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Vol. 25 No. 7 (2013): Vol 25 Issue 7

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Synthesis and Properties of Novel Polyazobenzene

https://doi.org/10.14233/ajchem.2013.13686
Weiwei Li
College of Chemistry, Chemical Engineering and Materials Science, National Engineering Laboratory for Modern Silk, Key Laboratory of Organic Synthesis of Jiangsu Province, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Soochow University, Suzhou, Jiangsu 215123, P.R. China
Dongmei Xu
College of Chemistry, Chemical Engineering and Materials Science, National Engineering Laboratory for Modern Silk, Key Laboratory of Organic Synthesis of Jiangsu Province, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, Soochow University, Suzhou, Jiangsu 215123, P.R. China

Corresponding Author(s) : Dongmei Xu

xdm.sd@163.com

Asian Journal of Chemistry, Vol. 25 No. 7 (2013): Vol 25 Issue 7

Abstract

A novel aromatic polyazo compound 1,2-bis[4-((4,6-bis((4-phenyl diazenyl)phenoxy)-1,3,5- triazin-2-yl)oxy)phenyl]diazene with five azobenzene units was facilely constructed by dehydrochlorination reaction between p-hydroxyazobenzene, 4,4'-dihydroxyazobenzene and cyanuric chloride under very mild conditions. Compared to azobenzene, the crystallinity of polyazo compound with five azobenzene units greatly decreased, while the thermostability remarkably improved. The maximal absorption wavelength of polyazo compound with five azobenzene units was close to that of azobenzene, but the molar extinction coefficient of polyazo compound with five azobenzene units was near five times of that of azobenzene. Polyazo compound with five azobenzene units exhibited typical reversible photoisomerization behaviours and was expected to be applied in photonic material areas.

Keywords

Azo compound Cyanuric chloride Crystallinity Thermostability Photoisomerization
Li, W., & Xu, D. (2013). Synthesis and Properties of Novel Polyazobenzene. Asian Journal of Chemistry, 25(7), 3625–3628. https://doi.org/10.14233/ajchem.2013.13686
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References
  1. N. Tamai and H. Miyasaka, Chem. Rev., 100, 1875 (2000).
  2. M. Pederzoli and J. Pittner, J. Phys. Chem. A, 115, 11136 (2011).
  3. T. Cusati, G. Granucci and M. Persico, J. Am. Chem. Soc., 133, 5109 (2011).
  4. G.S. Kumar and D.C. Neckers, Chem. Rev., 89, 1915 (1989).
  5. H. Rau, Photocromism: Mol. Syst., l, 165 (1990).
  6. I. Conti, M. Garavelli and G. Orlandi, J. Am. Chem. Soc., 130, 5216 (2008).
  7. J. Yao, Y. You, H. Liu, L. Dong and C. Xiong, J. Mater. Chem., 46, 3343 (2010).
  8. T. Ikeda and O. Tsutsumi, Science, 268, 1873 (1995).
  9. M. Suda, M. Nakagawa, T. Iyoda and Y. Einaga, J. Am. Chem. Soc., 129, 5538 (2007).
  10. W. Chen, Y. Lee and C. Chen, Org. Lett., 12, 1472 (2010).
  11. K.M. Lee and T.J. White, Polymer, 3, 1447 (2011).
  12. F.Z. Liu, K. Hashimoto and A. Fujishima, Nature, 347, 658 (1990).
  13. P.H. Rasmussen, P.S. Ramanujam, S. Hvilsted and R.H. Berg, J. Am. Chem. Soc., 121, 4738 (1999).
  14. H. Audorff, K. Kreger, R. Walker, D. Haarer, L. Kador and H.W. Schmidt, Adv. Polym. Sci., 228, 59 (2010).
  15. F.K. Bruder, R. Hagen, T. Rölle, M.S. Weiser and T. Fäcke, Angew. Chem. Int. Ed., 50, 4552 (2011).
  16. S. Spörlein, H. Carstens, H. Satzger, C. Renner, R. Behrendt, L. Moroder, P. Tavan, W. Zinth and J. Wachtveitl, Proc. Natl. Acad. Sci. USA, 99, 7998 (2002).
  17. C. Dugave and L. Demange, Chem. Rev., 103, 2475 (2003).
  18. A. Credi, Aust. J. Chem., 59, 157 (2006).
  19. T. Hugel, N.B. Holland, A. Cattani, L. Moroder, M. Seitz and H.E. Gaub, Science, 296, 1103 (2002).
  20. Y. Yu and T.J. Ikeda, Photochem. Photobiol. C, 5, 247 (2004).
  21. M. Chen, H.H. Uang, Y. Zhu, Z. Liu, X. Xing, F. Cheng and Y. Yu, Appl. Phys. A: Mater., 102, 667 (2011).
  22. X. Lv, H. Chang and H. Zhang, Opt. Commun., 284, 4991 (2011).
  23. H.A. Dabbagh, A. Teimouri and A.N. Chermahini, Dyes Pigments, 73, 239 (2007).
  24. M.P. Placidi, A.L. Villaraza, L.S. Natrajan, D. Sykes, A.M. Kenwright and S. Faulkner, J. Am. Chem. Soc., 131, 9916 (2009).
  25. J. Liu, F. Qiu, G. Cao, Q. Shen, Z. Cao and D. Yang, J. Appl. Polym. Sci., 121, 2567 (2011).
  26. X. Wang, J. Yin and X. Wang, Polymer, 52, 3344 (2011).
  27. H. Xie, S. Wang, G. Zhong, Y. Liu, H. Zhang and E. Chen, Macromolecules, 44, 7600 (2011).
  28. H. Sogawa, M. Shiotsuki, H. Matsuoka and F. Sanda, Macromolecules, 44, 3338 (2011).
  29. W. Zhang, K. Yoshida, M. Fujiki and X. Zhu, Macromolecules, 44, 5105 (2011).
  30. D. Ma, Y. Hou and Z. Sun, J. Nat. Sci. Heilongjiang Univ., 24, 446 (2007) In Chinese.
  31. X. Liu, X. Lin, D. Xu and K. Zhang, Sci. Technol. Chem. Ind., 14, 23 (2006) In Chinese.
  32. W. Chen, Y. Lee and C. Chen, Org. Lett., 12, 1472 (2010).
  33. M. Liu, X. Yan, M. Hu, X. Chen, M. Zhang, B. Zheng, X. Hu, S. Shao and F. Huang, Org. Lett., 12, 2558 (2010).
  34. Y. Morishima, M. Tsuji and M. Kamachi, Macromolecules, 25, 4406 (1992).
  35. C. Saravanan and P. Kannan, Polym. Degrad. Stab., 94, 1001 (2009).
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