Advances in materials Research

Techno-Press (테크노프레스)
권호 표지
DOI QR코드

DOI QR Code

Chemical synthesis of processable conducting polyaniline derivative with free amine functional groups

  • Kar, Pradip (Department of Chemistry, Birla Institute of Technology)
  • Received : 2014.02.10
  • Accepted : 2014.07.10
  • Published : 2014.06.25
⟨ Previous Next ⟩

Abstract

Processable conducting polyaniline derivative with free amine functional groups was successfully synthesized from the monomer o-phenylenediamine in aqueous hydrochloric acid medium using ammonium persulfate as an oxidative initiator. The synthesized poly(o-phenylenediamine) (PoPD) in critical condition was found to be completely soluble in common organic solvents like dimethyl sulfoxide, N,N-dimethyl formamide etc. From the intrinsic viscosity measurement, the optimum condition for the polymerization was established. The polymer was characterized by ultraviolet visible spectroscopy, Fourier transform infrared spectroscopy, proton magnetic resonance spectroscopy ($^1HNMR$) and thermogravimetric (TGA) analyses. The weight average molecular weights of the synthesized polymers were determined by the dynamic light scattering (DLS) method. From the spectroscopic analysis the structure was found to resemble that of polyaniline derivative with free amine functional groups attached to ortho/meta position in the phenyl ring. However, very little ladder unit was also present with in the polymer chain. The moderate thermal stability of the synthesized polymer could be found from the TGA analysis. The average DC conductivity of $2.8{\times}10^{-4}S/cm$ was observed for the synthesized polymer pellet after doping with hydrochloric acid.

Keywords

References

  1. Gowariker, V.R., Viswanathan, N.V. and Sreedhar J. (2005), Polymer Science (1st Ed.), New Age Publication, New Delhi, India.
  2. Huang, M.R., Ding, Y.B. and Li, X.G. (2013), "Lead-ion potentiometric sensor based on electrically conducting microparticles of sulfonic phenylenediamine copolymer", Analyst., 138, 3820-3829. https://doi.org/10.1039/c3an00346a
  3. Huang, M.R., Peng, Q.Y. and Li, X.G. (2006), "Rapid and effective adsorption of lead ions on fine poly(phenylenediamine) microparticles", Chem. Eur. J. 12(16), 4341-4350. https://doi.org/10.1002/chem.200501070
  4. Huang, M.R., Rao, X.W., Li, X.G. and Ding, Y.B. (2011), "Lead ion-selective electrodes based on polyphenylenediamine as unique solid ionophores", Talanta, 85(3), 1575-1584. https://doi.org/10.1016/j.talanta.2011.06.049
  5. Huang, M.R., Li, X.G. and Duan, W. (2005), "Effect of polymerization conditions on o-phenylenediamine and o-phenetidine oxidative copolymers", Polym. Int., 54(1), 70-82. https://doi.org/10.1002/pi.1618
  6. Huang, M.R., Li, X.G. and Yang, Y.L. (2001), "Oxidative polymerization of o-phenylenediamine and pyrimidylamine", Polym. Degrad. Stabil., 71(1), 31-38.
  7. Huang, M.R., Lu, H.J. and Li, X.G. (2012), "Synthesis and strong heavy-metal ion sorption of copolymer microparticles from phenylenediamine and its sulfonate", J. Mater. Chem., 22, 17685-17699. https://doi.org/10.1039/c2jm32361c
  8. Kar, P., Pradhan, N.C. and Adhikari, B. (2008), "Characterization of sulfuric acid doped conducting poly (m-aminophenol)", J. Polym. Mater., 25(3), 387-396.
  9. Kar, P., Pradhan N.C. and Adhikari, B. (2009), "Application of sulfuric acid doped poly (m-aminophenol) as aliphatic alcohol vapor sensor material", Sens. Actuators B: Chem., 140(2), 525-531. https://doi.org/10.1016/j.snb.2009.05.013
  10. Kar, P., Pradhan, N.C. and Adhikari B. (2010), "Isomeric effects on structures and properties of polyaminophenols synthesized in basic medium", J. Macromol. Sci. A: Pure Appl. Chem., 47(3), 282-290. https://doi.org/10.1080/10601320903527137
  11. Kar, P., Behera, A.K., Pradhan, N.C. and Adhikari, B. (2011), "Doping of the processable conducting poly(m-Aminophenol) with inorganic acids", J. Macromol. Sci. B: Phys., 50(9), 1822-1833 (2011). https://doi.org/10.1080/00222348.2010.549429
  12. Leclerc, M., Guay, J. and Dao, L.H. (1989), "Synthesis and characterization of poly (alkylanilines)" Macromolecules, 22(2), 649-653. https://doi.org/10.1021/ma00192a024
  13. Levin, O., Kondratiev, V. and Malev, V. (2005), "Charge transfer processes at poly-o-phenylenediamine and poly-o-aminophenol films", Electrochim. Acta, 50(7-8), 1573-1585. https://doi.org/10.1016/j.electacta.2004.10.028
  14. Li, X.G., Huang, M.R., Duan, W. and Yang, Y.L. (2002), "Novel multifunctional polymers from aromatic diamines by oxidative polymerizations", Chem. Rev., 102(9), 2925-3030. https://doi.org/10.1021/cr010423z
  15. Li, X.G., Huang, M.R. and Yang, Y. (2001), "Synthesis and characterization of o-phenylenediamine and xylidine copolymers", Polymer, 42(9), 4099-4107. https://doi.org/10.1016/S0032-3861(00)00661-3
  16. Li, X.G., Lu, Q.F. and Huang, M.R. (2008), "Self-stabilized nanoparticles of intrinsically conducting copolymers from 5-sulfonic-2-anisidine", Small, 4(8), 1201-1209. https://doi.org/10.1002/smll.200701002
  17. Li, X.G., Ma, X.L., Sun, J. and Huang, M.R. (2009), "Powerful reactive sorption of silver(I) and mercury(II) onto poly(o-phenylenediamine) microparticles", Langmuir, 25(3), 1675-1684. https://doi.org/10.1021/la802410p
  18. Li, X.G., Wang, H.Y. and Huang, M.R. (2007), "Synthesis, film-forming, and electronic properties of o-phenylenediamine copolymers displaying an uncommon tricolor", Macromolecules, 40(5), 1489-1496. https://doi.org/10.1021/ma062463g
  19. Lu, Q.F., Huang, M.R. and Li, X.G. (2007), "Synthesis and heavy-metal-ion sorption of pure sulfophenylenediamine copolymer nanoparticles with intrinsic conductivity and stability", Chem. Eur. J., 13(21), 6009-6018. https://doi.org/10.1002/chem.200700233
  20. Negi, Y.S. and Adhyapak, P.V. (2002), "Development in polyaniline conducting polymer", Polym. Rev. 42(1), 35-53.
  21. Pham, Q.L., Haldorai, Y., Nguyen, V.H., Tuma, D. and Shim, J.J. (2011), "Facile synthesis of poly(p-phenylenediamine)/MWCNT nanocomposites and characterization for investigation of structural effects of carbon nanotubes", Bull. Mater. Sci., 34(1), 37-43. https://doi.org/10.1007/s12034-011-0049-9
  22. Premasiri, A.H. and Euler, W.B. (1995), "Syntheses and characterization of poly(aminophenazines)", Macromol. Chem. Phys., 196(11), 3655-3666. https://doi.org/10.1002/macp.1995.021961118
  23. Rivas, B.L., Sanchez, C.O., Bernede, J.C. and Mollinie, P. (2002), "Synthesis, characterization, and properties of poly (2- and 3-aminophenol) and poly(2- and 3-aminophenol)-Cu(II) materials", Poly. Bull., 49(4), 257-264. https://doi.org/10.1007/s00289-002-0104-1
  24. Salavagione, H.J., Arias, J., Garces, P., Morallon, E., Barbero, C. and Vazquez, J.L. (2004) "Spectroelectrochemical study of the oxidation of aminophenols on platinum electrode in acid medium", J. Electroanal. Chem., 565(2), 375-383. https://doi.org/10.1016/j.jelechem.2003.11.005
  25. Salavagione, H.J., Pardilla, J.A., Perez, J.M., Vazquez, J.L., Morallon, E., Miras, M.C. and Barbero, C. (2005), "Study of redox mechanism of poly (o-aminophenol) using in situ techniques: evidence of two redox processes", J. Electroanal. Chem., 576(1), 139-145. https://doi.org/10.1016/j.jelechem.2004.10.013
  26. Sayyah, S.M., Bahgat, A.A., El-Salam, H.M.A. and Azooz, R.E. (2006), "Electropolymerization kinetics of o-aminophenol and characterization of the obtained polymer films", J. Appl. Polym. Sci., 99(6), 3093-3109. https://doi.org/10.1002/app.22915
  27. Schroder, D.K. (1990), Semiconductor material and device characterization, John Wiley & Sons, New York, USA.
  28. Yacynych, A.M. and Mark Jr. H.B. (1976), "The spectroelectrochemical study of the oxidation of 1,2-diaminobenzene: Alone and in the presence of Ni(II)", J. Electrochem. Soc., 123(9), 1346-1351. https://doi.org/10.1149/1.2133073
  29. Yue, J. and Epstein A.J. (1990), "Synthesis of self-doped conducting polyaniline", J. Am. Chem. Soc., 112(7), 2800-2801. https://doi.org/10.1021/ja00163a051
  30. Zhou, D.M., Dai, Y.Q. and Shiu, K.K. (2010), "Poly(phenylenediamine) film for the construction of glucose biosensors based on platinized glassy carbon electrode", J. Appl. Electrochem., 40(11), 1997-2003. https://doi.org/10.1007/s10800-010-0179-6

Cited by

  1. Structure and properties of conducting poly(o-phenylenediamine) synthesized in different inorganic acid medium vol.24, pp.4, 2016, https://doi.org/10.1007/s13233-016-4054-0
  2. Influence of pH of the Reaction Medium on the Structure and Property of Conducting Poly(o-Phenylenediamine) vol.2, pp.4-5, 2015, https://doi.org/10.1016/j.matpr.2015.07.046
  3. Influence of structure of poly(o-phenylenediamine) on the doping ability and conducting property vol.23, pp.4, 2017, https://doi.org/10.1007/s11581-016-1904-x
  4. Synthesis of poly(o -phenylenediamine) nanofiber with novel structure and properties vol.28, pp.7, 2017, https://doi.org/10.1002/pat.3981
  5. Versatile epoxy/polyaniline and derived nanocomposite: from strategic design to advance application vol.25, pp.6, 2014, https://doi.org/10.1080/14328917.2020.1813452