Synthesis of functionalized organic second-order nonlinear optical chromophores for electrooptic applications

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4289-4297

  Thayumanavan, S ^a   Mendez, Jeffrey ^a   Marder, Seth R ^a,b,c  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^c University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; OPTICS; POLYMERIZATION; REFRACTION INDEX; SYNTHESIS;

EID: 0033546259     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981707v     Document Type: Article

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21. For examples of second-order nonlinear optical chromophores with high μβ, see: (a) Ahlheim, M.; Barzoukas, M.; Bedworth, P. V.; Blanchard-Desce, M.; Fort, A.; Hu, Z.-Y.; Marder, S. R.; Perry, J. W.; Runser, C.; Staehelin, M.; Zysset, B. Science 1996, 277, 335. (b) Blanchard-Desce, M.; Alain, V.; Bedworth, P. V.; Marder, S. R.; Fort, A.; Runser, C.; Barzoukas, M.; Lebus, S.; Wortmann, R. Chem. Eur. J. 1997, 3, 1091 and references therein. (c) Dirk, C. W.; Katz, H. E.; Schilling, M. L.; King, L. A. Chem. Mater. 1990, 2, 700. (d) Blanchard-Desce, M.; Alain, V.; Midrier, L.; Wortmann, R.; Lebus, S.; Glania, C.; Krämer, P.; Fort, A.; Muller, J.; Barzoukas, M. J. Photochem. Photobiol. A 1997, 105, 115.
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50. For the covalent incorporation of a diarylamino donor-based chromophore into a polymeric system, see: (a) Verbiest, T.; Burland, D. M.; Jurich, M. C.; Lee, V. Y.; Miller, R. D.; Volksen, W. Science 1995, 268, 1604. (b) Verbiest, T.; Burland, D. M.; Jurich, M. C.; Lee, V. Y.; Miller, R. D.; Volksen, W. Macromolecules 1995, 28, 3005. (c) Miller, R. D.; Burland, D. M.; Jurich, M.; Lee, V. Y.; Moylan, C. R.; Thackara, J. I.; Twieg, R. J.; Verbiest, T.; Volksen, W. Macromolecules 1995, 28, 4970.
51. For the covalent incorporation of a diarylamino donor-based chromophore into a polymeric system, see: (a) Verbiest, T.; Burland, D. M.; Jurich, M. C.; Lee, V. Y.; Miller, R. D.; Volksen, W. Science 1995, 268, 1604. (b) Verbiest, T.; Burland, D. M.; Jurich, M. C.; Lee, V. Y.; Miller, R. D.; Volksen, W. Macromolecules 1995, 28, 3005. (c) Miller, R. D.; Burland, D. M.; Jurich, M.; Lee, V. Y.; Moylan, C. R.; Thackara, J. I.; Twieg, R. J.; Verbiest, T.; Volksen, W. Macromolecules 1995, 28, 4970.
52. For the covalent incorporation of a diarylamino donor-based chromophore into a polymeric system, see: (a) Verbiest, T.; Burland, D. M.; Jurich, M. C.; Lee, V. Y.; Miller, R. D.; Volksen, W. Science 1995, 268, 1604. (b) Verbiest, T.; Burland, D. M.; Jurich, M. C.; Lee, V. Y.; Miller, R. D.; Volksen, W. Macromolecules 1995, 28, 3005. (c) Miller, R. D.; Burland, D. M.; Jurich, M.; Lee, V. Y.; Moylan, C. R.; Thackara, J. I.; Twieg, R. J.; Verbiest, T.; Volksen, W. Macromolecules 1995, 28, 4970.
53. Thayumanavan, S. et al. Manuscript in preparation.
54. We are interested in analyzing the effect of the additional ethereal linkage, such as in 5, on the stability of the chromophores. Therefore, we targeted both 3 and 4 to analyze the effect of an additional ethereal linkage in the absence of other variables.
55. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217. (c) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215. For a recent review, see: (c) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
56. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217. (c) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215. For a recent review, see: (c) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
57. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217. (c) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215. For a recent review, see: (c) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
58. Thayumanavan, S.; Barlow, S.; Marder, S. R. Chem. Mater. 1997, 9, 3231.
59. Application of Vilsmeier-type reaction conditions to synthesize 3 from 10 resulted in the conversion of the -OTBS group to the -Cl group.
60. We also attempted to synthesize 13 directly from 11 by treating the lithiated intermediate with the TBS ether of 6-bromo-1-hexanol. However, the product had an inseparable impurity that was carried over from the preparation of the TBS ether of 6-bromo-1-hexanol. The origin of the impurity is ascribed to an inseparable impurity in the commercially available starting material.
61. We suggest that the low-yielding step in the reaction is the bromination reaction. During an independent effort to brominate 15, we realized that longer reaction times are needed for this type of substrate.
62. Tamo, K. In Comprehensive Organic Synthesis: Selectivity, Strategy, and Efficiency in Modern Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 2.2.
63. 16 However, the route reported here is useful since it allows for flexibility to introduce groups other than the hexyl at the 4-position.
64. The reason for the low yield in the synthesis of 28 under the current unoptimized reaction conditions is not clear.
65. This result is attributed to the difference in the strength of the dicyanovinyl and the 3-phenylisoxazolone acceptor. The stronger acceptor would have more attenuated bond length alternation and thus reduce the barrier to isomerization to the thermodynamically more stable trans isomer.