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.
Similar content being viewed by others
References
Mittal KL (ed) (1984) Polyimides: synthesis, characterization, and applications. Plenum Press, New York
Wilson D, Stenzenberger HD, Hergenrother PM (1990) Polyimides. Blackie, London
Ghost MK, Mittal LK (eds) (1996) Polyimide fundamental and applications. Marcel Dekker, New York
Liaw DJ, Wang KL, Huang YC, Lee KR, Lai JY, Ha CS (2012) Advanced polyimide materials: syntheses, physical properties and applications. Prog Polym Sci 37:907–974
Dhara MG, Banerjee S (2010) Fluorinated high-performance polymers: poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups. Prog Polym Sci 35:1022–1077
Liaw DJ, Chang FC, Leung MK, Chou MY, Muellen K (2005) High glass transition and rigid-rod of novel organosoluble polyimides and polyamides based on bulky and noncoplanar naphthalene group without ether linkage. Macromolecules 38:4024–4029
Patil YS, Salunkhe PH, Mahindrakar JN, Ankushrao SS, Kadam VN, Ubale VP, Ghanwat AA (2019) Synthesis and characterization of aromatic polyimides containing tetraphenylfuran–thiazole moiety. J Therm Anal Calorim 135:3057–3068
Patil YS, Mahindrakar JN, Salunkhe PH, Ubale VP, Ghanwat AA (2018) Synthesis, characterization and structure–property relationships of processable poly(amide-imide)s containing novel tetraphenylthiophene–thiazole diimide–diacid (TPTPThDIDA) moiety. J Macromol Sci Part A 55:572–581
Salunkhe PH, Patil YS, Kadam VN, Ankushrao SS, Ubale VP, Ghanwat AA (2019) Synthesis, characterization, wettability study and thermal behaviour of aromatic polyimides containing tetraphenylthiophene–quinoxaline unit. Polym Plast Technol Mater 59:95–105. https://doi.org/10.1080/25740881.2019.1625385
Mohagheghnezhad M, Rafiee Z (2019) Synthesis and characterization of two novel poly(amide-imide)s containing pendent (5-(4,5-diphenyl-1H-imidazol-2-yl)furan-2-yl)phenyl moieties and natural amino acids linkages for adsorption of Cu(II). Polym Bull. https://doi.org/10.1007/s00289-019-02992-9
Rafiee Z, Mohagheghnezhad M (2019) Synthesis and properties of organosoluble and thermal stable polyimides from 3,5-diamino-N-(4-(5-(4,5-diphenyl-1H-imidazol-2-yl)furan-2-yl)phenyl)benzamide. Polym Bull 76:3857–3877
Khalili S, Rafiee Z (2019) Synthesis and properties of highly organosoluble aromatic polyimides containing N-(4-(di(1H-indole-3-yl)methyl)phenyl) moieties. High Perform Polym. https://doi.org/10.1177/0954008319853031
Kim JB, Adler AD, Longo FR (1978) Porphyrin chemistry advances. In: Dolphin D (ed) The porphyrins. Academic, New York
Chou JH, Kosal ME, Nalwa HS, Rakow NA, Suslick KS (2000) Applications of porphyrins and metalloporphyrins to materials chemistry. In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook, volume 6/applications: past, present and future. Academic Press, New York
Ohkita H, Ogi T, Kinoshita R, Ito S, Yamamoto M (2002) Photoinduced electron transfer in nanostructures of ultrathin polyimide films containing porphyrin moieties. Polymer 43:3571–3577
Gentemann S, Medforth CJ, Forsyth TP, Nurco DJ, Smith KM, Fajer J, Holten D (1994) Photophysical properties of conformationally distorted metal-free porphyrins. Investigation into the deactivation mechanisms of the lowest excited singlet state. J Am Chem Soc 116:7363–7368
Natale CD, Monti D, Paolesse R (2010) Chemical sensitivity of porphyrin assemblies. A review. Mater Today 13:46–52
Fu F, Wang Q (2011) Removal of heavy metal ions from wastewaters: a review. J Environ Manage 92:407–418
Khulbe KC, Matsuura T (2018) Removal of heavy metals and pollutants by membrane adsorption techniques. Appl Water Sci 8:19–48
Pipi ARF, Neto SA, Barbosa PFP, Do Carmo DR (2019) The use of titanium (IV) phosphate for metal removal from aqueous and alcoholic samples. SN Appl Sci 1:929–937
Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J, Korsakoff L (1967) A simplified synthesis for meso-tetraphenylporphin. J Org Chem 32:476–477
Karimipour G, Ghaedi M, Behfar M, Andikaey Z, Kowkabi S, Orojloo AH (2012) Synthesis and application of new porphyrin derivatives for preparation of copper selective electrodes: influence of carbon nanotube on their responses. IEEE Sens J 12:2638–2647
Amundsen LH, Nelson LS (1951) Reduction of nitriles to primary amines with lithium aluminum hydride. J Am Chem Soc 73:242–244
Van Krevelen DW, Hoftyzer PJ (1976) Properties of polymer. Elsevier Scientific Publishing Company, New York
Funding
Funding was provided by Yasouj University (Grant No. Gryu-89131307).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that there is no conflict of interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-020-03118-2