Table of Contents
Journal of Polymers
Volume 2013, Article ID 167106, 8 pages
http://dx.doi.org/10.1155/2013/167106
Research Article

Synthesis of Polyethers Containing Triazole Units in the Backbone by Click Chemistry in a Tricomponent Reaction

Department of Polymer Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar 47416, Iran

Received 25 March 2013; Revised 23 July 2013; Accepted 13 August 2013

Academic Editor: Cyrille Boyer

Copyright © 2013 Moslem Mansour Lakouraj et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. J. Cotter, Engineering Plastics: A Handbook of Polyaryl Ethers, Gordon and Breach, Amsterdam, The Netherlands, 1995.
  2. I. S. Chung and S. Y. Kim, “Poly(arylene ether)s via nitro displacement reaction: synthesis of poly(biphenylene oxide)s containing trifluoromethyl groups from AB type monomers,” Macromolecules, vol. 33, no. 26, pp. 9474–9476, 2000. View at Publisher · View at Google Scholar · View at Scopus
  3. C. J. Hawker and K. L. Wooley, “The convergence of synthetic organic and polymer chemistries,” Science, vol. 309, no. 5738, pp. 1200–1205, 2005. View at Publisher · View at Google Scholar · View at Scopus
  4. S. Hecht, “Construction with macromolecules,” Materials Today, vol. 8, no. 3, pp. 48–55, 2005. View at Publisher · View at Google Scholar · View at Scopus
  5. H. C. Kolb, M. G. Finn, and K. B. Sharpless, “Click chemistry: diverse chemical function from a few good reactions,” Angewandte—Chemie International Edition, vol. 40, no. 11, pp. 2004–2021, 2001. View at Google Scholar
  6. R. Huisgen, S. Guenter, and M. Leander, “1.3-Dipolare cycloadditionen, XXXII. Kinetik der additionen organischer azide an CC-mehrfachbindungen,” Chemische Berichte, vol. 100, no. 8, pp. 2494–2507, 1967. View at Publisher · View at Google Scholar
  7. R. Huisgen, 1, 3-Dipolar Cycloaddition Chemistry, John Wiley & Sons, New York, NY, USA, 1984.
  8. V. V. Rostovtsev, L. G. Green, V. V. Fokin, and K. B. Sharpless, “A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes,” Angewandte—Chemie International Edition, vol. 41, no. 14, pp. 2596–2599, 2002. View at Google Scholar
  9. C. W. Tornøe, C. Christensen, and M. Meldal, “Peptidotriazoles on solid phase:  [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides,” The Journal of Organic Chemistry, vol. 67, no. 9, pp. 3057–3064, 2002. View at Publisher · View at Google Scholar
  10. A. J. Scheel, H. Komber, and B. I. Viot, “Novel hyperbranched poly([1,2,3]-triazole)s derived from AB2 monomers by a 1,3-dipolar cycloaddition,” Macromolecular Rapid Communications, vol. 25, no. 12, pp. 1175–1180, 2004. View at Publisher · View at Google Scholar
  11. P. Wu, A. K. Feldman, A. K. Nugent et al., “Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes,” Angewandte—Chemie International Edition, vol. 43, no. 30, pp. 3928–3932, 2004. View at Publisher · View at Google Scholar · View at Scopus
  12. D. J. V. C. van Steenis, O. R. P. David, G. P. F. van Strijdonck, J. H. Van Maarseveen, and J. N. H. Reek, “Click-chemistry as an efficient synthetic tool for the preparation of novel conjugated polymers,” Chemical Communications, no. 34, pp. 4333–4335, 2005. View at Publisher · View at Google Scholar · View at Scopus
  13. B. Helms, J. L. Mynar, C. J. Hawker, and J. M. J. Fréchet, “Dendronized linear polymers via “click chemistry”,” Journal of the American Chemical Society, vol. 126, no. 46, pp. 15020–15021, 2004. View at Publisher · View at Google Scholar
  14. B. Parrish, R. B. Breitenkamp, and T. Emrick, “PEG- and peptide-grafted aliphatic polyesters by click chemistry,” Journal of the American Chemical Society, vol. 127, no. 20, pp. 7404–7410, 2005. View at Publisher · View at Google Scholar · View at Scopus
  15. J. B. Carroll, B. J. Jordan, H. Xu et al., “Model systems for flavoenzyme activity: site-isolated redox behavior in flavin-functionalized random polystyrene copolymers,” Organic Letters, vol. 7, no. 13, pp. 2551–2554, 2005. View at Google Scholar
  16. J. A. Opsteen and J. C. M. van Hest, “Modular synthesis of block copolymers via cycloaddition of terminal azide and alkyne functionalized polymers,” Chemical Communications, no. 1, pp. 57–59, 2005. View at Publisher · View at Google Scholar · View at Scopus
  17. D. D. Díaz, S. Punna, P. Holzer et al., “Click chemistry in materials synthesis. 1. Adhesive polymers from copper-catalyzed azide-alkyne cycloaddition,” Journal of Polymer Science A, vol. 42, no. 17, pp. 4392–4403, 2004. View at Publisher · View at Google Scholar
  18. D. A. Ossipov and J. Hilborn, “Poly(vinyl alcohol)-based hydrogels formed by “click chemistry”,” Macromolecules, vol. 39, no. 5, pp. 1709–1718, 2006. View at Publisher · View at Google Scholar · View at Scopus
  19. Y. Nagao and A. Takasu, “Click polyester: synthesis of polyesters containing triazole units in the main chain by click chemistry and improved thermal property,” Macromolecular Rapid Communications, vol. 30, no. 3, pp. 199–203, 2009. View at Publisher · View at Google Scholar
  20. R. X. Yao, L. Kong, Z. S. Yin, and F. L. Qing, “Synthesis of novel aromatic ether polymers containing perfluorocyclobutyl and triazole units via click chemistry,” Journal of Fluorine Chemistry, vol. 129, no. 10, pp. 1003–1010, 2008. View at Publisher · View at Google Scholar
  21. P. Wu and V. V. Fokin, “Catalytic dipolar cycloaddition of azides and alkynes: reactivity and applications,” Aldrichimica Acta, vol. 40, no. 1, pp. 7–17, 2007. View at Google Scholar
  22. M. Meldal and C. W. Tornøe, “Cu-catalyzed azide-alkyne cycloaddition,” Chemical Reviews, vol. 108, no. 8, pp. 2952–3015, 2008. View at Publisher · View at Google Scholar
  23. G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba, and A. A. Genazzani, “Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes,” Medicinal Research Reviews, vol. 28, no. 2, pp. 278–308, 2008. View at Publisher · View at Google Scholar · View at Scopus
  24. V. D. Bock, H. Hiemstra, and J. V. Maarseveen, “CuI-catalyzed alkyne–azide “click” cycloadditions from a mechanistic and synthetic perspective,” European Journal of Organic Chemistry, vol. 2006, no. 1, pp. 51–68, 2006. View at Publisher · View at Google Scholar
  25. L. Wang, J. Li, and L. Wang, “Study on synthesis of paeks containing triazole units through click reaction and their properties,” Bulletin of the Korean Chemical Society, vol. 32, no. 9, pp. 3306–3310, 2011. View at Publisher · View at Google Scholar
  26. I. B. Mansour, K. Alouani, E. Chauveau, V. Martin, F. Schiets, and R. Mercier, “Synthesis and characterisation of poly(ester-amide)s from aromatic bisoxazoline precursors,” European Polymer Journal, vol. 46, no. 4, pp. 814–820, 2010. View at Publisher · View at Google Scholar · View at Scopus
  27. C. Saravanan, S. Senthil, and P. Kannan, “Click chemistry-assisted triazole-substituted azobenzene and fulgimide units in the pendant-based copoly(decyloxymethacrylate)s for dual-mode optical switches,” Journal of Polymer Science A, vol. 46, no. 23, pp. 7843–7860, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. B. Happ, C. Friebe, A. Winter, M. D. Hager, and U. S. Schubert, “Click chemistry meets polymerization: controlled incorporation of an easily accessible ruthenium(II) complex into a PMMA backbone via RAFT copolymerization,” European Polymer Journal, vol. 45, no. 12, pp. 3433–3441, 2009. View at Publisher · View at Google Scholar · View at Scopus