Syntheses and Spectroscopic and Quadratic Nonlinear Optical Properties of Extended Dipolar Complexes with Ruthenium(II) Ammine Electron Donor and N-Methylpyridinium Acceptor Groups

Journal of the American Chemical Society

Volumn 126, Issue 12, 2004, Pages 3880-3891

  Coe, Benjamin J ^a   Jones, Lathe A ^a   Harris, James A ^a   Brunschwig, Bruce S ^b,f   Asselberghs, Inge ^c   Clays, Koen ^c   Persoons, André ^c,d   Garín, Javier ^e   Orduna, Jesús ^e  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b BROOKHAVEN NATIONAL LABORATORY   (United States)

^c UNIVERSITY OF LEUVEN   (Belgium)

^d UNIVERSITY OF ARIZONA   (United States)

^e CSIC   (Spain)

^f CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; CHROMOPHORES; COMPLEXATION; ELECTRONS; NONLINEAR OPTICS; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL);

POLYENE; STARK SPECTROSCOPY;

RUTHENIUM COMPOUNDS;

AMPHOLYTE; ETHYLENE; METAL; N METHYLPYRIDINIUM; POLYENE; PYRIDINIUM DERIVATIVE; RUTHENIUM AMMINE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHARGE TRANSFER; DENSITY FUNCTIONAL THEORY; ELECTRICITY; ELECTRON TRANSPORT; FINITE FIELD CALCULATION; HYPERPOLARIZATION; LIGHT SCATTERING; MATHEMATICAL ANALYSIS; NONLINEAR SYSTEM; OPTICS; QUADRATIC NONLINEAR OPTICAL PROPERTY; RAYLEIGH SCATTERING; SPECTROSCOPY; STARK SPECTROSCOPY; SYNTHESIS;

EID: 1642339457     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0315412     Document Type: Article

References (89)

1. (a) Nonlinear Optical Properties of Organic Molecules and Crystals; Chemla, D. S., Zyss, J., Eds.; Academic Press: Orlando, FL, 1987; Vols. 1 and 2.
2. (b) Molecular Nonlinear Optics: Materials, Physics and Devices; Zyss, J., Ed.; Academic Press: Boston, 1994.
3. (c) Organic Nonlinear Optical Materials (Advances in Nonlinear Optics, Vol. 1.); Bosshard, Ch., Sutter, K., Prêtre, Ph., Hulliger, J., Flörsheimer, M., Kaatz, P., Günter, P., Eds.; Gordon & Breach: Amsterdam, The Netherlands, 1995.
4. (d) Nonlinear Optics of Organic Molecules and Polymers; Nalwa, H. S., Miyata, S., Eds.; CRC Press: Boca Raton, FL, 1997.
5. (a) Nalwa, H. S. Appl. Organomet. Chem. 1991, 5, 349-377.
6. (b) Marder, S. R. In Inorganic Materials, 2nd ed.; Bruce, D. W.; O'Hare, D., Eds.; Wiley: Chichester, United Kingdom; 1992; pp. 121-169.
7. (c) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195-242.
8. (d) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21-38.
9. (e) Whittall, I. R.; McDonagh, A. M.; Humphrey M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291-362.
10. (f) Whittall, I. R.; McDonagh, A. M.; Humphrey M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349-405.
11. (g) Heck, J.; Dabek, S.; Meyer-Friedrichsen, T.; Wong, H. Coord. Chem. Rev. 1999, 190-192, 1217-1254.
12. (h) Gray, G. M.; Lawson, C. M. In Optoelectronic Properties of Inorganic Compounds; Roundhill, D. M., Fackler, J. P., Jr., Eds.; Plenum: New York, U.S.A., 1999; pp. 1-27.
13. (i) Shi, S. In Optoelectronic Properties of Inorganic Compounds; Roundhill, D. M., Fackler, J. P., Jr., Eds.; Plenum: New York, U.S.A., 1999; pp 55-105.
14. (j) Le Bozec, H.; Renouard, T. Eur. J. Inorg. Chem. 2000, 229-239.
15. (k) Barlow, S.; Marder, S. R. Chem. Commun. 2000, 1555-1562.
16. (l) Lacroix, P. G. Eur. J. Inorg. Chem. 2001, 339-348.
17. (m) Di Bella, S. Chem. Soc. Rev. 2001, 30, 355-366.
18. (n) Coe, B. J. In Comprehensive Coordination Chemistry II; McCleverty J. A., Meyer, T. J., Eds.; Pergamon Press: Oxford, United Kingdom, 2004; Vol. 9, pp 621-687.
19. (a) Oudar, J. L.; Chemla, D. S. J. Chem. Phys. 1977, 66, 2664-2668.
20. (b) Oudar, J. L. J. Chem. Phys. 1977, 67, 446-457.
21. Note that the prefactor of 3 in eq 1 is not unique and that other two-state equations replace this factor by 6 of 3/2. See: Willetts, A.; Rice, J. E.; Burland, D. M.; Shelton, D. P. J. Chem. Phys. 1992, 97, 7590-7599.
22. See for examples: (a) Marder, S. R.; Cheng, L.-T.; Tiemann, B. G.; Friedli, A. C.; Blanchard-Desce, M.; Perry, J. W.; Skindhøj, J. Science 1994, 263, 511-514.
23. (b) Marder, S. R.; Gorman, C. B.; Meyers, F.; Perry, J. W.; Bourhill, G. ; Brédas, J.-L.; Pierce, B. M. Science 1994, 265, 632-635.
24. (c) Bublitz, G. U.; Ortiz, R.; Runser, C.; Fort, A.; Barzoukas, M.; Marder, S. R.; Boxer, S. G. J. Am. Chem. Soc. 1997, 119, 2311-2312.
25. (d) Lawrentz, U.; Grahn, W.; Lukaszuk, K.; Klein, C.; Wortmann, R.; Feldner, A.; Scherer, D. Chem. Eur. J. 2002, 8, 1573-1590.
26. 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.
27. See for examples: (a) Blanchard-Desce, M.; Runser, C.; Fort, A.; Barzoukas, M.; Lehn, J.-M.; Bloy, V.; Alain, V. Chem. Phys. 1995, 199, 253-261.
28. (b) Alain, V.; Fort, A.; Barzoukas, M.; Chen, C.-T.; Blanchard-Desce, M. ; Marder, S. R.; Perry, J. W. Inorg. Chim. Acta 1996, 242, 43-49.
29. (c) Wu, Z.; Ortiz, R.; Fort, A.; Barzoukas, M.; Marder, S. R. J. Organomet. Chem. 1997, 528, 217-219.
30. (d) Lee, I. S.; Seo, H.; Chung, Y. K. Organometallics 1999, 18, 1091-1096.
31. (e) Jayaprakash, K. N.; Ray, P. C.; Matsuoka, I.; Bhadbhade, M. M.; Puranik, V. G.; Das, P. K.; Nishihara, H.; Sarkar, A. Organometallics 1999,18, 3851-3858.
32. (f) Farrell, T.; Meyer-Friedrichsen, T.; Malessa, M.; Haase, D.; Saak, W.; Asselberghs, I.; Wostyn, K.; Clays, K.; Persoons, A.; Heck, J.; Manning, A. R. J. Chem. Soc., Dalton Trans. 2001, 29-36.
33. (g) Farrell, T.; Manning, A. R.; Murphy, T. C.; Meyer-Friedrichsen, T.; Heck, J.; Asselberghs, I.; Persoons, A. Eur. J. Inorg. Chem. 2001, 2365-2375.
34. (a) Terhune, R. W.; Maker, P. D.; Savage, C. M. Phys. Rev. Lett. 1965, 14, 681-684.
35. (b) Clays, K.; Persoons, A. Rev. Sci. Instrum. 1992, 63, 3285-3289.
36. (c) Hendrickx, E.; Clays, K.; Persoons, A. Acc. Chem. Res. 1998, 31, 675-683.
37. (a) Liptay, W. In Excited States, Vol. 1; Lim, E. C., Ed.; Academic Press: New York, 1974; pp. 129-229.
38. (b) Bublitz, G. U.; Boxer, S. G. Annu. Rev. Phys. Chem. 1997, 48, 213-242.
39. (a) Coe, B. J.; Chamberlain, M. C.; Essex-Lopresti, J. P.; Gaines, S.; Jeffery, J. C.; Houbrechts, S.; Persoons, A. Inorg. Chem. 1997, 36, 3284-3292.
40. (b) Coe, B. J.; Essex-Lopresti, J. P.; Harris, J. A.; Houbrechts S.; Persoons, A. Chem. Commun. 1997, 1645-1646.
41. (c) Coe, B. J.; Harris, J. A.; Harrington, L. J.; Jeffery, J. C.; Rees, L. H.; Houbrechts S.; Persoons, A. Inorg. Chem. 1998, 37, 3391-3399.
42. (d) Coe, B. J.; Harris, J. A.; Asselberghs, I.; Persoons, A.; Jeffery, J. C.; Rees, L. H.; Gelbrich T.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1999, 3617-3625.
43. (e) Coe, B. J.; Harris, J. A.; Clays, K.; Persoons, A.; Wostyn, K.; Brunschwig, B. S. Chem. Commun. 2001, 1548-1549.
44. (f) Coe, B. J.; Harris, J. A.; Brunschwig, B. S. J. Phys. Chem. A 2002, 106, 897-905.
45. (g) Coe, B. J.; Jones, L. A.; Harris, J. A.; Sanderson, E. E.; Brunschwig, B. S.; Asselberghs, I.; Clays, K.; Persoons, A. Dalton Trans. 2003, 2335-2341.
46. (a) Coe, B. J.; Houbrechts, S.; Asselberghs I.; Persoons, A. Angew. Chem. Int. Ed. 1999, 38, 366-369.
47. (b) Coe, B. J. Chem. Eur. J. 1999, 5, 2464-2471.
48. Coe, B. J.; Jones, L. A.; Harris, J. A.; Brunschwig, B. S.; Asselberghs, I.; Clays, K.; Persoons, A. J. Am. Chem. Soc. 2003, 125, 862-863.
49. Spangler, C. W.; McCoy, R. K. Synth. Commun. 1988, 18, 51-59.
50. Ichimura, K.; Watanabe, S. J. Polym. Sci., Polym. Chem. 1982, 20, 1419-1432.
51. Curtis, J. C.; Sullivan, B. P.; Meyer, T. J. Inorg. Chem. 1983, 22, 224-236.
52. Hendrickx, E.; Clays, K.; Persoons, A.; Dehu, C.; Brédas, J.-L. J. Am. Chem. Soc. 1995, 117, 3547-3555.
53. Houbrechts, S.; Clays, K.; Persoons, A.; Pikramenou, Z.; Lehn, J.-M. Chem. Phys. Lett. 1996, 258, 485-489.
54. Stähelin, M.; Burland, D. M.; Rice, J. E. Chem. Phys. Lett. 1992, 191, 245-250.
55. Shin, Y. K.; Brunschwig, B. S.; Creutz, C.; Sutin, N. J. Phys. Chem. 1996, 100, 8157-8169.
56. 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.; Baboul, A. G.; 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.; González, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
57. The B3P86 Functional consists of Becke's three parameter hybrid functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) with the nonlocal correlation provided by the Perdew 86 expression: Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
58. The B3P86 Functional consists of Becke's three parameter hybrid functional (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652) with the nonlocal correlation provided by the Perdew 86 expression: Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
59. D95 on first row: Dunning, T. H.; Hay P. J. In Modern Theoretical Chemistry: Schaefer, H. F., III, Ed.; Plenum: New York, 1976, vol. 3, 1.
60. Los Alamos ECP plus DZ on Na-Bi: (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
61. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
62. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
63. Selected examples: (a) Huang, Y.-Z.; Shi, L.-L.; Yang, J.-H. Tetrahedron Lett. 1985, 26, 6447-6448.
64. (b) Hagedorn, I.; Hohler, W. Angew. Chem., Int. Ed. Engl. 1975, 14, 486.
65. (c) Tolbert, L M.; Zhao, X.-D. J. Am. Chem. Soc. 1997, 119, 3253-3258.
66. (d) Leitis, L.; Jansone, D.; Skolmeistere, R.; Popelis, J.; Gavars, M.; Shimanskaya, M. V.; Maslii, L. K.; Nikol'skaya, G. S. Khim. Geterotsikl. Soedin. 1991, 77-80.
67. (a) Duhamel, L.; Ple, G.; Ramondenc, Y. Tetrahedron Lett. 1989, 30, 7377-7380.
68. (b) Ramondenc, Y.; Ple, G. Tetrahedron 1993, 49, 10 855-10 876.
69. Kunitake, M.; Nasu, K.; Manabe, O.; Nakashima, N. Bull. Chem. Soc. Jpn 1994, 67, 375-378.
70. - salts of the pyridyl pro-ligands are as follows (nm, in acetonitrile): 264 (n = 0), 316 (n = 1), 356 (n = 2), 394 (n = 3).
71. Woitellier, S.; Launay, J. P.; Spangler, C. W. Inorg. Chem. 1989, 28, 758-762.
72. (a) González, M.; Martín, N.; Segura, J. L.; Garín, J.; Orduna, J. Tetrahedron Lett. 1998, 39, 3269-3272.
73. (b) Garín, J.; Orduna, J.; Rupérez, J. I.; Alcalá, R.; Villacampa, B.; Sánchez, C.; Martín, N.; Segura, J. L.; González, M. Tetrahedron Lett. 1998, 39, 3577-3580,
74. (c) González, M.; Martín, N.; Segura, J. L.; Seoane, C.; Garín, J.; Orduna, J.; Alcalá, R.; Sánchez, C.; Villacampa, B. Tetrahedron Lett. 1999, 40, 8599-8602,
75. (d) González, M.; Segura, J. L.; Seoane, C.; Martín, N.; Garín, J.; Orduna, J.; Alcalá, R.; Villacampa, B.; Hernández, V.; López Navarrette, J. T. J. Org. Chem. 2001, 66, 8872-8882.
76. (e) Andreu, R.; Garín, J.; Orduna, J. Tetrahedron 2001, 57, 7883-7892.
77. Bryce, M. R.; Green, A.; Moore, A. J.; Perepichka, D. F.: Batsanov, A. S.; Howard, J. A. K.; Ledoux-Rak, I.; González, M.; Martín, N.; Segura, J. L.; Garín, J.; Orduna, J.; Alcalá, R.; Villacampa, B. Eur. J. Org. Chem. 2001, 1927-1935.
78. (a) Meier, H.; Petermann, R.; Gerold, J. Chem. Commun. 1999, 977-978.
79. (b) Mata, J. A.; Uriel, S.; Llusar, R.; Peris, E. Organometallics 2000, 19, 3797-3802.
80. (c) Meier, H.; Gerold, J.; Kolshorn, H.; Baumann, W.; Bletz, M. Angew. Chem., Int. Ed. 2002, 41, 292-295.
81. (d) Meier, H.; Gerold, J.; Jacob, D. Tetrahedron Lett. 2003, 44, 1915-1918.
82. (a) Alain, V.; Rédoglia, S.; Blanchard-Desce, M.; Lebus, S.; Lukaszuk, K.; Wortmann, R.; Gubler, U.; Bosshard, C.; Günter, P. Chem. Phys. 1999, 245, 51-71.
83. (b) Luo, J.-D.; Hua, J.-L.; Qin, J.-G.; Cheng, J.-Q.; Shen, Y.-C.; Lu, Z.-H.; Wang, P.; Ye, C. Chem. Commun. 2001, 171-172.
84. Barlow, S.; Bunting, H. E.; Ringham, C.; Green, J. C.; Bublitz, G. U.; Boxer, S. G.; Perry, J. W.; Marder, S. R. J. Am. Chem. Soc. 1999, 121, 3715-3723.
85. Kanis, D. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 10 338-10 357.
86. Calabrese, J. C.; Cheng, L.-T.; Green, J. C.; Marder, S. R.; Tam, W. J. Am. Chem. Soc. 1991, 113, 7227-7232.
87. 30 esu (n): -29.2 (0), -44.6 (1), -29.4 (2), -22.1 (3). Neither calculated MLCT maxima nor dipole parameters were quoted in this report.
88. Tozer, D. J.; Amos, R. D.; Handy, N. C.; Roos, B. O.; Serrano-Andrés, L. Mol. Phys. 1999, 97, 859-868.
89. Wiberg, K. B.; Stratmann, R. E.; Frish, M. J. Chem. Phys. Lett. 1998, 297, 60-64.