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Synthesis of novel aromatic polyamides containing cardo groups and triphenylphosphine oxide structures by a heterogeneous palladium-catalyzed carbonylation and condensation reaction

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Abstract

New aromatic polyamides containing cardo groups and triphenylphosphine oxide structures were synthesized by a heterogeneous palladium-catalyzed carbonylation and condensation of bis(4-(3-iodophenoxy)phenyl)phenylphosphine oxide (BIPPO), aromatic diamines bearing cardo groups, and carbon monoxide. Polycondensations were carried out in N,N-dimethylacetamide under 1 atm of CO at 120 °C in the presence of a magnetically recyclable heterogeneous palladium catalyst and 1,8-diaza-bicyclo[5,4,0]-7-undecene (DBU) and afforded novel aromatic polyamides with inherent viscosities between 0.72 and 0.76 dL/g. All the polyamides were quite soluble in dipolar aprotic solvents and pyridine and could be converted into transparent, flexible, and tough polyamide films by casting from DMAc solutions. These polymers exhibited high thermal and thermooxidative stability with the glass transition temperatures of 237 °C–256 °C, the temperatures at 5% weight loss of 448 °C–465 °C in air. All the phosphorus-containing polyamides self-extinguished as soon as the flame was removed, and the limited oxygen indices (LOIs) of these polymers were in the range of 39%–44%. The polymer films also showed good mechanical properties and high optical transparency.

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Acknowledgements

We thank the National Natural Science Foundation of China (Project 21664008), Natural Science Foundation of Jiangxi Province in China (Project 20181BAB203011) and Key Laboratory of Functional Small Organic Molecule, Ministry of Education (Grant No. KLFS-KF-201704) for financial support.

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  1. Key Laboratory of Functional Small Organic Molecule, Ministry of Education and College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330022, People’s Republic of China

    Li Wei, Huali Tang, Feihua Zou & Mingzhong Cai

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  1. Li Wei
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Correspondence to Mingzhong Cai.

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Wei, L., Tang, H., Zou, F. et al. Synthesis of novel aromatic polyamides containing cardo groups and triphenylphosphine oxide structures by a heterogeneous palladium-catalyzed carbonylation and condensation reaction. Polym. Bull. 78, 6797–6817 (2021). https://doi.org/10.1007/s00289-020-03447-2

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