Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Amine Donors in Nonlinear Optical Molecules: Methyl and Phenyl Substitution Effects on the First Hyperpolarizability

  • Park, Gyoo-Soon (Department of Chemistry, Kookmin University) ;
  • Ra, Choon-Sup (Department of Chemistry and Institute of Natural Sciences, Yeungnam University) ;
  • Cho, Bong-Rae (Molecular Opto-Electronics Laboratory, Department of Chemistry and Center for Electro- and Photo-Responsive Molecules, Korea University)
  • Published : 2003.11.20
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Abstract

The effects of amine donors ($a:NH_2,\;b:NMe_2,\;c:NMePh,\;d:NPh_2$) and conjugation length on the molecular hyperpolarizabilities of a series of dipolar molecules have been theoretically investigated by using CPHF/6-31G method. The first hyperpolarizabilities (${\beta}$) of p-nitrobenzene derivatives increase with the donor in the order, $NH_2\;<\;NMe_2\;<\;NMePh\;<\;NPh_2$, whereas slightly different order is observed in more conjugated derivatives, i.e., $NH_2\;<\;NPh_2\;<\;NMe_2\;<\;NMePh$. The result has been attributed to the extent of charge transfer and torsion angle. Moreover, the results show that "non-traditional" ${\pi}$-conjugation effect exists in small compounds and decreases as the conjugation length between donor and acceptor increases.

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References

  1. Marder, S. R.; Perry, J. W. Adv. Material. 1993, 5, 804. https://doi.org/10.1002/adma.19930051104
  2. Marder, S. R.; Kippelen, B.; Jen, A. K.-Y.; Peyghambarian, N.Nature 1997, 388, 845. https://doi.org/10.1038/42190
  3. Dalton, L. R.; Steier, W. H.; Robinson,B. H.; Zhang, C.; Ren, A.; Garner, S.; Chen, A.; Londergan, T.;Irwin, L.; Carlson, B.; Fifield, L.; Phelan, G.; Kincaid, C.; Amend,J.; Jen, A. J. Mater. Chem. 1999, 9, 1905. https://doi.org/10.1039/a902659b
  4. Shi, Y.; Zhang, C.;Zhang, H.; Bechtel, J. H.; Dalton, L. R.; Robinson, B. H.; Steier,W. H. Science 2000, 288, 119. https://doi.org/10.1126/science.288.5463.119
  5. Parasad, P. N.; Williams, D. J. Introduction to Nonlinear OpticalEffects in Molecules and Polymers; John Wiley & Sons: NewYork, 1991.
  6. Williams, D. J. Angew. Chem. Int. Ed. Engl. 1984, 23, 690. https://doi.org/10.1002/anie.198406901
  7. Long, N. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 21. https://doi.org/10.1002/anie.199500211
  8. Moylan, C. R.; Twieg, R. J.; Lee, V. Y.; Swanson, S. A.;Betterton, K. M.; Miller, R. D. J. Am. Chem. Soc. 1993, 115,12599. https://doi.org/10.1021/ja00079a055
  9. Kim, M. H.; Jin, J.-L.; Lee, C. J.; Kim, N.; Park, K. H.Bull. Korean Chem. Soc. 2002, 23, 964. https://doi.org/10.5012/bkcs.2002.23.7.964
  10. Cho, B. R.; Kim, Y. H.;Som, K. W.; Khalil, C.; Kim, Y. H.; Jeon, S.-J. Bull. KoreanChem. Soc. 2002, 23, 1253. https://doi.org/10.5012/bkcs.2002.23.9.1253
  11. Ra, C. S.; Park, G. Bull. KoreanChem. Soc. 2003, 24, 1051. https://doi.org/10.5012/bkcs.2003.24.8.1051
  12. Whitaker, C. M.; Patterson, E. V.; Kott, K. L.; McMahon, R. J. J.Am. Chem. Soc. 1996, 118, 9966. https://doi.org/10.1021/ja960284g
  13. Frisch, M. J. et al., Gaussian 98, Revision A.7; Gaussian, Inc.:Pittsburgh, PA, 2002.

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