Skip to main content
SpringerLink
Log in

Chitosan and functionalized graphene oxide nanocomposite as a novel and highly efficient catalyst for production of bis-coumarins under solvent-free conditions

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

Abstract

Chitosan and functionalized graphene oxide nanocomposite was used as efficient, sustainable, and recyclable catalyst in the production of bis-coumarins using 4-hydroxycoumarin and aromatic aldehydes under solvent-free conditions. Chitosan was first functionalized using chloroacetyl chloride. Afterward, graphene oxide was modified by aliphatic amine and then with dithioglycolic acid, giving rise to thiol (SH)-functionalized graphene oxide after reduction. The nanocomposite was prepared from the reaction of 2-chloroacetyl-functionalized chitosan and thiol-modified graphene oxide, followed by oxidization of thiols to SO3H groups using hydrogen peroxide. The nanocomposite (catalyst) was characterized using field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, thermogravimetric analysis, differential thermogravimetry, FT-IR, and MAP analysis. The nanocomposite showed superior properties over previously reported ones, including nontoxicity, environmental compatibility, solvent-free condition, simple work-up, no by-products, thermal stability, and recoverability.

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

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 5
Scheme 6
Fig. 9

Similar content being viewed by others

References

  1. S. Zangade, P. Patil, Curr. Org. Chem. 23, 2295 (2019)

    Article  CAS  Google Scholar 

  2. M.A. Ghasemzadeh, B. Mirhosseini-Eshkevari, M. Tavakoli, F. Zamani, Green Chem. 22, 7265 (2020)

    Article  CAS  Google Scholar 

  3. M.A. Gouda, M.A. Salem, M.H. Helal, Curr. Bioact. Compd. 16, 818 (2020)

    Article  CAS  Google Scholar 

  4. A. Detsi, C. Kontogiorgis, D. Hadjipavlou-Litina, Expert opin. Ther. Pat. 27, 1201 (2017)

    Article  CAS  PubMed  Google Scholar 

  5. M. Jokar, H. Naeimi, N.G. Bidhendi, Polycycl. Aromat. Compd. 41, 1 (2021)

    Article  Google Scholar 

  6. R. Rezaei, M.R. Sheikhi, Res. Chem. Intermed. 41, 1283 (2015)

    Article  CAS  Google Scholar 

  7. H. Bavandi, Z. Habibi, M. Yousefi, Bioorg. Chem. 103, 104139 (2020)

    Article  CAS  PubMed  Google Scholar 

  8. G. Brahmachari, S. Begam, ChemistrySelect 4, 5415 (2019)

    Article  CAS  Google Scholar 

  9. N. Daneshvar, O. Goli-Jolodar, R. Karimi-Chayjani, M. Safarpoor N. Langarudi, F. Shirini (2019) Chemistry Select 4, 1562.

  10. M. Gilanizadeh, B. Zeynizadeh, Polycycl. Aromat. Compd. 41, 15 (2021)

    Article  CAS  Google Scholar 

  11. N.O. Mahmoodi, Z. Jalalifard, G.P. Fathanbari, J. Chin. Chem. Soc. 67, 172 (2019)

    Article  Google Scholar 

  12. R. Teimuri-Mofrad, S. Tahmasebi, E. Payami, Appl. Organomet. Chem. 33, e4773 (2019)

    Article  Google Scholar 

  13. G. Kaur, D. Singh, A. Singh, B. Banerjee, Synth. Commun. 51, 1045 (2021)

    Article  CAS  Google Scholar 

  14. M. Biglari, F. Shirini, N.O. Mahmoodi, M. Zabihzadeh, M. Safarpoor, N. Langarudi, M.A. Khoshdel, Polycycl. Aromat. Compd. 41, 1 (2021)

    Article  Google Scholar 

  15. A. Sethiya, P. Teli, A. Manhas, D. Agarwal, J. Soni, N. Sahiba, P. Jha, S. Agarwal, Synth. Commun. 50, 2440 (2020)

    Article  CAS  Google Scholar 

  16. M. Faisal, F.A. Larik, A. Saeed, J. Porous Mater. 26, 455 (2019)

    Article  CAS  Google Scholar 

  17. B. Mitra, P. Ghosh, ChemistrySelect 6, 68 (2021)

    Article  CAS  Google Scholar 

  18. Z. Benzekri, S. Sibous, A. Ouasri, S. Boukhris, A. Hassikou, A. Rhandour, A. Souizi, J. Mol. Struct. 1230, 129890 (2021)

    Article  Google Scholar 

  19. B. Kharrngi, E.D. Dhar, G. Basumatary, D. Das, R.C. Deka, A.K. Yadav, G. Bez, J. Chem. Sci. 133, 1 (2021)

    Article  Google Scholar 

  20. F. Afsharnadery, K. Khosravi, M.A. Zolfigol, Appl. Organomet. Chem. e6297 (2021). https://doi.org/10.1002/aoc.6297

  21. R.C. Patil, S.K. Shinde, U.P. Patil, A.T. Birajdar, S.S. Patil, Res. Chem. Intermed. 47, 1675 (2021)

    Article  CAS  Google Scholar 

  22. L. Nazemi Nasirmahale, O. Goli Jolodar, F. Shirini, H. Tajik, (2021) Polycyclic Aromatic Compounds, 41, 199

  23. F. Ding, H. Li, Y. Du, X. Shi, Res. Chem. Intermed. 44, 4827 (2018)

    Article  CAS  Google Scholar 

  24. A. Muxika, A. Etxabide, J. Uranga, P. Guerrero, K. De La Caba, Int. J. Biol. Macromol. 105, 1358 (2017)

    Article  CAS  PubMed  Google Scholar 

  25. G.Z. Kyzas, D.N. Bikiaris, A.C. Mitropoulos, Polym. Int. 66, 1800 (2017)

    Article  CAS  Google Scholar 

  26. G. de Vargas Brião, J.R. de Andrade, M.G.C. da Silva, M.G.A. Vieira, Environ Chem. Lett. 18, 1145 (2020)

    Article  Google Scholar 

  27. G. Xu, T. Shi, M. Li, F. Yu, Y. Chen, Res. Chem. Intermed. 41, 8499 (2015)

    Article  CAS  Google Scholar 

  28. K. Pieklarz, M. Tylman, Z. Modrzejewska, Prog. Chem. Appl. Chitin Deriv. 23, 5 (2018)

    CAS  Google Scholar 

  29. W. Hummers, R. Offeman, J. Am. Chem. Soc. 80, 1339 (1958)

    Article  CAS  Google Scholar 

  30. J. Chen, B. Yao, C. Li, G. Shi, Carbon 64, 225 (2013)

    Article  CAS  Google Scholar 

  31. S. Naeim-Fallahiyeh, E. Rostami, H. Golchaman, S. Kaman-Torki, Res. Chem. Intermed. 46, 4141 (2020)

    Article  CAS  Google Scholar 

  32. S.M. Mousavi, S.A. Hashemi, Y. Ghasemi, A.M. Amani, A. Babapoor, O. Arjmand, Drug Metab. Rev. 51, 12 (2019)

    Article  CAS  PubMed  Google Scholar 

  33. K. Thakur, B. Kandasubramanian, J. Chem. Eng. Data 64, 833 (2019)

    Article  CAS  Google Scholar 

  34. P.P. Brisebois, M. Siaj, J. Mater. Chem. C 8, 1517 (2020)

    Article  CAS  Google Scholar 

  35. S.M. Anush, B. Vishalakshi, H.R. Chandan, B.R. Geetha, Sep. Sci. Technol. 53, 1979 (2018)

    Article  CAS  Google Scholar 

  36. D.C.P. Singh, S.R. Hashim, R.G. Singhal, E.-J. Chem. 8, 635 (2011)

    Article  CAS  Google Scholar 

  37. B.T. Gowda, Shilpa, J.K. Lakshmipathy, Z. Naturforsch. 61a, 595 (2006)

  38. M. Saeedi, F. Goli, M. Mahdavi, G. Dehghan, M.A. Faramarzi, A. Foroumadi, A. Shafiee, Iran. J. Pharm. Res. 13, 881 (2014)

    CAS  PubMed  PubMed Central  Google Scholar 

  39. D.M. Beaupre, R.G. Weiss, Molecules 26, 3332 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. T.Y. Samgina, K.A. Artemenko, V.A. Gorshkov, N.B. Poljakov, A.T. Lebedev, J. Am. Soc. Mass. Spectr. 19, 479 (2008)

    Article  CAS  Google Scholar 

  41. B. Amanulla, S. Palanisamy, S.M. Chen, V. Velusamy, T.W. Chiu, T.W. Chen, S.K. Ramaraj, J. Colloid Interface Sci. 487, 370 (2017)

    Article  CAS  PubMed  Google Scholar 

  42. P. Senthil Kumar, P.S.A. Fernando, R.T. Ahmed, R. Srinath, M. Priyadharshini, A.M. Vignesh, A. Thanjiappan, Chem. Eng. Commun. 201, 1526 (2014)

    Article  CAS  Google Scholar 

  43. A. Marcilla, A. Gómez, S. Menargues, J. Anal. Appl. Pyrolysis 74, 224 (2005)

    Article  CAS  Google Scholar 

  44. Z. Jovanović, I. Holclajtner-Antunović, D. Bajuk-Bogdanović, S. Jovanović, Ž Mravik, M. Vujković, Electrochem. Commun. 83, 36 (2017)

    Article  Google Scholar 

  45. W. Yan, Y. Xu, Y. Chen, J. Nanosci. Nanotechnol. 15, 2020 (2015)

    Article  CAS  PubMed  Google Scholar 

  46. M.K. Subramanian, P.M. Anbarasan, V. Ilangovan, N. Sundaraganesan, Mol. Simul. 34, 277 (2008)

    Article  CAS  Google Scholar 

  47. J. Wang, R. Huang, W. Qi, R. Su, B.P. Binks, Z. He, Appl. Catal. B-Environ. 254, 452 (2019)

    Article  CAS  Google Scholar 

  48. T. Zeng, Y. Yu, Z. Li, J. Zuo, Z. Kuai, Y. Jin, Y. Wang, A. Wu, C. Peng, Mater. Chem. Phys. 231, 105 (2019)

    Article  CAS  Google Scholar 

  49. A. Saeed, P.A. Channar, G. Shabir, F.A. Larik, J. fluoresce. 26, 1067 (2016)

    Article  CAS  Google Scholar 

  50. N. Manohar, J. Jayaramudu, S. Suchismita, K. Rajkumar, A.B. Reddy, E.R. Sadiku, R. Priti, D.J. Maurya, Polym. Test. 62, 447 (2017)

    Article  CAS  Google Scholar 

  51. M.N. Uddin, D.A. Chowdhury, M.M. Rony, M.E. Halim, Modern Chem. 2, 6 (2014)

    Article  CAS  Google Scholar 

  52. J. Lukose, C.Y. Panicker, P.S. Nayak, B. Narayana, B.K. Sarojini, C. Van Alsenoy, A.A. Al-Saadi, Spectrochim. Acta A Mol. Biomol. Spectrosc. 135, 608 (2015)

    Article  CAS  PubMed  Google Scholar 

  53. L.M. Ramenskaya, E.P. Grishina, J. Mol. Liq. 218, 133 (2016)

    Article  CAS  Google Scholar 

  54. T. Zeng, X.Q. Hu, H. Wu, J.W. Yang, H.B. Zhang, Int. J. Biol. Macromol. 131, 760 (2019)

    Article  CAS  PubMed  Google Scholar 

  55. A. Zimoch-Korzycka, J. Ambrozik-Haba, D. Kulig, A. Jarmoluk, Int. J. Polym. Sci. 2015, 1 (2015)

    Google Scholar 

  56. H.S. Patel, J.A. Patel, Polym. Plast. Technol. Eng. 48, 102 (2008)

    Article  Google Scholar 

  57. S. Ramachandran, G. Velraj, Rom. Journ. Phys. 57, 1128 (2012)

    CAS  Google Scholar 

  58. H.P. Zhao, G.C. Liang, S.M. Nie, X. Lu, C.X. Pan, X.X. Zhong, G.F. Su, D.L. Mo, Green Chem. 22, 404 (2020)

    Article  CAS  Google Scholar 

  59. N. Hsan, P.K. Dutta, S. Kumar, R. Bera, N. Das, Int. J. Biol. Macromol. 125, 300 (2019)

    Article  CAS  PubMed  Google Scholar 

  60. A.S.K. Kumar, S.J. Jiang, J. Environ. Chem. Eng. 4, 1698 (2016)

    Article  CAS  Google Scholar 

  61. S.K. Patil, D.V. Awale, M.M. Vadiyar, S.A. Patil, S.C. Bhise, S.S. Kolekar, Res. Chem. Intermed. 43, 5365 (2017)

    Article  CAS  Google Scholar 

  62. S.M. Banday, A. Amin, S. Bashir, R.A. Qadri, K.Z. Khan, M.A. Rizvi, Croat. Chem. Acta 90, 471 (2017)

    Article  CAS  Google Scholar 

  63. S.S. Kauthale, S.U. Tekale, K.M. Jadhav, R.P. Pawar, Mol. Divers. 20, 763 (2016)

    Article  CAS  PubMed  Google Scholar 

  64. A.R. Kiasat, L. Hemat-Alian, Res. Chem. Intermed. 41, 873 (2015)

    Article  CAS  Google Scholar 

  65. B. Akhlaghinia, P. Sanati, A. Mohammadinezhad, Z. Zarei, Res. Chem. Intermed. 45, 3215 (2019)

    Article  CAS  Google Scholar 

  66. P. Hayati, K. Eghbali, R. Rezaei, Res. Chem. Intermed. 45, 5067 (2019)

    Article  CAS  Google Scholar 

  67. J.M. Khurana, S. Kumar, Monatsh. Chem. 141, 561 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to appreciate the Payame Noor University (PNU) Research Council for supporting this research study.

Author information

Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

    Zhale Atashrouz, Esmael Rostami & Abdolkarim Zare

Authors
  1. Zhale Atashrouz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Esmael Rostami
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abdolkarim Zare
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Esmael Rostami.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 2610 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Atashrouz, Z., Rostami, E. & Zare, A. Chitosan and functionalized graphene oxide nanocomposite as a novel and highly efficient catalyst for production of bis-coumarins under solvent-free conditions. Res Chem Intermed 48, 179–201 (2022). https://doi.org/10.1007/s11164-021-04616-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04616-2

Keywords

Search

Navigation