Skip to main content
SpringerLink
Log in

Design and Synthesis of Supramolecular Polymer Network Equipped with Pd-porphyrin: An Efficient and Recoverable Heterogeneous Catalyst for C–C Coupling Reactions

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The present study aimed to explain a modern and attractive protocol for synthesizing hypercross-linked conjugated supramolecular polymer network contains palladium(II) porphyrin based on calix[4]resorcinarene as an efficient heterogeneous catalyst. Thus, characterizations were conducted by using spectroscopic methods including powder X-ray diffraction, energy dispersive spectroscopy, scanning electron microscopy, FT-IR, and UV–Vis spectroscopy. In addition, catalytic activity of Pd-porphyrin@polymer was evaluated for C–C coupling reactions. The catalyst demonstrated an excellent activity, which is highly potential for forming new bond under mild conditions.

Graphic Abstract

The synthesis of a novel, green and recoverable heterogeneous catalyst by grafting Pd-porphyrin on the surface of polymeric calix[4]resorcinarene for the synthesis of C–C coupling reactions.

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
Fig. 2
Fig. 3
Scheme 2
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Kinjo K, Hirao T, Kihara S, Katsumoto Y, Haino T (2015) Angew Chem 127:15043–15047

    Google Scholar 

  2. Brunsveld L, Folmer B, Meijer EW, Sijbesma R (2001) Chem Rev 101:4071–4098

    CAS  PubMed  Google Scholar 

  3. Guo D-S, Liu Y (2012) Chem Soc Rev 41:5907–5921

    CAS  PubMed  Google Scholar 

  4. Li S-L, Xiao T, Hu B, Zhang Y, Zhao F, Ji Y, Yu Y, Lin C, Wang L (2011) Chem Commun 47:10755–10757

    CAS  Google Scholar 

  5. Goldberg I (2000) Chem Eur J 6:3863–3870

    CAS  PubMed  Google Scholar 

  6. Barona-Castaño J, Carmona-Vargas C, Brocksom T, de Oliveira K (2016) Molecules 21:310

    PubMed  PubMed Central  Google Scholar 

  7. Betoni Momo P, Pavani C, Baptista MS, Brocksom TJ, Thiago de Oliveira K (2014) Eur J Org Chem 2014:4536–4547

    CAS  Google Scholar 

  8. Carvalho CMB, Fujita MA, Brocksom TJ, de Oliveira KT (2013) Tetrahedron 69:9986–9993

    CAS  Google Scholar 

  9. Ishihara S, Labuta J, Van Rossom W, Ishikawa D, Minami K, Hill JP, Ariga K (2014) Phys Chem Chem Phys 16:9713–9746

    CAS  PubMed  Google Scholar 

  10. Cornils B, Herrmann WA (2003) J Catal 216:23–31

    CAS  Google Scholar 

  11. Dioos BM, Vankelecom IF, Jacobs PA (2006) Adv Synth Catal 348:1413–1446

    CAS  Google Scholar 

  12. Zhang J, Zhao G-F, Popović Z, Lu Y, Liu Y (2010) Mater Res Bull 45:1648–1653

    Google Scholar 

  13. Sadegh F, Bagheri O, Moghadam M, Mirkhani V, Tangestaninejad S, Mohammadpoor-Baltork I (2014) J Organomet Chem 759:46–57

    CAS  Google Scholar 

  14. Bagheri O, Sadegh F, Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I, Safiri M (2014) Appl Organomet Chem 28:337–346

    CAS  Google Scholar 

  15. Mouradzadegun A, Mostafavi MA (2016) RSC Adv 6:42522–42531

    CAS  Google Scholar 

  16. Mouradzadegun A, Mostafavi MA (2018) Polym Eng Sci 58:1362–1370

    CAS  Google Scholar 

  17. Pieters RJ, Cuntze J, Bonnet M, Diederich F (1997) J Chem Soc Perkin Trans 2:1891–1900

    Google Scholar 

  18. Haba O, Haga K, Ueda M, Morikawa O, Konishi H (1999) Chem Mater 11(427):432

    Google Scholar 

  19. Nakayama T, Takahashi D, Takeshi K, Ueda M (1999) J Photopolym Sci Technol 12:347–352

    CAS  Google Scholar 

  20. Scarso A, Onagi H, Rebek J (2004) J Am Chem Soc 126:12728–12729

    CAS  PubMed  Google Scholar 

  21. Bell TW, Hext NM (2004) Chem Soc Rev 33:589–598

    CAS  PubMed  Google Scholar 

  22. Lu J-Q, Pang D-W, Zeng X-S, He X-W (2004) J Electroanal Chem 568:37–43

    CAS  Google Scholar 

  23. Ruderisch A, Iwanek W, Pfeiffer J, Fischer G, Albert K, Schurig V (2005) J Chromatogr 1095:40–49

    CAS  Google Scholar 

  24. Jain A, Gupta V, Singh L, Srivastava P, Raisoni J (2005) Talanta 65:716–721

    CAS  PubMed  Google Scholar 

  25. Barrett ES, Dale TJ, Rebek J (2007) J Am Chem Soc 129:3818–3819

    CAS  PubMed  Google Scholar 

  26. Jain V, Pillai S, Gupte H (2008) J Iran Chem Soc 5:646–656

    CAS  Google Scholar 

  27. Tancini F, Genovese D, Montalti M, Cristofolini L, Nasi L, Prodi L, Dalcanale E (2010) J Am Chem Soc 132:4781–4789

    CAS  PubMed  Google Scholar 

  28. Jiang W, Ajami D, Rebek J Jr (2012) J Am Chem Soc 134:8070–8073

    CAS  PubMed  Google Scholar 

  29. Mouradzadegun A, Kiasat AR, Fard PK (2012) Catal Commun 29:1–5

    CAS  Google Scholar 

  30. Mouradzadegun A, Elahi S, Abadast F (2014) RSC Adv 4:31239–31248

    CAS  Google Scholar 

  31. Mouradzadegun A, Elahi S, Abadast F (2014) Catal Lett 144:1636–1641

    CAS  Google Scholar 

  32. Mouradzadegun A, Ganjali MR, Mostafavi MA (2018) Appl Organomet Chem 32:e4214

    Google Scholar 

  33. Mouradzadegun A, Mostafavi MA, Ganjali MR (2018) J Incl Phenom Macrocycl Chem 91:25–36

    CAS  Google Scholar 

  34. Das P, Linert W (2016) Coord Chem Rev 311:1–23

    CAS  Google Scholar 

  35. Jeong E-Y, Burri A, Lee S-Y, Park S-E (2010) J Mater Chem 20:10869–10875

    CAS  Google Scholar 

  36. Amao Y, Asai K, Okura I (2000) J Porphyr Phthalocyanines 4:179–184

    CAS  Google Scholar 

  37. Tunstad LM, Tucker JA, Dalcanale E, Weiser J, Bryant JA, Sherman JC, Helgeson RC, Knobler CB, Cram DJ (1989) J Org Chem 54:1305–1312

    CAS  Google Scholar 

  38. Awad WH, Gilman JW, Nyden M, Harris RH Jr, Sutto TE, Callahan J, Trulove PC, DeLong HC, Fox DM (2004) Thermochim Acta 409:3–11

    CAS  Google Scholar 

  39. Fareghi-Alamdari R, Golestanzadeh M, Bagheri O (2016) RSC Adv 6:108755–108767

    CAS  Google Scholar 

  40. Prendergast K, Spiro TG (1992) J Am Chem Soc 114:3793–3801

    CAS  Google Scholar 

  41. Li N, Wang Z, Zhao K, Shi Z, Xu S, Gu Z (2010) J Nanosci Nanotechnol 10:6748–6751

    CAS  PubMed  Google Scholar 

  42. Chen J, Zhang J, Zhu D, Li T (2018) Appl Organomet Chem 32:e3996

    Google Scholar 

  43. Shang N, Gao S, Feng C, Zhang H, Wang C, Wang Z (2013) RSC Adv 3:21863–21868

    CAS  Google Scholar 

  44. Navidi M, Rezaei N, Movassagh B (2013) J Organomet Chem 743:63–69

    CAS  Google Scholar 

  45. Hoseini SJ, Heidari V, Nasrabadi H (2015) J Mol Catal A Chem 396:90–95

    CAS  Google Scholar 

Download references

Funding

Funding was provided by Shahid Chamran University of Ahvaz (Grant No. SCU.SC98.357).

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Shahid Chamran University of Ahvaz, Ahvaz, Iran

    Sheida Hamid & Arash Mouradzadegun

Authors
  1. Sheida Hamid
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Arash Mouradzadegun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Arash Mouradzadegun.

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 file1 (DOCX 1149 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hamid, S., Mouradzadegun, A. Design and Synthesis of Supramolecular Polymer Network Equipped with Pd-porphyrin: An Efficient and Recoverable Heterogeneous Catalyst for C–C Coupling Reactions. Catal Lett 151, 658–669 (2021). https://doi.org/10.1007/s10562-020-03344-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-020-03344-3

Keywords

Search

Navigation