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Synthesis of new poly(1,2,3-triazolyl-benzenesulfonamide)s via step-growth polymerization and characterization of their structures

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Abstract

In this article, three new poly(1,2,3-triazolyl-benzenesulfonamide)s (4-6) were synthesized from the new molecule 4-azido-N-(prop-2ʹ-yn-1ʹ-yl)benzenesulfonamide (3). The synthesis and step-growth click polyaddition reaction of a new AB-type monomer containing terminal alkyne and azide groups were described. Copper (I)-catalyzed azide-alkyne cycloaddition (CuAAC) and Huisgen click polymerization were performed to prepare sulfonamide, a derivative of poly(1,2,3-triazole)s. The CuAAC polymerization regioselectively led to 1,4-disubstituted triazole ring and hence to a stereoregular polymer. In contrast, the thermal polymerization also produced 1,5-disubstituted triazole units. The structure of the new poly(1,2,3-triazolyl-benzenesulfonamide)s (4-6) obtained from (4-azido-N-(prop-2ʹ-yn-1ʹ-yl)benzenesulfonamide) were characterized by FTIR, 1H-, and 13C- NMR spectroscopy. The resulting polymers had weight-average molecular weights in the 7,700-58,650 range and were determined by Gel Permeation Chromatography (GPC). The resulting polymers 4, 5 and 6, lossing about 50% of their weights, showed a decomposition temperature of 406, 474, and 451 °C in a nitrogen atmosphere, respectively. The glass transition temperature of all polymers were at 128 °C. In addition, the surface morphology was studied via Scanning Electron Microscopy with Energy Dispersive Spectroscopy (SEM/EDS). This paper is dedicated to the 100th Anniversary of the Republic of Türkiye.

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Acknowledgments

This study was financially supported by the Research Projects Coordination Office at Manisa Celal Bayar University (Project Number: 2022-026).

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  1. Department of Tobacco Technology Engineering, Manisa Celal Bayar University, Akhisar, Manisa, Türkiye

    Emriye Ay

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  1. Emriye Ay
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Ay, E. Synthesis of new poly(1,2,3-triazolyl-benzenesulfonamide)s via step-growth polymerization and characterization of their structures. J Polym Res 30, 360 (2023). https://doi.org/10.1007/s10965-023-03734-2

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