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.