Abstract
A series of new N-substituted poly (β-haloallylaniline)s were synthesized by the chemical oxidation method. Based on these polymers, various functionalized polyindoles of a new type were obtained. All the polymers were characterized by FTIR, UV–vis spectra, SEM and TGA techniques. Moreover, the antimicrobial activity of the samples synthesized was studied as antibacterial agents against Gram-positive bacteria Bacillus subtilis and Gram-negative bacteria Pseudomonas aureofaciens. It was confirmed that the polymer samples prepared in this study showed activity as antibacterial agents.
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References
Abbas M, Shafiee M (2020) An overview of maintenance management strategies for corroded steel structures in extreme marine environments. Mar Struct 71:102718. https://doi.org/10.1016/j.marstruc.2020.102718
Andriianova AN, Latypova LR, Vasilova LY, Kiseleva SV, Zorin VV, Abdrakhmanov IB, Mustafin AG (2021) Antibacterial properties of polyaniline derivatives. J App Polym Sci 138:51397. https://doi.org/10.1002/app.51397
Bagheri N, Lakouraj MM, Nabavi SR, Tashakkorian H, Mohseni M (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 10:25290–25304. https://doi.org/10.1039/D0RA03779F
Baker CO, Huang X, Nelson W, Kaner RB (2017) Polyaniline nanofibers: broadening applications for conducting polymers. Chem Soc Rev 46:1510–1525. https://doi.org/10.1039/C6CS00555A
Bogdanović U, Dimitrijević S, Škapin SD, Popović M, Rakočević Z, Leskovac A, Vodnik V (2018) Copper-polyaniline nanocomposite: role of physicochemical properties on the antimicrobial activity and genotoxicity evaluatio. Mater Sci Eng C 93:49–60. https://doi.org/10.1016/j.msec.2018.07.067
Cai W, Wang J, Quan X, Wang Z (2018) Preparation of bromo-substituted polyaniline with excellent antibacterial activity. J Appl Polym Sci 135:45657. https://doi.org/10.1002/app.45657
Dastjerdi R, Montazer MA (2010) Review on the application of inorganic nano-structured materials in the modification of textiles: focus on anti-microbial properties. Colloids Surf B 79:5–18. https://doi.org/10.1016/j.colsurfb.2010.03.029
De Muynck W, De Belie N, Verstraete W (2010) Microbial carbonate precipitation in construction materials: a review. Ecol Eng 36:118–136. https://doi.org/10.1016/j.ecoleng.2009.02.006
Dos Santos MR, Alcaraz-Espinoza JJ, da Costa MM, de Oliveira HP (2018) Usnic acid-loaded polyaniline/polyurethane foam wound dressing: preparation and bactericidal activity. Mater Sci Eng C 89:33–40. https://doi.org/10.1016/j.msec.2018.03.019
Elango M, Deepa M, Subramanian R, Saraswathy G (2018) Synthesis, structural characterization and antimicrobial activities of polyindole stabilized Ag-Co3O4 nanocomposite by reflux condensation method. Mater Chem Phys 216:305–315. https://doi.org/10.1016/j.matchemphys.2018.05.049
Filipović U, Dahmane RG, Ghannouchi S, Zore A, Bohinc K (2020) Bacterial adhesion on orthopedic implants. Adv Colloid Interface Sci 283:102228. https://doi.org/10.1016/j.cis.2020.102228
Flemming HC (2002) Biofouling in water systems–cases, causes and countermeasures. Appl Microbiol Biotechnol 59:629–640. https://doi.org/10.1007/s00253-002-1066-9
Flemming HC, Wuertz S (2019) Bacteria and archaea on Earth and their abundance in biofilms. Nat Rev Microbiol 17:247–260. https://doi.org/10.1038/s41579-019-0158-9
Gilbert P, Moore LE (2005) Cationic antiseptics: diversity of action under a common epithet. J Appl Microbiol 99:703–715. https://doi.org/10.1111/j.1365-2672.2005.02664.x
Handore K, Walunj D, Chhattise P, Chabukswar A, Mohite K, Dallavalle S, Chabukswar V (2017) ultrasound synthesis of polyindole–TiO2 nanocomposite and evaluation of antibacterial activity. Polym Plast Technol Eng 56:1259–1266. https://doi.org/10.1080/03602559.2016.1163581
Houlton BZ, Bai E (2009) Imprint of denitrifying bacteria on the global terrestrial biosphere. Proc Natl Acad Sci 106:21713–21716. https://doi.org/10.1073/pnas.0912111106
Javaherdashti R (2011) Impact of sulphate-reducing bacteria on the performance of engineering materials. Appl Microbiol Biotechnol 91:1507–1517. https://doi.org/10.1007/s00253-011-3455-4
Kausar A, Ilyas H, Siddiq M (2018) Aptitude of graphene oxide–silver in advance polymer nanocomposite: a review. Polym Plast Technol Eng 57:283–301. https://doi.org/10.1080/03602559.2017.1326135
Latypova LR, Andriianova AN, Salikhov SM, Mullagaliev IN, Salikhov RB, Abdrakhmanov IB, Mustafin AG (2020) Synthesis and physicochemical properties of poly [2-(2-chloro-1-methylbut-2-en-1-yl)aniline] obtained with various dopants. Polym Int 69:804–812. https://doi.org/10.1002/pi.6016
Lehmann J, Kleber M (2015) The contentious nature of soil organic matter. Nature 528:60–68. https://doi.org/10.1038/nature16069
Modarresi-Alam AR, Amirazizi HA, Movahedifar F, Farrokhzadeh A, Asli GR, Nahavandi H (2015) The first report of polymerization and characterization of aniline bearing chiral alkyl group on ring via covalent bond; poly [(±)-2-(sec-butyl) aniline]. J Mol Struct 1083:17–26. https://doi.org/10.1016/j.molstruc.2014.11.003
Mohd Norsham IN, Baharin SNA, Raoov M, Shahabuddin S, Jakmunee J, Sambasevam KP (2020) Optimization of waste quail eggshells as biocomposites for polyaniline in ammonia gas detection. Polym Eng Sci 60:3170–3182. https://doi.org/10.1002/pen.25545
Muhammad MH, Idris AL, Fan X, Guo Y, Yu Y, Jin X, Huang T (2020) Beyond risk: bacterial biofilms and their regulating approaches. Front Microbiol 11:928. https://doi.org/10.3389/fmicb.2020.00928
Mustafin AG, Latypova LR, Andriianova AN, Salikhov SM, Sattarova AF, Mullagaliev IN, Abdrakhmanov IB (2020) Synthesis and Physicochemical Properties of Poly(2-ethyl-3-methylindole). Macromolecules 53:8050–8059. https://doi.org/10.1021/acs.macromol.0c01308
Mustafin AG, Latypova LR, Andriianova AN, Mullagaliev IN, Salikhov SM, Salikhov RB, Usmanova GS (2021a) Polymerization of new aniline derivatives: synthesis, characterization and application as sensors. RSC Adv 11:21006–21016. https://doi.org/10.1039/D1RA02474D
Mustafin AG, Latypova LR, Andriianova AN, Usmanova GS (2021b) Poly[N-(2-chloroprop-2-en-1-yl) aniline]s: synthesis, polymer analogous reaction, and physicochemical properties. Polym Chem 12:5650–5661. https://doi.org/10.1039/D1PY00940K
Mustafin AG, Latypova LR, Andriianova AN (2021c) Synthesis and polymerization of 2-(1-methylbut-2-en-1-yl) aniline and its products modification. Polym Test 104:107351. https://doi.org/10.1016/j.polymertesting.2021.107351
Nazir R, Zaffar MR, Amin I (2019) Bacterial biofilms: the remarkable heterogeneous biological communities and nitrogen fixing microorganisms in lakes. Freshwater Microbiology. https://doi.org/10.1016/B978-0-12-817495-1.00008-6
Phasuksom K, Sirivat A (2016) Synthesis of nano-sized polyindole via emulsion polymerization and doping. Synth Met 219:142–153. https://doi.org/10.1016/j.synthmet.2016.05.033
Plachý T, Žitka J, Mrlík M, Bažant P, Kadlečková M, Trchová M, Stejskal J (2021) Electrorheology of polyindole. Polymer 217:123448. https://doi.org/10.1016/j.polymer.2021.123448
Podder S, Paul S, Basak P, Xie B, Fullwood NJ, Baldock SJ, Ghosh CK (2020) Bioactive Silver Phosphate/polyindole Nanocomposites. RSC Adv 10:11060–11073. https://doi.org/10.1039/D0RA01129K
Riaz U, Khan S, Islam MN, Ahmad S, Ashraf SM (2008) Evaluation of antibacterial activity of nanostructured poly(1-naphthylamine) and its composites. J Biomater Sci Polym Ed 19(11):1535–1546. https://doi.org/10.1163/156856208786140418
Shahabuddin S, Baharin SNA, Suhaimi NF, Yunus N, Sambasevam KP (2022) Preparation of shrimp-based chitin blend with polyaniline for chromium (VI) removal from aqueous solution. Mater Tod: Proceed 62:6940–6944. https://doi.org/10.1016/j.matpr.2021.12.299
Shahabuddin S, Mazlan NA, Baharin SNA, Sambasevam KP (2021) Introduction to conducting polymers. Advances in hybrid conducting polymer technology. Springer, Cham, pp 1–18. https://doi.org/10.1007/978-3-030-62090-5_1
Shoeb M, Mobin M, Rauf MA, Owais M, Naqvi AH (2018) In vitro and in vivo antimicrobial evaluation of graphene–polyindole (gr@ pin) nanocomposite against methicillin-resistant staphylococcus aureus pathogen. ACS Omega 3:9431–9440. https://doi.org/10.1021/acsomega.8b00326
Singh AP, Mishra M, Sambyal P, Gupta BK, Singh BP, Chandra A, Dhawan SK (2014) Encapsulation of γ-Fe 2 O 3 decorated reduced graphene oxide in polyaniline core–shell tubes as an exceptional tracker for electromagnetic environmental pollution. J Mater Chem 2:3581–3593. https://doi.org/10.1039/C3TA14212D
Siqueira JF Jr (2002) Endodontic infections: concepts, paradigms, and perspectives. Oral Surg Oral Med Oral Pathol Oral Radiol Endodontol 94:281–293. https://doi.org/10.1067/moe.2002.126163
Timofeeva L, Kleshcheva N (2011) Antimicrobial polymers: mechanism of action, factors of activity, and applications. Appl Microbiol Biotechnol 89:475–492. https://doi.org/10.1007/s00253-010-2920-9
Wang R, Ye G, Zhou W, Jiang F, Wu Y, Hou J, Du Y (2019) High-quality freestanding flexible poly(5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-1H-indole) film: electrosyntheses, characterization, and optical properties. J App Polym Sci 136:47016. https://doi.org/10.1002/app.47016
Yaroslavov AA, Efimova AA, Lobyshev VI, Kabanov VA (2002) Reversibility of structural rearrangements in the negative vesicular membrane upon electrostatic adsorption/desorption of the polycation. Biochim Bioph Acta Biomembr 1560:14–24. https://doi.org/10.1016/S0005-2736(01)00453-9
Yaroslavov AA, Melik-Nubarov NS, Menger FM (2006) Polymerinduced flip-flop in biomembranes. Acc Chem Res 39:702–710. https://doi.org/10.1021/ar050078q
Yebra DM, Kiil S, Dam-Johansen K (2004) Antifouling technology—past, present and future steps towards efficient and environmentally friendly antifouling coatings. Prog Org Coat 50:75–104. https://doi.org/10.1016/j.porgcoat.2003.06.001
Zhu B, Li Y, Huang F, Chen Z, Xie J, Ding C, Li J (2019) Promotion of the osteogenic activity of an antibacterial polyaniline coating by electrical stimulation. Biomater Sci 7:4730–4737. https://doi.org/10.1039/C9BM01203F
Acknowledgements
This study was supported by the Russian Science Foundation (RSF) within project No. 22-23-00623.
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Latypova, L.R., Usmanova, G.S., Vasilova, L.Y. et al. Synthesis and characterization of N-substituted polyanilines and polyindoles and their antibacterial activity. Chem. Pap. 77, 473–483 (2023). https://doi.org/10.1007/s11696-022-02506-4
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DOI: https://doi.org/10.1007/s11696-022-02506-4