DOI QR코드

DOI QR Code

Synthesis and Nonlinear Optical Properties of 1,3,5-Tricyano-2,4,6-tris[2-(thiophen-2-yl)vinyl]benzene Derivatives


Abstract

1,3,5-Tricyano-2,4,6-tris[2-(thiophen-2-yl)vinyl]benzene derivatives have been synthesized as a new type of octupolar nonlinear optical molecules and their linear and nonlinear optical properties were determined. The λmax values increa sed with the conjugation length and as the conjugation bridge was changed from phenyl to thienyl group. For phenyl and thiophene derivatives, the b value increased with conjugation length. In contrast, the $\beta$ values of the thiophene derivatives were much smaller than the corresponding phenyl derivatives.

Keywords

References

  1. Prasad, P. N.; William, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; John & Wiley: New York, 1991.
  2. 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
  3. 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
  4. Marder, S. R.; Cheng, L.-T.; Tiemann, A. C.; Blachard-Desce, M.; Perry, J. W.; Skindhoj, J. Science 1994, 263, 1706. https://doi.org/10.1126/science.263.5154.1706
  5. Varanasi, P. R.; Jen, K.-Y.; Chandrasekhar, J.; Namboothiri, I. N. N.; Rathna, A. J. Am. Chem. Soc. 1996, 118, 12443. https://doi.org/10.1021/ja960136q
  6. Cho, B. R.; Son, K. N.; Lee, S. J.; Kang, T. I.; Han, M. S.; Jeon, S. J.; Song, N. W.; Kim, D. Tetrahedron Lett. 1998, 39, 3167. https://doi.org/10.1016/S0040-4039(98)00450-X
  7. Cho, B. R.; Lee, S. H.; Lim, J. C.; Kang, T. I.; Jeon, S. J. Mol. Cryst. Liq. Cryst. 2001, 370, 77. https://doi.org/10.1080/10587250108030043
  8. Cho, B. R.; Lee, S. H.; Min, Y.; Kang, T. I.; Jeon, S. J. J. Photo Sci. 2001, 8, 79.
  9. Joffre, M.; Yaron, D.; Silbey, R. J.; Zyss, J. J. Chem. Phys. 1992, 97, 56.
  10. Zyss, J.; Ledoux, I. Chem. Rev. 1994, 94, 77. https://doi.org/10.1021/cr00025a003
  11. Dhnault, C. J.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339. https://doi.org/10.1038/374339a0
  12. Brasselet, S.; Zyss, J. Opt. Soc. Am. B 1998, 15, 257. https://doi.org/10.1364/JOSAB.15.000257
  13. del Rey, B.; Keller, U.; Torres, T.; Rojo, G.; Agullo-Lopez, F.; Nonell, S.; Marti, C.; Brasselet, S.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 1998, 120, 12808. https://doi.org/10.1021/ja980508q
  14. Wolff, J. J.; Wortman, R. Adv. Phys. Org. Chem. 1999, 32, 121. https://doi.org/10.1016/S0065-3160(08)60007-6
  15. Wolff, J. J.; Siegler, F.; Matschiner, R.; Wortman, R. Angew. Chem. Int. Ed. 2000, 39, 1436. https://doi.org/10.1002/(SICI)1521-3773(20000417)39:8<1436::AID-ANIE1436>3.0.CO;2-U
  16. Lambert, C.; Gaschler, W.; Schamlzlin, E.; Meerholz, K.; Brauchle, C. J. Chem. Soc. Perkin Trans. 2 1999, 577.
  17. Lambert, C.; Gaschler, W.; Noll, G.; Weber, M.; Schamlzlin, E.; Brauchle, C.; Meerholz, K. J. Chem. Soc. Perkin Trans. 2 2001, 964.
  18. Lee, Y.-K.; Jeon, S.-J.; Cho, M. J. Am. Chem. Soc. 1998, 120, 10921. https://doi.org/10.1021/ja9803456
  19. Lee, W.-H.; Lee, H.; Kim, J.-A.; Choi, J.-H.; Cho, M.; Jeon, S.-J.; Cho, B. R. J. Am. Chem. Soc. 2001, 123, 10658. https://doi.org/10.1021/ja004226d
  20. Thalladi, V. R.; Brasselet, S.; Weiss, H.-C.; Blaser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563. https://doi.org/10.1021/ja972830r
  21. Cho, B. R.; Lee, S. J.; Lee, S. H.; Son, K. H.; Kim, Y. H.; Doo, J.-Y.; Lee, G. J.; Kang, T. I.; Lee, Y. K.; Cho, M.; Jeon, S.-J. Chem. Mater. 2001, 13, 1438. https://doi.org/10.1021/cm000816z
  22. Cho, B. R.; Park, S. B.; Lee, S. J.; Son, K. H.; Lee, S. H.; Lee, M.-J.; Yoo, J.; Lee, Y. K.; Lee, G. J.; Kang, T. I.; Cho, M.; Jeon, S.-J. J. Am. Chem. Soc. 2001, 123, 6421. https://doi.org/10.1021/ja0025595
  23. Weiss, C. D. J. Org. Chem. 1962, 27, 2964. https://doi.org/10.1021/jo01055a535
  24. Hendricks, E.; Clay, K.; Persoons, A. Acc. Chem. Res. 1998, 31, 675. https://doi.org/10.1021/ar960233o
  25. Stadler, S.; Dietrich, R.; Bourhill, G.; Brauchle, Ch. Optics Lett. 1996, 21, 251. https://doi.org/10.1364/OL.21.000251
  26. Elandaloussi, E. H.; Frere, P.; Richomme, P.; Orduna, J.; Garin, J.; Roncali, J. J. Am. Chem. Soc. 1997, 119, 10774. https://doi.org/10.1021/ja9722739

Cited by

  1. First hyperpolarizabilities of 1,3,5-tricyano-2,4,6-tris(styryl)benzene derivatives:ab initio studies and Hammett correlation vol.18, pp.3, 2005, https://doi.org/10.1002/poc.809
  2. First hyperpolarizabilities of hexa(ethynyl)benzene derivatives: effect of conjugation length vol.16, pp.23, 2006, https://doi.org/10.1039/b601982j
  3. Synthesis and nonlinear optical properties of polyester containing 4-di-(2′-hydroxyethoxy)-4-diphenyl-hydrazonomethyl chromophore pp.10991581, 2010, https://doi.org/10.1002/pat.1478
  4. Second-order nonlinear optical properties of octupolar molecules structure–property relationship vol.19, pp.40, 2009, https://doi.org/10.1039/b906361g
  5. Synthesis, Characterization and Optical Properties of Novel Nonlinear Polysilylether vol.19, pp.4, 2009, https://doi.org/10.1007/s10904-009-9301-9
  6. Amine Donors in Nonlinear Optical Molecules: Methyl and Phenyl Substitution Effects on the First Hyperpolarizability vol.24, pp.11, 2003, https://doi.org/10.5012/bkcs.2003.24.11.1671
  7. Synthesis and Nonlinear Optical Properties of 1,3,5-Tricyano-2,4,6-tris[2-(thiophen-2-yl)vinyl]benzene Derivatives. vol.34, pp.7, 2003, https://doi.org/10.1002/chin.200307093
  8. Synthesis and Nonlinear Optical Properties of Novel Y-Type Polyester with High Thermal Stability of Second Harmonic Generation vol.25, pp.12, 2002, https://doi.org/10.5012/bkcs.2004.25.12.1941
  9. Synthesis and Nonlinear Optical Properties of Novel T-Type Polyimide with Exceptional High Thermal Stability of Second Harmonic Generation vol.25, pp.5, 2004, https://doi.org/10.5012/bkcs.2004.25.5.605
  10. Heterocyclic Nonlinear Optical Chromophores Composed of Phenothiazine or Carbazole Donor and 2-Cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran Acceptor vol.26, pp.1, 2002, https://doi.org/10.5012/bkcs.2005.26.1.077
  11. Synthesis and Nonlinear Optical Properties of Novel Polyurethanes with High Thermal Stability for Electro-Optic Applications vol.26, pp.5, 2002, https://doi.org/10.5012/bkcs.2005.26.5.841
  12. Preparation and Nonlinear Optical Properties of Novel Polyesters with Enhanced Thermal Stability of Second Harmonic Generation vol.29, pp.1, 2002, https://doi.org/10.5012/bkcs.2008.29.1.181
  13. Preparation of Novel T-type Polyurethanes with High Thermal Stability of Second Harmonic Generation and Their Nonlinear Optical Properties vol.29, pp.4, 2008, https://doi.org/10.5012/bkcs.2008.29.4.811
  14. Synthesis of Novel Y-type Nonlinear Optical Polyesters with Enhanced Thermal Stability of Dipole Alignment vol.29, pp.5, 2002, https://doi.org/10.5012/bkcs.2008.29.5.933
  15. Synthesis and Properties of Novel Y-type Nonlinear Optical Polyester Containing Cyanovinylthiophene with Enhanced Thermal Stability of Second Harmonic Generation vol.30, pp.3, 2002, https://doi.org/10.5012/bkcs.2009.30.3.661
  16. Synthesis and Nonlinear Optical Properties of Novel Polyester with 2,3-Dioxybenzylidenecyanoacetate vol.30, pp.3, 2002, https://doi.org/10.5012/bkcs.2009.30.3.731
  17. Preparation and Properties of A Novel Y-type Nonlinear Optical Polyester with Dioxybenzylidenecyanoacetate Groups vol.30, pp.5, 2009, https://doi.org/10.5012/bkcs.2009.30.5.1080
  18. Synthesis and Nonlinear Optical Properties of Novel T-type Polyester Containing Thiophene with Enhanced Thermal Stability vol.31, pp.2, 2010, https://doi.org/10.5012/bkcs.2010.31.02.429
  19. Synthesis of Novel Y-type Nonlinear Optical Polyester with Enhanced Thermal Stability of Second Harmonic Generation for Electro-Optic Applications vol.31, pp.6, 2002, https://doi.org/10.5012/bkcs.2010.31.6.1509
  20. On the protonation and deuteration of N , N ‐disubstituted 2‐aminothiophenes, 2‐aminothiazoles, and some 3‐amino substituted analogues vol.58, pp.7, 2002, https://doi.org/10.1002/jhet.4279