Skip to main content
Log in

Synthesis of polyfluorenes bearing lateral pyreneterminated alkyl chains for dispersion of single-walled carbon nanotubes

  • Papers
  • Published:
Chinese Journal of Polymer Science Aims and scope Submit manuscript

Abstract

Two kinds of polyfluorenes bearing two lateral pyrene terminated alkyl chains and two alkyl chains per repeating unit were synthesized by Suzuki polycondensation and used to disperse single-walled carbon nanotubes (SWCNT) in organic solvents. Stable polymer-SWCNT complex can be formed via the multivalent π-π stacking interaction of the lateral pyrene functional groups and the polyfluorene backbone with the outer surface of carbon nanotubes; meanwhile the lateral alkyl chains can impart good solubility to the complex. As expected, polyfluorenes bearing lateral pyrene functional groups and octyl chains exhibited much higher carbon nanotube solubility in common organic solvents than the corresponding polyfluorenes bearing only octyl chains. Photophysical studies indicated that the formation of polymer-SWCNT complex can effectively quench the fluorescence of polyfluorenes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Iijima, S., Nature, 1991, 354: 56

    Article  CAS  Google Scholar 

  2. Fowler, P.W. and Ceulemans, A., J. Phys. Chem., 1995, 99: 508

    Article  CAS  Google Scholar 

  3. Sorescu, D.C., Jordan, K.D. and Avouris, P., J. Phys. Chem. B: 2001, 105: 11227

    Article  CAS  Google Scholar 

  4. Philips, B., Xie, J., Chandrasekhar, A., Abraham, J. and Varadan, V.K., Smart Mater. Struct., 2004, 13: 295

    Article  Google Scholar 

  5. Chen, R. J., Zhang, Y., Wang, D. and Dai, H., J. Am. Chem. Soc., 2001, 123: 3838

    Article  CAS  Google Scholar 

  6. Geargakilas, V., Kordatos, K., Prato, M., Guldi, D.M., Holzinger, M. and Hirsch, A., J. Am. Chem. Soc., 2002, 124: 760

    Article  Google Scholar 

  7. Guldi, D.M., Rahnmen, G.M.A., Jux, N., Yagmatarchis, N. and Prato, M., Angew. Chem., Int. Ed., 2004, 43: 5526

    Article  CAS  Google Scholar 

  8. Nakashima, N., Tomonari, Y. and Murakami, H., Chem. Lett., 2002, 638

  9. Murakami, H., Nomura, T. and Nakashima, N., Chem. Phys. Lett., 2003, 378: 481

    Article  CAS  Google Scholar 

  10. Li, H.P., Zhou, B., Lin, Y., Gu, L.R., Wang, W., Fernando, K.A.S., Kumar, S., Allard, L.F. and Sun, Y.P., J. Am. Chem. Soc., 2004, 126: 1014

    Article  CAS  Google Scholar 

  11. Guldi, D.M., Rahman, G.M.A., Sgobba, V., Kotov, N.A., Bonifazi, D. and Prato, M., J. Am. Chem. Soc., 2006, 128: 2315

    Article  CAS  Google Scholar 

  12. Bahun, G.C.F., Homenick, C., Lawson, G., Zhu, J. and Adronov, A., in “Chemistry of carbon nanotubes”, ed. by Basiuk, V.A. and Basiuk, E.V., American Scientific Publishers, Stevenson Ranch, 2007

    Google Scholar 

  13. Zou, J.H., Khondaker, S.I., Huo, Q. and Zhai, L., Adv. Funct. Mater., 2008, 18: 1

    Article  Google Scholar 

  14. Cheng, F.Y. and Adronov, A., Chem. Eur. J., 2006, 12: 5053

    Article  CAS  Google Scholar 

  15. Grossiord, N., Loos, J., Regev, O. and Koning, C.E., Chem. Mater., 2006, 18: 1089

    Article  CAS  Google Scholar 

  16. Lim, E., Jung, B.J., Lee, J., Shim, H.K., Lee, J.I., Yang, Y.S. and Do, L.M., Macromolecules, 2005, 38: 4531

    Article  CAS  Google Scholar 

  17. Wang, J.O., Miao, H.M., Lu, B.Y., Xu, J.K., Li, Y.Z. and Zhang, H.L., Acta Polymerica Sinica (in Chinese), 2011, (3): 327

  18. Liu, J.J., Qin, H. and Ba, X.W., Acta Polymerica Sinica (in Chinese), 2011, (2): 217

    Article  Google Scholar 

  19. Zhu, Z.J., Li, Y.Z., Pei, M.S., Xu, J.K., Lu, B.Y., Li, L. and Shen, L.A., Acta Polymerica Sinica (in Chinese), 2010, (6): 714

    Article  Google Scholar 

  20. Bernius, M.T., Inbasekaran, M., O’Brien, J. and Wu, W.S., Adv. Mater., 2000, 12: 1737

    Article  CAS  Google Scholar 

  21. Snaith, H.J., Greenham, N.C. and Friend, R.H., Adv. Mater., 2004, 16: 1640

    Article  CAS  Google Scholar 

  22. He, F., Tang, Y., Wang, S., Li, Y. and Zhu, D., J. Am. Chem. Soc., 2005, 127: 12343

    Article  CAS  Google Scholar 

  23. He, F., Tang, Y., Yu, M., Feng, F., An, L., Sun, H., Wang, S., Li, Y., Zhu, D. and Bazan, G.C., J. Am. Chem. Soc., 2006, 128: 6764

    Article  CAS  Google Scholar 

  24. Cheng, F., Imin, P., Maunders, C., Botton, G. and Adronov, A., Macromolecules, 2008, 41: 2304

    Article  CAS  Google Scholar 

  25. Ozawa, H., Fujigaya, T., Niidome, Y., Hotta, N., Fujiki, M. and Nakashima, N., J. Am. Chem. Soc., 2011, 133: 2651

    Article  CAS  Google Scholar 

  26. Hwang, J.Y., Nish, A., Doig, J., Douven, S., Chen, C.W., Chen, L.C. and Nicholas, R.J., J. Am. Chem. Soc., 2008, 130: 3543

    Article  CAS  Google Scholar 

  27. Chen, F., Wang, B., Chen, Y. and Li, L., J. Nano Lett., 2007, 7: 3013

    Article  CAS  Google Scholar 

  28. Gao, J. and Loi, M.A., Eur. Phys. J. B, 2010, 75: 121

    Article  CAS  Google Scholar 

  29. Gao, J., Kwak, M., Wildeman, J., Herrmann, A. and Loi, M.A., Carbon, 2011, 49: 333

    Article  CAS  Google Scholar 

  30. Yuan, W.Z., Mao, Y., Zhao, H., Sun, J.Z., Xu, H.P., Jin, J.K., Zheng, Q. and Tang, B.Z., Macromolecules, 2008, 41: 701

    Article  CAS  Google Scholar 

  31. Zhao, H., Yuan, W.Z., Mei, J., Tang, L., Liu, X.Q., Yan, M., Shen, X.Y., Sun, J.Z., Qin, A.J. and Tang, B.Z., J. Polym. Sci. Part A: Polym. Chem., 2009, 47: 4995

    Article  CAS  Google Scholar 

  32. Tolman, C.A., Seidel, W.C. and Gerlach, D.H., J. Am. Chem. Soc., 1972, 94: 2669

    Article  CAS  Google Scholar 

  33. Beinhoff, M., Weigel, W., Jurczok, M., Rettig, W., Modrakowski, C., Bruedgam, I., Harti, H. and Schlueter, A.D., Eur. J. Org. Chem., 2001, 20: 3819

    Article  Google Scholar 

  34. Davidson, R.S., Goodin, J.W. and Kemp, G., Tetrahedron Lett., 1980, 21: 2911

    Article  CAS  Google Scholar 

  35. Xiao, X., Wu, Y., Zhou, J., Bo, Z., Li, L. and Chan, C.M., J. Polym. Sci. Part A: Polym. Chem., 2008, 46: 574

    Article  CAS  Google Scholar 

  36. Hou, Q., Xu, Y., Yang, W., Yuan, M., Peng, J. and Cao, Y., J. Mater. Chem., 2002, 12: 2887

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zhi-shan Bo  (薄志山).

Additional information

This work was financially supported by the NSF of China (Nos. 20834006 and 50821062) and the National Basic Research Program of China (973 Program: 2009CB623601).

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liu, Mf., Chen, Yl., Zhu, B. et al. Synthesis of polyfluorenes bearing lateral pyreneterminated alkyl chains for dispersion of single-walled carbon nanotubes. Chin J Polym Sci 30, 405–414 (2012). https://doi.org/10.1007/s10118-012-1131-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10118-012-1131-5

Keywords

Navigation