화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.60, 114-124, April, 2018
Fe3O4/SiO2 nanoparticles coated with polydopamine as a novel magnetite reductant and stabilizer sorbent for palladium ions: Synthetic application of Fe3O4/SiO2@PDA/Pd for reduction of 4-nitrophenol and Suzuki reactions
E-mail:
Polydopamine (PDA)-coated Fe3O4/SiO2 nanoparticles (Fe3O4/SiO2@PDA) were synthesized through a simple and green procedure. In this study, for the first time, successful deposition of Pd nanoparticles is described by using Fe3O4/SiO2@PDA as a magnetic reducing and stabilizing agent. In this approach, palladium ions were adsorbed on Fe3O4/SiO2@PDA surfaces by immersing the PDA-coated Fe3O4/SiO2 nanoparticles into a palladium plating bath. Then, they were reduced in situ to palladium nanoparticles by the help of PDA’s N-containing groups and reducing ability. The structure, morphology and physicochemical properties of the synthesized particles were characterized by different analytical techniques such as high resolution transmission electron microscopy (HRTEM), field emission scanning electron microscope (FESEM), energy-dispersive X-ray spectroscopy (EDS), wavelength-dispersive X-ray spectroscopy (WDX), X-ray diffraction analysis (XRD), vibrating sample magnetometer (VSM), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma (ICP) and FT-IR spectroscopy. Fe3O4/ SiO2@PDA/Pd nanoparticles illustrated high catalytic activity as a recyclable nanocatalyst in Suzuki. Miyaura cross-coupling reactions and reduction of 4-nitrophenol (4-NP), at room temperature. Furthermore, recovery and multiple reuse of the catalyst revealed no detectable activity loss.
  1. Ahn JH, Kim HS, Lee KJ, Jeon S, Kang SJ, Sun Y, Nuzzo RG, Rogers JA, Science, 314, 1754 (2006)
  2. Alivisatos P, Nat. Biotechnol., 22, 47 (2004)
  3. Langer R, Science, 293, 58 (2001)
  4. Lee BP, Messersmith PB, Israelachvili JN, Waite JH, Ann. Rev. Mater. Res., 41, 99 (2011)
  5. Lee H, Dellatore SM, Miller WM, Messersmith PB, Science, 318, 426 (2007)
  6. Lee H, Lee BP, Messersmith PB, Nature, 448, 338 (2007)
  7. Zhang WB, Xiao XM, An TC, Song ZG, Fu JM, Sheng GY, Cui MC, J. Chem. Technol. Biotechnol., 78(7), 788 (2003)
  8. Mand N, Crosby DG, J. Agric. Food Chem., 22, 849 (1974)
  9. Woo YT, Lai DY, Aromatic Amino and Nitro-Amino Compounds and Their Halogenated Derivatives. Patty’s Toxicology, Wiley, New York, 2001.
  10. Wang ZM, Xu CL, Gao GQ, Li X, RSC Adv., 4, 13644 (2014)
  11. Chen XM, Cai ZX, Chen X, Oyama M, J. Mater. Chem. A, 2, 5668 (2014)
  12. Jiang JF, Jiang DL, Hossain AMS, Qian K, Xie JM, Jiang ZF, Jiang DL, Hossain AMS, Qian K, Xie JM, Phys. Chem. Chem. Phys., 17, 2550 (2015)
  13. Evangelista V, Acosta B, Miridonov S, Smolentseva E, Fuentes S, Simakov A, Appl. Catal. B: Environ., 166-167, 518 (2015)
  14. Dong ZP, Le XD, Dong CX, Zhang W, Li XL, Ma JT, Appl. Catal. B: Environ., 162, 372 (2015)
  15. (a)Suzuki A, Diederich F, Stang PJ, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 49 (1998)., (b)Miyaura N, Suzuki A, Chem. Rev., 95, 2457 (1995).,(c)Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M, Chem. Rev., 102, 1359 (2002)., (d)Kirchhoff JH, Netherton MR, Hills ID, Fu GC, J. Am. Chem. Soc., 124, 13662 (2002)., (e)Dreher SD, Lim SE, Sandrock DL, Molander GA, J. Org. Chem., 74, 3626 (2009).
  16. (a)Markham A, Goa KL, Drugs, 54, 299 (1997)., (b)Capdeville R, Buchdunger E, Zimmermann J, A. Matter, Nat. Rev. Drug Discov., 1, 493 (2002).
  17. Tomori H, Fox JM, Buchwald SL, J. Org. Chem., 65, 5334 (2000)
  18. Kertesz M, Choi CH, Yang SJ, Chem. Rev., 105(10), 3448 (2005)
  19. (a)Lightowler S, Hird M, Chem. Mater., 17, 5538 (2005).,(b)Zhan X, Wang S, Liu Y, Wu X, Zhu D, Chem. Mater., 15, 1963 (2003).
  20. (a)Wolfe JP, Singer RA, Yang BH, Buchwald SL, J. Am. Chem. Soc., 122, 4020 (2000)., (b)Wolfe JP, Buchwald SL, Angew. Chem. Int. Ed., 38, 2413 (1999). (c)Grasa GA, Hillier AC, Nolan SP, Org. Lett., 3 , 1077 (2001)., (d)Lebaschi S, Hekmati M, Veisi H, J. Colloid Interface Sci., 485, 223 (2017). (e)Veisi H, Ghadermazi M, Naderi A, Appl. Organomet. Chem., 30, 341 (2016).
  21. Cozzi F, Adv. Synth. Catal., 348, 1367 (2006)
  22. (a)Bis A, Zecca M, Basato M, J. Mol. Catal. A Chem., 173, 249 (2001)., (b)Horniakova J, Raja T, Kubota Y, Sugi Y, J. Mol. Catal. A Chem., 217, 73 (2004)., (c)Yu K, Sommer W, Richardson JM, Weck M, Jones CW, Adv. Synth. Catal., 347, 161 (2005).
  23. Shylesh S, Schunemann V, Thiel WR, Angew. Chem.-Int. Edit., 49, 3428 (2010)
  24. (a)Wang Z, Xiao P, Shen B, He N, Colloids Surf. A, 276, 116 (2006)., (b)Schatz A, Hager M, Reiser O, Adv. Funct. Mater., 19, 2109 (2009). (c)Wittmann S, Schatz A, Grass RN, Stark WJ, Reiser O, Angew. Chem. Int. Ed. Engl., 49, 1867 (2010)., (d)Mondal J, Sen T, Bhaumik A, Dalton Trans., 41, 6173 (2012)., (e) Jin X, Zhang K, Sun J, Wang J, Dong Z, Li R, Catal. Commun., 26 , 199 (2012).,( f)Ma JM, Yang H, Li S, Ren R, Li J, Zhang X, Ma J, RSC Adv., 5, 97520 (2015)., (g)Gomez-Martinez M, Buxaderas E, Pastor IM, Alonso DA, J. Mol. Catal. A Chem., 404-405, 1 (2015).
  25. (a)Veisi H, Taheri S, Hemmati S, Green Chem., 18, 6337 (2016)., (b)Baeza A, Guillena G, Ramon DJ, ChemCatChem, 8, 49 (2016).,(c)Zhang L, He Y, Yang X, Yuan H, Du Z, Wu Y, Chem. Eng. J., 278, 129 (2015).,(d)Heidari F, Hekmati M, Veisi H, J. Colloid Interface Sci., 501, 175 (2017). (e)Kainz QM, Linhardt R, Grass RN, Vile G, Perez-Ramirez J, Stark WJ, Reiser O, Adv. Funct. Mater., 24, 2020 (2014).,(f)Nehlig E, Waggeh B, Millot N, Lalatonne Y, Motte L, Guenin E, Dalton Trans., 44, 501 (2015).
  26. (a)Lin YS, Haynes CL, Chem. Mater., 21, 3979 (2009)., (b)Deng Y, Cai Y, Sun Z, Liu J, Liu C, Wei J, Li W, Liu C, Wang Y, Zhao D, J. Am. Chem. Soc., 132, 8466 (2010).,(c)Veisi H, Pirhayati M, Kakanejadifard A, Tetrahedron Lett., 58, 4269 (2017)., (d)Sharma RK, Dutta S, Sharma S, Zboril R, Varma RS, Gawande MB, Green Chem., 18, 3184 (2016)., (e)Cano R, Ramon DJ, Yus M, Tetrahedron, 67, 5432 (2011)., (f)Dubey AV, Kumar AV, RSC Adv., 6, 4684 (2016)., (g)Cano R, Perez JM, Ramon DJ, McGlacken GP, Tetrahedron, 72, 1043 (2016)., (h)Pirhayati M, Veisi H, Kakanejadifard A, RSC Adv., 6, 27252 (2016)., (i)Khakiani BA, Pourshamsian K, Veisi H, Appl. Organomet. Chem., 29, 259 (2015).
  27. Aguilar-Arteaga K, Rodriguez JA, Barrado E, Anal. Chim. Acta, 674, 157 (2010)
  28. (a)Mazur M, Barras A, Kuncser V, Galatanu A, Zaitzev V, Turcheniuk KV, Woisel P, Lyskawa J, Laure W, Siriwardena A, Boukherroub R, Szunerits S, Nanoscale, 5, 2692 (2013)., (b)Bagtash M, Yamini Y, Tahmasebi E, Zolgharnein J, Dalirnasab Z, Microchim. Acta, 183, 449 (2016).
  29. (a)Veisi H, Gholami J, Ueda H, Mohammadi P, Noroozi M, J. Mol. Catal. A Chem., 396, 216 (2015)., (b)Veisi H, Hamelian M, Hemmati S, J. Mol. Catal. A: Chem., 395, 25 (2014)., (c)Veisi H, Sedrpoushan A, Maleki B, Hekmati M, Heidari M, Hemmati S, Appl. Organomet. Chem., 29, 517 (2015)., (d)Veisi H, Faraji AR, Hemmati S, Gil A, Appl. Organomet. Chem., 29, 517 (2015)., (e)Veisi H, Morakabati N, New J. Chem., 39, 2901 (2015)., (f)Bonyasi F, Hekmati M, Veisi H, J. Colloid Interface Sci., 496, 177 (2017)., (g)Veisi H, Masti R, Kordestani D, Safaei M, Sahin O, J. Mol. Catal. A: Chem., 385, 61 (2014)., (h)Veisi H, Hemmati S, Javaheri H, Tetrahedron Lett., 58, 3155 (2017)., (i)Veisi H, Maleki B, Hamelian M, Ashrafi SS, RSC Adv., 5, 6365 (2015).
  30. Ganguly A, Bhowmick AK, Nanoscale Res. Lett., 1, 36 (2008)
  31. Quang DV, Lee JE, Kim JK, Kim YN, Shao GN, Kim HT, Powder Technol., 2535, 221 (2013)
  32. Fotoohi B, Mercier L, Hydrometallurgy, 156, 28 (2015)
  33. Rao ZM, Wu TH, Peng SY, Acta Phys. Chim. Sin3, 11, 395 (1995)
  34. (a)Lee H, Dellatore SM, Miller WM, Messersmith PB, Science, 318, 426 (2007)., (b)Ye Q, Zhou F, Liu W, Chem. Soc. Rev., 40, 4244 (2011).
  35. Sun J, Fu Y, He G, Sun X, Wang X, Catal. Sci. Technol., 4, 1742 (2014)
  36. (a)Li XM, Zhang SL, Kulinich SA, Liu YL, Zeng HB, Sci. Rep., 4, 4976 (2014)., (b)Liu S, Tian J, Wang L, Zhang Y, Qin X, Luo Y, Asiri AM, Al-Youbi AO, Sun XO, Adv. Mater., 24, 2037 (2012).
  37. Schmid G, Chem. Rev., 92, 1709 (1992)
  38. Zhu YH, Shen JH, Zhou KF, Chen C, Yang XL, Li CZ, J. Phys. Chem. C, 115, 1614 (2011)
  39. Veisi H, Hajimoradi N, Mohammadi P, Appl. Organomet. Chem., 30, 890 (2016)
  40. Sreedhar B, Devi DK, Yada D, Catal. Commun., 12, 1009 (2011)
  41. Layek K, Kantam ML, Shirai M, Nishio-Hamane D, Sasaki T, Maheswaran H, Green Chem., 14, 3164 (2012)
  42. Kalbasi RJ, Nourbakhsh AA, Babaknezhad F, Catal. Commun., 12, 955 (2011)
  43. Rostami-Vartooni A, Nasrollahzadeh M, Alizadeh M, J. Colloid Interface Sci., 470, 268 (2016)
  44. Atarod M, Nasrollahzadeh M, Sajadi SM, J. Colloid Interface Sci., 462, 272 (2016)
  45. Shil AK, Sharma D, Guha NR, Das P, Tetrahedron Lett., 53, 4858 (2012)
  46. Wang P, Zhang F, Long Y, Xie M, Li R, Ma J, Catal. Sci. Technol., 3, 1618 (2013)
  47. Fortea-Perez FR, Schlegel I, Julve M, Armentano D, De Munno G, Stiriba SE, J. Organomet. Chem., 743, 102 (2013)
  48. Liu QX, Zhang W, Zhao XJ, Zhao ZX, Shi MC, Wang XG, Eur. J. Org. Chem., 2013, 1253 (2013)
  49. Ghiaci M, Zargani M, Moeinpour F, Khojastehnezhad A, Appl. Organomet. Chem., 28, 589 (2014)
  50. de Paula VI, Sato CA, Buffon R, J. Braz. Chem. Soc., 23, 258 (2012)
  51. Shakil Hussain SM, Ibrahim MB, Fazal A, Suleiman R, Fettouhi M, Ali BE, Polyhedron, 70, 39 (2014)
  52. Sobhani S, Ghasemzadeh MS, Honarmand M, Zarifi F, RSC Adv., 4, 44166 (2014)
  53. Sobhani S, Zarifi F, Chin. J. Catal., 555 (2015).