Lewis Acidic Borane Adducts of Pyridines and Stilbazoles for Nonlinear Optics

Chemistry of Materials

Volumn 10, Issue 5, 1998, Pages 1355-1365

  Lesley, M J Gerald ^a   Woodward, Alden ^a   Taylor, Nicholas J ^a   Marder, Todd B ^a,e   Cazenobe, Iréne ^b   Ledoux, Isabelle ^b   Zyss, Joseph ^b   Thornton, Anna ^c   Bruce, Duncan W ^c   Kakkar, Ashok K ^d  

^a UNIVERSITY OF WATERLOO   (Canada)

^b ORANGE LABS   (France)

^c UNIVERSITY OF EXETER   (United Kingdom)

^d MCGILL UNIVERSITY   (Canada)

^e DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000711729     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm9707519     Document Type: Article

References (68)

1. For reviews on materials for NLO see: (a) Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symp. Ser. 233; American Chemical Society: Washington, DC, 1983. (b) Nonlinear Optical Properties of Organic Molecules and Crystals; Vol. 1, 2. Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987. (c) Organic Materials for Nonlinear Optics; Hahn, R. A., Eds.; Spec. Publ. No. 69; The Royal Society of Chemistry: London, 1989. (d) Organic Materials for Nonlinear Optics II; Hahn, R. A., Bloor, D., Eds.; Spec. Publ. No. 91; The Royal Society of Chemistry: Cambridge, 1991. (e) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: Chichester, 1991. (f) Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1994.
2. For reviews on materials for NLO see: (a) Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symp. Ser. 233; American Chemical Society: Washington, DC, 1983. (b) Nonlinear Optical Properties of Organic Molecules and Crystals; Vol. 1, 2. Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987. (c) Organic Materials for Nonlinear Optics; Hahn, R. A., Eds.; Spec. Publ. No. 69; The Royal Society of Chemistry: London, 1989. (d) Organic Materials for Nonlinear Optics II; Hahn, R. A., Bloor, D., Eds.; Spec. Publ. No. 91; The Royal Society of Chemistry: Cambridge, 1991. (e) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: Chichester, 1991. (f) Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1994.
3. For reviews on materials for NLO see: (a) Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symp. Ser. 233; American Chemical Society: Washington, DC, 1983. (b) Nonlinear Optical Properties of Organic Molecules and Crystals; Vol. 1, 2. Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987. (c) Organic Materials for Nonlinear Optics; Hahn, R. A., Eds.; Spec. Publ. No. 69; The Royal Society of Chemistry: London, 1989. (d) Organic Materials for Nonlinear Optics II; Hahn, R. A., Bloor, D., Eds.; Spec. Publ. No. 91; The Royal Society of Chemistry: Cambridge, 1991. (e) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: Chichester, 1991. (f) Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1994.
4. For reviews on materials for NLO see: (a) Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symp. Ser. 233; American Chemical Society: Washington, DC, 1983. (b) Nonlinear Optical Properties of Organic Molecules and Crystals; Vol. 1, 2. Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987. (c) Organic Materials for Nonlinear Optics; Hahn, R. A., Eds.; Spec. Publ. No. 69; The Royal Society of Chemistry: London, 1989. (d) Organic Materials for Nonlinear Optics II; Hahn, R. A., Bloor, D., Eds.; Spec. Publ. No. 91; The Royal Society of Chemistry: Cambridge, 1991. (e) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: Chichester, 1991. (f) Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1994.
5. For reviews on materials for NLO see: (a) Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symp. Ser. 233; American Chemical Society: Washington, DC, 1983. (b) Nonlinear Optical Properties of Organic Molecules and Crystals; Vol. 1, 2. Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987. (c) Organic Materials for Nonlinear Optics; Hahn, R. A., Eds.; Spec. Publ. No. 69; The Royal Society of Chemistry: London, 1989. (d) Organic Materials for Nonlinear Optics II; Hahn, R. A., Bloor, D., Eds.; Spec. Publ. No. 91; The Royal Society of Chemistry: Cambridge, 1991. (e) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: Chichester, 1991. (f) Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1994.
6. For reviews on materials for NLO see: (a) Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symp. Ser. 233; American Chemical Society: Washington, DC, 1983. (b) Nonlinear Optical Properties of Organic Molecules and Crystals; Vol. 1, 2. Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987. (c) Organic Materials for Nonlinear Optics; Hahn, R. A., Eds.; Spec. Publ. No. 69; The Royal Society of Chemistry: London, 1989. (d) Organic Materials for Nonlinear Optics II; Hahn, R. A., Bloor, D., Eds.; Spec. Publ. No. 91; The Royal Society of Chemistry: Cambridge, 1991. (e) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: Chichester, 1991. (f) Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1994.
7. For reviews involving applications of NLO materials see: (a) Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics; Bredas, J. L., Chance, R. R., Eds.; NATO ARW Series E182; Kluwer Academic Publishers: Dordrecht, 1990. (b) Materials for Nonlinear Optics: Chemical Perspectives; Marder, S. R., Sohn, J. E., Stucky, G. D., Eds.; ACS Symp. Ser. 455; American Chemical Society: Washington, DC, 1991. (c) Molecular Nonlinear Optics: Materials, Physics, and Devices; Zyss, J., Ed.; Academic Press: New York, 1994. (d) Nonlinear Optical Properties of Organic Materials VII; Mohlmann, G. R., Ed.; Proc. SPIE, Vol. 2285; The International Society for Optical Engineering: Washington, DC, 1994. (e) Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications; Marder, S. R., Perry, J. W., Eds.; Proc. SPIE, Vol. 2143; The International Society for Optical Engineering: Washington, DC, 1994.
8. For reviews involving applications of NLO materials see: (a) Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics; Bredas, J. L., Chance, R. R., Eds.; NATO ARW Series E182; Kluwer Academic Publishers: Dordrecht, 1990. (b) Materials for Nonlinear Optics: Chemical Perspectives; Marder, S. R., Sohn, J. E., Stucky, G. D., Eds.; ACS Symp. Ser. 455; American Chemical Society: Washington, DC, 1991. (c) Molecular Nonlinear Optics: Materials, Physics, and Devices; Zyss, J., Ed.; Academic Press: New York, 1994. (d) Nonlinear Optical Properties of Organic Materials VII; Mohlmann, G. R., Ed.; Proc. SPIE, Vol. 2285; The International Society for Optical Engineering: Washington, DC, 1994. (e) Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications; Marder, S. R., Perry, J. W., Eds.; Proc. SPIE, Vol. 2143; The International Society for Optical Engineering: Washington, DC, 1994.
9. For reviews involving applications of NLO materials see: (a) Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics; Bredas, J. L., Chance, R. R., Eds.; NATO ARW Series E182; Kluwer Academic Publishers: Dordrecht, 1990. (b) Materials for Nonlinear Optics: Chemical Perspectives; Marder, S. R., Sohn, J. E., Stucky, G. D., Eds.; ACS Symp. Ser. 455; American Chemical Society: Washington, DC, 1991. (c) Molecular Nonlinear Optics: Materials, Physics, and Devices; Zyss, J., Ed.; Academic Press: New York, 1994. (d) Nonlinear Optical Properties of Organic Materials VII; Mohlmann, G. R., Ed.; Proc. SPIE, Vol. 2285; The International Society for Optical Engineering: Washington, DC, 1994. (e) Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications; Marder, S. R., Perry, J. W., Eds.; Proc. SPIE, Vol. 2143; The International Society for Optical Engineering: Washington, DC, 1994.
10. For reviews involving applications of NLO materials see: (a) Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics; Bredas, J. L., Chance, R. R., Eds.; NATO ARW Series E182; Kluwer Academic Publishers: Dordrecht, 1990. (b) Materials for Nonlinear Optics: Chemical Perspectives; Marder, S. R., Sohn, J. E., Stucky, G. D., Eds.; ACS Symp. Ser. 455; American Chemical Society: Washington, DC, 1991. (c) Molecular Nonlinear Optics: Materials, Physics, and Devices; Zyss, J., Ed.; Academic Press: New York, 1994. (d) Nonlinear Optical Properties of Organic Materials VII; Mohlmann, G. R., Ed.; Proc. SPIE, Vol. 2285; The International Society for Optical Engineering: Washington, DC, 1994. (e) Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications; Marder, S. R., Perry, J. W., Eds.; Proc. SPIE, Vol. 2143; The International Society for Optical Engineering: Washington, DC, 1994.
11. For reviews involving applications of NLO materials see: (a) Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics; Bredas, J. L., Chance, R. R., Eds.; NATO ARW Series E182; Kluwer Academic Publishers: Dordrecht, 1990. (b) Materials for Nonlinear Optics: Chemical Perspectives; Marder, S. R., Sohn, J. E., Stucky, G. D., Eds.; ACS Symp. Ser. 455; American Chemical Society: Washington, DC, 1991. (c) Molecular Nonlinear Optics: Materials, Physics, and Devices; Zyss, J., Ed.; Academic Press: New York, 1994. (d) Nonlinear Optical Properties of Organic Materials VII; Mohlmann, G. R., Ed.; Proc. SPIE, Vol. 2285; The International Society for Optical Engineering: Washington, DC, 1994. (e) Organic, Metallo-Organic, and Polymeric Materials for Nonlinear Optical Applications; Marder, S. R., Perry, J. W., Eds.; Proc. SPIE, Vol. 2143; The International Society for Optical Engineering: Washington, DC, 1994.
12. Marder, S. R.; Perry, J. W.; Yakymyshyn, C. P. Chem. Mater. 1994, 6, 1137.
13. For discussions of poling experiments with polymers see, for example: (a) Hubbard, M. A.; Marks, T. J.; Yang, J. Y.; Wong, G. K. Chem. Mater. 1989, 1, 167. (b) Xu, C.; Wu, B.; Dalton, L. R.; Shi, Y.; Ranon, P. M.; Steier, W. H. Macromolecules 1992, 25, 6714. (c) Ibid. 1992, 25, 6716. (d) Gilmour, S.; Montgomery, R. A.; Marder, S. R.; Cheng, L.-T.; Jen, A. K.-Y.; Cai, Y.; Perry, J. W.; Dalton, L. R. Chem. Mater. 1994, 6, 1603.
14. For discussions of poling experiments with polymers see, for example: (a) Hubbard, M. A.; Marks, T. J.; Yang, J. Y.; Wong, G. K. Chem. Mater. 1989, 1, 167. (b) Xu, C.; Wu, B.; Dalton, L. R.; Shi, Y.; Ranon, P. M.; Steier, W. H. Macromolecules 1992, 25, 6714. (c) Ibid. 1992, 25, 6716. (d) Gilmour, S.; Montgomery, R. A.; Marder, S. R.; Cheng, L.-T.; Jen, A. K.-Y.; Cai, Y.; Perry, J. W.; Dalton, L. R. Chem. Mater. 1994, 6, 1603.
15. For discussions of poling experiments with polymers see, for example: (a) Hubbard, M. A.; Marks, T. J.; Yang, J. Y.; Wong, G. K. Chem. Mater. 1989, 1, 167. (b) Xu, C.; Wu, B.; Dalton, L. R.; Shi, Y.; Ranon, P. M.; Steier, W. H. Macromolecules 1992, 25, 6714. (c) Ibid. 1992, 25, 6716. (d) Gilmour, S.; Montgomery, R. A.; Marder, S. R.; Cheng, L.-T.; Jen, A. K.-Y.; Cai, Y.; Perry, J. W.; Dalton, L. R. Chem. Mater. 1994, 6, 1603.
16. For discussions of poling experiments with polymers see, for example: (a) Hubbard, M. A.; Marks, T. J.; Yang, J. Y.; Wong, G. K. Chem. Mater. 1989, 1, 167. (b) Xu, C.; Wu, B.; Dalton, L. R.; Shi, Y.; Ranon, P. M.; Steier, W. H. Macromolecules 1992, 25, 6714. (c) Ibid. 1992, 25, 6716. (d) Gilmour, S.; Montgomery, R. A.; Marder, S. R.; Cheng, L.-T.; Jen, A. K.-Y.; Cai, Y.; Perry, J. W.; Dalton, L. R. Chem. Mater. 1994, 6, 1603.
17. (a) Nguyen, P.; Yuan, Z.; Agocs, L.; Lesley, G.; Marder, T. B. Inorg. Chim. Acta 1994, 220, 289.
18. (b) Marder, T. B.; Lesley, G.; Yuan, Z.; Fyfe, H. B.; Chow, P.; Stringer, G.; Jobe, I. R.; Taylor, N. J.; Williams, I. D.; Kurtz, S. K. In ref 2b, p 605.
19. (c) Nguyen, P.; Lesley, G.; Dai, C.; Taylor, N. J.; Marder, T. B.; Chu, V.; Viney, C.; Ledoux, I.; Zyss, J. In Applications of Organometallic Chemistry in the Preparation and Processing of Advanced Materials; Harrod, J. F., Laine, R. M., Eds.; NATO ASI Series E; Kluwer Academic Publishers: Dordrecht, 1995; Vol. 297, p 333.
20. (d) Nguyen, P.; Lesley, G.; Marder, T. B.; Ledoux, I.; Zyss, J. Chem. Mater. 1997, 9, 406.
21. (a) Cheng, L.-T.; Tam, W.; Marder, S. R.; Steigman, A. E.; Rikken, G. J. Phys. Chem. 1991, 95, 10631.
22. (b) Ibid. 1991, 95, 10634.
23. (c) Dirk, C. W.; Katz, H. E.; Schilling, M. L.; King, L. A. Chem. Mater. 1990, 2, 700.
24. (d) Jen, A. K.-Y.; Rao, V. P.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 90.
25. (e) Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. Ibid. 1993, 1118.
26. (f) Rao, V. P.; Cai, Y. M.; Jen, A. K.-Y. Ibid. 1994, 1689.
27. (g) Jen, A. K.-Y.; Rao, V. P.; Drost, K. J.; Wong, K. Y.; Cava, M. P. Ibid. 1994, 2057.
28. (a) Kurihara, T.; Tabei, H.; Kaino, T. J. Chem. Soc., Chem. Commun. 1987, 959.
29. (b) Tabei, H.; Kurihara, T.; Kaino, T. Appl. Phys. Lett. 1987, 50, 185.
30. (c) Steigman, A. E.; Miskowski, V. M.; Perry, K. J.; Coulter, D. R. J. Am. Chem. Soc. 1987, 709, 5884.
31. (d) Steigman, A. E.; Graham, E. M.; Perry, K. J.; Khundkar, L. R.; Cheng, L.-T.; Perry, J. W. J. Am. Chem. Soc. 1991, 113, 7658.
32. (e) Perry, J. W.; Steigman, A. E.; Marder, S. R.; Coulter, D. R.; Beratan, D. N.; Brinza, D. E.; Klavetter, F. L.; Grubbs, R. H. In Nonlinear Optical Properties of Organic Materials; Proc. SPIE, Vol. 971; The International Society for Optical Engineering: Washington, DC, 1988; p 17.
33. (f) Steigman, A. E.; Perry, J. W.; Cheng, L.-T. In ref 1d, p 149.
34. (g) Dehu, C.; Meyers, F.; Brédas, J. L. J. Am. Chem. Soc. 1993, 115, 6198.
35. (a) Etter, M. C.; Frankenbach, G. M. Chem. Mater. 1989, 1, 10.
36. (b) Etter, M. C.; Huang, K. S.; Frankenbach, G. M.; Adsmond, D. A. In ref 2b, p 457.
37. (c) Etter, M. C. J. Phys. Chem. 1991, 95, 4601.
38. (a) Blanchard-Desce, M.; Ledoux, I.; Lehn, J.-M.; Maithete, J.; Zyss, J. J. Chem. Soc., Chem. Commun. 1988, 737.
39. (b) Blanchard-Desce, M.; Lehn, J.-M.; Ledoux, I.; Zyss, J. In ref 1c, p 170.
40. (c) Zyss, J.; Ledoux, I.; Nicoud, J.-F. In ref 2c, p 129.
41. (d) Marder, S. R.; Cheng, L.-T.; Tiemann, B. G.; Friedli, A. C.; Blanchard-Desce, M.; Perry, J. W.; Skindhoj, J. Science 1994, 263, 511.
42. Meredith, G. R. In ref 1a, p 27.
43. Bruce, D. W.; Denning, R. G.; Grayson, M. G.; Le Lagadec, R.; Lai, K. K.; Pickup, B. T.; Thornton, A. Adv. Mater. Opt. Electron. 1994, 4, 293.
44. (a) Cheng. L.-T.; Tam, W.; Eaton, D. F. Organometallics 1990, 9, 2856.
45. (b) Cheng. L.-T.; Tam, W.; Meredith, G. R. Mol. Cryst. Liq. Cryst. 1990, 189, 137.
46. (c) The NLO properties of these and related compounds have recently been described in ref 13c, p 144.
47. (d) Kanis, D. R.; Lacroix, P. G.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10089.
48. (a) Bruce, D. W.; Thornton, A. Mol. Cryst. Liq. Cryst. 1993, 231, 253.
49. (b) Bruce, D. W.; Dunmur, D. A.; Lalinde, E.; Maitlis, P. M.; Styring, P. Liq. Cryst. 1988, 3, 385.
50. (c) The liquid-crystalline properties of related materials have been recently reviewed: Inorganic Materials, 2nd Ed.; Bruce, D. W., O'Hare D., Ed.; John Wiley and Sons: Chichester, England, 1996; Chapter 8.
51. (a) Bourgault, M.; Mountassir, C.; Le Bozec, H.; Ledoux, I.; Pucetti, G.; Zyss, J. J. Chem. Soc., Chem. Commun. 1993, 1623.
52. (b) Peng, Z.; Yu, L. J. Am. Chem. Soc. 1996, 118, 3777.
53. (a) Yuan, Z.; Taylor, N. J.; Marder, T. B.; Williams, I. D.; Kurtz, S. K.; Cheng, L.-T. J. Chem. Soc., Chem. Commun. 1990, 1489.
54. (b) Yuan, Z.; Taylor, N. J.; Marder, T. B.; Williams, I. D.; Kurtz, S. K.; Cheng, L.-T. In ref 1d, p 190.
55. (c) Yuan, Z.; Taylor, N. J.; Sun, Y.; Marder, T. B.; Williams, I. D.; Cheng, L.-T., J. Organomet. Chem. 1993, 449, 27.
56. (d) Yuan, Z.; Taylor, N. J.; Marder, T. B.; Cheng, L.-T., manuscript in preparation.
57. (e) Yuan, Z.; Taylor, N. J.; Ramachandran, R.; Marder, T. B. Appl. Organomet. Chem. 1996, 10, 305.
58. (f) Lequan, M.; Lequan, R. M.; Ching, K. C. J. Mater. Chem. 1991, 1, 997.
59. (g) Lequan, M.; Lequan, R. M.; Ching, K. C.; Barzoukas, M.; Fort, A.; Lahoucine, H.; Bravie, G.; Chasseau, D.; Gaultier, J. J. Mater. Chem. 1992, 2, 719.
60. 3 see: Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245. For the stilbazole reagents see refs 3 and 13b.
61. Guggenheim, E. A. Trans. Faraday Soc. 1949, 45, 203.
62. 13C NMR chemical shifts were calculated using a module developed for Chem Window 3.0.0 by Dr. Ernö Pretsch, Department of Organic Chemistry, ETH, Zurich, Switzerland, 1990-1993 Softshell International Ltd.
63. Both μβ and μβ(0) are given since the two-level model may not be accurate for these compounds due to the possible presence of low-lying excited states that may contribute to β.
64. Recently, a study involving ammonium/borate zwitterions has been reported in which phenyl, olefinic, and alkynyl backbones were examined for second-order NLO efficiency: Lambert, C.; Stadler, S.; Bourhill, G.; Bräuchte, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 644.
65. (a) Kurtz, S. K.; Perry, T. T. J. Appl. Phys. 1968, 39, 3798.
66. (b) Zyss, J.; Chemla, D. S.; Nicoud, J. F. J. Chem. Phys. 1981, 74, 4800.
67. (a) Ohms, U.; Guth, H. Z. Kristallogr. 1983, 162, 174.
68. (b) Ohms, U.; Guth, H. Z. Kristallogr. 1984, 766, 213.