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A Self-Doped Ionic Conjugated Polymer: Poly(2-ethynylpyridinium-Nbenzoylsulfonate) by the Activated Polymerization of 2-Ethynylpyridine with Ring-Opening of 2-Sulfobenzoic Acid Cyclic Anhydride

  • Gal, Yeong-Soon (Polymer Chemistry Laboratory, College of General Education, Kyungil University) ;
  • Jin, Sung-Ho (Department of Chemistry Education, Pusan National University)
  • Published : 2004.06.20

Abstract

Keywords

References

  1. Oosawa, F. Polyelectrolytes; Marcel-Dekker: New York, 1971.
  2. Dai, L.; Winkler, B.; Dong, L.; Tong, L.; Mau, A. W. H. Adv.Mater. 2001, 13, 915. https://doi.org/10.1002/1521-4095(200107)13:12/13<915::AID-ADMA915>3.0.CO;2-N
  3. Lowe, A. B.; McCormick, C. L. Chem.Rev. 2002, 102, 4177. https://doi.org/10.1021/cr020371t
  4. Tripathy, S. K.; Kumar, J.; Nalwa, H. S.Handbook of Polyelectrolytes and Their Applications; AmericanScientific Publishers: Calfornia, 2002.
  5. Ji, E. K.; Ahn, D. J.; Kim, J. M. Bull. Korean Chem. Soc. 2003, 24, 667. https://doi.org/10.5012/bkcs.2003.24.5.667
  6. Nguyen, M. T.; Kasai, P.; Miller, J. L.; Diaz, A. F. Macromolecules1994, 27, 3625. https://doi.org/10.1021/ma00091a026
  7. Buchhammer, H. M.; Petzold, G.; Lunkwitz, K. Langmuir 1999,15, 5306.
  8. Liu, R. C. W.; Morishima, Y.; Winnik, F. M. Macromolecules2001, 34, 9117. https://doi.org/10.1021/ma011260j
  9. Chien, J. C. W. Polyacetylene; Academic Press: New York, 1984.
  10. Toshima, N.; Hara, S. Prog. Polym. Sci. 1995, 20, 155. https://doi.org/10.1016/0079-6700(94)00029-2
  11. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev.2000, 100, 2537. https://doi.org/10.1021/cr9801014
  12. Ferraris, J. P.; Cowan, D. O.; Walatka, V. J.;Perlstein, J. H. J. Am. Chem. Soc. 1973, 95, 948. https://doi.org/10.1021/ja00784a066
  13. Chiang, C. K.; Park, Y. W.; Heeger, A. J.; Shirakawa, H.; Louis, E. J.;MacDiarmid, A. G. Phys. Rev. Lett. 1977, 39, 1098. https://doi.org/10.1103/PhysRevLett.39.1098
  14. Ito, T.; Shirakawa, H.; Ikeda, S. J. Polym, Sci.: Part A: Polym. Chem.1974, 12, 11. https://doi.org/10.1002/pol.1974.170120102
  15. Shirakawa, H. Angew. Chem. Int. Ed. 2001, 40, 2574. https://doi.org/10.1002/1521-3773(20010716)40:14<2574::AID-ANIE2574>3.0.CO;2-N
  16. Szafert, S.; Gladysz, J. A. Chem. Rev. 2003, 103, 4175. https://doi.org/10.1021/cr030041o
  17. Kim, E. J.; Park, J. W.; Kim, Y. R.; Park, Y. Bull. Korean Chem.Soc. 2003, 24, 484. https://doi.org/10.5012/bkcs.2003.24.4.484
  18. Chauser, M. G.; Rodinov, Yu. M.; Mishin, V. M.; Cherkashin,M. I. Russ. Chem. Rev. 1974, 45, 348. https://doi.org/10.1070/RC1976v045n04ABEH002642
  19. Masuda, T.; Higashimura, T. Acc. Chem. Res. 1981, 17, 51. https://doi.org/10.1021/ar00098a002
  20. Gal, Y. S. J. Chem. Soc. Chem. Commun. 1994, 327.
  21. Choi, S. K.; Lee, J. H.; Kang, S. J.; Jin, S. H. Prog. Polym. Sci. 1997, 22, 693. https://doi.org/10.1016/S0079-6700(97)00002-6
  22. Choi, S. K.; Gal, Y. S.; Jin, S. H.; Kim, H. K. Chem. Rev. 2000, 100, 1645. https://doi.org/10.1021/cr960080i
  23. Gal, Y. S.; Jin, S. H.; Lee, H. J.; Kim, S. H.; Lee, W. C.; Choi, S. K.Macromol. Res. 2003, 11, 80. https://doi.org/10.1007/BF03218334
  24. Jin, S. H.; Jin, J. Y.; Kim, Y. I.;Park, D. K.; Gal, Y. S. Macromol. Res. 2003, 11, 501. https://doi.org/10.1007/BF03218983
  25. Anders, U.; Nuyken, O.; Buchmeiser, M. R. J. Mol. Cat. A: Chem. 2004,213, 89. https://doi.org/10.1016/j.molcata.2003.10.052
  26. Gal, Y. S.; Jin, S. H.; Choi, S. K. J. Mol. Cat. A: Chem. 2004, 213, 115. https://doi.org/10.1016/j.molcata.2003.10.055
  27. Blumstein, A.; Subramanyam, S. US patent 5,037,916 (Aug. 6, 1991),
  28. Blumstein, A.; Samuelson, L. Adv. Mater. 1998, 10, 173. https://doi.org/10.1002/(SICI)1521-4095(199801)10:2<173::AID-ADMA173>3.0.CO;2-E
  29. Bhowmik, R. K.; Burchett, R. A.; Han, H.; Cebe, J. J. J.Polym. Sci.: Part A: Polym. Chem. 2001, 39, 2710. https://doi.org/10.1002/pola.1248
  30. Gui, T. L.; Jin, S. H.; Park, J. W.; Ahn, W. S.; Koh, K. N.; Kim, S. H.; Gal, Y.S. Opt. Mater. 2002, 21, 637. https://doi.org/10.1016/S0925-3467(02)00214-8
  31. Gal, Y. S.; Gui, T. L.; Jin, S. H.; Park, J. W.; Koh, K. N.; Lee, W. C.; Kim, S. H.; Kim, S. Y. Syn. Met. 2003, 135-136, 353. https://doi.org/10.1016/S0379-6779(02)00551-9
  32. Gui, T. L.; Jin, S. H.; Park, J. W.; Lim,K. T.; Kim, S. Y.; Gal, Y. S. Mater. Sci. & Eng. C 2004, 24, 217. https://doi.org/10.1016/j.msec.2003.09.055
  33. Patil, A. O.; Ikenoue, Y.; Basescu, N.; Colameri, N.; Chen, F.;Wudl, F.; Heeger, A. J. Syn. Met. 1987, 20, 151. https://doi.org/10.1016/0379-6779(87)90554-6
  34. Ikenoue, Y.; Votani, N.; Patil, A. O.; Wudl, F.; Heeger, A. J. Syn. Met. 1989, 30, 305. https://doi.org/10.1016/0379-6779(89)90653-X
  35. Chen, S. A.; Hua, M. Y. Macromolecules 1993, 26, 7108. https://doi.org/10.1021/ma00077a066
  36. Child, A. D.; Reynolds, J. R. Macromolecules 1994, 27, 1975. https://doi.org/10.1021/ma00085a050
  37. Lin, H. K.; Chen, S. A. Macromolecules 2000, 33, 811.
  38. Gal, Y. S.; Cho, H. N.; Kwon, S. K.; Choi, S. K. Polymer (Korea)1988, 12, 30.
  39. Gal, Y. S.; Lee, W. C.; Lee, S. J.; Park, J. W.; Ko, J. M.; Chun, J.H. J. Macromol. Sci.-Pure and Appl. Chem. 1999, A36, 1503.
  40. Gal, Y. S.; Lee, W. C.; Kim, S. Y.; Park, J. W.; Jin, S. H.; Koh, K. N.;Kim, S. H. J. Polym. Sci.: Part A: Polym. Chem. 2001, 39, 3151. https://doi.org/10.1002/pola.1297

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