Skip to main content
SpringerLink
Log in

Controlled lactide polymerization using diimine magnesium complex: synthesis of high-molecular-weight polylactide and evaluation of its cytotoxicity in vitro

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

Abstract

A mechanism of ring-opening polymerization of lactide in a solution using a magnesium coordination compound (dpp-bian)Mg(thf)3 (1) containing a chelating redox-active acenaphthenediimine ligand dpp-bian (1,2-bis-[(2,6- diisopropyl)phenylimino]acenaphthene) has been proposed. The reaction proceeds in the presence of a chain initiator/regulator ROH (R = H, alkyl, acyl), while the true polymerization catalyst is presumably the product of the interaction of complex 1, lactide, and ROH. It has been demonstrated that a decrease in the content of the initiating impurity in the initial monomer by precise purification of the latter makes it possible to control the molecular weight of polymer in order to obtain high molecular weight polylactide (Mw = 1.9 • 105, PDI 1.5). Due to non-toxic catalyst system, the resulting polymer shows no cytotoxicity, as confirmed by in vitro studies.

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

References

  1. https://www.plasticseurope.org/en/newsroom/news/eu-plastics-production-and-demand-first-estimates-2020.

  2. R. Geyer, J. R. Jambeckand, K. L. Law, Sci. Adv., 2017, 3, e1700782.

    Article  PubMed  PubMed Central  Google Scholar 

  3. A. Morão, F. de Bie, J. Polym. Environ., 2019, 27, 2523.

    Article  Google Scholar 

  4. S. Jacobsen, H. G. Fritz, P. Degée, P. Dubois, R. Jérôme, Polym. Eng. Sci., 1999, 39, 1311.

    Article  CAS  Google Scholar 

  5. J. Tuominen, J. Kylmä, A. Kapanen, O. Venelampi, M. Itävaara, J. Seppälä, Biomacromolecules, 2002, 3, 445.

    Article  CAS  PubMed  Google Scholar 

  6. T. A. Egiazaryan, V. M. Makarov, M. V. Moskalev, D. A. Razborov, I. L. Fedushkin, Mendeleev Commun., 2019, 29, 648–650.

    Article  CAS  Google Scholar 

  7. I. L. Fedushkin, M. V. Moskalev, D. A. Razborov, T. A. Egiazaryan, Pat. RF, No. 2695998; Bjul. Isobr. 2019, 22 (in Russian).

  8. I. L. Fedushkin, A. G. Morozov, V. A. Chudakova, G. K. Fukin, V. K. Cherkasov, Eur. J. Inorg. Chem., 2009, 4995.

  9. A. G. Morozov, E. S. Markelova, I. L. Fedyushkin, Russ. J. Appl. Chem., 2018, 91, 1044.

    Article  CAS  Google Scholar 

  10. S. Sagar, K. Bano, A. Sarkar, K. Pal, T. K. Panda, Eur. J. Inorg. Chem., 2022, e202200494.

  11. T. Rosen, J. Rajpurohit, S. Lipstman, V. Venditto, M. Kol, Chem. Eur. J. 2020, 26, 17183.

    Article  CAS  PubMed  Google Scholar 

  12. I. E. Nifant’ev, M. E. Minyaev, A. V. Shlyakhtin, P. V. Ivchenko, A. V. Churakov, Mendeleev Commun., 2017, 27, 341.

    Article  Google Scholar 

  13. P. McKeown, S. N. McCormick, M. F. Mahona, M. D. Jones, Polym. Chem., 2018, 9, 5339.

    Article  CAS  Google Scholar 

  14. A. G. Morozov, D. A. Razborov, T. A. Egiazaryan, M. A. Baten’kin, D. Ya. Aleynik, M. N. Egorikhina, Y. P. Rubtsova, I. N. Charikova, S. A. Chesnokov, I. L. Fedushkin, J. Polym. Environ., 2020, 28, 2652.

    Article  CAS  Google Scholar 

  15. O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev., 2004, 104, 12, 6147.

    Article  Google Scholar 

  16. S. R. Sandler, W. Karo, J. Bonesteel, E. M. Pearce, in Polymer Synthesis and Characterization: A Laboratory Manual, Academic Press, San Diego, 1998, p. 146.

    Google Scholar 

  17. S. Inkinen, M. Hakkarainen, A.-C. Albertsson, A. Södergård, Biomacromolecules, 2011, 12, 523; DOI: https://doi.org/10.1021/bm101302t.

    Article  CAS  PubMed  Google Scholar 

  18. I. L. Fedushkin, N. M. Khvoinova, A. Y. Baurin, G. K. Fukin, V. K. Cherkasov, M. P. Bubnov, Inorg. Chem., 2004, 43, 7807.

    Article  CAS  PubMed  Google Scholar 

  19. I. L. Fedushkin, N. M. Khvoinova, A. Y. Baurin, G. K. Fukin, Russ. Chem. Bull., 2006, 55, 451.

    Article  CAS  Google Scholar 

  20. Y. Wang, W. Zhao, X. Liu, D. Cui, E. Y. X. Chen, Macromolecules, 2012, 45, 6957.

    Article  CAS  Google Scholar 

  21. S. Shanmugam, B. Gopal, Appl. Surf. Sci., 2014, 303, 277.

    Article  CAS  Google Scholar 

  22. A. Paulovicova, U. El-Ayaan, K. Shibayama, T. Morita, Y. Fukuda, Eur. J. Inorg. Chem., 2001, 10, 2641.

    Article  Google Scholar 

  23. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, G. K. Fukin, H. Schumann, Eur. J. Inorg. Chem., 2003, 3336.

Download references

Author information

Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences, 49 ul. Tropinina, 630950, Nizhny Novgorod, Russian Federation

    A. G. Morozov, D. A. Razborov & I. L. Fedushkin

  2. Privolzhsky Research Medical University of the Ministry of Health Care of the Russian Federation, 10/1 pl. Minina i Pozharskogo, 603005, Nizhny Novgorod, Russian Federation

    D. Ya. Aleynik, M. N. Egorikhina & D. D. Linkova

Authors
  1. A. G. Morozov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. A. Razborov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. Ya. Aleynik
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. N. Egorikhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. D. Linkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. L. Fedushkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. G. Morozov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

The work was carried out within the framework of the “Priority 2030” program funded by the Ministry of Science and Higher Education of the Russian Federation, using the equipment of the Center for Collective Use “Analytical Center of G. A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences” with the support of the grant “Ensuring the development of the material and technical infrastructure of centers for the collective use of scientific equipment” (unique identifier RF 2296.61321X0017, agreement number 075-15-2021-670).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 3, pp. 778–784, March, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Morozov, A.G., Razborov, D.A., Aleynik, D.Y. et al. Controlled lactide polymerization using diimine magnesium complex: synthesis of high-molecular-weight polylactide and evaluation of its cytotoxicity in vitro. Russ Chem Bull 72, 778–784 (2023). https://doi.org/10.1007/s11172-023-3841-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3841-5

Key words

Search

Navigation