Skip to main content
SpringerLink
Log in

Cyclic Polymer of N-Vinylpyrrolidone via ATRP Protocol: Kinetic Study and Concentration Effect of Polymer on Click Chemistry in Solution

  • SYNTHESIS
  • Published:
Polymer Science, Series B Aims and scope Submit manuscript

Abstract

We hereby report the synthesis of a well-defined cyclic poly(N-vinylpyrrolidone) using propargyl-2-bromoisobutyrate as an ATRP initiator and NaN3 followed by the click reaction of alkynyl and azide groups. The decrease of polymer concentration is favorable for cyclization reaction, while the increase of polymer concentration leads to condensation reaction.

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.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.
Fig. 9.

Similar content being viewed by others

REFERENCES

  1. L. Yang, H. Sun, Y. Liu, W. Hou, Y. Yang, R. Cai, C. Cui, P. Zhang, X. Pan, X. Li, L. Li, B. S. Sumerlin, and W. Tan, Angew. Chem., Int. Ed. 57, 17048 (2018).

    Article  CAS  Google Scholar 

  2. V. Coessens, T. Pintauer, and K. Matyjaszewski, Prog. Polym. Sci. 26, 337 (2001).

    Article  CAS  Google Scholar 

  3. H. Sun, C. P. Kabb, M. B. Sims, and B. S. Sumerlin, Prog. Polym. Sci. 89, 61 (2019).

    Article  CAS  Google Scholar 

  4. H. C. Kolb, M. Finn, and K. B. Sharpless, Angew. Chem., Int. Ed. 40, 2004 (2001).

    Article  CAS  Google Scholar 

  5. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, and M. G. Finn, J. Am. Chem. Soc. 125, 3192 (2003).

    Article  CAS  Google Scholar 

  6. H. Sun, C. P. Kabb, Y. Dai, M. R. Hill, I. Ghiviriga, A. P. Bapat, and B. S. Sumerlin, Nat. Chem. 9, 817, (2017).

    Article  CAS  Google Scholar 

  7. V. Mishra, S.-H. Jung, J. M. Park, H. M. Jeong, and H.-I. Lee, Macromol. Rapid Commun. 35, 442 (2014).

    Article  CAS  Google Scholar 

  8. B. S. Sumerlin, N. V. Tsarevsky, G. Louche, R. Y. Lee, and K. Matyjaszewski, Macromolecules 38, 7540 (2005).

    Article  CAS  Google Scholar 

  9. Y. Li, J. Yang, and B. C. Benicewicz, J. Polym. Sci., Part A: Polym. Chem. 45, 4300 (2007).

    Article  CAS  Google Scholar 

  10. R. Riva, S. Schmeits, C. Jérôme, R. Jérôme, and P. Lecomte, Macromolecules 40, 796 (2007).

    Article  CAS  Google Scholar 

  11. J. F. Lutz, Angew. Chem., Int. Ed. 46, 1018 (2007).

    Article  CAS  Google Scholar 

  12. X. Jiang, M. C. Lok, and W. E. Hennink, Bioconjugate Chem. 18, 2077 (2007).

    Article  CAS  Google Scholar 

  13. W. H. Binder and R. Sachsenhofer, Macromol. Rapid Commun. 28, 15 (2007).

    Article  CAS  Google Scholar 

  14. V. Mishra, S.-H. Jung, H. M. Jeong, and H.-I. Lee, Polym. Chem. 5, 2411 (2014).

    Article  CAS  Google Scholar 

  15. N. V. Tsarevsky, B. S. Sumerlin, and K. Matyjaszewski, Macromolecules 38, 3558 (2005).

    Article  CAS  Google Scholar 

  16. K. Matyjaszewski and J. Xia, Chem. Rev. 101, 2921 (2001).

    Article  CAS  Google Scholar 

  17. V. Mishra and R. Kumar, J. Appl. Polym. Sci. 124, 4475 (2012).

    CAS  Google Scholar 

  18. V. Mishra and R. Kumar, Functional Controlled/Living Radical Polymers: Synthesis, Kinetics and Physico-Chemical Properties (Lambert Acad. Publ., GmbH, Germany, 2013), p. 133.

    Google Scholar 

  19. V. Mishra and R. Kumar, J. Appl. Polym. Sci. 128, 3295 (2013).

    Article  CAS  Google Scholar 

  20. A. Srivastava, V. Mishra, P. Singh, A. Srivastava, and R. Kumar, J. Therm. Anal. Calorim. 107, 211 (2012)

    Article  CAS  Google Scholar 

  21. A. Srivastava, V. Mishra, S. K. Singh, and R. Kumar, e-Polym. 6, 1 (2009).

  22. V. Mishra and R. Kumar, Trends Carbohydr. Res. 4 (3), 1 (2012).

    CAS  Google Scholar 

  23. V. Mishra and R. Kumar, Carbohydr. Polym. 83, 1534 (2011).

    Article  CAS  Google Scholar 

  24. F. Haaf, A. Sanner, and F. Straub, Polym. J. 17, 143 (1985).

    Article  CAS  Google Scholar 

  25. L. Nud’ga, V. Petrova, N. Klishevich, L. Litvinova, A. Y. Babenko, and V. Shelegedin, Russ. J. Appl. Chem. 75, 1678 (2002).

    Article  Google Scholar 

  26. M. J. O’Connell, P. Boul, L. M. Ericson, C. Huffman, Y. Wang, E. Haroz, C. Kuper, J. Tour, K. D. Ausman, and R. E. Smalley, Chem. Phys. Lett. 342, 265 (2001).

    Article  Google Scholar 

  27. Y. Nho and K. Park, J. Appl. Polym. Sci. 85, 1787 (2002).

    Article  CAS  Google Scholar 

  28. Q. Tang, J. Chen, Y. Zhao, and K. Zhang, Polym. Chem. 6, 6659 (2015).

    Article  CAS  Google Scholar 

  29. V. M. Treushnikov, N. V. Frolova, L. L. Pomerantseva, and A. V. Olenik, Polym. Sci. U.S.S.R. 20, 1371 (1978).

    Article  Google Scholar 

  30. S. Honda, T. Yamamoto, and Y. Tezuka, Nat. Commun. 4, 1574 (2013).

    Article  Google Scholar 

  31. R. Gilbert, M. Hess, A. Jenkins, R. Jones, P. Kratochvil, and R. Stepto, Pure Appl. Chem. 81, 351 (2009).

    Article  CAS  Google Scholar 

  32. X.-P. Qiu, F. Tanaka, and F. M. Winnik, Macromolecules 40, 7069 (2007).

    Article  CAS  Google Scholar 

  33. A. K. Nanda and K. Matyjaszewski, Macromolecules 36, 599 (2003).

    Article  CAS  Google Scholar 

  34. X.-S. Wang and S. Armes, Macromolecules 33, 6640 (2000).

    Article  CAS  Google Scholar 

  35. K. Matyjaszewski, T. E. Patten, and J. Xia, J. Am. Chem. Soc. 119, 674 (1997).

    Article  CAS  Google Scholar 

  36. A. T. Levy, M. M. Olmstead, and T. E. Patten, Inorg. Chem. 39, 1628 (2000).

    Article  CAS  Google Scholar 

  37. B. A. Laurent and S. M. Grayson, J. Am. Chem. Soc. 128, 4238 (2006).

    Article  CAS  Google Scholar 

  38. D. M. Eugene and S. M. Grayson, Macromolecules 41, 5082 (2008).

    Article  CAS  Google Scholar 

  39. D. E. Lonsdale, C. A. Bell, and M. J. Monteiro, Macromolecules 43, 3331 (2010).

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The author thanks the Department of Chemistry, BHU, Varanasi (India) and Department of Chemistry, the University of Delhi for providing spectral and analytical facilities and SERB, New Delhi for providing financial support in the form of National PDF.

Funding

This work was financially supported by a grant from SERB research Project Supported by the Department of Science and technology, New Delhi in the form of National-PDF (Grant no. PDF/2017/000952).

Author information

Authors and Affiliations

  1. Green Chemistry Network Centre, Department of Chemistry, University of Delhi, 110007, Delhi, India

    Vivek Mishra

  2. Green Process Material Research Group, Korea Institute of Industrial Technology, 331-822, Chungcheongnam-do, Republic of Korea

    Vivek Mishra

  3. Organic Polymer Chemistry Laboratory, Department of Chemistry, Institute of Science, Banaras Hindu University, UP-221005, Varanasi, India

    Rajesh Kumar

Authors
  1. Vivek Mishra
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rajesh Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vivek Mishra.

Ethics declarations

The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vivek Mishra, Rajesh Kumar Cyclic Polymer of N-Vinylpyrrolidone via ATRP Protocol: Kinetic Study and Concentration Effect of Polymer on Click Chemistry in Solution. Polym. Sci. Ser. B 61, 753–761 (2019). https://doi.org/10.1134/S1560090419060095

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1560090419060095

Search

Navigation