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Green Synthesis of Pd Nanoparticles Mediated by Thymbra Spicata Leaves Extract and Its Application as a Recyclable Nanocatalyst for Reduction of 4-Nitrophenol and Suzuki Reactions

  • Sepideh Tanreh
  • Sara Hallajian
  • Yasaman Pourdakheli Hamedani
  • Pooneh Nazari
  • Kiana Darvishi
  • Malak Hekmati
Article
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Abstract

A simple and ecological pathway for the procurement of palladium nanoparticles (Pd NPs) was developed, applying the non-toxic and sustainable natural extract from Thymbra spicata leaves as the reducing, stabilizing and capping agent. UV–vis spectroscopy, X-ray diffraction, Fourier transformed infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy and energy dispersive X-ray spectroscopy, were utilized to classify the synthesized Pd NPs@Thymbra spicata catalyst. The Pd NPs@Thymbra spicata demonstrated excellent behavior as a reusable nanocatalyst in Suzuki–Miyaura cross-coupling reactions and reduction of 4-nitrophenol at room temperature. The nanocatalyst was reused in numerous runs with excellent product yields and without any significant deduction in catalytic behavior.

Graphical Abstract

Keywords

Pd nanoparticles Thymbra spicata Green chemistry 4-Nitrophenol Suzuki 
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Notes

Acknowledgements

We are thankful to Department of Pharmaceutical Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran, for partial support of this work.

References

  1. 1.
    S. Iravani, Green Chem. 13, 2638 (2011)CrossRefGoogle Scholar
  2. 2.
    H. Zhu, M.L. Du, M. Zou, C. Xu, Y.Q. Fu, Dalton Trans. 41, 10465 (2012)CrossRefGoogle Scholar
  3. 3.
    P. Raveendran, J. Fu, S.L. Wallen, J. Am. Chem. Soc. 125, 13940 (2003)CrossRefGoogle Scholar
  4. 4.
    S.B. Kalidindi, B.R. Jagirdar, ChemSusChem 5, 65 (2012)CrossRefGoogle Scholar
  5. 5.
    R.S. Varma, Curr. Opin. Chem. Eng 1, 123 (2012)CrossRefGoogle Scholar
  6. 6.
    B. Nakhjavan, M.N. Tahir, F. Natalio, H. Gao, K. Schneider, T. Schladt, I. Ament, R. Branscheid, S. Weber, U. Kolb, C. Sönnichsen, L.M. Schreiber, W. Tremel, J. Mater. Chem 21, 8605 (2011)CrossRefGoogle Scholar
  7. 7.
    M.N. Tahir, F. Natalio, M.A. Cambaz, M. Panthöfer, R. Branscheid, U. Kolb, W. Tremel, Nanoscale 5, 9944 (2013)CrossRefGoogle Scholar
  8. 8.
    J.R. Peralta-Videa, L. Zhao, M.L. Lopez-Moreno, G. Rosa, J. Hong, J.L. Gardea-Torresdey, J. Hazard. Mater. 186, 1 (2011)CrossRefGoogle Scholar
  9. 9.
    K. Byrappa, S. Ohara, T. Adschiri, Adv. Drug Deliv. Rev. 60, 299 (2008)CrossRefGoogle Scholar
  10. 10.
    J.M. Campelo, D. Luna, R. Luque, J.M. Marinas, A.A. Romero, ChemSusChem. 2, 18 (2009)CrossRefGoogle Scholar
  11. 11.
    S.V. Otari, R.M. Patil, S.R. Waghmare, J. Ghosha, SH. Pawar, Dalton Trans. 42, 9966 (2013)CrossRefGoogle Scholar
  12. 12.
    T. Hennebel, S.D. Corte, W. Verstraete, N. Boon, Curr. Opin. Biotechnol. 23, 555 (2012)CrossRefGoogle Scholar
  13. 13.
    M.N. Tahir, F. Natalio, H.A. Therese, A. Yella, N. Mets, M.R. Shah, E. Mugnaioli, R. Berger, P. Theato, H.C. Schroeder, W.E.G. Mueller, W. Tremel, Adv. Funct. Mater. 19, 285 (2009)CrossRefGoogle Scholar
  14. 14.
    M.N. Tahir, P. Théato, W.E.G. Müller, H.C. Schröder, A. Boreijko, S. Faiß, A. Janshoff, J. Huth, W. Tremel, Chem. Commun. 44 5533 (2005)CrossRefGoogle Scholar
  15. 15.
    M.S. Akhtar, J. Panwar, Y.S. Yun, ACS Sustain. Chem. Eng 1, 591 (2013)CrossRefGoogle Scholar
  16. 16.
    A.K. Mittal, Y. Chisti, U.C. Banerjee, Biotechnol. Adv. 31, 346 (2013)CrossRefGoogle Scholar
  17. 17.
    H. Veisi, S. Hemmati, H. Shirvani, H. Veisi, Appl. Organomet. Chem. 30, 387 (2016)CrossRefGoogle Scholar
  18. 18.
    P.P. Gan, S.F.Y. Li, Rev. Environ. Sci. Biotechnol. 11, 169 (2012)CrossRefGoogle Scholar
  19. 19.
    F. Coccia, L. Tonucci, D. Bosco, M. Bressan, N. d’Alessandro, Green Chem. 14, 1073 (2012)CrossRefGoogle Scholar
  20. 20.
    F. Cheng, J.W. Betts, S.M. Kelly, J. Schaller, T. Heinze, Green Chem. 15, 989 (2013)CrossRefGoogle Scholar
  21. 21.
    K.M. Kumar, B.K. Mandal, S.K. Tammina, RSC Adv. 3, 4033 (2013)CrossRefGoogle Scholar
  22. 22.
    G. Zhang, M. Du, Q. Li, X. Li, J. Huang, X. Jiang, D. Sun, RSC Adv. 3, 1878 (2013)CrossRefGoogle Scholar
  23. 23.
    H.J. Lee, J.Y. Song, B.S. Kim, J. Chem. Technol. Biotechnol. 88, 1971 (2013)Google Scholar
  24. 24.
    P. Dauthal, M. Mukhopadhyay, Ind. Eng. Chem. Res. 51, 13014 (2012)CrossRefGoogle Scholar
  25. 25.
    Z. Shen, G. Han, X. Wang, J. Luo, R. Sun, J. Mater. Chem. B 5, 1155 (2017)CrossRefGoogle Scholar
  26. 26.
    G. Han, X. Li, J. Li, X. Wang, Y.S. Zhang, R. Sun, ACS Omega 2, 4938 (2017)CrossRefGoogle Scholar
  27. 27.
    Z. Shen, G. Han, C. Liu, X. Wang, R. Sun, J. Alloys Compd. 686, 82 (2016)CrossRefGoogle Scholar
  28. 28.
    K.D. Arunachalam, S.K. Annamalai, S. Hari, Int. J. Nanomed. 8, 1307 (2013)CrossRefGoogle Scholar
  29. 29.
    F. Zaera, Chem. Soc. Rev. 42, 2746 (2013)CrossRefGoogle Scholar
  30. 30.
    G.C. Fortman, S.P. Nolan, Chem. Soc. Rev. 40, 5151 (2011)CrossRefGoogle Scholar
  31. 31.
    A.J. Hickman, M.S. Sanford, Nature 484, 177 (2012)CrossRefGoogle Scholar
  32. 32.
    R. Ghorbani-Vaghei, S. Hemmati, M. Hashemi, H. Veisi, C. R. Chimie 18, 636 (2015)CrossRefGoogle Scholar
  33. 33.
    M. Pirhayati, H. Veisi, A. Kakanejadifard, RSC Adv. 6, 27252 (2016)CrossRefGoogle Scholar
  34. 34.
    B. Abbas Khakiani, K. Pourshamsian, H. Veisi, Appl. Organomet. Chem. 29, 259 (2015)CrossRefGoogle Scholar
  35. 35.
    M. Zhu, Y. Wang, C. Wang, W. Li, G. Diao, Catal. Sci. Technol. 3, 952 (2013)CrossRefGoogle Scholar
  36. 36.
    Y. Lu, H. Zhu, W. Li, B. Hu, S. Yu, J. Mater. Chem. A 1, 3783 (2013)CrossRefGoogle Scholar
  37. 37.
    S. Santra, P. Ranjan, P. Bera, P. Ghosh, S. K. Mandal, RSC Adv. 2, 7523 (2012)CrossRefGoogle Scholar
  38. 38.
    S. Deng, J. Lei, Y. Huang, X. Yao, L. Ding, H. Ju, Chem. Commun. 48, 9159 (2012)CrossRefGoogle Scholar
  39. 39.
    H. Itoh, H. Maeda, S. Yamada, Y. Hori, ChemCatChem 4, 1737 (2012)CrossRefGoogle Scholar
  40. 40.
    S. Cacchi, E. Caponetti, M.A. Casadei, A.D. Giulio, G. Fabrizi, G. Forte, A. Goggiamani, S. Moreno, P. Paolicelli, F. Petrucci, A. Prastaro, M.L. Saladino, Green Chem. 14, 317 (2012)CrossRefGoogle Scholar
  41. 41.
    H. Veisi, R. Masti, D. Kordestani, M. Safaei, O. Sahin, J. Mol. Catal. A 385, 61 (2014)CrossRefGoogle Scholar
  42. 42.
    M.P. Lorenzo, J. Phys. Chem. Lett. 3, 167 (2012)CrossRefGoogle Scholar
  43. 43.
    H. Veisi, M. Ghadermazi, A. Naderi, Appl. Organomet. Chem. 30, 341 (2016)CrossRefGoogle Scholar
  44. 44.
    H. Veisi, M. Pirhayati, A. Kakanejadifard, Tetrahedron Lett. 58, 4269 (2017)CrossRefGoogle Scholar
  45. 45.
    J. Cookson, Platinum Met. Rev. 56, 83 (2012)CrossRefGoogle Scholar
  46. 46.
    L. Liang, A.K. Diallo, L. Salmon, J. Ruiz, D. Astruc, Eur. J. Inorg. Chem. 17, 2950 (2012)CrossRefGoogle Scholar
  47. 47.
    D.J. Gavia, Y.S. Shon, Langmuir 28, 14502 (2012)CrossRefGoogle Scholar
  48. 48.
    W. Zhang, X. Xiao, T. An, Z. Song, J. Fu, G. Sheng, M. Cui, J. Chem. Technol. Biotechnol. 78, 788 (2003)CrossRefGoogle Scholar
  49. 49.
    N. Mand, D.G. Crosby, J. Agric, Food Chem. 22, 849 (1974)CrossRefGoogle Scholar
  50. 50.
    Y.-T. Woo, D.Y. Lai, Aromatic Amino and Nitro-Amino Compounds and Their Halogenated Derivatives: Patty’s Toxicology (Wiley, New York, 2001)Google Scholar
  51. 51.
    Z.M. Wang, C.L. Xu, G.Q. Gao, X. Li, RSC Adv. 4, 13644 (2014)CrossRefGoogle Scholar
  52. 52.
    X.M. Chen, Z.X. Cai, X. Chen, M. Oyama, J. Mater. Chem. A 2, 5668 (2014)CrossRefGoogle Scholar
  53. 53.
    Z.F. Jiang, D.L. Jiang, A.M.S. Hossain, K. Qian, J.M. Xie, Z.F. Jiang, D.L. Jiang, A.M.S. Hossain, K. Qian, J.M. Xie, Phys. Chem. Chem. Phys. 17, 2550 (2015)CrossRefGoogle Scholar
  54. 54.
    V. Evangelista, B. Acosta, S. Miridonov, E. Smolentseva, S. Fuentes, A. Simakov, Appl. Catal. B 166–167, 518 (2015)CrossRefGoogle Scholar
  55. 55.
    Z.P. Dong, X. Le, C.X. Dong, W. Zhang, X.L. Li, J.T. Ma, Appl. Catal. B 162, 372 (2015)CrossRefGoogle Scholar
  56. 56.
    H.J.D. Dorman, S.G. Deans, J. Appl. Microbiol. 88, 308 (2000)CrossRefGoogle Scholar
  57. 57.
    A. Shtayeh, Z. Yaniv, J. Mahajna, J. Ethnopharmacol. 73, 221 (2000)CrossRefGoogle Scholar
  58. 58.
    G. Tümen, N. Ermin, T. Özek, M. Kürkçüoğlu, K.H.C. Başer, J. Essent. Oil Res. 6, 463 (1994)CrossRefGoogle Scholar
  59. 59.
    H. Veisi, A.R. Faraji, S. Hemmati, A. Gil, Appl. Organomet. Chem. 29, 517 (2015)CrossRefGoogle Scholar
  60. 60.
    H. Veisi, R. Ghorbani-Vaghei, S. Hemmati, M. Haji Aliani, T. Ozturk, Appl. Organomet. Chem 29, 26 (2015)CrossRefGoogle Scholar
  61. 61.
    S. Lebaschi, M. Hekmati, H. Veisi, J. Colloid. Interface Sci. 485, 223 (2017)CrossRefGoogle Scholar
  62. 62.
    H. Veisi, A. Rashtiani, V. Barjasteh, Appl. Organomet. Chem. 30, 231 (2016)CrossRefGoogle Scholar
  63. 63.
    . H. Veisi, N. Hajimoradian Nasrabadi, P. Mohammadi, Appl. Organomet. Chem. 30, 890 (2016)CrossRefGoogle Scholar
  64. 64.
    S.A. Aromal, V.K. Vidhu, D. Philip, Spectrochim. Acta A 85, 99 (2012)CrossRefGoogle Scholar
  65. 65.
    S.L. Cumberland, G.F. Strouse, Langmuir 18, 269 (2002)CrossRefGoogle Scholar
  66. 66.
    D.S. Sheny, J. Mathew, D. Philip, Spectrochim. Acta A 79, 254 (2011)CrossRefGoogle Scholar
  67. 67.
    D. Philip, C. Unni, Physica E 43, 1318 (2011)CrossRefGoogle Scholar
  68. 68.
    H. Kostova, S.C. Joe, J. Pinzaru, Optoelectron. Biomed. Mater. 1, 188 (2009)Google Scholar
  69. 69.
    H. Veisi, A. Khazaei, M. Safaei, D. Kordestani, J. Mol. Catal. A 382, 106 (2014)CrossRefGoogle Scholar
  70. 70.
    F. Bonyasi, M. Hekmati, H. Veisi, J. Colloid. Interface Sci. 496, 177 (2017)CrossRefGoogle Scholar
  71. 71.
    H. Veisi, A. Sedrpoushan, B. Maleki, M. Hekmati, M. Heidari, S. Hemmati, Appl. Organomet. Chem. 29, 834 (2015)CrossRefGoogle Scholar
  72. 72.
    H. Veisi, M. Hekmati, S. Hemmati, J. Heterocyclic. Chem 54, 1630 (2017)CrossRefGoogle Scholar
  73. 73.
    M. Hajighorbani, M. Hekmati, RSC Adv. 6, 88916 (2016)CrossRefGoogle Scholar
  74. 74.
    F. Heidari, M. Hekmati, H. Veisi, J. Colloid Interface Sci. 501, 175 (2017)CrossRefGoogle Scholar
  75. 75.
    M.H. Rashid, T.K. Mandal, J. Phys. Chem. C 111, 16750 (2007)CrossRefGoogle Scholar
  76. 76.
    N. Sahiner, H. Ozay, O. Ozay, N. Aktas, Appl. Catal. A 385, 201 (2010)CrossRefGoogle Scholar
  77. 77.
    N. Sahiner, H. Ozay, O. Ozay, N. Aktas, Appl. Catal. B 101, 137 (2010)CrossRefGoogle Scholar
  78. 78.
    N. Sahiner, O. Ozay, Curr. Nanosci. 8, 367 (2012)CrossRefGoogle Scholar
  79. 79.
    F.R. Fortea-Pérez, I. Schlegel, M. Julve, D. Armentano, G. De Munno, S.E. Stiriba, J. Organomet. Chem. 743, 102 (2013)CrossRefGoogle Scholar
  80. 80.
    Q.X. Liu, W. Zhang, X.J. Zhao, Z.X. Zhao, M.C. Shi, X.G. Wang, Eur. J. Org. Chem. 2013, 1253 (2013)CrossRefGoogle Scholar
  81. 81.
    M. Ghiaci, M. Zargani, F. Moeinpour, A. khojastehnezhad, Appl. Organomet. Chem. 28, 589 (2014)CrossRefGoogle Scholar
  82. 82.
    V.I. de Paula, C.A. Sato, R. Buffon, J. Braz. Chem. Soc. 23, 258 (2012)Google Scholar
  83. 83.
    S.M. Shakil Hussain, M.B. Ibrahim, A. Fazal, R. Suleiman, M. Fettouhi, B. El Ali, Polyhedron 70, 39 (2014)CrossRefGoogle Scholar
  84. 84.
    S. Sobhani, M.S. Ghasemzadeh, M. Honarmand, F. Zarifi, RSC Adv. 4, 44166 (2014)CrossRefGoogle Scholar
  85. 85.
    S. Sobhani, F. Zarifi, Chin. J. Catal. 36 555 (2015)CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Sepideh Tanreh
    • 1
  • Sara Hallajian
    • 1
    • 2
  • Yasaman Pourdakheli Hamedani
    • 1
  • Pooneh Nazari
    • 1
  • Kiana Darvishi
    • 1
  • Malak Hekmati
    • 1
    • 2
  1. 1.Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical ChemistryPharmaceutical Sciences Branch, Islamic Azad University, (IAUPS)TehranIran
  2. 2.Young Researchers & elite ClubPharmaceutical Sciences Branch, Islamic Azad UniversityTehranIran

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