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Synthesis of N-alkyl- and N-alkenyl-substituted polyanilines. Properties and antibacterial activity study

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Abstract

Polyaniline derivatives were synthesized, characterized and evaluated for their antibacterial activities. By chemical oxidative polymerization, N-substituted polyaniline derivatives containing alkyl and alkenyl fragments in the main chain were obtained. NMR, UV-Vis, FT-IR were used to characterize the chemical structures of the polymers. SEM images revealed the different shapes and surface morphology of the polymers. In addition, the multi-step thermal degradation behavior of the polymers and the higher stability of the N-alkenyl PANIs compared to the N-alkyl PANIs were observed from the TGA plots. These polymers were used as antimicrobial agents against both gram-positive (Bacillus subtilis) and gram-negative (Pseudomonas aureofaciens) bacteria. For both gram-positive and gram-negative test strains, the highest antibacterial activity was observed for N-allyl-PANI and N-cyclohexenyl-PANI. The diameter of the inhibition zone was obtained within the range for Bacillus subtilis up to 23 mm and 24 mm, and for Pseudomonas aureofaciens up to 36 mm and 28 mm, respectively. Therefore, these polymers could be potential candidates for biomedical applications.

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All of the data sets that were included and/or examined in the present study can be obtained from the corresponding author upon request.

References

  1. Jubeh B, Breijyeh Z, Karaman R (2020) Resistance of gram-positive bacteria to current antibacterial agents and overcoming approaches. Molecules 25(12):2888

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Theuretzbacher U (2012) Accelerating resistance, inadequate antibacterial drug pipelines and international responses. Int J Antimicrob Agents 39(4):295–299

    Article  CAS  PubMed  Google Scholar 

  3. Bagheri N, Lakouraj MM, Nabavi SR et al (2020) Synthesis of bioactive polyaniline-b-polyacrylic acid copolymer nanofibrils as an effective antibacterial and anticancer agent in cancer therapy, especially for HT29 treatment. RSC Adv 10(42):25290–25304

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Alipour A, Lakouraj MM, Hasantabar V et al (2021) Evaluation of adsorption and biological activities of polyaniline-grafted-pectin as conductive nanogels. Carbohydr Polym 2:100151

    CAS  Google Scholar 

  5. Hasantabar V, Lakouraj MM, Zare EN et al (2017) Synthesis, characterization, and biological properties of novel bioactive Poly (xanthoneamide-triazole-ethersulfone) and its multifunctional nanocomposite with polyaniline. Adv Polym Technol 36(3):309–319

    Article  CAS  Google Scholar 

  6. Dos Santos MR, Alcaraz-Espinoza JJ, da Costa MM et al (2018) Usnic acid-loaded polyaniline/polyurethane foam wound dressing: preparation and bactericidal activity. Mater Sci Eng C 89:33–40

    Article  Google Scholar 

  7. Quan X, Wang J, Souleyman T et al (2018) Antibacterial and antifouling performance of bisphenol-A/Poly (ethylene glycol) binary epoxy coatings containing bromine-benzyl-disubstituted polyaniline. Prog Org Coat 124:61–70

    Article  CAS  Google Scholar 

  8. Cai W, Wang J, Quan X et al (2018) Preparation of bromo-substituted polyaniline with excellent antibacterial activity. J Appl Polym Sci 135(1):45657

    Article  Google Scholar 

  9. Sebastian J, Samuel JM (2020) Recent advances in the applications of substituted polyanilines and their blends and composites. Polym Bull 77(12):6641

    Article  CAS  Google Scholar 

  10. Kucekova Z, Humpolicek P, Kasparkova V et al (2014) Colloidal polyaniline dispersions: Antibacterial activity, cytotoxicity and neutrophil oxidative burst. Colloids Surf B 116:411–417

    Article  CAS  Google Scholar 

  11. Andriianova AN, Latypova LR, Vasilova LY et al (2021) Antibacterial properties of polyaniline derivatives. J Appl Polym Sci 138(47):51397

    Article  CAS  Google Scholar 

  12. Latypova LR, Usmanova GS, Vasilova LY et al (2023) Synthesis and characterization of N-substituted polyanilines and polyindoles and their antibacterial activity. Chem Zvesti 77(1):473–483

    CAS  Google Scholar 

  13. Mustafin AG, Latypova LR, Andriianova AN et al (2021) Poly [N-(2-chloroprop-2-en-1-yl) aniline] s: synthesis, polymer analogous reaction, and physicochemical properties. Polym Chem 12(39):5650–5661

    Article  CAS  Google Scholar 

  14. Chevalier JW, Bergeron JY, Dao LH (1992) Synthesis, characterization, and properties of poly (N-alkylanilines). Macromolecules 25(13):3325–3331

    Article  CAS  Google Scholar 

  15. Li T, Yuan C, Zhao Y et al (2013) Synthesis, characterization, and properties of aniline-p-phenylenediamine copolymers. High Perform Polym 25(3):348–353

    Article  Google Scholar 

  16. Savitha P, Swapna Rao P, Sathyanarayana DN (2005) Highly conductive new aniline copolymers: poly (aniline-co-aminoacetophenone) s. Polym Int 54(9):1243–1250

    Article  CAS  Google Scholar 

  17. Grigoras M, Catargiu AM, Tudorache F et al (2012) Chemical synthesis and characterization of self-doped N-propanesulfonic acid polyaniline derivatives. Iran Polym J 21:131–141

    Article  CAS  Google Scholar 

  18. Simagina LV, Gaynutdinov RV, Stepina ND et al (2010) Structural organization of films based on polyaniline/polysulfonic acid complexes depending on the synthesis method. Crystallogr Rep 55:681–687

    Article  CAS  Google Scholar 

  19. Chandrakanthi N, Careem MA (2000) Thermal stability of polyaniline. Polym Bull 44:101–108

    Article  CAS  Google Scholar 

  20. Jeevananda T, Seetharamu S, Saravanan S (2004) Synthesis and characterization of poly (aniline-co-acrylonitrile) using organic benzoyl peroxide by inverted emulsion method. Synth Met 140(2–3):247–260

    Article  CAS  Google Scholar 

  21. Abd El-Salam HM, Askalany HG (2017) Synthesis and characterization of crystalline poly (N-(2-hydroxyethyl) aniline) microspheres. High Perform Polym 29(2):227–236

    Article  CAS  Google Scholar 

  22. Mustafin AG, Latypova LR, Andriianova AN (2020) Synthesis and Physicochemical Properties of Poly (2-ethyl-3-methylindole). Macromolecules 53(18):8050–8059

    Article  CAS  Google Scholar 

  23. Abdolahi A, Hamzah E, Ibrahim Z et al (2014) Application of environmentally-friendly coatings toward inhibiting the microbially influenced corrosion (MIC) of steel: a review. Polym Rev 54(4):702–745

    Article  CAS  Google Scholar 

  24. Boomi P, Prabu HG, Mathiyarasu J (2014) Synthesis, characterization and antibacterial activity of polyaniline/Pt–Pd nanocomposite. Eur J Med Chem 72:18–25

    Article  CAS  PubMed  Google Scholar 

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Acknowledgment

This work was supported by the Ministry of Science and Higher Education of the Russian Federation as part of the state task no. 122031400278-2.

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Correspondence to Lyaysan R. Latypova.

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Latypova, L.R., Usmanova, G.S., Vasilova, L.Y. et al. Synthesis of N-alkyl- and N-alkenyl-substituted polyanilines. Properties and antibacterial activity study. J Polym Res 30, 315 (2023). https://doi.org/10.1007/s10965-023-03696-5

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