Skip to main content

Copper Nanoparticles in Polyvinyl Alcohol–Acrylic Acid Matrix: An Efficient Heterogeneous Catalyst for the Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Click Reaction

Journal of Inorganic and Organometallic Polymers and Materials volume 28, pages 1457–1467 (2018)Cite this article

Abstract

Copper nanoparticles (Cu(I) NPs) were immobilized in polyvinyl alcohol-grafted-acrylic acid (PVA-g-AA) matrix. This polymeric matrix was obtained via grafting of AA onto PVA chain by initiating system involving MEK-peroxide during sonication process. The Cu(I) NPs, in PVA–AA matrix was fully characterized by FT-IR, scanning electron microscopy, energy dispersive X-ray spectroscopy, ICP–OES, UV–Vis and TGA techniques. Then, this new synthesized and well-characterized copper nanocatalyst was examined as a catalyst and found being highly efficient and recyclable in the regioselective synthesis of 1,4-disubstitued 1,2,3-triazoles via click reaction. Moreover, a quantitative description for metal–ligand interactions in PVA-g-AA supported copper catalyst was presented via quantum chemistry calculations.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

Price includes VAT (USA)
Tax calculation will be finalised during checkout.

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

References

  1. R. Mirsafaei, M.M. Heravi, Sh Ahmadi, M.H. Moslemin, T. Hosseinnejad, J. Mol. Catal. A 402, 100 (2015)

    Article  CAS  Google Scholar 

  2. R. Mirsafaei, M.M. Heravi, T. Hosseinnejad, S. Ahmadi, App. Organomet. Chem. 30, 823 (2016)

    Article  CAS  Google Scholar 

  3. S. Sadjadi, T. Hosseinnejad, M. Malmir, M.M. Heravi, New J. Chem. 41, 13935 (2017)

    Article  CAS  Google Scholar 

  4. T. Baie Lashaki, H.A. Oskooie, T. Hosseinnejad, M.M. Heravi, J. Coord. Chem. 70, 1815 (2017)

    Article  CAS  Google Scholar 

  5. F. Ebrahimpour-Malmir, T. Hosseinnejad, R. Mirsafaei, M.M. Heravi, App. Organomet. Chem. (2017). https://doi.org/10.1002/aoc.3913

    Article  Google Scholar 

  6. T. Hossiennejad, M. Daraie, M.M. Heravi, N.N. Tajoddin, J. Inorg. Organomet. Polym. 27, 861 (2017()

    Article  CAS  Google Scholar 

  7. M. Salavati-Niasari, F. Davar, N. Mir, Polyhedron 27, 3514 (2008)

    Article  CAS  Google Scholar 

  8. R. Zhang, P.X. Ma, J. Biomed. Mater. Res. 52, 430 (2000)

    Article  CAS  PubMed  Google Scholar 

  9. F. Bauer, V. Sauerland, H. Glasel, J. Macromol. Mater. Eng. 287, 546 (2002)

    Article  CAS  Google Scholar 

  10. S.A. Jenekhe, S. Yi, Adv. Mater. 12, 1274 (2000)

    Article  CAS  Google Scholar 

  11. E.K. Athanassiou, R.N. Grass, W. Stark, J. Nanotechnol. 17, 1668 (2006)

    Article  CAS  Google Scholar 

  12. L. Chen, D. Zhang, J. Chen, H. Zhou, H. Wan, Mater. Sci. Eng. A 415, 156 (2006)

    Article  CAS  Google Scholar 

  13. B. Wang, S. Chen, J. Nie, X. Zhu, RSC Adv 4, 27381 (2014)

    Article  CAS  Google Scholar 

  14. S. Yallappa, J. Manjanna, M.A. Sindhe, N.D. Satyanarayan, S.N. Pramod, K. Nagaraja, Acta A-Mol. Biomol. Spectrosc. 110, 108 (2013)

    Article  CAS  Google Scholar 

  15. J.N. Solanki, R. Sengupta, Z.V.P. Murthy, Solid State Sci. 12, 1560 (2010)

    Article  CAS  Google Scholar 

  16. M. Saito, K. Yasukawa, T. Umeda, Y. Aoi, Opt. Mater. 30, 1201 (2008)

    Article  CAS  Google Scholar 

  17. S. Pilli, P. Bhunia, S. Yan, R.J. LeBlanc, R.D. Tyagi, R.Y. Surampalli, Ultrason. Sonochem. 18, 11 (2011)

    Article  CAS  Google Scholar 

  18. V. Saez, T.J. Mason, Molecules 14, 4284 (2009)

    Article  CAS  PubMed  Google Scholar 

  19. J.H. Bang, K.S. Suslick, Adv. Mater. 22, 1039 (2010)

    Article  CAS  PubMed  Google Scholar 

  20. P. Lei, F. Wang, X. Gao, Y. Ding, S. Zhang, J. Zhao, S. Liu, M. Yang, J. Hazard. Mater. 227, 185 (2012)

    Article  CAS  PubMed  Google Scholar 

  21. A.Y. Mitrofanov, A.V. Murashkina, I. Martín-García, F. Alonso, I.P. Beletskaya, Catal. Sci. Technol. 7, 4401 (2017)

    Article  CAS  Google Scholar 

  22. D. Solairaj, P. Rameshthangam, P. Muthukumaran, J. Wilson, Int. J. Biol. Macromol. 101, 668 (2017)

    Article  CAS  PubMed  Google Scholar 

  23. M.M. Heravi, S. Sadjadi, H.A. Oskooie, R.H. Shoar, F.F. Bamoharram, Catal. Commun. 9(4), 504 (2008)

    Article  CAS  Google Scholar 

  24. A. Kudo, Y. Miseki, Chem. Soc. Rev. 38(1), 253 (2009)

    Article  CAS  PubMed  Google Scholar 

  25. M.A. Fox, M.T. Dulay, Chem. Rev. 93(1), 341 (1993)

    Article  CAS  Google Scholar 

  26. Sh..M. Kuo, Sh..J. Chang, Y.J. Wang, J. Polym. Res. 6(3), 191 (1999)

    Article  CAS  Google Scholar 

  27. H.E. Assender, A.H. Windle, Polymer 39, 4303 (1998)

    Article  CAS  Google Scholar 

  28. Y. Iwakura, Y. Imai, Y. Ogiwara, Makromol. Chem. 98, 1 (1966)

    Article  CAS  Google Scholar 

  29. M. Uchiyama, J. Polym. Sci. A 7, 1479 (1969)

    Article  Google Scholar 

  30. Y. Mwara, T. Yasunaga, H. Kubota, J. Appl. Polym. Sci. 19, 1119 (1975)

    Article  Google Scholar 

  31. P. Hyczkowski, J. Kapko, H. Polaczek, J. Appl. Polym. Sci. 20, 3215 (1976)

    Article  Google Scholar 

  32. S. Gonen, D.H. Kohn, J. Polym. Sci. Polym. Chem. Ed. 19, 2215 (1981)

    Article  CAS  Google Scholar 

  33. P. Molyneux, Water-Soluble Synthetic Polymers, vol. 1 (CRC Press, Florida, 1983)

    Google Scholar 

  34. T. Hirai, T. Asada, T. Suzuki, S. Hayashi, J. Appl. Polym. Sci. 38, 491 (1989)

    Article  CAS  Google Scholar 

  35. A. Singh, M.S.M. Rawat, RRPL 4(3), 81 (2013)

    Google Scholar 

  36. M.L. Hallensleben, Polyvinyl Compounds, Ullmann’s Encyclopedia of Industrial Chemistry. (Wiley, Weinheim, 2000)

    Google Scholar 

  37. F. Arranz, M. Sanchez-Chaves, Angew. Makmmol. Chem. 92, 121 (1980)

    Article  CAS  Google Scholar 

  38. Z.A. Urban, E.Y. Danilova, E.N. Kulikova, L.A. Vol’f, A.I. Meos, Y.K. Kirilenko, Zh. Prikl. Khim. 42, 966 (1969)

    CAS  Google Scholar 

  39. J. Mathew, M. Kodama, Polym. J 24, 31 (1992)

    Article  CAS  Google Scholar 

  40. M.K. Beliakova, A.A. Aly, F.A. Abdel Mohdy, Starch-Starke 56, 409 (2004)

    Article  CAS  Google Scholar 

  41. N.A. El-Sawy, M.H. Abo-Shosha, M.A. Abd El-Ghaffar, N.A. Ibrahim, Am. Dyestuff Rep. 82(10), 60 (1993)

    CAS  Google Scholar 

  42. N.A. El-Sawy, M.H. Abo-Shosha, N.A. El-, N.A. Sawy, Ibrahim, Am. Dyestuff Rep. 82(4), 39 (1993)

    Google Scholar 

  43. S. Mishra, A. Panda, B.C. Sing, J. Appl. Polym. Sci. 73, 677 (1999()

    Article  CAS  Google Scholar 

  44. A. Hebeish, H.M. Fahmy, M.H. Abo-Shosha, N.A. Ibrahim, Polym. Plast. Technol. Eng. 45, 309 (2006)

    Article  CAS  Google Scholar 

  45. A. Chowdhurry, M. Banerjee, J. Appl. Polymer Sci. 70, 523 (1998)

    Article  Google Scholar 

  46. A. Panda, B.C. Singh, Polym. Plast. Technol. Eng. 35(3), 487 (1996)

    Article  CAS  Google Scholar 

  47. A. Panda, B.C. Singhi, J. Tuberc. Res. Chem. 2(2), 53 (1995)

    CAS  Google Scholar 

  48. Y. Gotoh, R. Igarashi, Y. Ohkoshi, M. Nagura, K. Akamatsub, S. Dekib, J. Mater. Chem. 10, 2548 (2000)

    Article  CAS  Google Scholar 

  49. X. Xu, Y. Yin, X. Ge, H. Wu, Z. Zhang, Mater. Lett. 37, 354 (1998)

    Article  CAS  Google Scholar 

  50. H. Morawetz, Polym. Chem. 17(85), 442 (1955)

    CAS  Google Scholar 

  51. H.P. Gregor, L.B. Luttinger, E.M. Loebl, J. Phys. Chem. 59(4), 366 (1955)

    Article  CAS  Google Scholar 

  52. H.P. Gregor, L.B. Luttinger, E.M. Loebl, J. Phys. Chem. 59(1), 34 (1955)

    Article  CAS  Google Scholar 

  53. O.G. Marambio, GdelC. Pizarro, M. Jeria-Orell, M. Huerta, C. Olea-Azar, W.D. Habicher, Polym. Chem. 43(20), 4933 (2005)

    Article  CAS  Google Scholar 

  54. S. Noji, K. Yamaoka, Macromolecules 12(6), 1110 (1979)

    Article  CAS  Google Scholar 

  55. Z. Zhou, W. Xu, D. He, J. Fan, F. Yu, F. Ren, J. Appl. Polym. Sci. 103, 848 (2007)

    Article  CAS  Google Scholar 

  56. S.V. Caro, C.S. Paik Sung, E.W. Merrill, J. Appl. Polym. Sci. 20, 3241 (1976)

    Article  CAS  Google Scholar 

  57. A.E. Rheineck, J. Am. Oil Chem. Soc. 28, 456 (1951)

    Article  CAS  Google Scholar 

  58. T.M. Hammad, J.K. Salem, S. Kuhn, N.M. Abu, R. Hempelmann, J. Lumin. 157, 88 (2015)

    Article  CAS  Google Scholar 

  59. C.-Y. Loo, P.M. Young, W.-H. Lee, R. Cavaliere, C.B. Whitchurch, R. Rohanizadeh, Biofouling 30, 773 (2014)

    Article  CAS  PubMed  Google Scholar 

  60. F. Hajipour, M. saleh, J. Iran. Chem. Soc. 12, 1339 (2015)

    Article  CAS  Google Scholar 

  61. X. Qi, Z. Wang, S. Ma, L. Wu, S. Yang, J. Xu, Polymer 55, 1183 (2014)

    Article  CAS  Google Scholar 

  62. W.Q. Fan, A.R. Katritzky, in Comprehensive Heterocyclic Chemistry II, eds. by A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Elsevier Science, Oxford, 1996)

    Google Scholar 

  63. R. Huisgen, Angew. Chem. Int. Ed. Engl. 2, 565 (1963)

    Article  Google Scholar 

  64. T. Jin, M. Yan, Y. Yamamoto, Chem. Cat. Chem. 4, 1217 (2012)

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  66. J.E. Moses, A.D. Moorhouse, Chem. Soc. Rev. 36, 1249 (2007)

    Article  CAS  PubMed  Google Scholar 

  67. R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry, ed. by A. Padwa (Wiley, New York, 1984)

    Google Scholar 

  68. C.W. Torne, C. Christensen, M. Meldal, J. Org. Chem.. 67, 3057 (2002)

    Article  CAS  Google Scholar 

  69. V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596 (2002)

    Article  CAS  Google Scholar 

  70. H. Dehne, in Methoden de Organischen Chemie (Houben-Weyl), ed. by E. Schumann (Thieme, Stuttgart, 1994)

    Google Scholar 

  71. H. Wamhoff, in Comprehensive Heterocyclic Chemistry, ed. by A.R. Katritzky, C.W. Rees (Pergamon, Oxford, 1984)

    Google Scholar 

  72. R. Bohm, C. Karow, Pharmazie 36, 243 (1981)

    CAS  PubMed  Google Scholar 

  73. M.M. Heravi, H. Hamidi, V. Zadsirjan, Curr. Org. Synth. 11, 647 (2014)

    Article  CAS  Google Scholar 

  74. F. Palacios, A.M. Ochoa de Retana, J. Pagalday, J.M. Sanchez, Org. Prep. Proced. Int. 27, 603 (1995)

    Article  CAS  Google Scholar 

  75. D.J. Hlasta, J.H. Ackerman, J. Org. Chem. 59, 6184 (1994)

    Article  CAS  Google Scholar 

  76. W.L. Mock, T.A. Irra, J.P. Wepsiec, M. Adhya, J. Org. Chem. 54, 5302 (1989)

    Article  CAS  Google Scholar 

  77. W. Peng, Sh. Zhu, Synlett, 2003, 187 (2003)

    Google Scholar 

  78. S. Kamijo, T. Jin, Z. Huo, Y. Yamamoto, J. Am. Chem. Soc. 125, 7786 (2003)

    Article  CAS  PubMed  Google Scholar 

  79. P. Appukkuttan, W. Dehaen, V.V. Fokin, E. Van der Eycken, Org. Lett. 6, 4223 (2004)

    Article  CAS  PubMed  Google Scholar 

  80. M.M. Heravi, G. Rajabzadeh, F. Bamoharram, J. Mol. Catal. A 256, 238 (2006)

    Article  CAS  Google Scholar 

  81. M.M. Heravi, K. Bakhtiari, A. Fatehi, F. Bamoharram, Catal. Commun. 9, 289 (2008)

    Article  CAS  Google Scholar 

  82. M.M. Heravi, E. Hashemia, Y.S. Beheshtiha, S. Ahmadi, T. Hosseinnejad, J. Mol. Cat. A 394, 74 (2014)

    Article  CAS  Google Scholar 

  83. S. Khaghaninejad, M.M. Heravi, T. Hosseinnejad, H.A. Oskooie, M. Bakavoli, Res. Chem. Intermed. 42, 1593 (2016)

    Article  CAS  Google Scholar 

  84. M.M. Heravi, Kh Bakhtiari, Z. Daroogheha, F. Bamoharram, Catal. Commun. 8, 1991 (2007)

    Article  CAS  Google Scholar 

  85. M.M. Heravi, M. Khorasani, F. Derikvand, H.A. Oskoole, F. Bamoharram, Catal. Commun. 8, 1886 (2007)

    Article  CAS  Google Scholar 

  86. T. Hosseinnejad, Phys. Chem. Res. 1, 175 (2013)

    CAS  Google Scholar 

  87. V. Zadsirjan, M.M. Heravi, M. Tajbakhsh, H.A. Oskooie, M. Shiri, T. Hosseinnejad, Res. Chem. Intermed. 42, 6407 (2016)

    Article  CAS  Google Scholar 

  88. V. Zadsirjan, M.M. Heravi, M. Shiri, T. Hosseinnejad, S.A. Shintre, N.A. Koorbanally, Res. Chem. Intermed. 43, 2119 (2017)

    Article  CAS  Google Scholar 

  89. E. Hashemi, Y.S. Beheshtiha, Sh Ahmadi, M.M. Heravi, Trans. Met. Chem. 39, 593 (2014)

    Article  CAS  Google Scholar 

  90. A. Fazeli, H.A. Oskooie, Y.S. Beheshtiha, M.M. Heravi, F.M. Moghaddam, B.K. Foroushani, Z. Naturforsch. B 68, 391–396 (2013)

    Article  CAS  Google Scholar 

  91. M.M. Heravi, A. Fazeli, H.A. Oskooie, Y.S. Beheshtiha, H. Valizadeh, Synlett 20, 2927 (2012)

    Article  CAS  Google Scholar 

  92. M.M. Heravi, M. Vazin Fard, Z. Faghihi, Green Chem. Lett. Rev. 6, 282 (2013)

    Article  CAS  Google Scholar 

  93. F. Heravi, N. Mousavizadeh, M. Ghobadi, Tetrahedron Lett. 55, 1226 (2014)

    Article  CAS  Google Scholar 

  94. M.M. Heravi, M. Tamimi, H. Yahyavi, T. Hosseinnejad, Curr. Org. Chem. 20, 1591 (2016)

    Article  CAS  Google Scholar 

  95. T. Hosseinnejad, M.M. Heravi, R. Firouzi, J. Mol. Model. 19, 951 (2013)

    Article  CAS  PubMed  Google Scholar 

  96. T. Hosseinnejad, B. Fattahi, M.M. Heravi, J.Mol. Model. 21, 264 (2015)

    Article  CAS  PubMed  Google Scholar 

  97. M.M. Heravi, T. Hosseinnejad, N. Nazari, Can. J. Chem. 92, 530 (2017)

    Article  CAS  Google Scholar 

  98. R. Mirsafaei, M.M. Heravi, T. Hosseinnejad, S. Ahmadi, Chem. Pap. 70, 418 (2016)

    Article  CAS  Google Scholar 

  99. T. Hosseinnejad, S. Dehghanpour, A. Hosseinjani, Comput. Theor. Chem. 1004, 31 (2013)

    Article  CAS  Google Scholar 

  100. T. Hosseinnejad, T. Kazemi, Mol. Cryst. Liq. Cryst. 637, 53 (2016)

    Article  CAS  Google Scholar 

  101. J. Masa, A. Zhao, W. Xia, Zh Sun, B. Mei, M. Muhler, W. Schuhmann, Electrochem. Commun. 34, 113 (2013)

    Article  CAS  Google Scholar 

  102. W. Oberhauser, C. Evangelisti, R.P. Jumde, G. Petrucci, M. Bartoli, M. Frediani, M. Mannini, L. Capozzoli, E. Passaglia, L. Rosi, J. Catal. 330, 187 (2015)

    Article  CAS  Google Scholar 

  103. S. Karahan, M. Zahmakıran, S. Ozkar, Chem. Commun. 48, 1180 (2012)

    Article  CAS  Google Scholar 

  104. G. Giachi, W. Oberhauser, M. Frediani, E. Passaglia, L. Capozzoli, L. Rosi, J. Polym. Sci. A 51, 2518 (2013)

    Article  CAS  Google Scholar 

  105. R.P. Jumde, M. Marelli, N. Scotti, A. Mandoli, R. Psaro, C. Evangelisti, J. Mol. Catal. A 414, 55 (2016)

    Article  CAS  Google Scholar 

  106. L. Bellamy, The Infrared Spectra of Complex Molecules (Chapman and Hall, London, 1975)

    Book  Google Scholar 

  107. A.D. Becke, J. Chem. Phys. 98, 1372 (1993)

    Article  CAS  Google Scholar 

  108. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988)

    Article  CAS  Google Scholar 

  109. H.N. Wu, J. Wang, W. Li, N.N. Ma, T. Zhang, S.Q. Shi, L.K. Yan, Z.M. Su, Comput. Theor. Chem. 1089, 28 (2016)

    Article  CAS  Google Scholar 

  110. Y. Zhao, D.G. Truhlar, J. Chem. Theory Comput. 4, 1849 (2008)

    Article  CAS  PubMed  Google Scholar 

  111. P.J. Hay, W.R. Wadt, J. Chem. Phys. 82, 284 (1985)

    Article  Google Scholar 

  112. P.J. Hay, W.R. Wadt, J. Chem. Phys. 82, 270 (1985)

    Article  CAS  Google Scholar 

  113. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S. Su, J. Comput. Chem. 14, 1347 (1993)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are thankful for partial financial supports from Alzahra research Council. M.M.H is grateful to Iran National Science Foundation (INSF) for partial financial support under granted individual research chair.

Author information

Authors and Affiliations

  1. Department of Chemistry, Alzahra University, Vanak, Tehran, Iran

    Afsaneh Taheri Kal-Kashvandi, Majid M. Heravi & Tayebeh Hosseinnejad

  2. Iran Polymer and Petrochemical Institute, Tehran, Iran

    Shervin Ahmadi

Authors
  1. Afsaneh Taheri Kal-Kashvandi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Majid M. Heravi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shervin Ahmadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tayebeh Hosseinnejad
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Majid M. Heravi.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Taheri Kal-Kashvandi, A., M. Heravi, M., Ahmadi, S. et al. Copper Nanoparticles in Polyvinyl Alcohol–Acrylic Acid Matrix: An Efficient Heterogeneous Catalyst for the Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via Click Reaction. J Inorg Organomet Polym 28, 1457–1467 (2018). https://doi.org/10.1007/s10904-018-0811-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-018-0811-1

Keywords

  • Heterogeneous catalysis
  • Copper nanoparticles
  • Polyvinyl alcohol
  • Acrylic acid
  • Click reaction
  • Density functional theory
  • Frontier molecular orbital analysis