Facile synthesis of new NLO-functionalized polyimides via Mitsunobu reaction

(Note: The full text of this document is currently only available in the PDF Version )

Chong-Bok Yoon and Hong-Ku Shim


Abstract

Three polyimides containing a nonlinear optical (NLO) chromophore were prepared through a new synthetic pathway. Coupling of dihydroxy and diimide compounds yielded the polyimide. Due to the mild conditions of polymerization, a chemically labile hemicyanine dye could be incorporated in the polyimide backbone successfully. The molecular weights of the polyimides obtained ranged from 8200 to 14[thin space (1/6-em)]400, and the glass transitions occurred between 135[thin space (1/6-em)]°C and 198[thin space (1/6-em)]°C. The second-order NLO properties were characterized by using the second harmonic generation (SHG) technique. The second-order NLO coefficients (χ(2)) of the polyimides were 82 pm V–1 and 122 pm V–1 with reference to quartz crystal, and the nonlinearity of those polymers was stable at 100[thin space (1/6-em)]°C without large loss.


References

  1. P. N. Prasad and D. J. Williams, in Introduction of Nonlinear Optical Effect in Molecules and Polymers, John Wiley & Sons, New York, 1991 Search PubMed .
  2. D. S. Chemla, in Nonlinear Optical Properties of Organic Materials and Crystals, ed. J. Zyss, Academic Press, New York, 1987 Search PubMed .
  3. S. R. Marder, B. Kippenlen, A. K.-Y. Jen and N. Pheyghambarian, Nature, 1997, 388, 845 CrossRef CAS .
  4. G. A. Lindsay and K. D. Singer, in Polymers for Second-order Nonlinear Optics, American Chemical Society, Washington, DC, 1995 Search PubMed .
  5. D. M. Burland, R. D. Miller and C. A. Walsh, Chem. Rev., 1994, 94, 31 CrossRef CAS .
  6. C. B. Yoon and H. K. Shim, Macromol. Chem. Phys., 1998, 199, 2433 CrossRef CAS .
  7. R. Dagani, Chem. Eng. News, 1996, 74, 22 .
  8. C. B. Yoon, K. J. Moon and H. K. Shim, Macromolecules, 1996, 29, 5754 CrossRef CAS .
  9. L. R. Dalton, A. W. Harper, R. Ghosn, W. H. Steier, M. Ziari, H. Fetterman, Y. Shi, R. V. Mustacich, A. K.-Y. Jen and K. J. Shea, Chem. Mater., 1995, 7, 1060 CrossRef CAS .
  10. T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller and W. Volksen, Science, 1995, 268, 1604 CAS .
  11. T. Verbiest, D. M. Burland, M. C. Jurich, V. Y. Lee, R. D. Miller and W. Volksen, Macromolecules, 1995, 28, 3005 CrossRef CAS .
  12. D. Yu and L. Yu, Macromolecules, 1994, 27, 6718 CrossRef CAS .
  13. T. A. Chen, A. K.-Y. Jen and Y. Cai, J. Am. Chem. Soc., 1995, 117, 7295 CrossRef CAS .
  14. K. S. Lee, K. J. Moon, H. Y. Woo and H. K. Shim, Adv. Mater., 1997, 9, 978 CrossRef CAS .
  15. O. Mitsunobu, Synthesis, 1981, 1 CrossRef CAS .
  16. O. K. Kim and L. S. Choi, Langmuir, 1994, 10, 2842 CrossRef CAS .
  17. K. J. Moon, H. K. Shim, K. S. Lee, J. Zieba and P. N. Prasad, Macromolecules, 1996, 29, 861 CrossRef CAS .
  18. K. S. Lee, S. W. Choi, H. Y. Woo, K. J. Moon, H. K. Shim, M. Jeong and T. K. Lim, J. Opt. Soc. Am. B Opt. Phys., 1998, 15, 393 Search PubMed .
  19. J. Jerphagnon and S. K. Kurtz, J. Appl. Phys., 1970, 41, 1667 CrossRef .
  20. W. N. Herman and L. M. Hayden, J. Opt. Soc. Am. B Opt. Phys., 1995, 12, 416 Search PubMed .
  21. D. Yu, A. Gharavi and L. Yu, J. Am. Chem. Soc., 1995, 117, 11680 CrossRef CAS .
  22. T. J. Marks and M. A. Rather, Angew. Chem., Int. Ed. Engl., 1995, 34, 155 CrossRef CAS .
  23. M. Kauranen, T. Verbiest, C. Boutton, M. N. Teerenstra, K. Clays, A. J. Schouten, R. J. M. Nolte and A. Persoons, Science, 1995, 270, 966 CAS .
Click here to see how this site uses Cookies. View our privacy policy here.