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Synthesis and Characterization of N-Substituted Polybenzimidazoles
Corresponding Author(s) : Lin Zhang
Asian Journal of Chemistry,
Vol. 25 No. 7 (2013): Vol 25 Issue 7
Abstract
Soluble N-substituted polybenzimidazoles have been prepared by aromatic nucleophilic displacement reaction of N-H sites in 1,3-bis(2-benzimidazolyl)benzene (mBBIB) with activated aromatic difluorides containing sulfonyl and carbonyl groups in sulfolane at 210 ºC in the presence of anhydrous potassium carbonate. 1,3-Bis(2-benzimidazolyl)benzene was synthesized from isophthalic acid and 1,2-phenylenediamine in polyphosphoric acid. The structure of 1,3-bis(2- benzimidazolyl)benzene was confirmed by FT-IR, HRMS, 1H and 13C NMR. The characterizations of the resulting polymers were performed with FT-IR, 1H NMR, elemental analysis, GPC, DSC, TGA and solubility tests. DSC and TG measurements showed that polymers had high glass transition temperatures (Tg > 210 ºC) and good thermal stability with high decomposition temperatures (TD > 430 ºC). These novel polymers also showed good solubility.
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References
R.H. Pater and P.A. Curto, Acta Astrunautica, 61, 1121 (2007).
H. Vogel and C.S. Marvel, J. Polym. Sci. A: Polym. Chem., 34, 1125 (1996).
J.A. Asensio, E.M. Sánchez and P. Gómez-Romero, Chem. Soc. Rev., 39, 3210 (2010).
M. Hua, H. Chen, R. Tsai, Y. Leu, Y. Liu and J. Lai, J. Mater. Chem., 21, 7254 (2011).
S. Kim, T. Kim, J. Jung and J. Lee, Polymer, 50, 3495 (2009).
H. Toiserkani, H. Sheibani and K. Saidi, Eur. Polym. J., 46, 185 (2010).
H. Xu, K. Chen, X. Guo, J. Fang and F. Yin, J. Polym. Sci. A: Polym. Chem., 45, 1150 (2007).
F.E. Johnson and I. Cabasso, Macromolecules, 43, 3634 (2010).
J.G. JR. Smith, J.W. Connell and P.M. Hergenrother, J. Polym. Sci. A: Polym. Chem., 31, 3099 (1993).
A.R. Hlil, S. Matsumura and A.S. Hay, Macromolecules, 41, 1912 (2008).
Y. Qi, Y. Gao, S. Tian, A.R. Hlil, J. Gaudet, D. Guay and A.S. Hay, J. Polym. Sci. A: Polym. Chem., 47, 1920 (2009).
Q. Li, J.O. Jensen, R.F. Savinell and N.J. Bjerrum, Prog. Polym. Sci., 34, 449 (2009).