Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Synthesis and characterization of a novel Schiff base polyamide ligand and its copper(II) complex for comparative removal of Pb(II) ions from aqueous solutions

  • 22 Accesses


A dicarboxylic acid Schiff base ligand was synthesized via condensation of 2-hydroxybenzaldehyde with 5-aminoisophthalic acid. The derived monomer was reacted with 4,4′-diaminodiphenyl ether and triphenyl phosphite (TPP) in tetrabutylammonium bromide (TBAB) molten ionic liquid as a green solvent to form an aromatic polyamide with a moderate yield (71%) and inherent viscosity (0.2 dL g−1). The nanostructured copper(II)/polyamide complex was then prepared. The structure, optical properties, and morphology of the compositions were confirmed by FT-IR, −1H-NMR, elemental analysis, UV-Vis, powder X-ray diffraction (XRD), thermogravimetric analysis (TGA) and field emission scanning electron microscopy (FE-SEM). The polyamide ligand and its nanostructured complex were comparatively applied in the elimination of Pb(II) ions from aqueous solutions.

Synthesis and characterization of a novel Schiff base polyamide ligand and its copper(II) complex for comparative removal of Pb(II) ions from aqueous solutions.

This is a preview of subscription content, log in to check access.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11


  1. 1.

    Feng Z, Zhu S, Martins de Godoi DR, Samia AC, Scherson D (2012) Adsorption of Cd2+ on carboxyl-terminated superparamagnetic iron oxide nanoparticles. Anal Chem 84:3764–3770

  2. 2.

    Ahmedna M, Marshall WE, Husseiny AA, Rao RM, Goktepe I (2004) The use of nutshell carbons in drinking water filters for removal of trace metals. Water Res 38:1062–1068

  3. 3.

    Krause-Nehring J, Brey T, Thorrold SR (2012) Centennial records of lead contamination in northern Atlantic bivalves (Arctica islandica). Mar Poll Bull 64:233–240

  4. 4.

    Yetilmezsoy K, Demirel S, Vanderbei RJ (2009) Response surface modeling of Pb (II) removal from aqueous solution by Pistacia vera L.: box–Behnken experimental design. J Hazard Mater 171:551–562

  5. 5.

    Ronteltap M, Maurer M, Gujer W (2007) The behaviour of pharmaceuticals and heavy metals during struvite precipitation in urine. Water Res 41:1859–1868

  6. 6.

    Mager EM, Brix KV, Gerdes RM, Ryan AC, Grosell M (2011) Effects of water chemistry on the chronic toxicity of lead to the cladoceran, Ceriodaphnia dubia. Ecotoxicol Environ Saf 74:238–243

  7. 7.

    Grover P, Rekhadevi PV, Danadevi K, Vuyyuri SB, Mahboob M, Rahman MF (2010) Genotoxicity evaluation in workers occupationally exposed to lead. Int J Hyg Environ Health 213:99–106

  8. 8.

    Murugesan GS, Sathishkumar M, Swaminathan K (2006) Arsenic removal from groundwater by pretreated waste tea fungal biomass. Bioresour Technol 97:483–487

  9. 9.

    Rao MM, Ramesh A, Rao GPC, Seshaiah K (2006) Removal of copper and cadmium from the aqueous solutions by activated carbon derived from Ceiba pentandra hulls. J Hazard Mater 129:123–129

  10. 10.

    Deng X, Lu L, Li H, Luo F (2010) The adsorption properties of Pb (II) and Cd (II) on functionalized graphene prepared by electrolysis method. J Hazard Mater 183:923–930

  11. 11.

    Nordberg GF, Flower BA, Nordberg M, Friberg L (2007) Handbook on the toxicology of metals academic press. The Netherlands, Amsterdam

  12. 12.

    Zhang X, Lin S, Lu XQ, Chen ZL (2010) Removal of Pb (II) from water using synthesized kaolin supported nanoscale zero-valent iron. Chem Eng J 163:243–248

  13. 13.

    Fu F, Wang Q (2011) Removal of heavy metal ions from wastewaters: a review. J Environ Manag 92:407–418

  14. 14.

    Singh CK, Sahu JN, Mahalik KK, Mohanty CR, Mohan BR, Meikap BC (2008) Studies on the removal of Pb (II) from wastewater by activated carbon developed from tamarind wood activated with sulphuric acid. J Hazard Mater 153:221–228

  15. 15.

    Park HG, Kim TW, Chae MY, Yoo IK (2007) Activated carbon-containing alginate adsorbent for the simultaneous removal of heavy metals and toxic organics. Process Biochem 42:1371–1377

  16. 16.

    Mohan D, Pittman Jr CU, Bricka M, Smith F, Yancey B, Mohammad J, Steele PH, Alexandre-Franco MF, Gomez-Serrano V, Gong H (2007) Sorption of arsenic, cadmium, and lead by chars produced from fast pyrolysis of wood and bark during bio-oil production. J Colloid Interface Sci 310:57–73

  17. 17.

    Dong L, Zhu Z, Qiu Y, Zhao J (2010) Removal of lead from aqueous solution by hydroxyapatite/magnetite composite adsorbent. Chem Eng J 165:827–834

  18. 18.

    Recillas S, García A, González E, Casals E, Puntes V, Sánchez A, Font X (2011) Use of CeO2, TiO2 and Fe3O4 nanoparticles for the removal of lead from water: toxicity of nanoparticles and derived compounds. Desalination 277:213–220

  19. 19.

    Samiey B, Cheng CH, Wu J (2014) Organic-inorganic hybrid polymers as adsorbents for removal of heavy metal ions from solutions: a review. Materials 7:673–726

  20. 20.

    Mercier L, Pinnavaia TJ (1998) Heavy metal ion adsorbents formed by the grafting of a thiol functionality to mesoporous silica molecular sieves: factors affecting hg (II) uptake. Environ Sci Technol 32:2749–2754

  21. 21.

    Kaşgöz H, Durmuş A, Kaşgöz A (2008) Enhanced swelling and adsorption properties of AAm-AMPSNa/clay hydrogel nanocomposites for heavy metal ion removal. Polym Adv Technol 19:213–220

  22. 22.

    Craciunescu I, Petran A, Liebscher J, Vekas L, Turcu R (2017) Synthesis and characterization of size-controlled magnetic clusters functionalized with polymer layer for wastewater depollution. Mater Chem Phys 185:91–97

  23. 23.

    Aiba M, Higashihara T, Ashizawa M, Otsuka H, Matsumoto H (2016) Triggered structural control of dynamic covalent aromatic polyamides: effects of thermal reorganization behavior in solution and solid states. Macromolecules 49:2153–2161

  24. 24.

    Banerjee S, Maji S (2011) Aromatic polyamides. High-performance processable aromatic polyamides. In: Mittal V (ed) High performance polymers and engineering plastics. Wiley, Hoboken, 111–166

  25. 25.

    Iwan A, Sek D (2008) Processible polyazomethines and polyketanils: from aerospace to light-emitting diodes and other advanced applications. Prog Polym Sci 33:289–345

  26. 26.

    Grigoras M, Catanescu O, Simionescu CI (2001) Poly (azomethine) s. Rev Roum Chim 46:927–939

  27. 27.

    Grigoras M, Catanescu CO (2004) Imine oligomers and polymers. J Macromol Sci C Polym Rev 44:131–173

  28. 28.

    Zhang LJ, Qi L, Chen XY, Liu F, Liu LJ, Ding WL, Li DL, Yuan GC, Tong JZ, Chen FY, Huang HJ (2018) Synthesis, crystal structure and photophysical properties of two reduced Schiff bases derived from 5-Aminoisophthalic acid. J Chem Crystallogr 1–7

  29. 29.

    Aghaei M, Kianfar AH, Dinari M (2019) Green synthesis of nanostructure Schiff base complex based on aromatic polyamide and manganese (III) for elimination of Hg (II) and Cd (II) from solutions. JICS 1–12

  30. 30.

    Rasool R, Hasnaina S, Nishata N (2014) Metal-based Schiff base polymers: preparation, spectral, thermal and their in vitro biological investigation. Des Monomers Polym 17:217–226

  31. 31.

    Lacroix PG, Di Bella S, Ledoux I (1996) Synthesis and second-order nonlinear optical properties of new copper (II), nickel (II), and zinc (II) Schiff-base complexes. Toward a role of inorganic chromophores for second harmonic generation. Chem Mater 8:541–545

  32. 32.

    Vitalini D, Mineo P, Di Bella S, Fragala I, Maravigna P, Scamporrino E (1996) Synthesis and matrix-assisted laser desorption ionization− time of flight characterization of an exactly alternating Copolycarbonate and two random Copolyethers containing Schiff Base copper (II) complex nonlinear optical units in the Main chain. Macromolecules 29:4478–4485

  33. 33.

    Kumar S, Jha RR, Yadav S, Gupta R (2015) Pd (II) complexes with amide-based macrocycles: syntheses, properties and applications in cross-coupling reactions. New J Chem 39:2042–2051

  34. 34.

    Tyagi M, Chandra S (2014) Synthesis and spectroscopic studies of biologically active tetraazamacrocyclic complexes of Mn (II), co (II), Ni (II), Pd (II) and Pt (II). J Saudi Chem Soc 18:53–58

  35. 35.

    Ebrahimipour SY, Mague JT, Akbari A, Takjoo R (2012) Synthesis, characterization, crystal structure and thermal behavior of 4-Bromo-2-(((5-chloro-2-hydroxyphenyl)imino)methyl phenol and its oxido-vanadium (V) complexes. J Mol Struct 1028:148–155

  36. 36.

    Kirupha SD, Murugesan A, Vidhyadevi T, Baskaralingam P, Sivanesan S, Ravikumar L (2012) Novel polymeric adsorbents bearing amide, pyridyl, azomethine and thiourea binding sites for the removal of Cu (II) and Pb (II) ions from aqueous solution. Sep Sci Technol 48:254–262

  37. 37.

    Dinari M, Haghighi A (2017) Efficient removal of hexavalent chromium and lead from aqueous solutions by s-triazine containing nanoporous polyamide. Polym Adv Technol 28:1683–1689

  38. 38.

    Dinari M, Mohammadnezhad G, Soltani R (2016) Fabrication of poly (methyl methacrylate)/silica KIT-6 nanocomposites via in situ polymerization approach and their application for removal of Cu 2+ from aqueous solution. RSC Adv 6:11419–11429

  39. 39.

    Mohammadnezhad G, Dinari M, Soltani R (2016) The preparation of modified boehmite/PMMA nanocomposites by in situ polymerization and the assessment of their capability for Cu 2+ ion removal. New J Chem 40:3612–3621

  40. 40.

    Zhengang L, Fu-Shen Z (2009) Removal of lead from water using biochars prepared from hydrothermal liquefaction of biomass. J Hazard Mater 167:933–939

  41. 41.

    Mishra PC, Patel RK (2009) Removal of lead and zinc ions from water by low cost adsorbents. J Hazard Mater 168:319–325

  42. 42.

    Kumari M, Pittman Jr CU, Mohan D (2014) Heavy metals [chromium (VI) and Lead (II)] removal from water using Mesoporous magnetite (Fe3O4) Nanospheres. J Colloid Interface Sci 442:120–132

  43. 43.

    El-Reash YA, Otto M, Kenawy IM, Ouf AM (2011) Adsorption of Cr (VI) and as (V) ions by modified magnetic chitosan chelating resin. Int J Biol Macromol 49:513–522

  44. 44.

    Langmuir I (1918) The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc 40:1361–1403

  45. 45.

    Naiya TK, Bhattacharya AK, Das SK (2008) Removal of Cd (II) from aqueous solutions using clarified sludge. J Colloid Interface Sci 325:48–56

Download references


The authors appreciate Isfahan University of Technology (IUT) for partial financial support of this work.

Author information

Correspondence to Ali Hossein Kianfar.

Ethics declarations

Conflict of interest

The authors expressed that they own no conflicts of interest in current research.

Additional information

Publisher’s note

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


• The new PA containing Schiff base, was prepared in green solvent of TBAB.

• The synthesized PA was coordinated to Cu(II) ion to form metal polymer complex.

• The nanostructured PA ligand and its Cu(II) complex were comparatively applied to eliminate Pb(II) from water.

• The best adsorption was occurred at pH =6.

Electronic supplementary material


(DOCX 2.52 mb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Aghaei, M., Kianfar, A.H. & Dinari, M. Synthesis and characterization of a novel Schiff base polyamide ligand and its copper(II) complex for comparative removal of Pb(II) ions from aqueous solutions. J Polym Res 27, 54 (2020).

Download citation


  • Green chemistry
  • Lead
  • Metal ion adsorption
  • Nanostructure polyamide complex
  • Schiff base polymer