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<p>A novel biocompatible polyamide incorporating Schiff base moiety, N,N′-bis(4-aminoglutamic acid-ortho-hydroxyacetophenone)ethylenediamine (AEHPED), was successfully synthesized via a four-step route involving condensation, nitration, reduction, and amide polymerization. The chemical structure was confirmed by Fourier Transform Infrared (FTIR), <sup>1</sup>H and <sup>13</sup>C NMR, and elemental analysis. The polymer’s structure was further validated by micro elemental analysis and NMR spectroscopy, confirming the incorporation of Schiff base and amide functionalities. The polymer exhibited high crystallinity (74.8%), hierarchical porous structure (Brunauer–Emmett–Teller (BET) surface area 0.71 m<sup>2</sup> g⁻<sup>1</sup>, average pore diameter 48 nm), excellent thermal stability (T<sub>5</sub> = 350&#xa0;°C, T<sub>max</sub> = 439&#xa0;°C), and remarkable water solubility (50 mg/mL in Phosphate-Buffered Saline (PBS), pH 7.4) owing to pendant carboxylic acid groups. DFT (Density Functional Theory) calculations (B3LYP/6-31G(d,p)) support the experimental thermodynamic data. The combination of photosensitive Schiff base, high thermal robustness, and biocompatibility makes AEHPED a promising candidate for drug delivery, optical pH sensing, and heavy metal scavenging applications. This work addresses the limitations of traditional polyamides by enhancing aqueous solubility and thermal stability, motivated by the need for multifunctional materials in biomedical and environmental applications.</p>

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Synthesis, Characterization, and DFT Computational Study of a Novel Schiff Base-Containing Polyamide: N,N′-Bis(4-Aminoglutamic Acid-ortho-hydroxyacetophenone)ethylenediamine (AEHPED)

  • 期刊论文

  • 发表日期：

    2026年1月29日

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  • Mohammad Saki,
  • Leila Mahdavian,
  • Azam Marjani,
  • Fatemeh Shafiei

摘要

A novel biocompatible polyamide incorporating Schiff base moiety, N,N′-bis(4-aminoglutamic acid-ortho-hydroxyacetophenone)ethylenediamine (AEHPED), was successfully synthesized via a four-step route involving condensation, nitration, reduction, and amide polymerization. The chemical structure was confirmed by Fourier Transform Infrared (FTIR), 1H and 13C NMR, and elemental analysis. The polymer’s structure was further validated by micro elemental analysis and NMR spectroscopy, confirming the incorporation of Schiff base and amide functionalities. The polymer exhibited high crystallinity (74.8%), hierarchical porous structure (Brunauer–Emmett–Teller (BET) surface area 0.71 m2 g⁻1, average pore diameter 48 nm), excellent thermal stability (T5 = 350 °C, Tmax = 439 °C), and remarkable water solubility (50 mg/mL in Phosphate-Buffered Saline (PBS), pH 7.4) owing to pendant carboxylic acid groups. DFT (Density Functional Theory) calculations (B3LYP/6-31G(d,p)) support the experimental thermodynamic data. The combination of photosensitive Schiff base, high thermal robustness, and biocompatibility makes AEHPED a promising candidate for drug delivery, optical pH sensing, and heavy metal scavenging applications. This work addresses the limitations of traditional polyamides by enhancing aqueous solubility and thermal stability, motivated by the need for multifunctional materials in biomedical and environmental applications.