Table of Contents Author Guidelines Submit a Manuscript
International Journal of Polymer Science
Volume 2012 (2012), Article ID 170912, 18 pages
http://dx.doi.org/10.1155/2012/170912
Review Article

Novel Complex Polymers with Carbazole Functionality by Controlled Radical Polymerization

Department of Polymer Science and Engineering, Department of Organic Device Engineering, Graduate School of Science and Engineering, Yamagata University, 4-3-16, Jonan, Yonezawa 992-8510, Japan

Received 27 September 2011; Accepted 8 December 2011

Academic Editor: Toshifumi Satoh

Copyright © 2012 Kazuhiro Nakabayashi and Hideharu Mori. 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. J. V. Grazulevicius, P. Strohriegl, J. Pielichowski, and K. Pielichowski, “Carbazole-containing polymers: synthesis, properties and applications,” Progress in Polymer Science, vol. 28, no. 9, pp. 1297–1353, 2003. View at Publisher · View at Google Scholar · View at Scopus
  2. P. L. T. Boudreault, S. Beaupré, and M. Leclerc, “Polycarbazoles for plastic electronics,” Polymer Chemistry, vol. 1, no. 2, pp. 127–136, 2010. View at Publisher · View at Google Scholar · View at Scopus
  3. S. Beaupré, P. L. T. Boudreault, and M. Leclrec, “Solar-energy production and energy-efficient lighting: photovoltaic devices and white-light-emitting diodes using poly(2,7-fluorene), poly(2,7-carbazole), and poly(2,7-dibenzosilole) derivatives,” Advanced Materials, vol. 22, no. 8, pp. E6–E27, 2010. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  4. J. Li and A. C. Grimsdale, “Carbazole-based polymers for organic photovoltaic devices,” Chemical Society Reviews, vol. 39, no. 7, pp. 2399–2410, 2010. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  5. T. Uryu, H. Ohkawa, and R. Oshima, “Synthesis and High Hole Mobility of Isotactic Poly(2-N-carbazolylethyl acrylate),” Macromolecules, vol. 20, p. 705, 1987. View at Google Scholar
  6. C. J. Hu, R. Oshima, S. Sato, and M. Seno, “Synthesis and photoinduced discharge characteristics of polyacrylates with pendant carbazole group,” Journal of Polymer Science Part C, vol. 26, no. 10, pp. 441–446, 1988. View at Google Scholar · View at Scopus
  7. M. Keyanpour-Rad, A. Ledwith, A. Hallam et al., “Some photophysical properties of five new carbazole-containing methacrylate polymers,” Macromolecules, vol. 11, no. 6, pp. 1114–1118, 1978. View at Google Scholar · View at Scopus
  8. F. S. Du, Z. C. Li, W. Hong, Q. Y. Cao, and F. M. Li, “Vinyl monomers bearing chromophore moieties and their polymers. XI. Synthesis and photochemical behavior of carbazole-containing methacrylic monomers and their polymers,” Journal of Polymer Science Part A, vol. 38, no. 4, pp. 679–688, 2000. View at Publisher · View at Google Scholar · View at Scopus
  9. A. Ledwith, N. J. Rowley, and S. M. Walker, “Fluorescence emission from poly[2-(9-ethyl)carbazolyl-methylmethacrylate],” Polymer, vol. 22, no. 4, pp. 435–436, 1981. View at Google Scholar · View at Scopus
  10. S. Barik and S. Valiyaveettil, “Synthesis and self-assembly of copolymers with pendant electroactive units,” Macromolecules, vol. 41, no. 17, pp. 6376–6386, 2008. View at Publisher · View at Google Scholar · View at Scopus
  11. T. Kanbara, Y. Yokokawa, and K. Hasegawa, “Palladium-catalyzed modification of poly(p-bromostyrene) with carbazole and related heteroarenes containing an N-H bond and their properties,” Journal of Polymer Science Part A, vol. 38, no. 1, pp. 28–34, 2000. View at Publisher · View at Google Scholar · View at Scopus
  12. Y. S. Cho, S. W. Kim, C. S. Ihn, and J. S. Lee, “Anionic polymerization of 4-(9-carbazolyl)methylstyrene,” Polymer, vol. 42, no. 18, pp. 7611–7616, 2001. View at Publisher · View at Google Scholar · View at Scopus
  13. S. Förster and T. Plantenberg, “From self-organizing polymers to nanohybrid and biomaterials,” Angewandte Chemie International Edition, vol. 41, no. 5, pp. 688–714, 2002. View at Google Scholar
  14. T. Liu, C. Burger, and B. Chu, “Nanofabrication in polymer matrices,” Progress in Polymer Science, vol. 28, no. 1, pp. 5–26, 2003. View at Publisher · View at Google Scholar · View at Scopus
  15. D. E. Discher and A. Eisenberg, “Polymer vesicles,” Science, vol. 297, no. 5583, pp. 967–973, 2002. View at Publisher · View at Google Scholar · View at PubMed
  16. M. Sauer and W. Meier, “Polymer nanocontainers with controlled permeability,” Australian Journal of Chemistry, vol. 54, no. 3, pp. 149–151, 2001. View at Publisher · View at Google Scholar · View at Scopus
  17. G. Riess, “Micellization of block copolymers,” Progress in Polymer Science, vol. 28, no. 7, pp. 1107–1170, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, and A. P. H. J. Schenning, “About supramolecular assemblies of π-conjugated systems,” Chemical Reviews, vol. 105, no. 4, pp. 1491–1546, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  19. J. Liu, E. Sheina, T. Kowalewski, and R. D. McCullough, “Tuning the electrical conductivity and self-assembly of regioregular polythiophene by block copolymerization: nanowire morphologies in new di-and triblock copolymers,” Angewandte Chemie International Edition, vol. 41, no. 2, pp. 329–332, 2002. View at Publisher · View at Google Scholar · View at Scopus
  20. R. A. Segalman, B. McCulloch, S. Kirmayer, and J. J. Urban, “Block copolymers for organic optoelectronics,” Macromolecules, vol. 42, no. 23, pp. 9205–9216, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. I. Botiz and S. B. Darling, “Optoelectronics using block copolymers,” Materials Today, vol. 13, no. 5, pp. 42–51, 2010. View at Publisher · View at Google Scholar
  22. G. Moad, M. Chen, M. Häussler, A. Postma, E. Rizzardo, and S. H. Thang, “Functional polymers for optoelectronic applications by RAFT polymerization,” Polymer Chemistry, vol. 2, no. 3, pp. 492–519, 2011. View at Publisher · View at Google Scholar
  23. A. de Cuendias, R. C. Hiorns, E. Cloutet, L. Vignau, and H. Cramail, “Conjugated rod-coil block copolymers and optoelectronic applications,” Polymer International, vol. 59, no. 11, pp. 1452–1476, 2010. View at Publisher · View at Google Scholar
  24. C. J. Hawker, A. W. Bosman, and E. Harth, “New polymer synthesis by nitroxide mediated living radical polymerizations,” Chemical Reviews, vol. 101, no. 12, pp. 3661–3688, 2001. View at Publisher · View at Google Scholar · View at Scopus
  25. R. B. Grubbs, “Nitroxide-mediated radical polymerization: limitations and versatility,” Polymer Reviews, vol. 51, no. 2, pp. 104–137, 2011. View at Publisher · View at Google Scholar
  26. K. Matyjaszewski and J. Xia, “Atom transfer radical polymerization,” Chemical Reviews, vol. 101, no. 9, pp. 2921–2990, 2001. View at Publisher · View at Google Scholar · View at Scopus
  27. M. Kamigaito, T. Ando, and M. Sawamoto, “Metal-catalyzed living radical polymerization,” Chemical Reviews, vol. 101, no. 12, pp. 3689–3745, 2001. View at Publisher · View at Google Scholar · View at Scopus
  28. J. Chiefari, Y. K. Chong, F. Ercole et al., “Living free-radical polymerization by reversible addition—fragmentation chain transfer: the RAFT process,” Macromolecules, vol. 31, no. 16, pp. 5559–5562, 1998. View at Google Scholar · View at Scopus
  29. C. Barner-Kowollik, T. P. Davis, J. P. A. Heuts, M. H. Stenzel, P. Vana, and M. Whittaker, “RAFTing down under: tales of missing radicals, fancy architectures, and mysterious holes,” Journal of Polymer Science Part A, vol. 41, no. 3, pp. 365–375, 2003. View at Publisher · View at Google Scholar · View at Scopus
  30. G. Moad, E. Rizzardo, and S. H. Thang, “Living radical polymerization by the RAFT process,” Australian Journal of Chemistry, vol. 58, no. 6, pp. 379–410, 2005. View at Publisher · View at Google Scholar · View at Scopus
  31. C. L. McCormick and A. B. Lowe, “Aqueous RAFT polymerization: recent developments in synthesis of functional water-soluble (Co)polymers with controlled structures,” Accounts of Chemical Research, vol. 37, no. 5, pp. 312–325, 2004. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  32. S. Perrier and P. Takolpuckdee, “Macromolecular design via reversible addition-fragmentation chain transfer (RAFT)/xanthates (MADIX) polymerization,” Journal of Polymer Science Part A, vol. 43, no. 22, pp. 5347–5393, 2005. View at Publisher · View at Google Scholar · View at Scopus
  33. A. Favier and M. T. Charreyre, “Experimental requirements for an efficient control of free-radical polymerizations via the reversible addition-fragmentation chain transfer (RAFT) process,” Macromolecular Rapid Communications, vol. 27, no. 9, pp. 653–692, 2006. View at Publisher · View at Google Scholar · View at Scopus
  34. G. Moad, E. Rizzardo, and S. H. Thang, “Living radical polymerization by the RAFT process—a first update,” Australian Journal of Chemistry, vol. 59, no. 10, pp. 669–692, 2006. View at Publisher · View at Google Scholar · View at Scopus
  35. A. B. Lowe and C. L. McCormick, “Reversible addition-fragmentation chain transfer (RAFT) radical polymerization and the synthesis of water-soluble (co)polymers under homogeneous conditions in organic and aqueous media,” Progress in Polymer Science, vol. 32, no. 3, pp. 283–351, 2007. View at Publisher · View at Google Scholar · View at Scopus
  36. C. Barner-Kowollik, M. Buback, B. Charleux et al., “Mechanism and kinetics of dithiobenzoate-mediated RAFT polymerization. I. The current situation,” Journal of Polymer Science Part A, vol. 44, no. 20, pp. 5809–5831, 2006. View at Publisher · View at Google Scholar · View at Scopus
  37. M. L. Coote, E. H. Krenske, and E. I. Izgorodina, “Computational studies of RAFT polymerization-mechanistic insights and practical applications,” Macromolecular Rapid Communications, vol. 27, no. 7, pp. 473–497, 2006. View at Publisher · View at Google Scholar · View at Scopus
  38. L. Barner, T. P. Davis, M. H. Stenzel, and C. Barner-Kowollik, “Complex macromolecular architectures by reversible addition fragmentation chain transfer chemistry: theory and practice,” Macromolecular Rapid Communications, vol. 28, no. 5, pp. 539–559, 2007. View at Publisher · View at Google Scholar · View at Scopus
  39. A. Goto and T. Fukuda, “Kinetics of living radical polymerization,” Progress in Polymer Science, vol. 29, no. 4, pp. 329–385, 2004. View at Publisher · View at Google Scholar · View at Scopus
  40. G. Moad, E. Rizzardo, and S. H. Thang, “Radical addition-fragmentation chemistry in polymer synthesis,” Polymer, vol. 49, no. 5, pp. 1079–1131, 2008. View at Publisher · View at Google Scholar · View at Scopus
  41. C. Barner-Kowollik, Handbook of RAFT Polymerization, Wiley-VCH, Weinheim, Germany, 2007.
  42. B. M. Rosen and V. Percec, “Single-electron transfer and single-electron transfer degenerative chain transfer living radical polymerization,” Chemical Reviews, vol. 109, no. 11, pp. 5069–5119, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  43. S. Yamago, “Precision polymer synthesis by degenerative transfer controlled/living radical polymerization using organotellurium, organostibine, and organobismuthine chain-transfer agents,” Chemical Reviews, vol. 109, no. 11, pp. 5051–5068, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  44. M. Hurtgen, C. Detrembleur, C. Jerome, and A. Debuigne, “Insight into organometallic-mediated radical polymerization,” Polymer Reviews, vol. 51, no. 2, pp. 188–213, 2011. View at Publisher · View at Google Scholar
  45. M. Sawamoto, J. Fujimori, and T. Higashimura, “Living cationic polymerization of N-vinylcarbazole initiated by hydrogen iodide,” Macromolecules, vol. 20, no. 5, pp. 916–920, 1987. View at Google Scholar · View at Scopus
  46. T. Fukuda, T. Terauchi, A. Goto, Y. Tsujii, T. Miyamoto, and Y. Shimizu, “Well-defined block copolymers comprising styrene-acrylonitrile random copolymer sequences synthesized by “living” radical polymerization,” Macromolecules, vol. 29, no. 8, pp. 3050–3052, 1996. View at Publisher · View at Google Scholar · View at Scopus
  47. H. Baethge, S. Butz, C. H. Han, and G. Schmidt-Naake, “Rate enhancement of the N-oxyl-controlled free radical copolymerization of styrene with N-vinylcarbazole,” Die Angewandte Makromolekulare Chemie, vol. 267, pp. 52–56, 1999. View at Google Scholar · View at Scopus
  48. H. Baethge, S. Butz, and G. Schmidt-Naake, “‘Living’ free radical copolymerization of styrene and N-vinylcarbazole,” Macromolecular Rapid Communications, vol. 18, no. 10, pp. 911–916, 1997. View at Google Scholar · View at Scopus
  49. M. Nowakowska, S. Zapotoczny, and A. Karewicz, “Polymeric photosensitizers. Part 4. Synthesis of poly(sodium styrenesulfonate-block-N-vinylcarbazole) by nitroxide-mediated free radical polymerization,” Polymer, vol. 42, no. 5, pp. 1817–1823, 2001. View at Google Scholar · View at Scopus
  50. J. Hua, D. B. Chen, Y. L. Yu et al., “Preparation of C60 bonded poly(N-vinylcarbazole) with C60Cln/CuCl/Bpy catalyst system,” Polymer Bulletin, vol. 48, no. 2, pp. 135–141, 2002. View at Publisher · View at Google Scholar · View at Scopus
  51. J. Hua, D. Chen, X. Jing, L. Xu, Y. Yu, and Y. Zhang, “Preparation and photoconducting property of C60Cln-m-bonded poly(N-vinylcarbazole) with C60Cln/CuCl/Bpy catalyst system,” Journal of Applied Polymer Science, vol. 87, no. 4, pp. 606–609, 2003. View at Publisher · View at Google Scholar · View at Scopus
  52. J. Brandrup and E. H. Immergut, Polymer Handbook, John Wiley & Sons, New York, NY, USA, 3rd edition, 1991.
  53. H. Mori, H. Ookuma, S. Nakano, and T. Endo, “Xanthate-mediated controlled radical polymerization of N-vinylcarbazole,” Macromolecular Chemistry and Physics, vol. 207, no. 12, pp. 1005–1017, 2006. View at Publisher · View at Google Scholar · View at Scopus
  54. D. Charmot, P. Corpart, H. Adam, S. Z. Zard, T. Biadatti, and G. Bouhadir, “Controlled radical polymerization in dispersed media,” Macromolecular Symposia, vol. 150, pp. 23–32, 2000. View at Google Scholar · View at Scopus
  55. D. Taton, A. Z. Wilczewska, and M. Destarac, “Direct synthesis of double hydrophilic statistical di-and triblock copolymers comprised of acrylamide and acrylic acid units via the MADIX process,” Macromolecular Rapid Communications, vol. 22, no. 18, pp. 1497–1503, 2001. View at Publisher · View at Google Scholar · View at Scopus
  56. M. Destarac, D. Taton, S. Z. Zard, T. Saleh, and Y. Six, “On the importance of xanthate substituents in the MADIX process,” in Advances in Controlled/Living Radical Polymerization, K. Matyjaszewski, Ed., vol. 854 of ACS Symposinum Series, chapter 37, pp. 536–550, American Chemical Society, Washington, DC, USA, 2003. View at Publisher · View at Google Scholar
  57. M. H. Stenzel, L. Cummins, G. E. Roberts, T. P. Davis, P. Vana, and C. Barner-Kowollik, “Xanthate mediated living polymerization of vinyl acetate: a systematic variation in MADIX/RAFT agent structure,” Macromolecular Chemistry and Physics, vol. 204, no. 9, pp. 1160–1168, 2003. View at Publisher · View at Google Scholar · View at Scopus
  58. M. L. Coote and L. Radom, “Substituent effects in xanthate-mediated polymerization of vinyl acetate: Ab initio evidence for an alternative fragmentation pathway,” Macromolecules, vol. 37, no. 2, pp. 590–596, 2004. View at Publisher · View at Google Scholar · View at Scopus
  59. M. H. Stenzel, T. P. Davis, and C. Barner-Kowollik, “Poly(vinyl alcohol) star polymers prepared via MADIX/RAFT polymerisation,” Chemical Communications, vol. 10, no. 13, pp. 1546–1547, 2004. View at Google Scholar · View at Scopus
  60. M. Destarac, D. Charmot, X. Franck, and S. Z. Zard, “Dithiocarbamates as universal reversible addition-fragmentation chain transfer agents,” Macromolecular Rapid Communications, vol. 21, no. 15, pp. 1035–1039, 2000. View at Google Scholar · View at Scopus
  61. T. L. U. Nguyen, K. Eagles, T. P. Davis, C. Barner-Kowollik, and M. H. Stenzel, “Investigation of the influence of the architectures of poly(vinyl pyrrolidone) polymers made via the reversible addition-fragmentation chain transfer/macromolecular design via the interchange of xanthates mechanism on the stabilization of suspension polymerizations,” Journal of Polymer Science Part A, vol. 44, no. 15, pp. 4372–4383, 2006. View at Publisher · View at Google Scholar · View at Scopus
  62. D. Wan, K. Satoh, M. Kamigaito, and Y. Okamoto, “Xanthate-mediated radical polymerization of N-vinylpyrrolidone in fluoroalcohols for simultaneous control of molecular weight and tacticity,” Macromolecules, vol. 38, no. 25, pp. 10397–10405, 2005. View at Publisher · View at Google Scholar · View at Scopus
  63. R. Devasia, R. L. Bindu, R. Borsali, N. Mougin, and Y. Gnanou, “Controlled radical polymerization of N-vinylpyrrolidone by reversible addition-fragmentation chain transfer process,” Macromolecular Symposia, vol. 229, pp. 8–17, 2005. View at Publisher · View at Google Scholar · View at Scopus
  64. Y. Maki, H. Mori, and T. Endo, “Xanthate-mediated controlled radical polymerization of N-vinylindole derivatives,” Macromolecules, vol. 40, no. 17, pp. 6119–6130, 2007. View at Publisher · View at Google Scholar · View at Scopus
  65. Y. Maki, H. Mori, and T. Endo, “Controlled RAFT polymerization of N-vinylphthalimide and its hydrazinolysis to poly(vinyl amine),” Macromolecular Chemistry and Physics, vol. 208, no. 24, pp. 2589–2599, 2007. View at Publisher · View at Google Scholar · View at Scopus
  66. Y. Maki, H. Mori, and T. Endo, “Synthesis of well-defined alternating copolymers by RAFT copolymerization of N-vinylnaphthalimide,” Macromolecules, vol. 41, no. 22, pp. 8397–8404, 2008. View at Publisher · View at Google Scholar · View at Scopus
  67. Y. Maki, H. Mori, and T. Endo, “Synthesis of amphiphilic and double-hydrophilic block copolymers containing polyvinyl amine segments by RAFT polymerization of N-vinylphthalimide,” Macromolecular Chemistry and Physics, vol. 211, no. 1, pp. 45–56, 2010. View at Publisher · View at Google Scholar
  68. H. Mori, M. Yanagi, and T. Endo, “RAFT polymerization of N-vinylimidazolium salts and synthesis of thermoresponsive ionic liquid block copolymers,” Macromolecules, vol. 42, no. 21, pp. 8082–8092, 2009. View at Publisher · View at Google Scholar · View at Scopus
  69. G. Moad, J. Chiefari, Y. K. Chong et al., “Living free radical polymerization with reversible addition—fragmentation chain transfer (the life of RAFT),” Polymer International, vol. 49, no. 9, pp. 993–1001, 2000. View at Google Scholar
  70. M. Destarac, W. Bzducha, D. Taton, I. Gauthier-Gillaizeau, and S. Z. Zard, “Xanthates as chain-transfer agents in controlled radical polymerization (MADIX): structural effect of the O-alkyl group,” Macromolecular Rapid Communications, vol. 23, no. 17, pp. 1049–1054, 2002. View at Publisher · View at Google Scholar · View at Scopus
  71. A. Favier, C. Barner-Kowollik, T. P. Davis, and M. H. Stenzel, “A detailed on-line FT/NIR and 1H NMR spectroscopic investigation into factors causing inhibition in xanthate-mediated vinyl acetate polymerization,” Macromolecular Chemistry and Physics, vol. 205, no. 7, pp. 925–936, 2004. View at Publisher · View at Google Scholar · View at Scopus
  72. B. Y. K. Chong, T. P. T. Le, G. Moad, E. Rizzardo, and S. H. Thang, “More versatile route to block copolymers and other polymers of complex architecture by living radical polymerization: the RAFT process,” Macromolecules, vol. 32, no. 6, pp. 2071–2074, 1999. View at Publisher · View at Google Scholar · View at Scopus
  73. R. T. A. Mayadunne, E. Rizzardo, J. Chiefari et al., “Living polymers by the use of trithiocarbonates as reversible addition-fragmentation chain transfer (RAFT) agents: ABA triblock copolymers by radical polymerization in two steps,” Macromolecules, vol. 33, no. 2, pp. 243–245, 2000. View at Publisher · View at Google Scholar · View at Scopus
  74. Y. A. Vasilieva, D. B. Thomas, C. W. Scales, and C. L. McCormick, “Direct controlled polymerization of a cationic methacrylamido monomer in aqueous media via the RAFT process,” Macromolecules, vol. 37, no. 8, pp. 2728–2737, 2004. View at Publisher · View at Google Scholar · View at Scopus
  75. P. Vana, T. P. Davis, and C. Barner-Kowollik, “Kinetic analysis of reversible addition fragmentation chain transfer (RAFT) polymerizations: conditions for inhibition, retardation, and optimum living polymerization,” Macromolecular Theory and Simulations, vol. 11, no. 8, pp. 823–835, 2002. View at Publisher · View at Google Scholar · View at Scopus
  76. H. Mori, E. Kudo, Y. Saito, A. Onuma, and M. Morishima, “RAFT polymerization of vinyl sulfonate esters for the controlled synthesis of poly(lithium vinyl sulfonate) and sulfonated block copolymers,” Macromolecules, vol. 43, no. 17, pp. 7021–7032, 2010. View at Publisher · View at Google Scholar · View at Scopus
  77. C. F. Huang, J. A. Yoon, and K. Matyjaszewski, “Synthesis of N-vinylcarbazole-N-vinylpyrrolidone amphiphilic block copolymers by xanthate-mediated controlled radical polymerization,” Canadian Journal of Chemistry, vol. 88, no. 3, pp. 228–235, 2010. View at Publisher · View at Google Scholar · View at Scopus
  78. N. Hu, W. X. Ji, Y. Y. Tong, Z. C. Li, and E. Q. Chen, “Synthesis of diblock copolymers containing poly(N-vinylcarbazole) by reversible addition-fragmentation chain transfer polymerization,” Journal of Polymer Science Part A, vol. 48, no. 20, pp. 4621–4626, 2010. View at Publisher · View at Google Scholar · View at Scopus
  79. N. Suchao-in, S. Chirachanchai, and S. Perrier, “pH-and thermo-multi-responsive fluorescent micelles from block copolymers via reversible addition fragmentation chain transfer (RAFT) polymerization,” Polymer, vol. 50, no. 17, pp. 4151–4158, 2009. View at Publisher · View at Google Scholar · View at Scopus
  80. W. Y. Tam, C. S. K. Mak, A. M. C. Ng, A. B. Djurišič, and W. K. Chan, “Multifunctional poly(N-vinylcarbazole)-based block copolymers and their nanofabrication and photosensitizing properties,” Macromolecular Rapid Communications, vol. 30, no. 8, pp. 622–626, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  81. M. Benaglia, J. Chiefari, Y. K. Chong, G. Moad, E. Rizzardo, and S. H. Thang, “Universal (Switchable) RAFT agents,” Journal of the American Chemical Society, vol. 131, no. 20, pp. 6914–6915, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  82. D. J. Keddie, C. Guerrero-Sanchez, G. Moad, E. Rizzardo, and S. H. Thang, “Switchable reversible addition-fragmentation chain transfer (raft) polymerization in aqueous solution, n, n -dimethylacrylamide,” Macromolecules, vol. 44, no. 17, pp. 6738–6745, 2011. View at Publisher · View at Google Scholar
  83. Y. Yan, W. Zhang, Y. Qiu et al., “Universal xanthate-mediated controlled free radical polymerizations of the “less activated” vinyl monomers,” Journal of Polymer Science Part A, vol. 48, no. 22, pp. 5206–5214, 2010. View at Publisher · View at Google Scholar · View at Scopus
  84. M. Heo, J. Kim, J. Y. Kim, and C. Yang, “A first approach to white organic electroluminescence device from a single rod-coil poly[thiophene-block-(N-vinylcarbazole)] diblock copolymer,” Macromolecular Rapid Communications, vol. 31, no. 23, pp. 2047–2052, 2010. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  85. A. S. Brar and S. Kaur, “Atom transfer radical polymerization of N-vinyl carbazole: optimization to characterization,” Journal of Polymer Science Part A, vol. 44, no. 5, pp. 1745–1757, 2006. View at Publisher · View at Google Scholar · View at Scopus
  86. N. Haridharan and R. Dhamodharan, “Controlled polymerization of carbazole-based vinyl and methacrylate monomers at ambient temperature: a comparative study through ATRP, SET, and SET-RAFT polymerizations,” Journal of Polymer Science Part A, vol. 49, no. 4, pp. 1021–1032, 2011. View at Publisher · View at Google Scholar
  87. W. Zhang, Y. Yan, N. Zhou et al., “Controlled synthesis and fluorescent properties of poly(9-(4-vinylbenzyl)-9H-carbazole) via nitroxide-mediated living free-radical polymerization,” European Polymer Journal, vol. 44, no. 10, pp. 3300–3305, 2008. View at Publisher · View at Google Scholar · View at Scopus
  88. Y. K. Fang, C. L. Liu, and W. C. Chen, “New random copolymers with pendant carbazole donor and 1,3,4-oxadiazole acceptor for high performance memory device applications,” Journal of Materials Chemistry, vol. 21, no. 13, pp. 4778–4786, 2011. View at Publisher · View at Google Scholar
  89. B. Lessard, E. J. Y. Ling, M. S. T. Morin, and M. Marić, “Nitroxide-mediated radical copolymerization of methyl methacrylate controlled with a minimal amount of 9-(4-vinylbenzyl)-9H-carbazole,” Journal of Polymer Science Part A, vol. 49, no. 4, pp. 1033–1045, 2011. View at Publisher · View at Google Scholar
  90. X. Zhu, N. Zhou, Z. Zhang et al., “Cyclic polymers with pendent carbazole units: enhanced fluorescence and redox behavior,” Angewandte Chemie International Edition, vol. 50, no. 29, pp. 6615–6618, 2011. View at Publisher · View at Google Scholar · View at PubMed
  91. H. Mori, S. Nakano, and T. Endo, “Controlled synthesis of poly(N-ethyl-3-vinylcarbazole) and block copolymers via RAFT polymerization,” Macromolecules, vol. 38, no. 20, pp. 8192–8201, 2005. View at Publisher · View at Google Scholar · View at Scopus
  92. H. Mori, H. Iwaya, and T. Endo, “Structures and chiroptical properties of thermoresponsive block copolymers containing L-proline moietiesa,” Macromolecular Chemistry and Physics, vol. 208, no. 17, pp. 1908–1918, 2007. View at Publisher · View at Google Scholar · View at Scopus
  93. H. Mori, H. Iwaya, and T. Endo, “Controlled synthesis of thermoresponsive polymer via RAFT polymerization of an acrylamide containing l-proline moiety,” Reactive and Functional Polymers, vol. 67, no. 10, pp. 916–927, 2007. View at Publisher · View at Google Scholar · View at Scopus
  94. H. Mori and S. Okabayashi, “Synthesis, assembled structure, and chiroptical properties of amino acid-based amphiphilic block copolymers containing carbazole moiety,” Reactive and Functional Polymers, vol. 69, no. 7, pp. 441–449, 2009. View at Publisher · View at Google Scholar · View at Scopus
  95. J. D. Quinn and R. A. Register, “Nitroxide-mediated radical polymerization of N-ethyl-2-vinylcarbazole,” Polymers for Advanced Technologies, vol. 19, no. 6, pp. 556–559, 2008. View at Publisher · View at Google Scholar · View at Scopus
  96. K. Ogino, T. Goma, D. Kageyama, H. Sato, and N. Yonezawa, “Multifunctional block copolymers for organic photorefractive materials,” Journal of Photopolymer Science and Technology, vol. 19, no. 3, pp. 419–424, 2006. View at Publisher · View at Google Scholar · View at Scopus
  97. P. Zhao, Q. D. Ling, W. Z. Wang, J. Ru, S. B. Li, and W. Huang, “Reversible addition-fragmentation chain transfer polymerization of methacrylates containing hole-or electron-transporting groups,” Journal of Polymer Science Part A, vol. 45, no. 2, pp. 242–252, 2007. View at Publisher · View at Google Scholar · View at Scopus
  98. D. Neugebauer, D. Charasim, A. Swinarew et al., “Polymethacrylates with anthryl and carbazolyl groups prepared by atom transfer radical polymerization,” Polymer Journal, vol. 43, no. 5, pp. 448–454, 2011. View at Publisher · View at Google Scholar
  99. C. Ulbricht, C. R. Becer, A. Winter, D. Veldman, and U. S. Schubert, “Copolymers containing phosphorescent iridium(III) complexes obtained by free and controlled radical polymerization techniques,” Macromolecular Rapid Communications, vol. 29, no. 24, pp. 1919–1925, 2008. View at Publisher · View at Google Scholar · View at Scopus
  100. N. Hadjichristidis, M. Pitsikalis, S. Pispas, and H. Iatrou, “Polymers with complex architecture by living anionic polymerization,” Chemical Reviews, vol. 101, no. 12, pp. 3747–3792, 2001. View at Publisher · View at Google Scholar · View at Scopus
  101. A. Hirao, M. Hayashi, S. Loykulnant et al., “Precise syntheses of chain-multi-functionalized polymers, star-branched polymers, star-linear block polymers, densely branched polymers, and dendritic branched polymers based on iterative approach using functionalized 1,1-diphenylethylene derivatives,” Progress in Polymer Science, vol. 30, no. 2, pp. 111–182, 2005. View at Publisher · View at Google Scholar · View at Scopus
  102. H. Mori and A. H. E. Müller, “New polymeric architectures with (meth)acrylic acid segments,” Progress in Polymer Science, vol. 28, p. 1403, 2003. View at Google Scholar
  103. N. Hadjichristidis, H. Iatrou, M. Pitsikalis, S. Pispas, and A. Avgeropoulos, “Linear and non-linear triblock terpolymers. Synthesis, self-assembly in selective solvents and in bulk,” Progress in Polymer Science, vol. 30, no. 7, pp. 725–782, 2005. View at Publisher · View at Google Scholar · View at Scopus
  104. K. V. Bernaerts and F. E. du Prez, “Dual/heterofunctional initiators for the combination of mechanistically distinct polymerization techniques,” Progress in Polymer Science, vol. 31, no. 8, pp. 671–722, 2006. View at Publisher · View at Google Scholar · View at Scopus
  105. Y. Yagci and M. A. Tasdelen, “Mechanistic transformations involving living and controlled/living polymerization methods,” Progress in Polymer Science, vol. 31, no. 12, pp. 1133–1170, 2006. View at Publisher · View at Google Scholar · View at Scopus
  106. D. Taton, Y. Gnanou, R. Matmour et al., “Controlled polymerizations as tools for the design of star-like and dendrimer-like polymers,” Polymer International, vol. 55, no. 10, pp. 1138–1145, 2006. View at Publisher · View at Google Scholar · View at Scopus
  107. H. Mori, H. Ookuma, and T. Endo, “Synthesis of star polymers based on xanthate-mediated controlled radical polymerization of N-vinylcarbazole,” Macromolecular Symposia, vol. 249-250, pp. 406–411, 2007. View at Publisher · View at Google Scholar
  108. H. Mori, H. Ookuma, and T. Endo, “Poly(N-vinylcarbazole) star polymers and amphiphilic star block copolymers by xanthate-mediated controlled radical polymerization,” Macromolecules, vol. 41, no. 19, pp. 6925–6934, 2008. View at Publisher · View at Google Scholar · View at Scopus
  109. N. Hadjichristidis, S. Pispas, M. Pitsikalis, H. Iatrou, and C. Vlahos, “Asymmetric star polymers: synthesis and properties,” Advances in Polymer Science, vol. 142, pp. 71–127, 1999. View at Google Scholar · View at Scopus
  110. W. Zhang, W. Zhaing, Z. Zhang et al., “Thermo-responsive fluorescent micelles from amphiphilic A3B miktoarm star copolymers prepared via a combination of SET-LRP and RAFT polymerization,” Journal of Polymer Science Part A, vol. 48, no. 19, pp. 4268–4278, 2010. View at Publisher · View at Google Scholar · View at Scopus
  111. Y. Tao, Q. Xu, N. Li, J. Lu, L. Wang, and X. Xia, “Synthesis and photoluminescent property of star polymers with carbzole pendent and a zinc porphyrin core by ATRP,” Polymer, vol. 52, no. 19, pp. 4261–4267, 2011. View at Publisher · View at Google Scholar
  112. A. A. Farah and W. J. Pietro, “Atom transfer radical polymerization of N-(ω-alkylcarbazolyl) methacrylates via the use of novel heteroleptic Ru(II) polypyridyl initiator,” Inorganica Chimica Acta, vol. 357, no. 13, pp. 3813–3824, 2004. View at Publisher · View at Google Scholar
  113. A. A. Farah and W. J. Pietro, “Synthesis and characterization of multifunctional polymers via atom transfer radical polymerization of N-(ω′-alkylcarbazolyl) methacrylates initiated by Ru(II) polypyridyl chromophores,” Journal of Polymer Science Part A, vol. 43, no. 23, pp. 6057–6072, 2005. View at Publisher · View at Google Scholar · View at Scopus
  114. C. Chang, J. Zhu, Z. Zhang, N. Zhou, Z. Cheng, and X. Zhu, “Synthesizing and characterization of comb-shaped carbazole containing copolymer via combination of ring opening polymerization and nitroxide-mediated polymerization,” Polymer, vol. 51, no. 9, pp. 1947–1953, 2010. View at Publisher · View at Google Scholar · View at Scopus
  115. J. Shen, H. Masaoka, K. Tsuchiya, and K. Ogino, “Synthesis and properties of a novel brush-type copolymers bearing thiophene backbone and 3-(N-carbazolyl)propyl acrylate side chains for light-emitting applications,” Polymer Journal, vol. 40, no. 5, pp. 421–427, 2008. View at Publisher · View at Google Scholar · View at Scopus
  116. B. Zhang, J. Wang, Y. U. Chen et al., “Multiwalled carbon nanotubes covalently functionalized with poly(N-vinylcarbazole) via RAFT polymerization: synthesis and imonliner optical properties,” Journal of Polymer Science Part A, vol. 48, no. 14, pp. 3161–3168, 2010. View at Publisher · View at Google Scholar · View at Scopus
  117. B. Zhang, Y. U. Chen, X. Zhuang et al., “Poly(N-vinylcarbazole) chemically modified graphene oxide,” Journal of Polymer Science Part A, vol. 48, no. 12, pp. 2642–2649, 2010. View at Publisher · View at Google Scholar · View at Scopus
  118. B. Zhang, Y. Chen, L. Xu et al., “Growing poly(N-vinylcarbazole) from the surface of graphene oxide via RAFT polymerization,” Journal of Polymer Science Part A, vol. 49, no. 9, pp. 2043–2050, 2011. View at Publisher · View at Google Scholar
  119. J. Hua, D. Chen, X. Jing, L. Xu, Y. Yu, and Y. Zhang, “Preparation and Photoconducting Property of C60Cln-m-Bonded Poly(N-vinylcarbazole) with C60Cln/CuCl/Bpy Catalyst System,” Journal of Applied Polymer Science, vol. 84, 2003. View at Google Scholar
  120. J. Hua, W. Yang, and Y. Zhu, “Optical-limiting effect of C60 bonded poly(N-vinylcarbazole) initiated with C60Cln/CuCl/Bpy catalyst system,” Materials Letters, vol. 59, p. 644, 2005. View at Google Scholar
  121. T.-L. Wang, C.-H. Yang, Y.-T. Shieh, A.-C. Yeh, L.-W. Juan, and H. C. Zeng, “Synthesis of new nanocrystal-polymer nanocomposite as the electron acceptor in polymer bulk heterojunction solar cells,” European Polymer Journal, vol. 46, p. 634, 2009. View at Google Scholar
  122. T. L. Wang, C. H. Yang, Y. T. Shieh, and A. C. Yeh, “Synthesis of CdSe-Poly(N-vinylcarbazole) nanocomposite by atom transfer radical polymerization for potential optoelectronic applications,” Macromolecular Rapid Communications, vol. 30, no. 19, pp. 1679–1683, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  123. M. Feng, Y. Chen, N. He et al., “Ultrasound-assisted bulk synthesis of CdS-PVK nanocomposites via RAFT polymerization,” Journal of Polymer Science Part A, vol. 46, no. 16, pp. 5702–5707, 2008. View at Publisher · View at Google Scholar · View at Scopus
  124. M. Sato, A. Kawata, S. Morito, Y. Sato, and I. Yamaguchi, “Preparation and properties of polymer/zinc oxide nanocomposites using functionalized zinc oxide quantum dots,” European Polymer Journal, vol. 44, no. 11, pp. 3430–3438, 2008. View at Publisher · View at Google Scholar · View at Scopus
  125. J. Liu, W. He, L. Zhang et al., “Bifunctional Nanoparticles with Fluorescence and Magnetism via Surface-Initiated AGET ATRP Mediated by an Iron Catalyst,” Langmuir, vol. 27, pp. 12684–12692, 2011. View at Google Scholar
  126. Q. Li, L. Zhang, L. Bai et al., “Multistimuli-responsive hybrid nanoparticles with magnetic core and thermoresponsive fluorescence-labeled shell via surface-initiated RAFT polymerization,” Soft Matter, vol. 7, no. 15, pp. 6958–6966, 2011. View at Publisher · View at Google Scholar
  127. T. M. Fulghum, P. Taranekar, and R. C. Advincula, “Grafting hole-transport precursor polymer brushes on ITO electrodes: surface-initiated polymerization and conjugated polymer network formation of PVK,” Macromolecules, vol. 41, no. 15, pp. 5681–5687, 2008. View at Publisher · View at Google Scholar · View at Scopus
  128. M. C. Tria, K. S. Liao, N. Alley, S. Curran, and R. Advincula, “Electrochemically crosslinked surface-grafted PVK polymer brushes as a hole transport layer for organic photovoltaics,” Journal of Materials Chemistry, vol. 21, no. 28, pp. 10261–10264, 2011. View at Publisher · View at Google Scholar
  129. Y. Wei, D. Gao, L. Li, and S. Shang, “Memory effect in polymer brushes containing pendant carbazole groups,” Polymer, vol. 52, no. 6, pp. 1385–1390, 2011. View at Publisher · View at Google Scholar