Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Steric Effect on the Molecular Hyperpolarizabilities of β-Nitrostyrene Derivatives

  • Published : 1996.08.20
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Abstract

The steric effect on the first order hyperpolarizability of the β-nitrostyrene derivatives has been investigated by comparing the β values and the dihedral angles between the aryl and nitroalkenyl groups. In general the β value increased with the electron-donating ability of the substituent. The larger β value for 3,4-dimethoxy-β-nitrostyrene than that for p-methoxy-β-nitrostyrene has been attributed to the lower charge transfer energy for the former. The most striking substituent effect was observed in the β-methyl-β-nitrostyrene derivatives. Thus the β values for 3,4-dimethoxy- and p-methoxy derivatives of the latter decreased to near zero, probably because of the large distortion from planarity caused by the steric repulsion between the β-methyl and the aryl groups. The larger β value for p-dimethylamino-β-methyl-β-nitrostyrene has been interpreted with an increased electron-donating ability of the substituent and increased co-planarity.

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References

  1. Introduction to Nonlinear Optical Effects in Molecules and Polymers Prasad, P. N.;William, D. J.
  2. Materials for Nonlinear Optics, Chemical Perspectives; ACS Symposium Series 455 Marder, S. R.(ed);Sohn, J. F.(ed);Stucky, G. D.(ed)
  3. Adv. Materials v.5 Marder, S. R.;Perry, J. W.
  4. Science v.263 Marder, S. R.;Perry, J. W.
  5. Science v.245 Marder, S. R.;Perry, J. W.;Schaeffer, W. P.
  6. Science v.252 Marder, S. R.;Beratan, D. N.;Cheng, L.-T.
  7. J. Am. Chem. Soc. v.115 Marder, S. M.;Gorman, C. B.;Tiemann, B. G.;Cheng, L.-T.
  8. J. Am. Chem. Soc. v.116 Bourhill, G.;Bredas, J.-T.;Cheng, L.-T.;Marder, S. R.;Meyers, F.;Perry, J. W.;Tiemann, B. G.
  9. Science v.263 Marder, S. R.;Cheng, L.-T.;Tiemann, B. G.;Friedli, A. C.;Blanchard-Desce, M.;Perry, J. W.;Skindhoj, Jorgen
  10. J. Chem. Soc. Faraday Trans. v.87 Morley, J. O.
  11. Angew. Chem. Int. Ed. Engl. v.23 William, D. J.
  12. J. Org. Chem. v.18 Gairaud, C. B.;Lapin, G. R.
  13. Org. Synth. Collect. Vol.Ⅰ v.413 Worrall, D. E.
  14. Synth. Commun. v.510 Karmarkar, S. N.;Kelkar, S. L.;Wadia, M. S.
  15. J. Phys. Chem. v.99 Song, O. K.;Wang, C. H.;Je, J. T.;Cho, B. R.
  16. J. Chem. Soc. Perkin Trans 2 v.311 Pedireddi, V. R.;Sarma, J. A. R. P.;Desiraju, G. R.
  17. Acta Cryst. v.C49 Boys, D.;Manriquez, V.;Cassels, B. K.
  18. J. Phys. Chem. v.95 Cheng, L.-T.;Tam, W.;Marder, S. R.;Stiegman, A. E.;Rikken, G.;Spangler, C. W.
  19. Mechanism and Theory in Organic Chemistry Lowry, T. H.;Richardson, K. S.
  20. J. Chem. Soc. Perkin Trans 2 Cho, B. R.;Je, J. T.;Lee, S. H.;Lee, S. H.;Kim, H. S.;Jeon, S. J.;Song, O. K.;Wang, C. H.
  21. Crystal Engineering Dejiraju, G. R.