Synthesis, crystal structure, and second-order nonlinear optical properties of a new bis(salicylaldiminato)nickel(II) metal complex

Chemistry of Materials

Volumn 11, Issue 4, 1999, Pages 995-1002

  Averseng, Frédéric ^a   Lacroix, Pascal G ^a   Malfant, Isabelle ^a   Lenoble, Géraldine ^a   Cassoux, Patrick ^a   Nakatani, Keitaro ^a   Maltey Fanton, Isabelle ^a   Delaire, Jacques A ^a   Aukauloo, Ally ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000616586     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm980650q     Document Type: Article

References (87)

1. (a) Molecular Nonlinear Optics; Zyss, J., Ed.; Academic Press: New York, NY, 1994.
2. (b) Nonlinear Optical Properties of Organic Molecules and Crystals; Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987; Vols 1 and 2
3. (c) Prasad, N. P.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: New York, 1991.
4. Nonlinear Optical Properties of Organic Materials; Proceedings of SPIE 1988-1994, Vols. 971, 1147, 1337, 1560, 1775, 2025, 2285.
5. for recent reviews, see: (a) Dalton, L. R.; Harper, A. W.; Ghosn, R.; Steier, W. H.; Ziari, M.; Fetterman, H.; Shi, Y.; Mustacich, R. V.; Jen, A. K. Y.; Shea, K. J. Chem. Mater. 1995, 7, 1060.
6. (b) Benning, R. G. J. Mater. Chem. 1995, 5, 365.
7. (c) Special issue: Optical Nonlinearities in Chemistry. Chem. Rev. 1994, 94 (1).
8. (d) Marder, S. R.; Beratan, D. N.; Cheng, L. T. Science 1991, 252, 103.
9. (e) Verbiest, T.; Houbrechts, S.; Kauranen, M.; Clays, K.; Persoons, A. J. Mater. Chem. 1997, 7, 2175.
10. Williams, D. J. Ang. Chem., Int. Ed. Engl. 1984, 23, 690.
11. For a recent reviews on NLO organometallics, see: (a) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21.
12. (b) Marder, S. R. In Inorganic Materials; Bruce, D. W., O'Hare, D., Eds.; John Wiley & Sons: New York, 1992; p 115.
13. (a) Whittall, I. R.; Humphrey, M. G.; Persoons, A.; Houbrechts, S. Organometallics 1996, 15, 1935.
14. (b) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738.
15. (c) Whittall, I. R.; Humphrey, M. G.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Organometallics 1995, 14, 3970.
16. (a) Kanis, D. R.; Lacroix, P. G.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10089.
17. (b) Kanis, D. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 10338.
18. (a) Coe, B. J.; Hamor, T. A.; Jones, C. J.; McCleverty, J. A.; Bloor, D.; Cross, G. H.; Axon, T. L. J. Chem. Soc., Dalton Trans. 1995, 673.
19. (b) Coe, B. J.; Foulon, J. D.; Hamor, T. A.; Jones, C. J.; McCleverty, J. A.; Bloor, D.; Cross, G. H.; Axon, T. L. J. Chem. Soc., Dalton Trans. 1994, 3427.
20. (c) Houlton, A.; Jasim, N.; Roberts, R. M. G.; Silver, J.; Cunningham, D.; Mcardle, P.; Higgins, T. J. Chem. Soc., Dalton Trans. 1992, 2235.
21. (a)Loucif-Saïbi, R.; Delaire, J. A.; Bonazzola, L.; Doisneau, G.; Balavoine, G.; Fillebeen-Khan, T.; Ledoux, I.; Puccetti, G. Chem. Phys. 1992, 167, 369.
22. (b) Balavoine, G. G. A.; Daran, J.-C.; Iftime, G.; Lacroix, P. G.; Manoury, E.; Maltey-Fanton, I.; Nakatani, K.; Delaire, J. A.; Di Bella, S. J. Am. Chem. Soc. Submitted.
23. (a) Wright, M. E.; Toplikar, E. G.; Lackritz, H. S.; Kerney, J. T. Macromolecules 1994, 27, 3016.
24. (b) Wright, M. E.; Sigman, M. S. Macromolecules 1992, 25, 6055.
25. (c) Wright, M. E.; Toplikar, E. G. Macromolecules 1992, 25, 6050.
26. Cheng, L. T.; Tam, W.; Meredith, G. R.; Marder, S. R. Mol. Cryst. Liq. Cryst. 1990, 189, 137.
27. Bougault, M.; Mountassir, C.; Le Bozec, H.; Ledoux, I.; Pucetti, G.; Zyss J. J. Chem. Soc., Chem. Commun. 1993, 1623.
28. Zyss, J.; Dhénaut, C.; Chauvan, T.; Ledoux, I. Chem. Phys. Lett. 1993, 206, 409.
29. Thami, T.; Bassoul, P.; Petit, M. A.; Simon, J.; Fort, A.; Barzoukas, M.; Villaeys, A. J. Am. Chem. Soc. 1992, 114, 915.
30. Cummings, S. D.; Cheng, L. T.; Eisenberg, R. Chem. Mater. 1997, 9, 440.
31. (a) Di Bella, S.; Fragalà , I.; Ledoux, I.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 9481.
32. (b) Di Bella, S.; Fragalà , I.; Ledoux, I.; Diaz-Garcia, M. A.; Lacroix, P. G.; Marks, T. J. Chem. Mater. 1994, 6, 881.
33. (c) Di Bella, S.; Fragalà , I.; Ledoux, I.; Diaz-Garcia, M. A.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 9550.
34. (a) Lacroix, P. G.; Di Bella, S.; Ledoux, I. Chem. Mater. 1996, 8, 541
35. (b) Lenoble, G.; Lacroix, P. G.; Daran, J. C.; Di Bella, S.; Nakatani, K. Inorg. Chem. 1998, 37, 2158.
36. (a) Lecours, S. M.; Guan, H.-W.; Dimagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497.
37. (b) Priyadarshy, S.; Therien, M. J.; Beratan, D. N. J. Am. Chem. Soc. 1996, 118, 1504.
38. (a) Geoffroy, G. L.; Wrighton, M. S. Organometallic Photochemistry; Academic Press: New York, 1979.
39. (b) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
40. Kahn, O. Molecular Magnetism; VCH Publishers: New York, 1993.
41. For a general discussion of EFISH technique, see: (a) Levine, B. F.; Bethea, C. G. J. Chem. Phys. 1976, 65, 2429
42. (b) Singer, K. D.; Garito, A. F. J. Chem. Phys. 1981, 75, 3572.
43. Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195.
44. Cheeseman, G. W. H. J. Chem. Soc. 1962, 1170.
45. (a) Arshady, R.; Kenner, G. W.; Ledwith, A. J. Polym. Science: Polym. Chem. Ed. 1974, 12, 2017
46. (b) Lacroix, P. G.; Lin, W.; Wong, G. W. Chem. Mater. 1995, 7, 1293.
47. See for example: (a) 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.
48. (b) Bosnich, B. J. Am. Chem. Soc. 1968, 90, 627.
49. Sheldrick, G. M. SHELXS86, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1986.
50. Prince, E. Mathematical Techniques in Crystallography; Springer-Verlag: Berlin, 1982.
51. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. CRYSTALS Issue 10; Chemical Crystallography Laboratory, University of Oxford, Oxford, 1996.
52. Watkin, D. J.; Prout, C. K.; Pearce, L. J. CAMERON; Chemical Crystallography Laboratory, University of Oxford, Oxford, 1996.
53. Maltey, I.; Delaire, J. A.; Nakatani, K.; Wang, P.; Shi, X.; Wu, S. Adv. Mater. Opt. Electronics 1996, 6, 233.
54. Nicoud, J. F.; Twieg, R. J. In ref 1(b), Vol. 2, p 251.
55. (a) Zerner, M.; Loew, G.; Kirchner, R.; Mueller-Westerhoff, U. J. Am. Chem. Soc. 1980, 102, 589.
56. (b) Anderson, W. P.; Edwards, D; Zerner, M. C. Inorg. Chem. 1986, 25, 2728.
57. Ward, J. F. Rev. Mod. Phys. 1965, 37, 1.
58. (a) Singh Nalwa, H.; Watanabe, T.; Miyata, S. Adv. Mater. 1995, 7, 754.
59. (a) Singh Nalwa, H.; Nakajima, K.; Watanabe, T.; Nakamora, K.; Yamada, A.; Miyata, S. J. Appl. Phys. 1991, 30, 983.
60. Wöhrle, D.; Buttner, P. Polym. Bull. (Berlin) 1985, 13, 57.
61. Manfredotti, A. G.; Guastini, C. Acta Crystallogr. 1983, C39, 863.
62. Paley, M. S.; Harris, J. M.; Looser, H.; Baumert, J. C.; Bjorklund, G. C.; Jundt, D.; Twieg, R. J. J. Org. Chem. 1989, 54, 3774.
63. for a review of the solvent polarity scales, see: Buncel, E.; Rajagopal, S. Acc. Chem. Res. 1990, 23, 226.
64. Reichardt, C.; Harbusch-Görnet, E. Liebigs Ann. Chem. 1983, 5, 721.
65. Oudar, J. L. J. Chem. Phys. 1977, 67, 446.
66. S. R. Marder, D. N. Beratan and L. T. Cheng, Science 1991, 252, 103.
67. D. R. Kanis, Marks, T. J.; Ratner, M. A. Int. J. Quantum Chem. 1992, 43, 61.
68. (a) Cheng, L. T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.; Rikken, G.; Marder, S. R. J. Phys. Chem. 1991, 95, 10631.
69. (b) Cheng, L. T.; Tam, W.; Marder, S. R.; Stiegman, A. E.; Rikken, G.; Spangler, C. W. J. Phys. Chem. 1991, 95, 10643.
70. Handbook of Chemistry and Physics, 63rd ed.; CRC Press: Boca Raton, FL, 1982; D195.
71. Nonlinear Optics of Organic Molecules and Polymers; Nalwa, H. S., Miyata, S., Eds.; CRC Press: New York, 1997; 89.
72. Dagani, R. C&EN 1996, March 4, 22.
73. Oudar, J. L.; Zyss, J. Phys. Rev. 1982, A26, 2016.
74. (a) Meredith, G. R.; Van Dusen, J. G.; Williams, D. J. Macromolecules 1982, 15, 1385.
75. (b) Meredith, G. R.; Van Dusen, J. G.; Williams, D. J. In Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symposium Series 233; American Chemical Society: Washington, DC, 1984; p 109.
76. Williams, D. J. In ref 1b, Vol. 1, p 405.
77. Singer, K. D.; Lalama, S. J.; Sohn, J. E.; Small, S. D. In ref 1b, Vol. 1, p 437.
78. see for example: (a) Pushkana Rao, V.; Jen, A. K.-Y.; Chandrasekhar, J.; Namboothiri, I. N. N.; Rathna, A. J. Am. Chem. Soc. 1996, 118, 12443.
79. (b) Dalton, L. R.; Harper, A. W.; Ghosn, R.; Steier, W. H.; Ziari, M.; Fetterman, H.; Shi, Y.; Mustacich, R. V.; Jen, A. K.- Y.; Shea, K. J. Chem. Mater. 1995, 7, 1060.
80. Nalwa, H. S.; Watanabe, T.; Miyata, S. In ref 44, p 89.
81. Park, J.; Marks, T. J.; Yang, J.; Wong, G. K. Chem. Mater. 1990, 2, 229.
82. Vitalini, D.; Mineo, P.; Di Bella, S.; Fragala, I.; Maravigna, P.; Scamporrino, E. Macromolecules 1996, 29, 4478.
83. For recent reports on such high Tg polymers, see: (a) Yu, D.; Gharavi, A.; Yu, L. Appl. Phys. Lett. 1995, 66, 1050
84. (b) Verbiest, T.; Burland, D. M.; Jurich, M. C.; Lee, V. Y.; Miller, R. D.; Volksen, W. Macromolecules 1995, 28, 3005.
85. (c) Jen, A. K.-Y.; Wu, X.; Ma, H. Chem. Mater. 1998, 10, 471.
86. (a) Comprehensive Supramolecular Chemistry; Atwood, J. L., Lehn, J. M., Eds.; Pergamon Press: Oxford, 1996
87. (b) Supramolecular Chemistry: Concepts and Perspectives; Lehn, J. M., Ed.; VCH: Weinheim, Germany, 1995.