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Synthesis and characterization of photoconductive C60–N-vinylcarbazole copolymers

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Abstract

Soluble C60–N-vinylcarbazole copolymers with different C60 contents were synthesized in lithium naphthalene-initiated anionic polymerization reactions. 13C nuclear magnetic resonance (NMR) results provided strong evidence for the covalent attachment of poly(N-vinylcarbazole; PVK) units to the C60 cores. The chemical shifts located at 142.16, 143.21, 144.70, 145.61, 146.65, 147.09, 149.08 and 170.28 p.p.m. in the 13C NMR spectrum of the copolymer are assigned to the unsaturated carbon signals of the substituted C60 cage. Its ultraviolet–visible absorption spectrum tends to move to the longer wavelength compared with those of the N-vinylcarbazole (NVC) monomer and PVK, and the peak range also extended from about 350 to 640 nm due to “charge-transfer” interaction between C60 and N-ethylcarbazole units. X-ray diffraction evidence suggests that the structure of the resultant copolymer might be a layered structure. Like the C60 chemically modified PVK, this material also exhibits good photoconductivity and temperature sensitivity. An unusual temperature dependence of the ESR spectrum is observed. In addition, it is also found that both [60] fullerene polyanion salts [(Cn-60) M+n, M=Li, Na, K] and fullerene itself are unable to initiate the polymerization of such monomers as N-vinylcarbazole, styrene and acrylonitrile, etc. © 1998 Kluwer Academic Publishers

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References

  1. G. Yu, J. Gao, J. C. Hummelen, F. Wudl and A. J. Heeger, Science 270 (1995) 1789.

    Google Scholar 

  2. T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti and P. Sozzani, Angew. Chem. Int. Ed. Engl. 35 (1996) 648.

    Google Scholar 

  3. E. Cloutet, Y. Gnanou, J. L. Fillaut and D. Astruc, Chem. Commun. (1996) 1565.

  4. C. J. Hawker, Macromolecules 27 (1994) 4836.

    Google Scholar 

  5. Y. Chen, R. F. Cai, Z. E. Huang and S. Q. Kong, Polym. Bull. 35 (1995) 705.

    Google Scholar 

  6. O. Patil and G. W. Schriver, Macromol. Symp. 91 (1995) 73.

    Google Scholar 

  7. A. G. Camp, A. Lary and W. T. Ford, Macromolecules 28 (1995) 7959.

    Google Scholar 

  8. L. Y. Chiang, L. Y. Wang and C. S. Kuo, ibid. 28 (1995) 7574.

    Google Scholar 

  9. N. Manolova, I. Rashkov, H. van Damme and F. Beguim, Polym. Bull. 33 (1994) 175.

    Google Scholar 

  10. Y. Chen, Z. E. Huang, R. Cai, S. Kong, S. Chen, Q. Shao, X. Yan, F. Zhao and D. Fu, J. Polym. Sci. A, Polym. Chem. 34 (1996) 3297.

    Google Scholar 

  11. R. Taylor and D. R. M. Walton, Nature 363 (1993) 685.

    Google Scholar 

  12. D. E. Bergbreiter and H. N. Gray, J. Chem. Soc., Chem. Commun. (1993) 645.

  13. B. Nie and V. M. Rotello, Macromolecules 30 (1997) 3949.

    Google Scholar 

  14. R. F. Cai, X. Bai, Y. Chen and Z. E. Huang, Eur. Polym. J. 34 (1998) 7.

    Google Scholar 

  15. H. Nagashima, A. Nakaoka, Y. Saito, M. Kato, T. Kawanishi and K. Itoh, J. Chem. Soc., Chem. Commun. (1992) 377.

  16. Y. Wang, Nature 356 (1992) 585.

    Google Scholar 

  17. Y. Wang, R. West and C. H. Yuan, J. Amer. Chem. Soc. 115 (1993) 3844.

    Google Scholar 

  18. Z. Xu, W. Chen, Y. Long, Y. Xu, W. Li and M. Wang, J. Mater. Sci. Lett. 14 (1995) 1030.

    Google Scholar 

  19. N. S. Sariciftci, L. Smilowitz, A. J. Heeger and F. Wudl, Science 258 (1992) 1474.

    Google Scholar 

  20. C. H. Lee, G. Yu, D. Moses, K. Pakbaz, C. Zhang, N. S. Sariciftci, A. J. Heeger and F. Wudl, Phys. Rev. B 48 (1993) 15425.

    Google Scholar 

  21. S. Morita, A. A. Zakhidov and K. Yoshino, Jpn. J. Appl. Phys. 32 (1993) L873.

    Google Scholar 

  22. Y. Wei, J. Jian, A. G. Macdiarmid, J. G. Masters, A. L. Smith and D. Li, J. Chem. Soc., Chem. Commun. (1993) 603.

  23. S. Kazaoui, R. Ross and N. Minami, Solid State Commun. 90 (1994) 623.

    Google Scholar 

  24. A. Watanabe and O. Ito, J. Chem. Soc., Chem. Commun. (1994) 1285.

  25. Y. Chen, R. F. Cai, Z. E. Huang, X. Bai, B. C. Yu, W. Jin, D. C. Pan and S. T. Wang, Polym. Bull. 36 (1996) 203.

    Google Scholar 

  26. Y. Chen, Z. E. Huang and R. F. Cai, J. Polym. Sci. B, Polym. Phys. 34 (1996) 631.

    Google Scholar 

  27. Y. Chen, Z. E. Huang, R. F. Cai, X. M. Yan, S. M. Chen, W. Jin, D. C. Pan and S. T. Wang, J. Appl. Polym. Sci. 61 (1996) 2185.

    Google Scholar 

  28. Z. E. Huang, Y. Chen, R. F. Cai, C. G. Rui and F. P. Zhang, ibid. 60 (1996) 573.

    Google Scholar 

  29. Z. E. Huang, Y. Chen, R. F. Cai, W. Ma, X. Hou, Q. Shao, F. Zhao, D. Fu, G. Shi, X. Sheng, W. Jin, S. Wang and D. Pan, J. Phys. Chem. Solids 58 (1997) 107.

    Google Scholar 

  30. Y. Chen, Z. E. Huang, R. F. Cai, B. C. Yu, O. Ito, J. Zhang, W. Ma, C. Zhong, L. Zhao, Y. Li, L. Zhu, F. Mamoru and A. Watanabe, J. Polym. Sci. B, Polym. Phys. 35 (1997) 1185.

    Google Scholar 

  31. A. Hirsch, T. Grosser, A. Skiebe and A. Soi, Chem. Ber. 126 (1993) 1061.

    Google Scholar 

  32. P. J. Fagan, J. Amer. Chem. Soc. 114 (1992) 9697.

    Google Scholar 

  33. Y. Chen, B. C. Yu, R. F. Cai, Z. E. Huang, H. K. Yu, H. M. Wu and J. F. Xu, Synth. Commun. 26 (1996) 3699.

    Google Scholar 

  34. E. T. Samulski, J. M. Desimone, M. O. Hunt, Jr., Y. Z. Menceloglu, R. C. Jarnagin, G. A. York, K. B. Labat and H. Wang, Chem. Mater. 4 (1992) 1153.

    Google Scholar 

  35. G. D. Wignall, K. A. Affholter, G. J. Bunick, M. O. Hunt, Jr., Y. Z. Menceloglu, J. M. Desimone and E. T. Samulski, Macromolecules 28 (1995) 6000.

    Google Scholar 

  36. B. C. Yu, Y. Chen, R. F. Cai, Z. E. Huang, and Y. W. Xiao, Eur. Polym. J. 33 (1997) 1049.

    Google Scholar 

  37. Y. Chen, W. S. Huang, Z. E. Huang, R. F. Cai, H. K. Yu, S. M. Chen and X. M. Yan, Eur. Polym. J. 33 (1997) 823.

    Google Scholar 

  38. L. Isaacs, A. Wehrisg and F. Diederich, Helv. Chim. Acta 76 (1993) 1231.

    Google Scholar 

  39. J. Stinchcombe, A. Penicaud, P. Bhyrappa, P. D. W. Boyd and C. A. Reed, J. Amer. Chem. Soc. 115 (1993) 5212.

    Google Scholar 

  40. J. E. Fischer and P. A. Heiney, J. Phys. Chem. Solids 54 (1993) 1725.

    Google Scholar 

  41. A. F. Hebard, M. J. Rosseinsky, R. C. Haddon, D. W. Murphy, S. H. Glarum, T. T. M. Palstra, A. P. Ramirez and A. R. Kortan, Nature 350 (1991) 600.

    Google Scholar 

  42. F. Zhou, C. Jehoulet and A. J. Bard, J. Amer. Chem. Soc. 114 (1992) 11 004.

    Google Scholar 

  43. M. M. Khaled, R. T. Carlin, P. C. Trulove, G. R. Eaton, and S. S. Eaton, ibid. 116 (1994) 3465.

    Google Scholar 

  44. C. Bossard, S. Rigaut, D. Astruc, M. H. Delville, G. Felix, A. F. Bouvier, J. Amiell, S. Flandrois and P. Delhaes, J. Chem. Soc., Chem. Commun. (1993) 333.

  45. J. Chen, Z. E. Huang, R. F. Cai, Q. F. Shao, S. M. Chen and H. J. Ye, ibid. (1994) 2177.

  46. P. D. W. Boyd, P. Bhyrappa, P. Paul, J. Stinchcombe, R. D. Bolskar, Y. Sun and C. A. Reed, J. Amer. Chem. Soc. 117 (1995) 2907.

    Google Scholar 

  47. J. W. Bausch, G. K. S. Prakash and G. A. Olah, ibid. 113 (1991) 3205.

    Google Scholar 

  48. T. Suzuki, Q. Li, K. C. Khemani and F. Wudl, ibid. 114 (1992) 7301.

    Google Scholar 

  49. J. P. Hare, Chem. Phys. Lett. 117 (1991) 394.

    Google Scholar 

  50. C. H. Griffiths, J. Polym. Sci. 13 (1975) 1167.

    Google Scholar 

  51. G. C. Richard, Macromolecules 4 (1971) 370.

    Google Scholar 

  52. A. Kimura, S. Yoshimolo, Y. Akana, H. Hirata, S. Kusabayashi, H. Mikawa and N. Kassai, J. Polym. Sci. A2 8 (1970) 643.

    Google Scholar 

  53. D. J. Willians, Macromolecules 3 (1970) 602.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Fudan University, Shanghai, 200433, People's Republic of China

    Yu Chen, Rui-FANG Cai, Li-XIANG Xiao & Zu-EN Huang

  2. Department of Applied Chemistry, Shanghai Jiaotong University, Shanghai, 200240, People's Republic of China

    Daocheng Pan

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Chen, Y., Cai, RF., Xiao, LX. et al. Synthesis and characterization of photoconductive C60–N-vinylcarbazole copolymers. Journal of Materials Science 33, 4633–4641 (1998). https://doi.org/10.1023/A:1004441426521

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