Sliwa, J. Abe, J. Am. Chem. Soc. 141, 17744 (2019)

    Article  CAS  Google Scholar 

  25. S. Aiken, R.J.L. Edgar, C.D. Gabbutt, B.M. Heron, P.A. Hobson, Dyes Pigm. 149, 92 (2018)

    Article  CAS  Google Scholar 

  26. V.A. Barachevsky, Rev. J. Chem. 7, 334 (2017)

    Article  CAS  Google Scholar 

  27. V.K. Johns, P. Peng, J. DeJesus, Z. Wang, Y. Liao, Chem. Eur. J. 20, 689 (2014)

    Article  CAS  Google Scholar 

  28. C. Yang, T. Khalil, Y. Liao, RSC Adv. 6, 85420 (2016)

    Article  CAS  Google Scholar 

  29. M.Yu. Belikov, M.Yu. Ievlev, S.V. Fedoseev, O.V. Ershov, New J. Chem. 43, 8414 (2019)

    Article  CAS  Google Scholar 

  30. M.Yu. Belikov, M.Yu. Ievlev, S.V. Fedoseev, O.V. Ershov, Res. Chem. Intermed. 45, 4625 (2019)

    Article  CAS  Google Scholar 

  31. M.Yu. Belikov, S.V. Fedoseev, O.V. Ershov, M.Yu. Ievlev, V.A. Tafeenko, Tetrahedron Lett. 57, 4101 (2016)

    Article  CAS  Google Scholar 

  32. S.V. Fedoseev, M.Yu. Belikov, M.Yu. Ievlev, O.V. Ershov, V.A. Tafeenko, Res. Chem. Intermed. 44, 3565 (2018)

    Article  CAS  Google Scholar 

  33. S.V. Fedoseev, M.Yu. Belikov, M.Yu. Ievlev, O.V. Ershov, V.A. Tafeenko, Dyes Pigment 165, 451 (2019)

    Article  CAS  Google Scholar 

  34. S.V. Fedoseev, M.Yu. Belikov, M.Yu. Ievlev, O.V. Ershov, New J. Chem. 43, 17923 (2019)

    Article  CAS  Google Scholar 

  35. K. Ayub, R. Zhang, S.G. Robinson, B. Twamley, R.V. Williams, R.H. Mitchell, J. Org. Chem. 73, 451 (2008)

    Article  CAS  Google Scholar 

  36. N. Khan, N.S. Sheikh, A.F. Khan, R. Ludwig, T. Mahmood, W. Rehman, Y.S.S. Al-Faiyz, K. Ayub, J. Mol. Model. 21, 148 (2015)

    Article  Google Scholar 

  37. B. Saima, N. Khan, Y.S.S. Al-Faiyz, R. Ludwig, W. Rehman, M. Habib-ur-Rehman, N.S. Sheikh, K. Ayub, J. Mol. Graph. Model. 88, 261 (2019)

    Article  CAS  Google Scholar 

  38. H.C. Brown, Y. Okamoto, J. Am. Chem. Soc. 80, 4979 (1958)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The research was performed under the financial support of the Russian Science Foundation (Grant No. 18-73-10065).

Author information

Authors and Affiliations

  1. Ulyanov Chuvash State University, Moskovsky pr., 15, Cheboksary, Russia, 428015

    Mikhail Yu. Belikov, Mikhail Yu. Ievlev, Sergey V. Fedoseev & Oleg V. Ershov

Authors
  1. Mikhail Yu. Belikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mikhail Yu. Ievlev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sergey V. Fedoseev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Oleg V. Ershov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mikhail Yu. Ievlev.

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 (DOCX 3374 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Belikov, M.Y., Ievlev, M.Y., Fedoseev, S.V. et al. Synthesis and fine-tuning of thermal stability of the negative nitrile-rich photochromes of hydroxytricyanopyrrole (HTCP) series. Res Chem Intermed 46, 3477–3490 (2020). https://doi.org/10.1007/s11164-020-04157-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04157-0

Keywords

Search

Navigation