Propeller-Shaped Octupolar Molecules Derived from Triphenylbenzene for Nonlinear Optics: Synthesis and Optical Studies

Chemistry of Materials

Volumn 15, Issue 21, 2003, Pages 4139-4148

  Brunel, Jérémie ^a   Mongin, Olivier ^b   Jutand, Anny ^a   Ledoux, Isabelle ^c   Zyss, Joseph ^c   Blanchard Desce, Mireille ^b  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; CORRELATION METHODS; LIGHT ABSORPTION; LIGHT EMISSION; OLIGOMERS; SYNTHESIS (CHEMICAL);

NONLINEAR RESPONSES;

AROMATIC COMPOUNDS;

BENZENE DERIVATIVE; TRIPHENYLBENZENE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CORRELATION ANALYSIS; ELECTRON TRANSPORT; ION TRANSPORT; NONLINEAR SYSTEM; OPTICS; SYNTHESIS; WITTIG REACTION;

EID: 0142183589     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm030392j     Document Type: Article

References (88)

1. Chemla, D. S., Zyss, J., Eds. Nonlinear Optical Properties of Organic Molecules and Crystals; Academic Press: New York, 1987; Vols. 1 and 2.
2. Zyss, J.; Ledoux, I. Chem. Rev. 1994, 94, 77-105.
3. Goovaerts, E.; Wenseleers, W. E.; Garcia, M. H.; Cross, G. H. In Handbook of Advanced Electronic and Photonic Materials and Devices; Nalwa, H. S., Ed.; Academic Press: New York, 2001; Vol. 9: Nonlinear Optical Materials, pp 127-191.
4. Shi, Y.; Zhang, C.; Zhang, H.; Bechtel, J. H.; Dalton, L. R.; Robinson, B. H.; Steier, W. H. Science 2000, 288, 119-122.
5. Parthenopoulos, D. A.; Rentzepis, P. M. Science 1989, 245, 843-845.
6. Maruo, S.; Nakamura, O.; Kawata, S. Opt. Lett. 1997, 22, 132-134.
7. Cumpston, B. H.; Ananthavel, S. P.; Barlow, S.; Dyer, D. L.; Ehrlich, J. E.; Erskine, L. L.; Heikal, A. A.; Kuebler, S. M.; Lee, I.-Y. S.; McCord-Maughon, D.; Qin, J.; Röckel, H.; Rumi, M.; Wu, X. L.; Marder, S. R.; Perry, J. W. Nature 1999, 398, 51-54.
8. Kawata, S.; Sun, H.-B.; Tanaka, T.; Takada, K. Nature 2001, 412, 697-698.
9. Denk, W.; Strickler, J. H.; Webb, W. W. Science 1990, 248, 73-76.
10. Moreaux, L.; Sandre, O.; Charpak, S.; Blanchard-Desce, M.; Mertz, J. Biophys. J. 2001, 80, 1568-1574.
11. 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, 1091-1104.
12. Alain, V.; Blanchard-Desce, M.; Ledoux-Rak, I.; Zyss, J. Chem. Commun. 2000, 353-354.
13. Ledoux, I.; Zyss, J.; Siegel, J. S.; Brienne, J.; Lehn, J.-M. Chem. Phys. Lett. 1990, 172, 440-444.
14. Zyss, J. J. Chem. Phys. 1993, 98, 6583-6599.
15. Wolff, J. J.; Wortmann, R. J. Prakt. Chem. 1998, 340, 99-111.
16. Wolff, J. J.; Wortmann, R. Adv. Phys. Org. Chem. 1999, 32, 121-217.
17. Joffre, M.; Yaron, D.; Silbey, R. J.; Zyss J. J. Chem. Phys. 1992, 97, 5607-5615.
18. Brédas, J.-L.; Meyers, F.; Pierce, B. M.; Zyss, J. J. Am. Chem. Soc. 1992, 114, 4928-4929.
19. Verbiest, T.; Clays, K.; Samyn, C.; Wolff, J.; Reinhoudt, D.; Persoons, A. J. Am. Chem. Soc. 1994, 116, 9320-9323.
20. Ray, P. C.; Das, P. K. Chem. Phys. Lett. 1995, 244, 153-156.
21. Noordman, O. F. J.; van Hulst, N. F. Chem. Phys. Lett. 1996, 253, 145-150.
22. Wortmann, R.; Glania, C.; Krämer, P.; Matschiner, R.; Wolff, J. J.; Kraft, S.; Treptow, B.; Barbu, E.; Längle, D.; Görlitz, G. Chem. Eur. J. 1997, 3, 1765-1773.
23. Wolff, J. J.; Siegler, F.; Matschiner, R.; Wortmann, R. Angew. Chem., Int. Ed. 2000, 39, 1436-1439.
24. 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, 1438-1440.
25. 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, 6421-6422.
26. Cho, B. R.; Chajara, K.; Oh, H. J.; Son, K. H.; Jeon, S.-J. Org. Lett. 2002, 4, 1703-1706.
27. Cho, B. R.; Kim, Y. H.; Son, K. W.; Khalil, C.; Kim, Y. H.; Jeon, S.-J. Bull. Korean Chem. Soc. 2002, 23, 1253-1256.
28. Zyss, J.; Brasselet, S.; Thalladi, V. R.; Desiraju, G. R. J. Chem. Phys. 1998, 109, 658-669.
29. Thalladi, V., R.; Brasselet, S.; Weiss, H.-C.; Bläser, D.; Katz, A. K.; Carrel, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563-2577.
30. Thalladi, V. R.; Boese, R.; Brasselet, S.; Ledoux, I.; Zyss, J.; Jetti, R. K. R.; Desiraju, G. R. Chem. Commun. 1999, 1639-1640.
31. Brasselet, S.; Cherioux, F.; Audebert, P.; Zyss, J. Chem. Mater. 1999, 11, 1915-1920.
32. Stadler, S.; Feiner, F.; Bräuchle, C.; Brandl, S.; Gompper, R. Chem. Phys. Lett. 1995, 245, 292-296.
33. Stadler, S.; Bräuchle, C.; Brandl, S.; Gompper, R. Chem. Mater. 1996, 8, 414-417.
34. Lambert, C.; Gaschler, W.; Schmälzlin, E.; Meerholz, K.; Bräuchle, C. J. Chem. Soc., Perkin Trans. 2 1999, 577-587.
35. Lambert, C.; Gaschler, W.; Noll, G.; Weber, M.; Schmalzlin, E.; Brauchle, C.; Meerholz, K. J. Chem. Soc., Perkin Trans. 2 2001, 964-974.
36. Cho, B. R.; Lee, S. K.; Kim, K. A.; Son, K. N.; Kang, T. I.; Jeon, S. J. Tetrahedron Lett. 1998, 39, 9205-9208.
37. Kenis, P. J. A.; Noordman, O. F. J.; Houbrechts, S.; Van Hummel, G. J.; Harkema, S.; Van Veggel, F. C. J. M.; Clays, K.; Engbersen, J. F. J.; Persoons, A.; Van Hulst, N. F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1998, 120, 7875-7883.
38. Verbiest, T.; Clays, K.; Persoons, A.; Meyers, F.; Brédas, J.-L. Opt. Lett. 1993, 18, 525-527.
39. Zyss, J.; Chau Van, T.; Dhenaut, C.; Ledoux, I. Chem. Phys. 1993, 177, 281-296.
40. Chui, T. W.; Wong, K. Y. J. Chem. Phys. 1998, 109, 1391-1396.
41. Greve, D. R.; Schougaard, S. B.; Geisler, T.; Petersen, J. C.; Bjørnholm, T. Adv. Mater. 1997, 9, 1113-1116.
42. Stadler, S.; Bräuchle, C.; Brandl, S.; Gompper, R. Chem. Mater. 1996, 8, 676-678.
43. Lequan, M.; Branger, C.; Simon, J.; Thami, T.; Chauchard, E.; Persoons, A. Adv. Mater. 1994, 6, 851-853.
44. Lambert, C.; Schmälzlin, E.; Meerholz, K.; Bräuchle, C. Chem. Eur. J. 1998, 4, 512-521.
45. Blanchard-Desce, M.; Baudin, J.-B.; Ruel, O.; Jullien, L.; Brasselet, S. ; Zyss, J. Opt. Mater. 1998, 9, 276-279.
46. Blanchard-Desce, M.; Baudin, J.-B.; Jullien, L.; Lorne, R.; Ruel, O.; Brasselet, S.; Zyss, J. Opt. Mater. 1999, 12, 333-338.
47. Bourgogne, C.; Le Fur, Y.; Juen, P.; Masson, P.; Nicoud, J.-F.; Masse, R. Chem. Mater. 2000, 12, 1025-1033.
48. Bartholomew, G. P.; Ledoux, I.; Mukamel, S.; Bazan, G. C.; Zyss, J. J. Am. Chem. Soc. 2002, 124, 13480-13485.
49. Sastre, A.; Torres, T.; Díaz-García, M. A.; Agulló-López, F.; Dhenaut, C.; Brasselet, S.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 1996, 118, 2746-2747.
50. del Rey, B.; Keller, U.; Torres, T.; Rojo, G.; Agulló-Ló pez, F.; Nonell, S.; Martí, C.; Brasselet, S.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 1998, 120, 12808-12817.
51. Zyss, J.; Dhenaut, C.; Chauvan, T.; Ledoux, I. Chem. Phys. Lett. 1993, 206, 409-414.
52. Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339-342.
53. McDonagh, A. M.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B.; Houbrechts, S.; Wada, T.; Sasabe, H.; Persoons, A. J. Am. Chem. Soc. 1999, 121, 1405-1406.
54. Vance, F. W.; Hupp, J. T. J. Am. Chem. Soc. 1999, 121, 4047-4053.
55. Renouard, T.; Le Bozec, H.; Brasselet, S.; Ledoux, I.; Zyss, J. Chem. Commun. 1999, 871-872.
56. Sénéchal, K.; Maury, O.; Le Bozec, H.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 2002, 124, 4561-4562.
57. Novak, J. P.; Brousseau, L. C. I.; Vance, F. W.; Johnson, R. C.; Lemon, B. I.; Hupp, J. T.; Feldheim, D. L. J. Am. Chem. Soc. 2000, 122, 12029-12030.
58. Brunel, J.; Ledoux, I.; Zyss, J.; Blanchard-Desce, M. Chem. Commun. 2001, 923-924.
59. Brunel, J.; Jutand, A.; Ledoux, I.; Zyss, J.; Blanchard-Desce, M. Synth. Met. 2001, 124, 195-199.
60. Mongin, O.; Porrès, L.; Moreaux, L.; Mertz, J.; Blanchard-Desce, M. Org. Lett. 2002, 4, 719-722.
61. Ndayikengurukiye, H.; Jacobs, S.; Tachelet, W.; Van Der Looy, J.; Pollaris, A.; Geise, H. J.; Claeys, M.; Kauffmann, J. M.; Janietz, S. Tetrahedron 1997, 53, 13811-13828.
62. Shim, H. K.; Kang, I. N.; Jang, M. S.; Zyung, T.; Jung, S. D. Macromolecules 1997, 30, 7749-7752.
63. Franke, A.; Frickel, F.-F.; Schlecker, R.; Thieme, P. C. Synthesis 1979, 712-714.
64. Ulman, A.; Willand, C. S.; Köhler, W.; Robello, D. R.; Williams, D. J.; Handley, L. J. Am. Chem. Soc. 1990, 112, 7083-7090.
65. Lyle, R. E.; DeWitt, E. J.; Nichols, N. M.; Cleland, W. J. Am. Chem. Soc. 1953, 75, 5959-5961.
66. Weber, E.; Hecker, M.; Koepp, E.; Orlia, W.; Czugler, M.; Csöregh, I. J. Chem. Soc., Perkin Trans. 2 1988, 1251-1257.
67. Terhune, R. W.; Maker, P. D.; Savage, C. M. Phys. Rev. Lett. 1965, 14, 681-684.
68. ex2-which shows the highest fluorescence quantum yield of the series (Table 2)-and checked that the TPA cross section vanishes totally at wavelengths longer than 940 nm.
69. Jutand, A.; Negri, S. Eur. J. Org. Chem. 1998, 1811-1821.
70. Elmorsy, S. S.; Pelter, A.; Smith, K. Tetrahedron Lett. 1991, 32, 4175-4176.
71. Plater, M. J.; McKay, M.; Jackson, T. J. Chem. Soc., Perkin Trans. 1 2000, 2695-2701.
72. Fiorini, C.; Charra, F.; Nunzi, J.-M.; Samuel, I. D. W.; Zyss, J. Opt. Lett. 1995, 20, 2469-2471.
73. Brasselet, S.; Zyss, J. Opt. Lett. 1997, 22, 1464-1466.
74. Brasselet, S.; Zyss, J. J. Opt. Soc. Am. B 1998, 15, 257-288.
75. It has been pointed out before that solvent effects do influence in a signilficant way the optical properties (including nonlinear properties) of octupolar derivatives, these effects deriving mainly from dipolar interactions: Luo, Y.; Norman, P.; Ågren, H. 1998, 120, 11188-11189.
76. In agreement with the value of resonance contribution (R = -0.37) to the Hammett constant: Swain, C. G.; Lupton, E. C., Jr. J. Am. Chem. Soc. 1968, 90, 4328-4337. Swain, C. G.; Unger, S. H.; Rosenquist, N. R.; Swain, M. S. J. Am. Chem. Soc. 1983, 105, 492-502.
77. In agreement with the value of resonance contribution (R = -0.37) to the Hammett constant: Swain, C. G.; Lupton, E. C., Jr. J. Am. Chem. Soc. 1968, 90, 4328-4337. Swain, C. G.; Unger, S. H.; Rosenquist, N. R.; Swain, M. S. J. Am. Chem. Soc. 1983, 105, 492-502.
78. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
79. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
80. Willets, A.; Rice, J. E.; Burland, D. M.; Shelton, D. P. J. Chem. Phys. 1992, 97, 7590-7599.
81. The β-σ correlation for octupolar molecules has been theoretically predicted by Cho and colleagues (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, 10658-10667), and to the best of our knowledge, this is the first experimental corroboration.
82. We note that this strategy has proven to be successful in other types of octupolar molecules.25
83. 2Me remains soluble enough to allow NMR cbaracterization and HRS experiments in solution.
84. MDICT has also been shown to give rise to large TPA responses in octupolar systems: (a) Joshi, M. P.; Swiatkiewicz, J.; Xu, F.; Prasad, P. N.; Reinhardt, B. A.; Kannan, R. Opt. Lett. 1998, 23, 1742-1744.
85. (b) Chung, S.-J.; Kim, K.-S.; Lin, T.-C.; He, G. S.; Swiatkiewicz, J.; Prasad, P. N. J. Phys. Chem. B 1999, 103, 10741-10745.
86. (c) He, G. S.; Swiatkiewicz, J.; Jiang, Y.; Prasad, P. N.; Reinhardt, B. A.; Tan, L.-S.; Kannan, R. J. Phys. Chem. A 2000, 104, 4805-4810.
87. (d) Cho, B. R.; Son, K. H.; Sang, H. L.; Song, Y.-S.; Lee, Y.-Y.; Jeon, S.-J.; Choi, J. H.; Lee, H.; Cho, M. J. Am. Chem. Soc. 2001, 123, 10039-10045.
88. (e) Mongin, O.; Brunel, J.; Porrès, L.; Blanchard-Desce, M. Tetrahedron Lett. 2003, 44, 2813-2816.