Polyunsaturated dicarboxylate tethers connecting dimolybdenum redox and chromophoric centers: Absorption spectra and electronic structures

Journal of the American Chemical Society

Volumn 125, Issue 18, 2003, Pages 5486-5492

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

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CHARGE TRANSFER; ELECTRIC EXCITATION; ELECTRONIC STRUCTURE; PIGMENTS; REDOX REACTIONS;

LINKERS;

UNSATURATED POLYMERS;

ACETYLENE DICARBOXYLATE; DICARBOXYLIC ACID DERIVATIVE; FUMARIC ACID; LIGAND; METAL; MOLYBDENUM; MUCONIC ACID; OXALIC ACID; TAMUATE; TEREPHTHALIC ACID; TEXATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOPHORE; COLOR; ELECTRICITY; ENERGY ABSORPTION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION;

ALKENES; DICARBOXYLIC ACIDS; MODELS, MOLECULAR; MOLYBDENUM; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0038137603     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0343555     Document Type: Article

References (53)

1. (a) Comorosan, S.; Jieanu, V.; Morlova, I.; Paslaru, L.; Rozoveanu, P.; Toroiman, E.; Vasilco, R. Physiol. Chem. Phys. Med. NMR 1988, 20, 319.
2. (b) Comorosan, S. J. Biol. Phys. 1990, 17, 151.
3. (c) Brixner, T.; Damrauer, N. H.; Gerber, G. Adv. At., Mol., Opt. Phys. 2001, 46, 1.
4. Wang, Y.; Hu, X. J. Am. Chem. Soc. 2002, 124, 8445.
5. (a) Ruban, A. V.; Phillip, D.; Young, A. J.; Horton, P. Biochemistry 1997, 36, 7855.
6. (b) Frank, H. A.; Bautista, J. A.; Josue, J. S.; Young, A. J. Biochemistry 2000, 39, 2831.
7. Rando, R. R. Chem. Rev. 2001, 101, 1881.
8. For example, see: Nishino, H. In Functional Foods for Disease Prevention 1; Shibamoto, T., Terao, J., Osawa, T., Eds.: ACS Symposium Series 701; American Chemical Society: Washington, DC, 1998; p 59 and references therein.
9. (a) Mortensen, A.; Skibsted, L. H. J. Agric. Food Chem. 1997, 45, 2970.
10. (b) Kappus, H. In Free Radicals and Food Additives, Arouma, O. I., Halliwell, B., Eds.; Taylor and Francis: London, 1991; p 59.
11. (c) Garavelli, M.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1998, 120, 10210.
12. (d) Mortensen, A.; Everett, S. A.; Skibstead, L. H. In Phytochemicals and Phytopharmaceuticals; Shahidi, F., Ho, C.-T., Eds; AOCS Press: Champaign, IL 2000; p 185.
13. (a) Cotton, F. A.; Walton, R. A. Multiple Bonds Between Metal Atoms; Clarendon: Oxford, 1993.
14. (b) Hopkins, M. D.; Gray, H. B.; Miskowski, V. M. Polyhedron 1987, 6, 705.
15. (c) Miskowski, V. M.; Hopkins, M. D.; Winkler, J. R.; Gray, H. B. In Inorganic Electronic Structure and Spectroscopy; Solomon, E. I., Lever, A. B. P., Eds.; Wiley: New York. 1999; Vol. 2, pp 343-402.
16. (d) Beers, W. W.; McCarley, R. E.; Martin, D. S.; Miskowski, V. M.; Gray, H. B.; Hopkins, M. D. Coord. Chem. Rev. 1999, 187, 103.
17. (e) Cotton, F. A.; Nocera, D. G. Acc. Chem. Res. 2000, 33, 483.
18. (a) Cotton, F. A.; Martin, D. S.; Fanwick, P. E.; Peters, T. J.; Webb, T. R. J. Am. Chem. Soc. 1976, 98, 4681.
19. (b) Martin, D. S.; Newman, R. A.; Fanwick, P. E. Inorg. Chem. 1979, 18, 2511.
20. (c) Cotton, F. A.; Martin, D. S.; Webb, T. R.; Peters, T. J. Inorg. Chem. 1976, 15, 1199.
21. (d) Martin, D. S.; Huang, H.-W. Inorg. Chem. 1990, 29, 3674.
22. (e) Cotton, F. A.; Zhong, B. J. Am. Chem. Soc. 1990, 112, 2256.
23. (f) Chisholm, M. H.; Huffman, J. C.; Iyer, S. S.; Lynn, M. A. Inorg. Chim. Acta 1996, 243, 283.
24. (a) Cotton, F. A.; Donahue, J. P.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 1234.
25. (b) Cotton, F. A.; Donahue, J. P.; Murillo, C. A. J. Am. Chem. Soc. 2003, 125, 5436.
26. Cotton, F. A.; Feng, X.; Matusz, M. Inorg. Chem. 1989, 28, 594.
27. (a) Bursten, B. E.; Chisholm, M. H.; Hadad, C. M.; Li, J.; Wilson, P. J. Chem. Commun. 2001, 2382.
28. (b) Bursten, B. E.; Chisholm, M. H.; Clark, R. J. H.; Firth, S.; Hadad, C. M.; MacIntosh, A. M.; Wilson, P. J.; Woodward, P. M.; Zaleski, J. M. J. Am. Chem. Soc. 2002, 124, 3050
29. (c) Bursten, B. E.; Chisholm, M. H.; Clark, R. J. H.; Firth, S.; Hadad, C. M.; Wilson, P. J.; Woodward, P. M.; Zaleski, J. M. J. Am. Chem. Soc. 2002, 124, 12244.
30. Arrhenius, T. S.; Blanchard-Desce, M.; Dvolaitzky, M.; Lehn, J.-M.; Malthete, J. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 5355.
31. Slama-Schwok, A.; Blanchard-Desce, M.; Lehn, J.-M. J. Phys. Chem. 1990, 94, 3894.
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revisions A.6, A.7, and A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
33. Dunning, T. H.; Hay, P. J. Methods of Electronic Structure Theory; Schaefer, H. F., III, Ed.; Plenum Press: New York, 1977; Vol. 3.
34. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
35. -8.
36. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
37. (a) Becke, A. D. Phys. Rep. A. 1998, 38, 3098.
38. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
39. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
40. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rep. B 1998, 37, 785.
41. Casida, M. E.; Jaorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439.
42. Other instances are available in the literature in which the construct of a particle in a one-dimensional box is employed as a model for the description of conjugated systems. For example, see: (a) Calzaferri, G. Chimia 1987, 41, 248. (b) Chernyak, V.; Volkov, S. N.; Mukamel, S. J. Phys. Chem. A 2001, 105, 1988. (c) Rogers, J. E.; Cooper, T. M.; Fleitz, P. A.; Glass, D. J.; McLeans, D. G. J. Phys. Chem. A. 2002, 106, 10108.
43. Other instances are available in the literature in which the construct of a particle in a one-dimensional box is employed as a model for the description of conjugated systems. For example, see: (a) Calzaferri, G. Chimia 1987, 41, 248. (b) Chernyak, V.; Volkov, S. N.; Mukamel, S. J. Phys. Chem. A 2001, 105, 1988. (c) Rogers, J. E.; Cooper, T. M.; Fleitz, P. A.; Glass, D. J.; McLeans, D. G. J. Phys. Chem. A. 2002, 106, 10108.
44. Other instances are available in the literature in which the construct of a particle in a one-dimensional box is employed as a model for the description of conjugated systems. For example, see: (a) Calzaferri, G. Chimia 1987, 41, 248. (b) Chernyak, V.; Volkov, S. N.; Mukamel, S. J. Phys. Chem. A 2001, 105, 1988. (c) Rogers, J. E.; Cooper, T. M.; Fleitz, P. A.; Glass, D. J.; McLeans, D. G. J. Phys. Chem. A. 2002, 106, 10108.
45. The energy separations between the HOMO and HOMO-1 are 6.7, 4.9, 4.0, 3.5, and 3.2 kcal/mol for molecules 6, 8, 12, 13, and 14, respectively.
46. The dicarboxylic acid analogue of the dicarboxylate linkers in 6, 8, 12, 13, and 14 were optimized at the B3LYP level of theory (shown in Figure S2). The C-C optimized values were then used for the C-C bond distances of the dicarboxylate linker in 6, 8, 12, 13, and 14.
47. Because the DFT calculations are sensitive to minor changes in the structural parameters, the high esd's (which are commonly observed) in the carbon-carbon bond lengths (∼0.01 Å) of the polyolefinic linker render the results of the calculations susceptible to the sort of undulation seen in the blue trace in Figure 6.
48. (a) Woodcock, H. L.; Schaefer, H. F., III: Schreiner, P. R. J. Phys. Chem. A, 2002, 106, 11923.
49. (b) Plattner, D. A.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4405.
50. (a) Longuet, Higgins, H. C.; Salem, L. Proc. R. Soc. London 1959, A251, 172.
51. (b) Yannoni, C. S.; Clarke, T. C. Phys. Rev. Lett. 1983, 51, 1191.
52. (c) Guo, H.; Paldus, J. Int. J. Quantum Chem. 1997, 63, 345.
53. Woitellier, S.; Launey, J. P.; Spangler, C. W. Inorg. Chem. 1989, 28, 758.