Copolymerization of aniline and gallic acid: Novel electroactive materials with antioxidant and antimicrobial activities
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2022
Authors
Janošević-Ležaić, AleksandraPašti, Igor
Gledović, Ana
Antić-Stanković, Jelena
Božić, Dragana
Uskoković-Marković, Snežana
Ćirić-Marjanović, Gordana
Article (Published version)
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Novel electroactive PANI-GA micro/nanostructured functional copolymers/co-oligomers were synthesized by the oxidative copolymerization of aniline and gallic acid (GA) in an aqueous solution, using ammonium peroxydisulfate (APS) as an oxidant and different initial mole ratios of GA to aniline ([GA]/[aniline]=0.1, 0.25, 0.5 and 1.0). It was found that the yield, molecular structure, morphology, electrical conductivity, electrochemical behavior, antioxidant and antimicrobial properties of PANI-GA strongly depend on [GA]/[aniline] ratio. The highest conductivity (3.8 × 10–3 S cm 1) showed PANI-GA with dominant polyaniline (PANI) emeraldine salt segments and nanorod morphology, synthesized at [GA]/[aniline] = 0.1. FTIR spectroscopy confirmed the presence of covalently bonded GA and PANI-type structural segments in PANI-GA. The antioxidant activity of PANI-GA was explored by the spectrophotometric 2,2′ -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assay and electrochemical test ...for superoxide anion radical, •O2 . All protonated PANI-GA showed good scavenging activity toward ABTS•+ and •O2 radicals, whereby the highest activity exhibited PANI-GA produced at [GA]/[aniline] = 1. The radical scavenging activity of protonated PANI-GA samples toward ABTS•+ was much higher than that of PANI. The antimicrobial properties of the PANI-GA against bacteria S. aureus and E. coli, as well as against fungus C. albicans were evaluated. All synthesized protonated PANI-GA were more effective as S. aureus growth inhibitors than pristine GA and PANI. Highest effectiveness against E. coli and C. albicans, higher than that of pristine GA and PANI, showed conductive PANI-GA synthesized at [GA]/[aniline]= 0.1. Based on the obtained experimental results the mechanism of GA and aniline oxidative copolymerization is proposed.
Keywords:
Antioxidant activity / Aniline / Antimicrobial activity / Copolymerization / Gallic acidSource:
Synthetic Metals, 2022, 286Publisher:
- Elsevier Ltd
Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200146 (University of Belgrade, Faculty of Physical Chemistry) (RS-200146)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200161 (University of Belgrade, Faculty of Pharmacy) (RS-200161)
DOI: 10.1016/j.synthmet.2022.117048
ISSN: 0379-6779
WoS: 000787688700003
Scopus: 2-s2.0-85125835685
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Institution/Community
PharmacyTY - JOUR AU - Janošević-Ležaić, Aleksandra AU - Pašti, Igor AU - Gledović, Ana AU - Antić-Stanković, Jelena AU - Božić, Dragana AU - Uskoković-Marković, Snežana AU - Ćirić-Marjanović, Gordana PY - 2022 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4067 AB - Novel electroactive PANI-GA micro/nanostructured functional copolymers/co-oligomers were synthesized by the oxidative copolymerization of aniline and gallic acid (GA) in an aqueous solution, using ammonium peroxydisulfate (APS) as an oxidant and different initial mole ratios of GA to aniline ([GA]/[aniline]=0.1, 0.25, 0.5 and 1.0). It was found that the yield, molecular structure, morphology, electrical conductivity, electrochemical behavior, antioxidant and antimicrobial properties of PANI-GA strongly depend on [GA]/[aniline] ratio. The highest conductivity (3.8 × 10–3 S cm 1) showed PANI-GA with dominant polyaniline (PANI) emeraldine salt segments and nanorod morphology, synthesized at [GA]/[aniline] = 0.1. FTIR spectroscopy confirmed the presence of covalently bonded GA and PANI-type structural segments in PANI-GA. The antioxidant activity of PANI-GA was explored by the spectrophotometric 2,2′ -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assay and electrochemical test for superoxide anion radical, •O2 . All protonated PANI-GA showed good scavenging activity toward ABTS•+ and •O2 radicals, whereby the highest activity exhibited PANI-GA produced at [GA]/[aniline] = 1. The radical scavenging activity of protonated PANI-GA samples toward ABTS•+ was much higher than that of PANI. The antimicrobial properties of the PANI-GA against bacteria S. aureus and E. coli, as well as against fungus C. albicans were evaluated. All synthesized protonated PANI-GA were more effective as S. aureus growth inhibitors than pristine GA and PANI. Highest effectiveness against E. coli and C. albicans, higher than that of pristine GA and PANI, showed conductive PANI-GA synthesized at [GA]/[aniline]= 0.1. Based on the obtained experimental results the mechanism of GA and aniline oxidative copolymerization is proposed. PB - Elsevier Ltd T2 - Synthetic Metals T1 - Copolymerization of aniline and gallic acid: Novel electroactive materials with antioxidant and antimicrobial activities VL - 286 DO - 10.1016/j.synthmet.2022.117048 ER -
@article{ author = "Janošević-Ležaić, Aleksandra and Pašti, Igor and Gledović, Ana and Antić-Stanković, Jelena and Božić, Dragana and Uskoković-Marković, Snežana and Ćirić-Marjanović, Gordana", year = "2022", abstract = "Novel electroactive PANI-GA micro/nanostructured functional copolymers/co-oligomers were synthesized by the oxidative copolymerization of aniline and gallic acid (GA) in an aqueous solution, using ammonium peroxydisulfate (APS) as an oxidant and different initial mole ratios of GA to aniline ([GA]/[aniline]=0.1, 0.25, 0.5 and 1.0). It was found that the yield, molecular structure, morphology, electrical conductivity, electrochemical behavior, antioxidant and antimicrobial properties of PANI-GA strongly depend on [GA]/[aniline] ratio. The highest conductivity (3.8 × 10–3 S cm 1) showed PANI-GA with dominant polyaniline (PANI) emeraldine salt segments and nanorod morphology, synthesized at [GA]/[aniline] = 0.1. FTIR spectroscopy confirmed the presence of covalently bonded GA and PANI-type structural segments in PANI-GA. The antioxidant activity of PANI-GA was explored by the spectrophotometric 2,2′ -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assay and electrochemical test for superoxide anion radical, •O2 . All protonated PANI-GA showed good scavenging activity toward ABTS•+ and •O2 radicals, whereby the highest activity exhibited PANI-GA produced at [GA]/[aniline] = 1. The radical scavenging activity of protonated PANI-GA samples toward ABTS•+ was much higher than that of PANI. The antimicrobial properties of the PANI-GA against bacteria S. aureus and E. coli, as well as against fungus C. albicans were evaluated. All synthesized protonated PANI-GA were more effective as S. aureus growth inhibitors than pristine GA and PANI. Highest effectiveness against E. coli and C. albicans, higher than that of pristine GA and PANI, showed conductive PANI-GA synthesized at [GA]/[aniline]= 0.1. Based on the obtained experimental results the mechanism of GA and aniline oxidative copolymerization is proposed.", publisher = "Elsevier Ltd", journal = "Synthetic Metals", title = "Copolymerization of aniline and gallic acid: Novel electroactive materials with antioxidant and antimicrobial activities", volume = "286", doi = "10.1016/j.synthmet.2022.117048" }
Janošević-Ležaić, A., Pašti, I., Gledović, A., Antić-Stanković, J., Božić, D., Uskoković-Marković, S.,& Ćirić-Marjanović, G.. (2022). Copolymerization of aniline and gallic acid: Novel electroactive materials with antioxidant and antimicrobial activities. in Synthetic Metals Elsevier Ltd., 286. https://doi.org/10.1016/j.synthmet.2022.117048
Janošević-Ležaić A, Pašti I, Gledović A, Antić-Stanković J, Božić D, Uskoković-Marković S, Ćirić-Marjanović G. Copolymerization of aniline and gallic acid: Novel electroactive materials with antioxidant and antimicrobial activities. in Synthetic Metals. 2022;286. doi:10.1016/j.synthmet.2022.117048 .
Janošević-Ležaić, Aleksandra, Pašti, Igor, Gledović, Ana, Antić-Stanković, Jelena, Božić, Dragana, Uskoković-Marković, Snežana, Ćirić-Marjanović, Gordana, "Copolymerization of aniline and gallic acid: Novel electroactive materials with antioxidant and antimicrobial activities" in Synthetic Metals, 286 (2022), https://doi.org/10.1016/j.synthmet.2022.117048 . .