Skip to main content
SpringerLink
Log in

New TEMPO containing polymers for all polymeric oxidation procedure

  • ORIGINAL PAPER
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

2,2,6,6-Tetramethylpiperidine 1-oxyl (TEMPO) is a versatile compound which is used mainly in organic oxidation reactions and organic battery applications. Incorporating TEMPO into a polymer could provide many applications into its repertoire. In this study, new polymeric TEMPO derivatives are synthesized and characterized to be used as catalysts in the presence of another polymer which constitutes N-halamine functionality. These polymeric mixtures were superior since the mixture could easily be separated from the reaction medium by simple filtration and reused in some other oxidation reactions numerous times. In turn, an all polymeric oxidation method was developed for oxidation of primary alcohols.

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
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. Lu J, Toy PH (2009). Chem Rev 109(2):815–838

    Article  CAS  Google Scholar 

  2. Zarchi MAK, Mousavi SZ (2014). J Polym Res 21:330

    Article  Google Scholar 

  3. Eames J, Watkinson M (2001) Eur. J. Org. Chem. 1213

  4. Chen C, Yang Z, Da Z, Qui F, Cao G, Guan Y, Yang D (2015) J Polym. Res. 22, 10, 188

  5. Dickerson TJ, Reed NN, Janda KD (2002). Chem Rev 102(10):3325–3344

    Article  CAS  Google Scholar 

  6. Salimi H, Rahimi A, Pourjavadi A (2007). Monatsh Chem 138(4):363–379

    Article  CAS  Google Scholar 

  7. Tsutsuba T, Sogawa H, Takata T (2017). Polym Chem 8:1445–1448

    Article  CAS  Google Scholar 

  8. Tzschucke CC, Markert C, Bannwarth W, Roller S, Hebel A, Haag R (2002) Angew. Chem. Int. Ed., 41-3964

  9. Sertkol SB, Sinirlioglu D, Esat B (2015) J. Polym. Res. 22-136

  10. Lewandowski M, Gwozdzinski K (2017) Int. J. Mol. Sci. 18(11)

  11. Soule BP, Hyodo F, Matsumoto K, Simone NL, Cook JA, Krishna MC, Mitchell JB (2007). Free Radic Biol Med 42:1632–1650

    Article  CAS  Google Scholar 

  12. Krishna MC, Grahame DA, Samuni A, Mitchell JB, Russo A (1992). Proc Natl Acad Sci 89:5537–5541

    Article  CAS  Google Scholar 

  13. Adam W, Saha-Möller CR, Ganeshpure PA (2001). Chem Rev 101:3499–3548

    Article  CAS  Google Scholar 

  14. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J Am Chem Soc 2013, 135, 2357–2367

  15. Dijksman A, Marino-González A, Payeras A, Arends I, Sheldon R (2001). J Am Chem Soc 123:6826–6833

    Article  CAS  Google Scholar 

  16. Dickerson TJ, Reed NN, Janda KD (2002). Chem Rev 102:3325–3344

    Article  CAS  Google Scholar 

  17. Benaglia M, Puglisi A, Cozzi F (2003). Chem Rev 103:3401–3429

    Article  CAS  Google Scholar 

  18. Tsubokawa, N.; Kimoto, T.; Endo, T. J Mol Catal 1995, 101, 45–50

  19. Le D, Dilger M, Pertici V, Diabaté S, Gigmes D, Weiss C, Delaittre G (2019). Angew Chem Int Ed Engl 58(14):4725–4731

    Article  CAS  Google Scholar 

  20. de Nooy AEJ, Besemer AC, van Bekkum H (1995). Synthesis:1153–1174

  21. Vogler, T.; Studer, A (2008) Synthesis 1979–1993

  22. Bobbitt JM, Flores MCL (1988). Heterocycles 27:509–533

    Article  CAS  Google Scholar 

  23. Cella, J.A.; Kelley J.A.; Kenehan, E. F. J Org Chem 1975, 40, 1860–1862

  24. Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J Org Chem 1987, 52, 2559–2562

  25. De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J Org Chem 1997, 62, 6974–6977

  26. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J Org Chem 1996, 61, 7452–7454

  27. Akdag A, Öztürk P (2013). Synlett 24:2451–2453

    Article  CAS  Google Scholar 

  28. Sun, G.; B. Wheatle, W.B.; Worley, S. D. Ind. Eng. Chem. Res.1994331168-170

  29. Akdag A, Webb T, Worley SD (2006). Tetrahedron Lett 47:3509–3510

    Article  CAS  Google Scholar 

  30. Akdag, A.; Okur, S.; McKee, M. L.; Worley S.D. J Chem Theory Comput, 2006, 2, 879-884

  31. Ren X, Akdag A, Kocer HB, Worley SD, Broughton RM, Huang TS (2009) Carbohydr. Polym. 220-226

  32. Demir B, Broughton RM, Qiao M, Huang T-S, Worley SD (2017). Molecules 22:1582

    Article  Google Scholar 

  33. Potier J, Commarieu B, Soldera A, Claverie JP (2018). ACS Catal 8:6047–6054

    Article  CAS  Google Scholar 

  34. Grubbs, R.H.; Trnka, T.M. Ruthenium in Organic Synthesis, Murahashi, S. (Ed.) Wiley-VCH: Weinheim, Germany, 2005: 6, 156-158

  35. Rintoul L, Micallef AS, Bottle SE (2008) Spectrochim. Acta Part A Mol Biomol Spectrosc 70:713–717

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We would like to acknowledge Middle East Technical University Research Funds (BAP): BAP-01-03-2015-003, BAP-07-02-2014-007-690, BAP-08-11-2012-120.

Author information

Authors and Affiliations

  1. Middle East Technical University, Department of Chemistry, Universiteler Mah, Dumlupinar Blv. No:1, 06800, Ankara, Turkey

    Perihan Öztürk, Ece Ayça Yücel & Akın Akdag

Authors
  1. Perihan Öztürk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ece Ayça Yücel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Akın Akdag
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Akın Akdag.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

ESM 1

(DOCX 13.0 MB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Öztürk, P., Yücel, E.A. & Akdag, A. New TEMPO containing polymers for all polymeric oxidation procedure. J Polym Res 27, 30 (2020). https://doi.org/10.1007/s10965-019-1996-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-019-1996-x

Keywords

Search

Navigation