Design and synthesis of pendant naphthalene-based aromatic polyesters: structure-property relationship, solubility, and thermal behavior
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Shivaji D. Ghodke
,
Arati V. Diwate
,
Pravin S. Bhale
,
Monali P. Patil
and
Noormahmad N. Maldar
Abstract
Aromatic polyesters were synthesized from 3,5-dihydroxy-N-(4-(naphthalen-8-yloxy)phenyl)benzamide via interfacial polycondensation with varying molar ratios of isophthaloyl chloride (IPC) and terephthaloyl chloride (TPC). The diol precursor was synthesized by Yamazaki condensation and characterized using FT-IR, 1H NMR, and 13C NMR spectroscopy. The resulting polyesters were obtained in high yields (84–93 %) with inherent viscosities in the range of 0.37–0.54 dL g−1, confirming moderate chain lengths. Solubility studies revealed that all polyesters were soluble in NMP, DMF, DMAc, and DMSO, partially soluble in THF and m-cresol, and poorly soluble in chloroform and dichloromethane. Thermogravimetric analysis (TGA) indicated good thermal stability, with initial decomposition temperatures of 151–169 °C, 10 % weight-loss temperatures (T10 %) of 369–425 °C, and residual weights of 34–53 % at 800 °C. Differential scanning calorimetry (DSC) showed glass transition temperatures (Tg) ranging from 109 to 129 °C. The incorporation of bulky naphthyl pendant units and ether linkages disrupted chain packing, enhancing solubility while retaining thermal stability. These results suggest that the synthesized polyesters possess a balanced combination of solubility and thermal resistance, making them potential candidates for applications in membranes, coatings, and other processable high-performance materials.
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Research ethics: Not applicable.
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Informed consent: Not applicable.
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Author contributions: All authors have accepted responsibility for the entire content of this manuscript and approved its submission.
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Use of Large Language Models, AI and Machine Learning Tools: None declared.
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Conflict of interest: The authors state no conflict of interest.
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Research funding: None declared.
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Data availability: Not applicable.
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