Preparation and properties of polyimides having porphyrin moieties for heavy metals removal

Abstract

A tetramine monomer containing porphyrin moiety is prepared in high purity by the propionic acid-mediated condensation of pyrrole with 4-cyanobenzaldehyde and then reduction in the tetracyano intermediate. The thermally stable porphyrin-based polyimides (PI)s are prepared using tetramine and four aromatic tetracarboxylic dianhydrides via a two-step method in quantitative yields with inherent viscosities of 0.34–0.63 dL/g. The PIs are soluble in some organic solvents such as N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide and dimethyl sulfoxide. The resultant PIs had high glass transition temperatures and displayed outstanding thermal stability up to 500 °C. The resulting polymers revealed strong UV–Vis absorption band around 422 nm in DMF. Wide-angle XRD measurements exhibited that the PIs were amorphous. The polymer films had tensile strengths 101–128 MPa, elongates at break of 7–11% and tensile moduli of 2.0–2.2 GPa. One of the PIs was applied to examine the adsorption properties of two heavy metal ions (Cd2+ and Hg2+) at pH 7. The results revealed that the applied PI was an outstanding sorbent for heavy metal ions. The goal of this study is the preparation of hydrophobic PIs for ion-selective membranes and chemical sensors to adsorb of toxic heavy metals.

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Funding

Funding was provided by Yasouj University (Grant No. Gryu-89131307).

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Correspondence to Zahra Rafiee.

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Rafiee, Z., Golriz, L., Karimipour, G. et al. Preparation and properties of polyimides having porphyrin moieties for heavy metals removal. Polym. Bull. 78, 481–492 (2021). https://doi.org/10.1007/s00289-020-03118-2

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Keywords

  • Polyimide
  • Porphyrin
  • Tetramine
  • Direct polycondensation
  • Thermal stability
  • Heavy metal