A five-center redox system: Molecular coupling of two noninnocent imino-o-benzoquinonato-ruthenium functions through a π acceptor bridge

Journal of the American Chemical Society

Volumn 131, Issue 25, 2009, Pages 8895-8902

  Das, Atanu Kumar ^a   Sarkar, Biprajit ^a   Fiedler, Jan ^b   Zális, Stanislav ^b   Hartenbach, Ingo ^a   Strobel, Sabine ^a   Lahiri, Goutam Kumar ^c   Kaim, Wolfgang ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^c INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION BAND; ACTIVE COMPONENTS; ANTI ISOMERS; ANTIFERROMAGNETIC COUPLING; BRIDGING LIGANDS; DFT CALCULATION; ELECTRON TRANSFER; EPR SPECTRA; G FACTORS; HYPERFINE; METAL CENTERS; METAL REDUCTION; MOLECULAR COUPLING; MONOANION; NEAR INFRA RED; NEW SYSTEM; ONE-ELECTRON TRANSFER; ORBITAL INTERACTION; OXIDATION STATE; PYRAZINE; PYRIDYL; RADICAL COMPLEXES; REDOX SYSTEMS; REDOX-ACTIVE; SPECTROSCOPIC CHARACTERIZATION; STRUCTURE-BASED; TETRAKIS; UV-VIS-NIR;

ABSORPTION; ANISOTROPY; ANTIFERROMAGNETISM; CYCLIC VOLTAMMETRY; DYES; ELECTRON RESONANCE; ELECTRON TRANSITIONS; FREE RADICAL REACTIONS; INFRARED DEVICES; OXIDATION; PARAMAGNETIC RESONANCE; QUANTUM THEORY; REDUCTION; RUTHENIUM; RUTHENIUM COMPOUNDS; SPECTROELECTROCHEMISTRY;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

2,3,5,6 TETRAKIS(2 PYRIDYL)PYRAZINE; 4,6 2 TERT BUTYL N PHENYL 2 IMINOBENZOQUINONE; BENZOQUINONE DERIVATIVE; CHLORINE; IMINO 1,2 BENZOQUINONE RUTHENIUM; IMINOSEMIQUINONE; LIGAND; METAL; PYRAZINE DERIVATIVE; QUINONE DERIVATIVE; RUTHENIUM COMPLEX; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ANISOTROPY; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ENERGY YIELD; ISOMER; ISOMERIZATION; MOLECULAR INTERACTION; NEAR INFRARED SPECTROSCOPY; OXIDATION; OXIDATION REDUCTION REACTION; SPECTROELECTROCHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 67649573996     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja901746x     Document Type: Article

References (108)

1. Creutz, C. Prog. Inorg. Chem. 1983, 30, 1.
2. (b) Richardson, D. E.;Taube, H. Coord. Chem. Rev. 1984, 60, 107.
3. (c) Crutchley, R. J. Adv. Inorg. Chem. 1994, 41, 273.
4. (d) Demadis, K. D.; Hartshorn, D. C; Meyer, T. J. Chem. Rev. 2001, 101, 2655.
5. Salsman, J. C.; Kubiak, C. P.; Ito, T. J. Am. Chem. Soc. 2005, 127, 2382.
6. (b) Londergan, C. H.; Salsman, J. C.; Lear, B. J.; Kubiak, C. P. Chem. Phys. 2006, 324, 57.
7. Braun-Sand, S. B.; Wiest, O. J. Phys. Chem. B 2003, 107, 9624.
8. (b) Braun-Sand, S. B.; Wiest, O. J. Phys. Chem. A 2003, 107, 285.
9. (c) Wang, Y.; Lieberman, M. IEEE Trans. Nanotech. 2004, 3, 368.
10. (d) Zhao, P.; Woolard, D.; Seminario, J. M.; Trew, R. Int. J. High Speed Electronics 2006, 16, 705.
11. Heyduk, A. F.; Nocera, D. G. Science 2001, 293, 1639.
12. (b) Esswein, A. J.; Veige, A. S.; Piccoli, P. M. B.; Schultz, A. J.; Nocera, D. G. Organometallics 2008, 27, 1073.
13. Hush, N. S. Prog. Inorg. Chem. 1967, 8, 391.
14. (b) Hush, N. S. Coord. Chem. Rev. 1985, 64, 135.
15. (c) Creutz, C.; Newton, M. D.; Sutin, N. J. Photochem. Photobiol. A 1994, 82, 47.
16. Petrov, V.; Hupp, J. T.; Mottley, C.; Mann, L. C. J. Am. Chem. Soc. 1994, 116, 2171.
17. (b) Oh, D. H.; Sano, M.; Boxer, S. G. J. Am. Chem. Soc. 1991, 113, 6880.
18. (c) Rocha, R. C.; Brown, M. G.; Londergan, C. H.; Salsman, J. C.; Kubiak, C. P.; Shreve, A. P. J. Phys. Chem. A 2005, 109, 9006.
19. Prassides, K, Ed. Mixed Valency Systems - Applications in Chemistry, Physics and Biology; Kluwer Academic Publishers: Dordrecht, 1991.
20. (b) Fabre, M.; Bonvoisin, J. J. Am. Chem. Soc. 2007, 129, 1434.
21. Hupp, J. T. In Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier Science: Amsterdam, 2003; p 709.
22. (b) Crutchley, R. J. In Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier Science: Amsterdam, 2003; p 235.
23. Kaim, W.; Klein, A.; Glöckle, M. Acc. Chem. Res. 2000, 33, 755.
24. (b) Kaim, W.; Sarkar, B. Coord. Chem. Rev. 2007, 251, 584.
25. (c) Kaim,W.; Lahiri, G. K. Angew. Chem. 2007, 119, 1808;
26. Angew. Chem., Int. Ed. 2007, 46, 1778.
27. Baumann, F.; Kaim, W.; Denninger, G.; Kümmerer, H. J.; Fiedler, J. Organometallics 2005, 24, 1966.
28. (b) Kaim, W. In New Trends in Molecular Electrochemistry; Pombeiro, A. J. L., Ed.; Fontis Media: Lausanne, 2004; p 127.
29. Singh, P.; Sieger, M.; Fiedler, J.; Su, C.-Y.; Kaim, W. Dalton Trans. 2008, 868.
30. Haga, M.; Dodsworth, E. S.; Lever, A. B. P. Inorg. Chem. 1986, 25, 447.
31. (b) Masui, H.; Lever, A. B. P.; Auburn, P. Inorg. Chem. 1991, 30, 2402.
32. (c) Ebadi, M.; Lever, A. B. P. Inorg. Chem. 1999, 38, 467.
33. (d) Lever, A.B. P.; Auburn, P. R.; Dodsworth, E. S.; Haga, M.; Liu, W.; Melnik, M.; Nevin, W. A. J. Am. Chem. Soc. 1988, 110, 8076.
34. (e) Auburn, P. R.; Dodsworth, E. S.; Haga, M.; Liu, W.; Nevin, W. A.; Lever, A. B. P. Inorg. Chem. 1991, 30, 3502.
35. (f) Poddel'sky, A. I.; Cherkasov, V. K.; Abakumov, G. A. Coord. Chem. Rev. 2009, 253, 291.
36. Chaudhuri, P.; Verani, C. N.; Bill, E.; Bothe, E.; Weyhermüller, T.; Wieghardt, K. J. Am. Chem. Soc. 2001, 123, 2213.
37. Chanda, N.; Sarkar, B.; Fiedler, J.; Kaim, W.; Lahiri, G. K. Inorg. Chem. 2004, 43, 5128.
38. (b) Ghumaan, S.; Sarkar, B.; Chanda, N.; Sieger, M.; Fiedler, J.; Kaim, W.; Lahiri, G. K. Inorg. Chem. 2006, 45, 7955.
39. (c) Koley, M.; Sarkar, B.; Ghumaan, S.; Bulak, E.; Fiedler, J.; Kaim, W.; Lahiri, G. K. Inorg. Chem. 2007, 46, 3736.
40. (d) Rocha, R. C.; Rein, F. M.; Jude, H.; Shreve, A. P.; Concepcion, J. J.; Meyer, T. J. Angew. Chem. 2008, 120, 513;
41. Angew. Chem., Int. Ed. 2008, 47, 503.
42. (e) Chanda, N.; Laye, R. H.; Chakraborty, S.; Paul, R. L.; Jeffery, J. C.; Ward, M. D.; Lahiri, G. K. J. Chem. Soc., Dalton Trans. 2002, 3496.
43. (f) Carranza, J.; Sletten, J.; Brennan, C.; Lloret, F.; Cano, J.; Julve, M. Dalton Trans. 2004, 3997.
44. Fantacci, S.; De Angelis, F.; Wang, J.; Bernhard, S.; Selloni, A. J. Am. Chem. Soc. 2004, 126, 9715.
45. (b) Flores-Torres, S.; Hutchison, G. R.; Soltzberg, L. J.; Abruña, H. D. J. Am. Chem. Soc. 2006, 126, 1513.
46. Kalinina, D.; Dares, C.; Kaluarachchi, H.; Potvin, P. G.; Lever, A. B. P. Inorg. Chem. 2008, 47, 10110.
47. Ernst, S.; Hänel, P.; Jordanov, J.; Kaim, W.; Kasack, V.; Roth, E. J. Am. Chem. Soc. 1989, 111, 1733.
48. (b) Schwederski, B.; Kasack, V.; Kaim, W.; Roth, E.; Jordanov, J. Angew. Chem. 1990, 102, 74;
49. Angew. Chem., Int. Ed. Engl. 1990, 29, 78.
50. (c) Ernst, S.; Kasack, V.; Bessenbacher, C.; Kaim, W. Z. Naturforsch. 1987, 42b, 425.
51. Patra, S.; Sarkar, B.; Mobin, S. M.; Kaim, W.; Lahiri, G. K. Inorg. Chem. 2003, 42, 6469.
52. Kaim, W.; Ernst, S.; Kasack, V. J. Am. Chem. Soc. 1990, 112, 173.
53. (b) Waldhör, E.; Schwederski, B.; Kaim, W. J. Chem. Soc., Perkin Trans. 2 1993, 2109.
54. (c) Ye, S.; Sarkar, B.; Duboc, C.; Fiedler, J.; Kaim, W. Inorg. Chem. 2005, 44, 2843.
55. Remenyi, C.; Kaupp, M. J. Am. Chem. Soc. 2005, 127, 11399.
56. Maji, S.; Sarkar, B.; Mobin, S. M.; Fiedler, J.; Urbanos, F. A.; Jimenez-Aparicio, R.; Kaim, W.; Lahiri, G. K. Inorg. Chem. 2008, 47, 5204.
57. (b) Ghumaan, S.; Sarkar, B.; Maji, S.; Puranik, V. G.; Fiedler, J.; Urbanos, F. A.; Jimenez-Aparicio, R.; Kaim, W.; Lahiri, G. K. Chem. - Eur. J. 2008, 14, 10816.
58. (c) Mitra, K. N.; Peng, S.-M.; Goswami, S. Chem. Commun. 1998, 1685.
59. (d) Bill, E.; Bothe, E.; Chaudhuri, P.; Chlopek, K.; Herbian, D.; Kokatam, S.; Ray, K.; Weyhermüller, T.; Neese, F.; Wieghardt, K. Chem. - Eur. J. 2005, 11, 204.
60. Kobayashi, K.; Ohtsu, H.; Wada, T.; Kato, T.; Tanaka, K. J. Am. Chem. Soc. 2003, 125, 6729.
61. (b) Miyazato, Y.; Wada, T.; Muckerman, J. T.; Fujita, E.; Tanaka, K. Angew. Chem. 2007, 119, 5830;
62. Angew. Chem., Int. Ed. 2007, 46, 5728.
63. Muckerman, J. T.; Polyansky, D. E.; Wada, T.; Tanaka, K.; Fujita, E. Inorg. Chem. 2008, 47, 1787.
64. Krejèik, M.; Danek, M.; Hartl, F. J. Electroanal. Chem. Interfacial Electrochem. 1991, 317, 179.
65. Hartshorn, C. M.; Daire, N.; Tondreau, V.; Loeb, B.; Meyer, T. J.; White, P. S. Inorg. Chem. 1999, 38, 3200.
66. Sheldrick, G. M. Program for Crystal Structure Solution and Refinement; Universität Göttingen, 1997.
67. Herrendorf, W.; Bärnighausen, H. Program HABITUS; Karlsruhe; Germany, 1993.
68. Frisch, M. J.; Trucks, G.; Schlegel, H. B. et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT; 2004.
69. te Velde, G.; Bickelhaupt, F. M.; van Gisbergen, S. J. A.; Fonseca Guerra, C.; Baerends, E. J.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931.
70. (b) ADF 2008 01, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, http://www.scm.com.
71. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
72. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
73. Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123.
74. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
75. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
76. (b) Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244.
77. van Lenthe, E.; van der Avoird, A.; Wormer, P. E. S. J. Chem. Phys. 1997, 107, 2488.
78. (b) van Lenthe, E.; van der Avoird, A.; Wormer, P. E. S. J. Chem. Phys. 1998, 108, 4783.
79. Reduced pyrazines exhibit characteristic CC bond shortening and CN bond lengthening. (a) Kaim, W. Rev. Chem. Intermed. 1987, 8, 247.
80. (b) Kaim, W.; Schulz, A.; Hilgers, F.; Hausen, H.-D.; Moscherosch, M.; Lichtblau, A.; Jordanov, J.; Roth, E.; Zalis, S. Res. Chem. Intermed. 1993, 19, 603.
81. Kokatam, S.; Weyhermüller, Th.; Bothe, E.; Chaudhuri, P.; Wieghardt, K. Inorg. Chem. 2005, 44, 3709.
82. (b) Bhattacharya, S.; Gupta, P.; Basuli, F.; Pierpont, C. G. Inorg. Chem. 2002, 41, 5810.
83. For a related example, see: Sieger, M.; Vogler, C.; Klein, A.; Knödler, A.; Wanner, M.; Fiedler, J.; Zalis, S.; Snoeck, T. L.; Kaim, W. Inorg. Chem. 2005, 44, 4637.
84. Kaim, W. Angew. Chem. 1983, 95, 201;
85. Angew. Chem., Int. Ed. Engl. 1983, 22, 171.
86. Poppe, J.; Moscherosch, M.; Kaim, W. Inorg. Chem. 1993, 32, 2640.
87. Creutz, C.; Chou, M. H. Inorg. Chem. 1987, 26, 2995.
88. Miller, J. S.; Min, K. S. Angew. Chem. 2008, 121, 268;
89. Angew. Chem., Int. Ed. 2008, 48, 262.
90. (a) Evangelio, E.; Ruiz.-Molina, D. Eur. J. Inorg. Chem. 2005, 2957.
91. (b) Sato, O.; Cui, A.; Matsuda, R.; Tao, J.; Hayami, S. Acc. Chem. Res. 2007, 40, 361.
92. (c) Dei, A.; Gatteschi, D.; Sangregorio, C.; Sorace, L. Acc. Chem. Res. 2004, 37, 827.
93. (d) Hendrickson, D. N.; Pierpont, C. G. Top. Curr. Chem. 2004, 234, 63.
94. Samanta, S.; Singh, P.; Fiedler, J.; Zalis, S.; Kaim, W.; Goswami, S. Inorg. Chem. 2008, 47, 1625.
95. Moscherosch, M.; Waldhör, E.; Binder, H.; Kaim, W.; Fiedler, J. Inorg. Chem. 1995, 34, 4326.
96. (b) Záliš, S.; Kaim, W.; Sarkar, B.; Duboc, C. Chem. Monthly, in print.
97. (c) Schwederski, B.; Kasack, V.; Kaim, W.; Roth, E.; Jordanov, J. Angew. Chem. 1990, 102, 74;
98. Angew. Chem., Int. Ed. Engl. 1990, 29, 78.
99. (b) Waldhör, E.; Schwederski, B.; Kaim, W. J. Chem. Soc., Perkin Trans. 2 1993, 2109.
100. Stegmann, H. B.; Ulmschneider, K. B.; Hieke, K.; Scheffler, K. J. Organomet. Chem. 1976, 118, 259.
101. Ye, S.; Sarkar, B.; Lissner, F.; Schleid, Th.; van Slageren, J.; Fiedler, J.; Kaim, W. Angew. Chem. 2005, 117, 2140;
102. Angew. Chem., Int. Ed. 2005, 44, 2103.
103. Ward, M. D.; McCleverty, J. A. J. Chem. Soc., Dalton Trans. 2002, 275.
104. Salsman, J. C.; Ronco, S.; Londergan, C. H.; Kubiak, C. P. Inorg. Chem. 2006, 45, 547.
105. (b) Adams, H.; Costa, P. J.; Newell, M.; Vickers, S. J.; Ward, M. D.; Félix, V.; Thomas, J. A. Inorg. Chem. 2008, 47, 11633.
106. (a) Nelsen, S. F. Chem.-Eur. J. 2000, 6, 581.
107. (b) Lambert, C.; Nöll, G.; Schelter, J. Nat. Mater. 2002, 1, 69.
108. Zalis, S.; Kaim, W. Main Group Chem. 2007, 6, 267.