Synthesis, linear, and quadratic-nonlinear optical properties of octupolar D3 and D2d bipyridyl metal complexes

Chemistry - A European Journal

Volumn 10, Issue 18, 2004, Pages 4454-4466

  Maury, Olivier ^a   Viau, Lydie ^a   Sénéchal, Katell ^a   Corre, Brigitte ^a   Guégan, Jean Paul ^a   Renouard, Thierry ^a   Ledoux, Isabelle ^b   Zyss, Joseph ^b   Le Bozec, Hubert ^a  

^a CNRS   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Absorption; Coordination chemistry; Fluorescence; Ligand design; N ligands; Nonlinear optics

Indexed keywords

ABSORPTION; LIGHT SCATTERING; NONLINEAR OPTICS; ORGANOMETALLICS; POLARIZATION; SYNTHESIS (CHEMICAL);

HARMONIC LIGHT SCATTERING; OCTUPOLAR METAL COMPLEXES;

OPTICAL PROPERTIES;

2,2' BIPYRIDINE; 4,4' OLIGOPHENYLENEVINYLENE; BIPYRIDINE DERIVATIVE; IRON; LEWIS ACID; METAL COMPLEX; RUTHENIUM; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ACIDITY; ARTICLE; HYPERPOLARIZATION; LIGHT SCATTERING; LINEAR SYSTEM; NONLINEAR SYSTEM; OPTICS; PHASE TRANSITION; SYNTHESIS; THERMAL ANALYSIS;

2,2'-DIPYRIDYL; METALS, HEAVY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 4744356690     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400012     Document Type: Article

References (106)

1. a) T. Verbiest, S. Houbrechts, M. Kauranen, K. Clays, A. Persoons, J. Mater. Chem. 1997, 7, 2175-2189;
2. b) N. J. Long, Angew. Chem. 1995, 107, 37-56; Angew. Chem. Int. Ed. Engl. 1995, 34, 21-38;
3. b) N. J. Long, Angew. Chem. 1995, 107, 37-56; Angew. Chem. Int. Ed. Engl. 1995, 34, 21-38;
4. c) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167-187; Angew. Chem. Int. Ed. Engl. 1995, 34, 155-173;
5. c) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167-187; Angew. Chem. Int. Ed. Engl. 1995, 34, 155-173;
6. d) H. Le Bozec, T. Renouard, Eur. J. Inorg. Chem. 2000, 229-239.
7. J. Zyss, I. Ledoux, Chem. Rev. 1994, 94, 77-105.
8. For a review, see: O. Riant, G. Bluet, S. Brasselet, N. Druze, I. Ledoux, F. Lefloch, A. Skibniewski, J. Zyss, Mol. Cryst. Liq. Cryst. 1998, 322, 35-42.
9. a) I. Ledoux, J. Zyss, J. S. Siegel, J. Brienne, J. M. Lehn, Chem. Phys. Lett. 1990, 172, 440-444;
10. b) T. Verbiest, K. Clays, C. Semyr, J. Wolff, D. Reihoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320-9323;
11. c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928-4929;
12. d) J. J. Wolff, D. Längle, D. Hillenbrand, R. Wortmann, R. Matschiner, C. Glania, P. Krämer, Adv. Mater. 1997, 9, 138-143;
13. e) R. Wortmann, C. Glania, P. Krämer, R. Matschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chem. Eur. J. 1997, 3, 1765-1773;
14. f) C. Lambert, G. Nöll, E. Schmälzlin, K. Meerholz, C. Bräuchle, Chem. Eur. J. 1998, 4, 2129-2135;
15. g) B. R. Cho, S. K. Lee, K. A. Kim, K. N. Son, T. I. Kang, S. J. Jeon, Tetrahedron Lett. 1998, 39, 9205-9208;
16. h) A. M. McDonagh, M. G. Humphrey, M. Samoc, B. Luther-Davies, S. Houbrechts, T. Wada, H. Sasabe, A. Persoons, J. Am. Chem. Soc. 1999, 121, 1405-1406;
17. i) C. Andraud, T. Zabulon, A. Collet, J. Zyss, Chem. Phys. 1999, 245, 243-261;
18. j) A. Omenat, J. Barbera, J. L. Serrano, S. Houbrechts, A. Persoons, Adv. Mater. 1999, 11, 1292-1295;
19. k) B. R. Cho, S. J. Lee, S. H. Lee, K. H. Son, Y. H. Kim, I.-Y. Doo, G. J. Lee, T. I. Kang, Y. K. Lee, M. Cho, S.-J. Jeon, Chem. Mater. 2001, 13, 1438-1440;
20. l) J. Brunel, I. Ledoux, J. Zyss, M. Blanchard-Desce, Chem. Commun. 2001, 923-924;
21. m) B. R. Cho, S. B. Park, S. J. Lee, K. H. Son, S. H. Lee, M.-J. Lee, J. Yoo, Y. K. Lee, G. J. Lee, T. I. Kang, M. Cho, S.-J. Jeon, J. Am. Chem. Soc. 2001, 123, 6421-6422.
22. a) S. Brasselet, F. Cherioux, P. Audebert, J. Zyss, Chem. Mater. 1999, 11, 1915-1920;
23. b) V. R. Thalladi, R. Boese, S. Brasselet, I. Ledoux, J. Zyss, R. K. R. Jetti, G. R. Desiraju, Chem. Commun. 1999, 1639-1640;
24. c) F. Cherioux, H. Maillotte, P. Audebert, J. Zyss, Chem. Commun. 1999, 2083-2084;
25. d) J. J. Wolff, F. Siegler, R. Matschiner, R. Wortmann, Angew. Chem. 2000, 112, 1494-1498; Angew. Chem. Int. Ed. 2000, 39, 1436-1439.
26. d) J. J. Wolff, F. Siegler, R. Matschiner, R. Wortmann, Angew. Chem. 2000, 112, 1494-1498; Angew. Chem. Int. Ed. 2000, 39, 1436-1439.
27. G. Alcaraz, L. Euzenat, O. Mongin, C. Katan, I. Ledoux, J. Zyss, M. Blanchard-Desce, M. Vaultier, Chem. Commun. 2003, 2766-2767.
28. For carbocations, see: a) J. Zyss, T. Chauvan, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281-296;
29. b) A. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320-9323;
30. c) Y.-K. Lee, S.-J. Jeon, M. Cho, J. Am. Chem. Soc. 1998, 120, 10921-10927. For carbanions, see: T. Verbiest, K. Clays, A. Persoons, F. Meyers, J.-L. Brédas, Opt. Lett. 1993, 18, 525-527; for carbon radicals, see: I. Ratera, S. Marcen, S. Montant, D. Molina-Ruiz, C. Rovira, J. Veciana, J.-F. Letard, E. Freysz, Chem. Phys. Lett. 2002, 363, 245-251.
31. c) Y.-K. Lee, S.-J. Jeon, M. Cho, J. Am. Chem. Soc. 1998, 120, 10921-10927. For carbanions, see: T. Verbiest, K. Clays, A. Persoons, F. Meyers, J.-L. Brédas, Opt. Lett. 1993, 18, 525-527; for carbon radicals, see: I. Ratera, S. Marcen, S. Montant, D. Molina-Ruiz, C. Rovira, J. Veciana, J.-F. Letard, E. Freysz, Chem. Phys. Lett. 2002, 363, 245-251.
32. c) Y.-K. Lee, S.-J. Jeon, M. Cho, J. Am. Chem. Soc. 1998, 120, 10921-10927. For carbanions, see: T. Verbiest, K. Clays, A. Persoons, F. Meyers, J.-L. Brédas, Opt. Lett. 1993, 18, 525-527; for carbon radicals, see: I. Ratera, S. Marcen, S. Montant, D. Molina-Ruiz, C. Rovira, J. Veciana, J.-F. Letard, E. Freysz, Chem. Phys. Lett. 2002, 363, 245-251.
33. a) S. Stadler, C. Braüchle, S. Brandl, R. Gompper, Chem. Mater. 1996, 8, 414-417;
34. b) C. Lambert, W. Gaschler, E. Schmälzlin, K. Meerholz, C. Bräuchle, J. Chem. Soc. Perkin Trans. 2 1999, 577-587.
35. P. D. Maker, Phys. Rev. A 1970, 1, 923.
36. a) C. Bourgogne, Y. Le Fur, P. Juen, P. Masson, J.-F. Nicoud, R. Masse, Chem. Mater. 2000, 12, 1025-1033;
37. b) C. Lambert, E. Schmälzlin, K. Meerholz, C. Bräuchle, Chem. Eur. J. 1998, 4, 512-521.
38. M. Lequan, C. Branger, J. Simon, T. Thami, E. Chauchard, A. Persoons, Adv. Mater. 1994, 6, 851-853.
39. a) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Dhenaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746-2747;
40. b) B. del Rey, U. Keller, T. Torres, G. Rojo, F. Agullo-Lopez, S. Nonell, C. Marti, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1998, 120, 12808-12817.
41. a) M. Blanchard-Desce, J.-B. Baudin, O. Ruel, L. Jullien, S. Brasselet, J. Zyss, Opt. Mater. 1998, 9, 276-279;
42. b) M. Blanchard-Desce, J.-B. Baudin, L. Jullien, R. Lorne, O. Ruel, S. Brasselet, J. Zyss, Opt. Mater. 1999, 12, 333-338.
43. P. Mukhopadhyay, P. K. Bharadwaj, G. Savitha, A. Krishnan, P. K. Das, Chem. Commun. 2000, 1815-1816.
44. J. Zyss, I. Ledoux, S. Volkov, V. Cherniak, S. Mukamel, G. P. Bartholomew, G. C. Bazan, J. Am. Chem. Soc. 2000, 122, 11956-11962.
45. J. Zyss, C. Dhenaut, T. Chau Van, I. Ledoux, Chem. Phys. Lett. 1993, 206, 409.
46. a) W. Lin, Z. Wang, L. Ma, J. Am. Chem. Soc. 1999, 121, 11249-11250;
47. b) W. Lin, L. Ma, O. R. Evans, Chem. Commun. 2000, 2263-2264;
48. c) O. R. Evans, W. Lin, Chem. Mater. 2001, 13, 2705-2712;
49. d) O. R. Evans, W. Lin, Acc. Chem. Res. 2002, 35, 511-522.
50. a) C. Dhenaut, I. Ledoux, I. D. W. Samuel, J. Zyss, M. Bourgault, H. Le Bozec, Nature 1995, 374, 339-342;
51. b) T. Renouard, H. Le Bozec, I. Ledoux, J. Zyss, Chem. Commun. 1999, 871-872;
52. c) H. Le Bozec, T. Renouard, M. Bourgault, C. Dhenaut, S. Brasselet, I. Ledoux, J. Zyss, Synth. Met. 2001, 124, 185-189;
53. d) T. Le Bouder, O. Maury, H. Le Bozec, I. Ledoux, J. Zyss, Chem. Commun. 2001, 2430-2431;
54. e) H. Le Bozec, T. Le Bouder, O. Maury, A. Bondon, J. Zyss, I. Ledoux, Adv. Mater. 2001, 13, 1677-1681;
55. f) K. Sénéchal, O. Maury, H. Le Bozec, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 2002, 124, 4561-4562;
56. g) L. Viau, M. Even, O. Maury, D. Haddleton, H. Le Bozec, Macromol. Rapid Commun. 2003, 24, 630-635;
57. h) T. Le Bouder, O. Maury, H. Le Bozec, A. Bondon, K. Costuas, E. Amouyal, J. Zyss, I. Ledoux, J. Am. Chem. Soc. 2003, 125, 12884-12899.
58. O. Maury, J.-P. Guégan, T. Renouard, A. Hilton, P. Dupau, N. Sandon, L. Toupet, H. Le Bozec, New J. Chem. 2001, 25, 1553-1566.
59. L. Viau, K. Sénéchal, O. Maury, J.-P. Guégan, P. Guégan, P. Dupau, L. Toupet, H. Le Bozec, Synthesis 2003, 577-582.
60. This ligand was preliminary reported in: L. Viau, O. Maury, H. Le Bozec, Tetrahedron Lett. 2004, 45, 125-128.
61. a) J. Lacour, C. Glinglinger, C. Grivet, G. Bernardelli, Angew. Chem. 1997, 109, 660-662; Angew. Chem. Int. Ed. Engl. 1997, 36, 608-610;
62. a) J. Lacour, C. Glinglinger, C. Grivet, G. Bernardelli, Angew. Chem. 1997, 109, 660-662; Angew. Chem. Int. Ed. Engl. 1997, 36, 608-610;
63. b) O. Maury, J. Lacour, H. Le Bozec, Eur. J. Inorg. Chem. 2001, 201-204, and references therein.
64. a) A. K.-J. Jen, X. Wu, H. Ma, Chem. Mater. 1998, 10, 471-473;
65. b) C.-F. Shu, Y.-C. Shu, Z.-H. Gong, S.-M. Peng, G. H. Lee, A. K.-J. Jen, Chem. Mater 1998, 10, 3284-3286;
66. c) Y.-C. Shu, Z.-H. Gong, C.-F. Shu, E. M. Breitung, R. J. McMahon, G. H. Lee, A. K.-J. Jen, Chem. Mater. 1999, 11, 1628-1632;
67. d) X. Wu, J. Wu, Y. Liu, A. K.-J. Jen, Chem. Commun. 1999, 2391-2392;
68. e) J.-M. Raimundo, P. Blanchard, I. Ledoux-Rak, R. Hierle, L. Michaud, J. Roncali, Chem. Commun. 2000, 1597-1598.
69. +, m/z: 1311.7972 (found 1311.8043). Similar behavior was observed for 3b.
70. a) C. O. Dietrich-Brucheker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810;
71. b) J.-P. Sauvage, Acc. Chem. Res. 1990, 23, 319-327.
72. For a complete NMR study in the case of copper complexes, see: A. J. Pallenberg, K. S. Koenig, D. M. Barnhart, Inorg. Chem. 1995, 34, 2833-2840.
73. A. J. Pallenberg, T. M. Marsher, D. M. Barnhart, Polyhedron 1997, 16, 2711-2719.
74. For Lewis acidity scale of metal chlorides, see S. Kobahashi, T. Busujima, S. Nagamaya, Chem. Eur. J. 2000, 6, 3491-3494.
75. M. H. Ford-Smith, N. Sutin, J. Am. Chem. Soc. 1961, 83, 1830.
76. F. W. Vance, J. T. Hupp, J. Am. Chem. Soc. 1999, 121, 4047-4053.
77. T. Renouard, PhD Thesis of Rennes I University, 1998.
78. M. J. Cook, A. P. Lewis, G. S. G. McAuliffe, V. Skarda, A. J. Thomson, J. L. Glasper, D. J. Robbins, J. Chem. Soc. Perkin Trans. 2 1984, 1293-1301.
79. For a recent review, see N. Armaroli, Chem. Soc. Rev. 2001, 30, 113-124, and references therein; for recent examples, see E. C. Constable, C. E. Housecroft, M. Neuburger, I. Poleschak, M. Zehnder, Polyhedron 2003, 22, 93-108.
80. For a recent review, see N. Armaroli, Chem. Soc. Rev. 2001, 30, 113-124, and references therein; for recent examples, see E. C. Constable, C. E. Housecroft, M. Neuburger, I. Poleschak, M. Zehnder, Polyhedron 2003, 22, 93-108.
81. a) R. W. Terhune, P. D. Maker, C. M. Savage, Phys. Rev. 1965, 14, 681;
82. b) K. Clays, A. Persoons, Phys. Rev. Lett. 1991, 66, 2980.
83. I. D. Morrison, R. G. Denning, W. M. Laidlaw, M. A. Stammers, Rev. Sci. Instrum. 1996, 67, 1445.
84. a) M. Cho, H.-S. Kim, S.-J. Jeon, J. Chem. Phys. 1998, 108, 7114-7120;
85. b) Y.-K. Lee, S.-J. Jeon, M. Cho, J. Am. Chem. Soc. 1998, 120, 10921-10927;
86. c) H. Lee, S.-Y. An, M. Cho, J. Phys. Chem. B 1999, 103, 4992-4996.
87. -30 esu). Since this NLO activity is one order of magnitude lower than those of the cations, its contribution to the global NLO activity can be considered to be negligible.
88. a) V. P. Rao, A.-K. Jen, K. Y. Wong, K. J. Drost, Tetrahedron Lett. 1993, 34, 1747-1750;
89. b) A.-K. Jen, V. P. Rao, K. Y. Wong, K. J. Drost, J. Chem. Soc. Chem. Commun. 1993, 90-92;
90. c) A.-K. Jen, Y. Cai, P. V. Bedworth, S. R. Marder, Adv. Mater. 1997, 9, 132-135;
91. d) V. P. Rao, A.-K. Jen, K. Y. Wong, K. J. Drost, J. Chem. Soc. Chem. Commun. 1993, 1118-1110;
92. e) X. Wu, J. Wu, Y. Liu, A.-K. Jen, J. Am. Chem. Soc. 1999, 121, 472-473;
93. f) V. P. Rao, A. K.-Y. Jen, Y. Cai, Chem. Commun. 1996, 1237-1238.
94. T. L. Gilchrist, Heterocycle Chemistry, Wiley, New York, 1985.
95. a) I. D. L. Albert, T. J. Marks, M. A. Ratner, J. Am. Chem. Soc. 1997, 119, 6575-6582;
96. b) E. M. Breitung, C.-F. Shu, R. J. McMahon, J. Am. Chem. Soc. 2000, 122, 1154-1160.
97. a) A. Hilton, T. Renouard, O. Maury, H. Le Bozec, I. Ledoux, J. Zyss, Chem. Commun. 1999, 2521-2522;
98. b) I. R. Whittall, M. G. Humphrey, A. Persoons, S. Houbrechts, Organometallics 1996, 15, 1935-1941;
99. c) I. R. Whittall, M. G. Humphrey, S. Houbrechts, A. Persoons, D. C. Hockless, Organometallics 1996, 15, 5738-5745;
100. d) for C=C containing chromophores, see: S.-S. P. Chou, D.-J. Sun, J. Y. Huang, P.-K. Yang, H. C. Lin, Tetrahedron Lett. 1996, 37, 7279-7282;
101. e) for related imino molecules, see: S.-S. P. Chou, D.-J. Sun, H. C. Lin, P.-K. Yang, Chem. Commun. 1996, 1045-1046.
102. T. Tsunekawa, K. Yamaguchi, J. Phys. Chem. 1992, 96, 10268-10275.
103. -1): f = 1.97 (6b′, M = Ag) and 1.90 (1b′, M = Zn). In the case of 5b′ (M = Cu), f could not be determined on account of an overlap between both ILCT and MLCT transitions.
104. I. P. Evans, A. Spencer, G. Wilkinson, J. Chem. Soc. Dalton Trans. 1973, 204-209.
105. J. Zyss, J.-F. Nicoud, M. Coquillay, J. Chem. Phys. 1984, 81, 4160.
106. S. G. Yan, J. T. Hupp, J. Phys. Chem. 1996, 100, 6867-6870.