Polyunsaturated dicarboxylate tethers connecting dimolybdenum redox and chromophoric centers: Syntheses, structures, and electrochemistry

Journal of the American Chemical Society

Volumn 125, Issue 18, 2003, Pages 5436-5450

  Cotton, F Albert ^a   Donahue, James P ^a   Murillo, Carlos A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIFFERENTIAL PULSE VOLTAMMETRY;

CHEMICAL BONDS; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; MOLECULES; OXIDATION; REDOX REACTIONS; SPECTROSCOPIC ANALYSIS; X RAY CRYSTALLOGRAPHY;

UNSATURATED POLYMERS;

ALLENE 1,3 DICARBOXYLATE; ALLENE DERIVATIVE; DICARBOXYLIC ACID; MALEIC ACID; MOLYBDENUM; MUCONIC ACID; TAMUATE; TAXATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHROMATOPHORE; CYCLIC POTENTIOMETRY; DIFFERENTIAL PULSE VOLTAMMETRY; ELECTRICITY; ELECTROCHEMISTRY; ISOMERISM; OXIDATION; OXIDATION REDUCTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

DICARBOXYLIC ACIDS; ELECTROCHEMISTRY; ISOMERISM; LIGANDS; MODELS, MOLECULAR; MOLYBDENUM; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION;

EID: 0038413962     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029101i     Document Type: Article

References (108)

1. (a) Lippard, S. J.; Berg, J. M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, California, 1994.
2. (b) Schuster, G. B. Acc. Chem. Res. 2000, 33, 253.
3. (a) Endicott, J. F.; Kumar, K.; Ramasami, T.; Rotzinger, F. P. Prog. Inorg. Chem. 1983, 30, 141.
4. (b) Barigelletti, F.; Flamigni, L. Chem. Soc. Rev. 2000, 29, 1.
5. (a) Wosnick, J. H.; Swager, T. M. Curr. Opin. Chem. Biol. 2000, 4, 715.
6. (b) Tour, J. M.; Rawlett, A. M.; Kozaki, M.; Yao, Y.; Jagessar, R. C.; Dirk, S. M.; Price, D. W.; Reed, M. A.; Zhou, C.-W.; Chen, J.; Wang, W.; Campbell, I. Chem.-Eur. J. 2001, 7, 5118.
7. (c) Launay, J.-P. Chem. Soc. Rev. 2001, 30, 386.
8. (d) Cahen, D.; Hodes, G. Adv. Mater. 2002, 14, 789.
9. (e) Ratner, M. A. Mater. Today 2002, 5, 20.
10. (f) Kwok, K. S.; Ellenbogen, J. C. Mater. Today 2002, 5, 28.
11. (a) Ortega, J. V.; Hong, B.; Ghosal, S.; Hemminger, J. C.; Breedlove, B.; Kubiak, C. P. Inorg. Chem. 1999, 38, 5102.
12. (b) Chisholm, M. H. Acc. Chem. Res. 2000, 33, 53.
13. (a) Kahn, O. Molecular Magnetism; Wiley-VCH: New York, 1993.
14. (b) Seddon, E. J.; Yoo, J.; Folting, K.; Huffman, J. C.; Hendrickson, D. N.; Christou, G. J. Chem. Soc., Dalton Trans. 2000, 3640.
15. (c) Sañudo, E. C.; Grillo, V. A.; Knapp, M. J.; Bollinger, J. C.; Huffman, J. C.; Hendrickson, D. N.; Christou, G. Inorg. Chem. 2002, 41, 2441.
16. (a) Pourtois, G.; Beljonne, D.; Cornil, J.; Ratner, M. A.; Brédas, J. L. J. Am. Chem. Soc. 2002, 124, 4436.
17. (b) Niyogi, K. K. Curr. Opin. Plant Biol. 2000, 3, 455.
18. For example, see: Richardson, D. E.; Taube, H. Inorg. Chem. 1981, 20, 1278.
19. (a) Creutz, C. Prog. Inorg. Chem. 1983, 30, 1.
20. (b) Brunschwig, B. S.; Creutz, C.; Sutin, N. Chem. Soc. Rev. 2002, 31, 168.
21. Villata, L. S.; Féliz, M. R.; Capparelli, A. L. Coord. Chem. Rev. 2000, 196, 65.
22. Cotton, F. A.; Donahue, J. P.; Murillo, C. A. Inorg. Chem. 2001, 40, 2229.
23. Cotton, F. A.; Lin, C.; Murillo, C. A. J. Am. Chem. Soc. 2001, 123, 2670.
24. (a) Coat, F.; Lapinte, C. Organometallics 1996, 15, 477.
25. (b) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. J. Am. Chem. Soc. 2000, 122, 810.
26. (c) Ren, T.; Zou, G.; Alvarez, J. C. Chem. Commun. 2000, 1197.
27. (d) Wong, K.-T.; Lehn, J.-M.; Peng, S.-M.; Lee, G.-H. Chem. Commun. 2000, 2259.
28. (a) Arrhenius, T. S.; Blanchard-Desce, M.; Dvolaitzky, M.; Lehn, J.-M.; Malthete, J. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 5355.
29. (b) Slama-Schwok, A.; Blanchard-Desce, M.; Lehn, J.-M. J. Phys. Chem. 1990, 94, 3894.
30. (c) Etzenhouser, B. A.; Cavanaugh, M. D.; Spurgeon, H. N.; Sponsler, M. B. J. Am. Chem. Soc. 1994, 116, 2221.
31. (d) Ribou, A.-C.; Launay, J.-P.; Sachtleben, M. L.; Li, H.; Spangler, C. W. Inorg. Chem. 1996, 35, 3735.
32. (e) Hapiot, P.; Kispert, L. D.; Konovalov, V. V.; Savéant, J.-M. J. Am. Chem. Soc. 2001, 123, 6669.
33. Kingsborough, R. P.; Swager, T. M. Prog. Inorg. Chem. 1999, 48, 123.
34. (a) Lacoste, M.; Varret, F.; Toupet, L.; Astruc, D. J. Am. Chem. Soc. 1987, 109, 6504.
35. (b) Collin, J.-P.; Lainé, P.; Launay, J.-P.; Sauvage, J.-P.; Sour, A. J. Chem. Soc., Chem. Commun. 1993, 434.
36. (c) Rabaâ, H.; Lacoste, M.; Delville-Desbois, M.-H.; Ruiz, J.; Gloaguen, B.; Ardoin, N.; Astruc, D.; Le Beuze, A.; Saillard, J.-Y.; Linares, J.; Varret, F.; Dance, J.-M.; Marquestaut, E. Organometallics 1995, 14, 5078.
37. (d) Galán-Mascarós, J. R.; Dunbar, K. R. Chem. Commun. 2001, 217.
38. (e) Campos-Fernández, C. S.; Clérac, R.; Koomen, J. M.; Russell, D. H.; Dunbar, K. R. J. Am. Chem. Soc. 2001, 123, 773.
39. (a) Morán, M.; Casado, C. M.; Cuadrado, I.; Losada, J. Organometallics 1993, 12, 4327.
40. (b) Constable, E. C.; Edwards, A. J.; Marcos, M. D.; Raithby, P. R.; Martínez-Máñez, R.; Tendero, M. J. L. Inorg. Chim. Acta 1994, 224, 11.
41. (c) Astruc, D. Acc. Chem. Res. 1997, 30, 383.
42. (d) Alvarez, J.; Ren, T.; Kaifer, A. E. Organometallics 2001, 20, 3543.
43. (e) Alvarez, J.; Ni, Y.; Ren, T.; Kaifer, A. E. J. Supramol. Chem. 2001, 1, 7.
44. (f) Zakaria, C. M.; Ferguson, G.; Lough, A. J.; Glidewell, C. Acta Crystallogr. 2002, B58, 786.
45. (a) Crossley, M. J.; Burn, P. L. J. Chem. Soc., Chem. Commun. 1991, 1569.
46. (b) Iengo, E.; Zangrando, E.; Minatel, R.; Alessio, E. J. Am. Chem. Soc. 2002, 124, 1003.
47. (a) Sutton, J. E.; Taube, H. Inorg. Chem. 1981, 20, 3125.
48. (b) Woitellier, S.; Launay, J. P.; Spangler, C. W. Inorg. Chem. 1989, 28, 758.
49. (c) Reimers, J. R.; Hush, N. S. Inorg. Chem. 1990, 29, 3686.
50. (d) McWhinnie, S. L. W.; Thomas, J. A.; Hamor, T. A.; Jones, C. J.; McCleverty, J. A.; Collison, D.; Mabbs, F. E.; Harding, C. J.; Yellowlees, L. J.; Hutchings, M. G. Inorg. Chem. 1996, 35, 760.
51. (a) Cotton, F. A.; Lin, C.; Murillo, C. A. Acc. Chem. Res. 2001, 34, 759.
52. (b) Cotton, F. A.; Lin, C.; Murillo, C. A. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4810.
53. Cotton, F. A.; Daniels, L. M.; Donahue, J. P.; Liu, C. Y.; Murillo, C. A. Inorg. Chem. 2002, 41, 1354.
54. Cotton, F. A.; Liu, C. Y.; Murillo, C. A. Unpublished results.
55. Cotton, F. A.; Walton, R. A. Multiple Bonds between Metal Atoms: Clarendon: Oxford, 1993.
56. Cotton, F. A.; Donahue, J. P.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 1234.
57. The second report is in a succeeding paper in this issue: Cotton, F. A.; Donahue, J. P.; Murillo, C. A.; Pérez, L. M. J. Am. Chem. Soc. 2003, 125, 5486.
58. Cotton, F. A.; Daniels, L. M.; Jordan, G. T., IV; Lin, C.; Murillo, C. A. J. Am. Chem. Soc. 1998, 120, 3398.
59. Ikeda, I.; Honda, K.; Osawa, E.; Shiro, M.; Aso, M.; Kanematsu, K. J. Org. Chem. 1996, 61, 2031.
60. van der Zanden, J. M. Recl. Trav. Chim. Pays-Bas 1935, 54, 289.
61. Dreiding, A. S.; Pratt, R. J. J. Am. Chem. Soc. 1953, 75, 4580.
62. Abarbri, M.; Parrain, J.-L.; Cintrat, J.-C.; Duchêne, A. Synthesis 1996, 82.
63. Jones, E. R. H.; Shaw, B. L.; Whiting, M. C. J. Chem. Soc. 1954, 3212.
64. Reppe, W. et al. Justus Liebigs Ann. Chem. 1955, 596, 72.
65. Pflugrath, J.; Messerschmitt, A. MADNES, Munich Area Detector (New EEC) System, version EEC 11/1/89; with enhancements by Nonius Corporation; Delft, The Netherlands. A description of MADNES appears in the following: Messerschmitt, A.; Pflugrath, J. J. Appl. Crystallogr. 1987, 20, 306.
66. Pflugrath, J.; Messerschmitt, A. MADNES, Munich Area Detector (New EEC) System, version EEC 11/1/89; with enhancements by Nonius Corporation; Delft, The Netherlands. A description of MADNES appears in the following: Messerschmitt, A.; Pflugrath, J. J. Appl. Crystallogr. 1987, 20, 306.
67. (a) Kabsch, W. J. Appl. Crystallogr. 1988, 21, 67.
68. (b) Kabsch, W. J. Appl. Crystallogr. 1988, 21, 916.
69. Blessing, R. H. Acta Crystallogr. 1995, A51, 33.
70. SMART for Windows NT, version 5.059; Bruker Analytical X-ray Systems; 1997-1998.
71. SAINT+ for NT, version 6.02; Bruker Analytical X-ray Systems; 1997-1999.
72. Sheldrick, G. M. SHELX-97 Programs for Crystal Structure Analysis. Institut für Anorganische Chemie der Universität: Tammanstrasse 4, D-3400 Göttingen, Germany, 1998.
73. 14 has been reported: Cotton, F. A.; Donahue, J. P.; Lin, C.; Murillo, C. A.; Rockwell, J. Acta Crystallogr. 2002, E58, m298.
74. 2).
75. (a) Kuhn, R.; Grundmann, C. Chem. Ber. 1936, 69, 1979.
76. (b) Kuhn, R.; Grundmann, C. Chem. Ber. 1937, 70, 1318.
77. (c) Shaw, B. L.; Whiting, M. C. J. Chem. Soc. 1954, 3217.
78. (a) Longuet-Higgins, H. C.; Salem, L. Proc. R. Soc. London 1959, A251, 172.
79. (b) Yannoni, C. S.; Clarke, T. C. Phys. Rev. Lett. 1983, 51, 1191.
80. (c) Guo, H.; Paldus, J. Int. J. Quantum Chem. 1997, 63, 345.
81. For n = 2, both cis and trans isomers are possible, but only the cis isomer has proven sufficiently stable to be isolated and studied.
82. Chisholm, M. H.; Cotton, F. A.; Daniels, L. M.; Folting, K.; Huffman, J. C.; Iyer, S. S.; Lin, C.; Macintosh, A. M.; Murillo, C. A. J. Chem. Soc., Dalton Trans. 1999, 1387.
83. Bera, J. K.; Fanwick, P. E.; Walton, R. A. J. Chem. Soc., Dalton Trans. 2001, 109.
84. Taylor, J. R. An Introduction to Error Analysis; University Science Books: Sausalito, California, 1997.
85. Gilbert, T. M.; Hadley, F. J.; Simmons, M. D.; Bauer, C. B.; Rogers, R. D. J. Organomet. Chem. 1996, 510, 83.
86. Rando, R. R. Chem. Rev. 2001, 101, 1881.
87. Hong, B. Comments Inorg. Chem. 1999, 20, 177.
88. Adams, R. D.; Huang, M. Organometallics 1996, 15, 4437.
89. Adams, R. D.; Huang, M. Chem. Ber. 1996, 129, 1447.
90. Adams, R. D.; Huang, M.; Zhang, L. J. Cluster Sci. 1997, 8, 101.
91. 4 obtained using our experimental conditions differs from a value previously published by another research group: Cf. Lin, C.; Protasiewicz, J. D.; Smith, E. T.; Ren, T. Inorg. Chem. 1996, 35, 6422. We will use our experimental number for reference.
92. Cotton, F. A.; Daniels, L. M.; Hillard, E. A.; Murillo, C. A. Inorg. Chem. 2002, 41, 1639.
93. Serjeant, E. P.; Dempsey, B. Ionisation Constants of Organic Acids in Aqueous Solution; Pergamon: Oxford, 1979.
94. Oszczapowicz, J.; Orliński, R.; Hejchman, E. Pol. J. Chem. 1979, 53, 1259.
95. 1/2 versus d is similar to that of the published figure. More importantly, the discussion presented in ref 23 is not affected.
96. Kiehl, A.; Eberhardt, A.; Adam, M.; Enkelmann, V.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 1588.
97. Märkl, G.; Pöll, A.; Aschenbrenner, N. G.; Schmaus, C.; Troll, T.; Kreitmeier, P.; Nöth, H.; Schmidt, M. Helv. Chim. Acta 1996, 79, 1497.
98. Gebhardt, V.; Bacher, A.; Thelakkat, M.; Stalmach, U.; Meier, H.; Schmidt, H.-W.; Haarer, D. Adv. Mater. 1999, 11, 119.
99. Deng, Y.; Gao, G.; He, Z.; Kispert, L. D. J. Phys. Chem. B 2000, 104, 5651.
100. Heinze, J.; Tschuncky, P. In Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: New York, 1998; Chapter 9.
101. Kaim, W.; Klein, A.; Glöckle, M. Acc. Chem. Res. 2000, 33, 755.
102. Demadis, K. D.; Hartshorn, C. M.; Meyer, T. J. Chem. Rev. 2001, 101, 2655.
103. (a) Elvidge, J. A.; Linstead, R. P.; Sims, P.; Orkin, B. A. J. Chem. Soc. 1950, 2235.
104. (b) Elvidge, J. A.; Linstead, R. P.; Sims, P. J. Chem. Soc. 1953, 1793.
105. (a) Gust, D.; Moore, T. A.; Moore, A. L.; Barrett, D.; Harding, L. O.; Makings, L. R.; Liddell, P. A.; De Schryver, F. C.; Van der Auweraer, M.; Bensasson, R. V.; Rougée, M. J. Am. Chem. Soc. 1988, 110, 321.
106. (b) Gust, D.; Moore, T. A.; Moore, A. L.; Lee, S.-J.; Bittersmann, E.; Luttrull, D. K.; Rehms, A. A.; DeGraziano, J. M.; Ma, X. C.; Gao, F.; Belford, R. E.; Trier, T. T. Science 1990, 248, 199.
107. (c) Hung, S.-C.; Macpherson, A. N.; Lin, S.; Liddell, P. A.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 1995, 117, 1657.
108. (d) Liddell, P. A.; Kuciauskas, D.; Sumida, J. P.; Nash, B.; Nguyen, D.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 1997, 119, 1400.