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Thiophene-containing Schiff base polymers: synthesis, characterization, and anti-bacterial properties

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Abstract

We synthesized the Schiff bases and their polymers, which contain thiophene units. For the synthesis process, first, hydroxynaphthalene di- and triol-derived Schiff bases that are abbreviated as (A1) and (A2) were prepared by a common condensation reaction. Second, their polymers named as B1 and B2 were separately synthesized from the oxidative polycondensation of the Schiff base monomers with (NH4)2S2O8 in an aqueous alkaline medium. The new polymeric structures that are abbreviated as B1-S and B2-S, containing thiophene groups, were synthesized by HBr elimination using B1 and B2 polymers. The characterization processes of the synthesized products were carried out using spectroscopic techniques such as FTIR, UV–Vis, 1H and 13C NMR, TG-DTG analysis, and MALDI-TOF MS. According to the TG analysis results, except for A2, the thermal stabilities of the other compounds were good since they left about 50% residue at 800°C. SEM images of the compounds were recorded at different sizes, and also they were found to be quite different from each other. For example, A1 was like a ball. Additionally, A1, A2, B1, B2, B1-S, and B2-S were tested for their anti-bacterial activities against some bacteria types. Minimum inhibitory concentration (MIC) method was used for the anti-bacterial activity tests. The MIC test results showed that the synthesized polymers could be used as antimicrobial agents for surfaces with P. vulgaris NRRL-B-123 bacteria at lower concentrations such as 15.625 and 31.25 µg/mL.

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Acknowledgements

We would like to thank Dr. Neslihan DEMİR (Çanakkale Onsekiz Mart University, Faculty of Sciences and Arts, Department of Biology, Çanakkale¸ Turkey) for her help on anti-microbial tests. Additionally, the authors thank the Çanakkale Onekiz Mart University Scientific Research Projects Coordination Unit (Project No.: FYL-2022-4007).

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Authors and Affiliations

  1. Chemistry Research Laboratory, Department of Mathematics and Science Education, Faculty of Education, Çanakkale Onsekiz Mart University, Çanakkale, Turkey

    Aysel Aydın Kocaeren

  2. Department of Chemistry Education, School of Graduate Studies, Çanakkale Onsekiz Mart University, Çanakkale, Turkey

    Elifnur Karatağ

  3. Department of Mathematics and Science Education, School of Graduate Studies, Çanakkale Onsekiz Mart University, Çanakkale, Turkey

    Elifnur Karatağ

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  1. Aysel Aydın Kocaeren
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Correspondence to Aysel Aydın Kocaeren.

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Kocaeren, A.A., Karatağ, E. Thiophene-containing Schiff base polymers: synthesis, characterization, and anti-bacterial properties. Iran Polym J 32, 1405–1419 (2023). https://doi.org/10.1007/s13726-023-01211-7

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