100
Views
2
CrossRef citations to date
0
Altmetric
Research Articles

Polyaniline/Aza-Bicyclo Composites Containing P, S, and Si Atoms: Synthesis, Characterization, Molecular Orbital Calculations, Electrical Conductivity, and Biocidal Activities against Some Biofouling-Causing Organisms

, &
Pages 2392-2409 | Received 21 Jun 2020, Accepted 02 Oct 2020, Published online: 30 Oct 2020

References

  • A. Aboelnaga, M. Hagar, and S. Soliman, “Ultrasonic Synthesis, Molecular Structure and Mechanistic Study of 1,3-Dipolar Cycloaddition Reaction of 1-Alkynylpyridinium-3-Olate and Acetylene Derivatives,” Molecules 21, no. 7 (2016): 848.
  • A. Aboelnaga and S. Abbady, “Ball Milling Assisted 1,3-Dipolar Cycloaddition Reaction of 1-(4-Nitrobenzyl)-Pyridinium-3-Olate,” Indian Journal of Heterocyclic Chemistry 27, no. 4 (2017): 423–30.
  • N. Dennis, A. R. Katritzky, and Y. Takeuchi, “Synthetic Applications of Heteroaromatic Betaines with Six-Membered Rings,” Angewandte Chemie 15, no. 1 (1976): 1–9.
  • S. L. Shapiro, K. Weinberg, and L. Freedman, “N-Substituted-3-Oxypyridyl Betaines,” Journal of the American Chemical Society 81, no. 19 (1959): 5140–5.
  • M. R. Safenaz and M. Sheikha, “Synthesis and Electrical Properties of Polyaniline Composite with Silver Nanoparticles,” Advances in Materials Physics and Chemistry 2012, (2012).
  • S. Bhadra, D. Khastgir, N. K. Singha, and J. H. Lee, “Progress in Preparation, Processing and Applications of Polyaniline,” Progress in Polymer Science 34, no. 8 (2009): 783–810.
  • A. G. MacDiarmid, “Polyaniline and Polypyrrole: Where Are We Headed?” Synthetic Metals 84, no. 1–3 (1997): 27–34.
  • S. M. Reda and S. M. Al-Ghannam, “Synthesis and Electrical Properties of Polyaniline Composite with Silver Nanoparticles,” Advances in Materials Physics and Chemistry 2, no. 2 (2012): 75–81.
  • Shumaila, G. B. V. S. Lakshmi, M. Alam, A. M. Siddiqui, M. Zulfequar, and M. Husain. “Synthesis and Characterization of Se Doped Polyaniline,” Current Applied Physics 11, no. 2 (2011): 217–22.
  • S. Umare, B. Shambharkar, and R. Ningthoujam, “Synthesis and Characterization of Polyaniline–Fe3O4 Nanocomposite: Electrical Conductivity, Magnetic, Electrochemical Studies,” Synthetic Metals 160, no. 17–18 (2010): 1815–21.
  • T. Jeevananda and J. H. Lee, “Preparation of Polyaniline Nanostructures Using Sodium Dodecylsulphate,” Materials Letters 62, no. 24 (2008): 3995–8.
  • D. Harvey, Modern Analytical Chemistry (Boston, MA: McGraw-Hill, 2000).
  • F. Fifield and D. Kealey, Principles and Practice of Analytical Chemistry (USA: Blackwell Science Ltd., 2000), 270–6.
  • D. E. Mohamed, M. A. Abbas, N. A. Fatthallah, and M. R. Mishrif, “Corrosion Inhibition and Antimicrobial Activity of Some Ethoxylated Sulphanilamides on Carbon Steel in Acidic Medium,” MSAIJ 10, no. 2 (2014): 57–71.
  • M. A. Hassan, G. H. Sayed, A. M. El-Nagar, and A. M. Hussien, “A Convenient Synthesis of Some Diarylurea and Thiourea Derivatives as Antimicrobial Compounds,” Chemical and Process Engineering Research 25 (2014): 1–11.
  • D. J. Finney, Probit Analysis, 3rd ed. (London, UK: Cambridge University Press, 1971).
  • P. Murray, E. J. Baron, M. A. Pfaller, F. C. Tenover, and R. H. Yolken, “Manual of Clinical Microbiology (6th Edn),” Trends in Microbiology 3, no. 11 (1995): 449.
  • P. Olurinola, A Laboratory Manual of Pharmaceutical Microbiology, vol. 69 (Idu, Abuja, Nigeria: National Institute for Pharmaceutical Research and Development, 1996), 1–105.
  • A. Sen and A. Batra, “Evaluation of Antimicrobial Activity of Different Solvent Extracts of Medicinal Plant: Melia azedarach L,” International Journal of Current Pharmaceutical Research 4, no. 2 (2012): 67–73.
  • K. Bisetty and P. Singh, “Cycloaddition Reactions of Azatrienes with Sulfene,” International Journal of Organic Chemistry 2, no. 2 (2012): 121–5.
  • A. A. Syed and M. K. Dinesan, “Anion-Exchange Studies on Electrically Conducting Polymers: Polyanilines,” Reactive Polymers 17, no. 2 (1992): 145–57.
  • C. E. Stephan, “Methods for calculating an LC50,” in Aquatic Toxicology and Hazard Evaluation, edited by F. L. Mayer and J. L. Hamelink (Philadelphia, PA: ASTM International, 1977), 65–84.
  • J. Lu, Y. Qian, M. Altieri, H. Dong, J. Wang, K. Raina, J. Hines, J. D. Winkler, A. P. Crew, K. Coleman, et al. “Hijacking the E3 Ubiquitin Ligase Cereblon to Efficiently Target BRD4,” Chemistry & Biology 22, no. 6 (2015): 755–63.
  • A. R. Katritzky and N. Dennis, “Cycloaddition Reactions of Heteroaromatic Six-Membered Rings,” Chemical Reviews 89, no. 4 (1989), 827–61.
  • M. Trchová, I. Šeděnková, E. Tobolková, and J. Stejskal, “FTIR Spectroscopic and Conductivity Study of the Thermal Degradation of Polyaniline Films,” Polymer Degradation and Stability 86, no. 1 (2004): 179–85.
  • M. Khalid and F. Mohammad, “Preparation, FTIR Spectroscopic Characterization and Isothermal Stability of Differently Doped Fibrous Conducting Polymers Based on Polyaniline and Nylon-6,6,” Synthetic Metals 159, no. 1–2 (2009): 119–22.
  • T. Prabhakaran and J. Hemalatha, “Synthesis and Characterization of Magnetoelectric Polymer Nanocomposites,” Journal of Polymer Science Part B: Polymer Physics 46, no. 22 (2008): 2418–22.
  • C. Zhou, J. Han, G. Song, and R. Guo, “Fabrication of Poly(Aniline‐Co‐Pyrrole) Hollow Nanospheres with Triton X‐100 Micelles as Templates,” Journal of Polymer Science Part A: Polymer Chemistry 46, no. 11 (2008): 3563–72.
  • S. Zhou, T. Wu, and J. Kan, “Effect of Co2+, Ni2+, Cu2+, or Zn2+ on Properties of Polyaniline Nanoparticles,” Journal of Applied Polymer Science 106, no. 1 (2007): 652–8.
  • L. Yan and W. Tao, “Synthesis of Achiral PEG‐PANI Rod‐Coil Block Copolymers and Their Helical Superstructures,” Journal of Polymer Science Part A: Polymer Chemistry 46, no. 1 (2008): 12–20.
  • X. Lei and Z. Su, “Conducting Polyaniline‐Coated Nano Silica by In Situ Chemical Oxidative Grafting Polymerization,” Polymers for Advanced Technologies 18, no. 6 (2007): 472–6.
  • W. F. Alves, E. C. Venancio, F. L. Leite, D. H. F. Kanda, L. F. Malmonge, J. A. Malmonge, and L. H. C. Mattoso, “Thermo-Analyses of Polyaniline and Its Derivatives,” Thermochimica Acta 502, no. 1–2 (2010): 43–6.
  • S. H. Hosseini and A. A. Entezami, “Studies of Thermal and Electrical Conductivity Behaviours of Polyaniline and Polypyrrole Blends with Polyvinyl Acetate, Polystyrene and Polyvinyl Chloride,” Iranian Polymer Journal 14, no. 3 (2005): 201–9.
  • J. Bhadra, N. J. Al-Thani, N. K. Madi, and M. A. Al-Maadeed, “Effects of Aniline Concentrations on the Electrical and Mechanical Properties of Polyaniline Polyvinyl Alcohol Blends,” Arabian Journal of Chemistry 10, no. 5 (2017): 664–72.
  • J. C. Spain, “Biodegradation of Nitroaromatic Compounds,” Annual Review of Microbiology 49, no. 1 (1995): 523–55.
  • D. Traversi, R. Degan, R. De Marco, G. Gilli, C. Pignata, S. Villani, and R. Bono, “Mutagenic Properties of PM2.5 Urban Pollution in the Northern Italy: The Nitro-Compounds Contribution,” Environment International 35, no. 6 (2009): 905–10.
  • P. R. Race, A. L. Lovering, R. M. Green, A. Ossor, S. A. White, P. F. Searle, C. J. Wrighton, and E. I. Hyde, “Structural and Mechanistic Studies of Escherichia coli Nitroreductase with the Antibiotic Nitrofurazone Reversed Binding Orientations in Different Redox States of the Enzyme,” The Journal of Biological Chemistry 280, no. 14 (2005): 13256–64.
  • C. Bryant and W. McElroy, Chemistry and Biochemistry of Flavoenzymes (Boca Raton, FL: CRC Press, 1991), 295–7.
  • J. Lee, I. B. C. Matheson, F. Müller, D. J. O’Kane, J. Vervoort, and A. J. W. G. Visser, “The Mechanism of Bacterial Bioluminescence,” in Chemistry and Biochemistry of Flavoenzymes, vol. 2, edited by F. Müller (Boca Raton, FL: CRC Press, 1991), 109–51.
  • D. W. Bryant, D. R. McCalla, M. Leeksma, and P. Laneuville, “Type I Nitroreductases of Escherichia coli,” Canadian Journal of Microbiology 27, no. 1 (1981): 81–6.
  • C. Ren, T. Wang, X. Zhang, J. Pan, J. Xu, and Y. Bai, “Asymmetric Bioreduction of γ-and δ-Keto Acids by Native Carbonyl Reductases from Saccharomyces cerevisiae,” Chinese Journal of Chemical Engineering (2020).
  • O. S. Bains, M. J. Karkling, T. A. Grigliatti, R. E. Reid, and K. W. Riggs, “Two Non-Synonymous Single Nucleotide Polymorphisms of Human Carbonyl Reductase 1 Demonstrate Reduced In Vitro Metabolism of Daunorubicin and Doxorubicin,” Drug Metabolism and Disposition 37, no. 5 (2009): 1107–14.
  • J. A. Doorn, E. Maser, A. Blum, D. J. Claffey, and D. R. Petersen, “Human Carbonyl Reductase Catalyzes Reduction of 4-Oxonon-2-Enal,” Biochemistry 43, no. 41 (2004): 13106–14.
  • Y. El-Hawari, A. D. Favia, E. S. Pilka, M. Kisiela, U. Oppermann, H.-J. Martin, and E. Maser, “Analysis of the Substrate-Binding Site of Human Carbonyl Reductases CBR1 and CBR3 by Site-Directed Mutagenesis,” Chemico-Biological Interactions 178, no. 1–3 (2009): 234–41.
  • D. Ghosh, M. Sawicki, V. Pletnev, M. Erman, S. Ohno, S. Nakajin, and W. L. Duax, “Porcine Carbonyl Reductase: Structural Basis for a Functional Monomer in Short-Chain Dehydrogenases/Reductases,” The Journal of Biological Chemistry 276, no. 21 (2001): 18457–63.
  • S. Tchatalbachev, R. Ghai, H. Hossain, and T. Chakraborty, “Gram-Positive Pathogenic Bacteria Induce a Common Early Response in Human Monocytes,” BMC Microbiology 10, no. 1 (2010): 275.
  • A. M. Gilbert, A. Failli, J. Shumsky, Y. Yang, A. Severin, G. Singh, W. Hu, D. Keeney, P. J. Petersen, A. H. Katz, et al. “Pyrazolidine-3,5-Diones and 5-Hydroxy-1H-Pyrazol-3(2H)-Ones, Inhibitors of UDP-N-Acetylenolpyruvyl Glucosamine Reductase,” Journal of Medicinal Chemistry 49, no. 20 (2006): 6027–36.
  • W. W. Navarre and O. Schneewind, “Surface Proteins of Gram-Positive Bacteria and Mechanisms of Their Targeting to the Cell Wall Envelope,” Microbiology and Molecular Biology Reviews: MMBR 63, no. 1 (1999): 174–229.
  • A. Badawi and A. Hafiz, “Synthesis and Immunomodulatory Activity of Some Novel Amino Acid Germinates,” Journal of the Iranian Chemical Society 4, no. 1 (2007): 107–13.
  • R. M. Mohareb, A. M. Badawi, M. R. Noor El-Din, N. A. Fatthalah, and M. R. Mahrous, “Synthesis and Characterization of Cationic Surfactants Based on N-Hexamethylenetetramine as Active Microfouling Agents,” Journal of Surfactants and Detergents 18 (2015): 529–35.
  • N. Kawabata and M. Nishiguchi, “Antibacterial Activity of Soluble Pyridinium-Type Polymers,” Applied and Environmental Microbiology 54, no. 10 (1988): 2532–35.
  • S. Gurunathan, J. W. Han, A. A. Dayem, V. Eppakayala, and J.-H. Kim, “Oxidative Stress-Mediated Antibacterial Activity of Graphene Oxide and Reduced Graphene Oxide in Pseudomonas aeruginosa,” International Journal of Nanomedicine 7 (2012): 5901–14.
  • Y. Li, W. Zhang, J. Niu, and Y. Chen, “Mechanism of Photogenerated Reactive Oxygen Species and Correlation with the Antibacterial Properties of Engineered Metal-Oxide Nanoparticles,” ACS Nano 6, no. 6 (2012): 5164–73.
  • Z. Peng, J. Ni, K. Zheng, Y. Shen, X. Wang, G. He, S. Jin, and T. Tang, “Dual Effects and Mechanism of TiO2 Nanotube Arrays in Reducing Bacterial Colonization and Enhancing C3H10T1/2 Cell Adhesion,” International Journal of Nanomedicine 8 (2013): 3093–105.
  • X.-H. Wang, J. Li, J.-Y. Zhang, Z.-C. Sun, L. Yu, X.-B. Jing, F.-S. Wang, Z.-X. Sun, and Z.-J. Ye, “Polyaniline as Marine Antifouling and Corrosion-Prevention Agent,” Synthetic Metals 102, no. 1–3 (1999): 1377–80.
  • D. R. Livingstone, “Organic Xenobiotic Metabolism in Marine Invertebrates,” in Advances in Comparative and Environmental Physiology , edited by R. Gilles, Liege, P. J. Butler, Birmingham R. Greger, Freiburg Ch. P. Mangum, Williamsburg G. N. Somero, La Jolla K. Takahashi, Tokyo and R. E. Weber, Aarhus (Berlin: Springer, 1991), 45–185.
  • K.-S. Ju and R. E. Parales, “Nitroaromatic Compounds, from Synthesis to Biodegradation,” Microbiology and Molecular Biology Reviews: MMBR 74, no. 2 (2010): 250–72.
  • S. Moreno and R. Docampo, “Mechanism of Toxicity of Nitro Compounds Used in the Chemotherapy of Trichomoniasis,” Environmental Health Perspectives 64 (1985): 199–208.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.