Structural Changes upon Reduction of Dipyrido[2,3-a:3′,2′ -c]phenazine Probed by Vibrational Spectroscopy, ab Initio Calculations, and Deuteration Studies

Inorganic Chemistry

Volumn 43, Issue 9, 2004, Pages 2876-2887

  Howell, Sarah L ^a   Matthewson, Benjamin J ^a   Polson, Matthew I J ^a   Burrell, Anthony K ^b   Gordon, Keith C ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b LOS ALAMOS NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; DEUTERIUM; DIPYRIDO[2,3 A:3',2' C]PHENAZINE; LIGAND; PHENANTHROLINE; PHENAZINE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ABSORPTION; ARTICLE; CALCULATION; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; ELECTROCHEMICAL ANALYSIS; INFRARED RADIATION; RAMAN SPECTROMETRY; REDUCTION; SPECTROSCOPY; VIBRATION; VIBRATIONAL SPECTROSCOPY;

EID: 2142698621     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic030225l     Document Type: Article

References (65)

1. (a) Nazeeruddin, M. K.; Kay, A.; Rodicio, I.; Humphrey-Baker, R.; Mueller, E.; Liska, P.; Vlachopoulos, N.; Gratzel, M. J. Am. Chem. Soc. 1993, 115, 6382.
2. (b) Kalyanasundaram, K.; Gratzel, M. Coord. Chem. Rev. 1998, 177, 347.
3. (c) Moser, J. E.; Bonnote, P.; Gratzel, M. Coord. Chem. Rev. 1998, 177, 245.
4. (d) Bignozzi, C. A.; Schoonover, J. R.; Scandola, F. Prog. Inorg. Chem. 1997, 44, 1.
5. (a) Scandola, F.; Indelli, M. T.; Chiorboli, C.; Bignozzi, C. A. Top. Curr. Chem. 1990, 158, 73.
6. (b) Balzani, V.; Campagna, S.; Denti, G.; Juris, A.; Serroni, S.; Venturi, M. Acc. Chem. Res. 1998, 31, 26.
7. (c) Balzani, V.; Gomez-Lopez, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405.
8. (d) Venturi, M.; Serroni, S.; Juris, A.; Campagna, S.; Balzani, V. Top. Curr. Chem. 1998, 197, 193.
9. (e) Ziessel, R.; Hissler, M.; El-Ghayoury, A.; Harriman, A. Coord. Chem. Rev. 1998, 180, 1251.
10. (f) Ziessel, R.; Harriman, A. Coord. Chem. Rev. 1998, 171, 331.
11. (g) Scandola, F.; Argazzi, R.; Bignozzi, C. A.; Chiorboli, C.; Indelli, M. T.; Rampi, M. A. In Supramolecular Chemistry; Balzani, V., DeCola, L., Eds.; Kluwer: Dordrecht, The Netherlands, 1992; p 235.
12. DeArmond, M. K.; Myrick, M. L. Acc. Chem. Res. 1989, 22, 364.
13. Bradley, P. G.; Kress, N.; Hornberger, B. A.; Dallinger, R. F.; Woodruff, W. H. J. Am. Chem. Soc. 1981, 103, 7441-7446.
14. Diaz-Acosta, I.; Baker, J.; Cordes, W.; Pulay, P. J. Phys. Chem. A 2001, 105, 238.
15. (a) Zheng, K. C.; Wang, J. P.; Peng, W. L.; Shen, Y.; Yun, F. C. Inorg. Chim. Acta 2002, 328, 247.
16. (b) Zheng, K. C.; Wang, J. P.; Peng, W. L.; Shen, Y.; Yun, F. C. J. Chem. Soc., Dalton Trans. 2002, 111.
17. Damrauer, N. H.; Weldon, B. T.; McCusker, J. K. J. Phys. Chem. A 1998, 102, 3382.
18. Dattelbaum, D. M.; Omberg, K. M.; Schoonover, J. R.; Martin, R. L.; Meyer, T. J. Inorg. Chem. 2002, 41, 6071.
19. Treadway, J. A.; Loeb, B.; Lopez, R.; Anderson, P. A.; Keene, R. F.; Meyer, T. J. Inorg. Chem. 1996, 35, 2242.
20. (a) Chen, W.; Turro, C.; Friedman, L. A.; Barton, J. K.; Turro, N. J. J. Phys. Chem. B 1997, 101, 6995.
21. (b) Friedman, A. E.; Chambron, J.-C.; Sauvage, J.-P.; Turro, N. J.; Barton, J. K. J. Am. Chem. Soc. 1990, 112, 4960.
22. (c) Hiort, C.; Lincoln, P.; Nordén, B. J. Am. Chem. Soc. 1993, 115, 3448.
23. (d) Jenkins, Y.; Friedman, A. E.; Turro, N. J.; Barton, J. K. Biochemistry 1992, 31, 10809.
24. (e) Turro, C.; Bossmann, S. H.; Jenkins, Y.; Barton, J.; Turro, N. J. J. Am. Chem. Soc. 1995, 117, 9026.
25. Matthewson, B. J.; Flood, A.; Polson, M. I. J.; Armstrong, C.; Phillips, D. L.; Gordon, K. C. Bull. Chem. Soc. Jpn. 2002, 75, 933-942.
26. Gordon, K. C.; Al-Obaidi, A. H. R.; Jayaweera, P. M.; McGarvey, J. J.; Malone, J. F.; Bell, S. E. J. J. Chem. Soc., Dalton Trans. 1996, 1591-1596.
27. (a) Dobson, J. F.; Green, B. E.; Healy, P. C.; Kennard, C. H. L.; Pakawatchai, C.; White, A. H. Aust. J. Chem. 1984, 37, 649.
28. (b) Hämäläinen, R.; Ahlgrén, M.; Turpeinen, U.; Raikas, T. Cryst. Struct. Commun. 1979, 8, 75.
29. (c) Dessy, G.; Fares, V. Cryst. Struct. Commun. 1979, 8, 507.
30. (d) Burke, P. J.; Henrick, K.; McMillin, D. R. Inorg. Chem. 1982, 21, 1881.
31. (e) Burke, P. J.; McMillin, D. R.; Robinson, W. R. Inorg. Chem. 1980, 19, 1211.
32. Jameson, R. F. In Metal Ions in Biological Systems, Vol. 12; Sigul, H., Ed.; Marcel Dekker: New York, 1981; Chapter 1.
33. A complete listing of all of the calculated vibrational data is given in Table S1 in the Supporting Information.
34. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
35. (a) Grafton, A. K.; Wheeler, R. A. Comput. Phys. Commun. 1998, 113, 78.
36. (b) Grafton, A. K.; Wheeler, R. A. J. Comput. Chem. 1998, 19, 1663.
37. Baerends, E. J.; Riccardi, G.; Rosa, A.; van Gisbergen, S. J. A. Coord. Chem. Rev. 2002, 230, 5.
38. 2 the transitions lie at: 400 nm, HOMO - 2 → LUMO, f = 0.0014; 360 nm, a combination of HOMO - 1 → LUMO + 1 and HOMO → LUMO, f = 0.0075 and 342 nm, a combination of HOMO - 1 → LUMO and HOMO → LUMO + 1, f = 0.12.
39. (a) Sherborne, J.; Scott, S. M.; Gordon, K. C. Inorg. Chim. Acta 1997, 260, 199.
40. (b) Sherborne, J.; Gordon, K. C. Asian J. Spectrosc. 1998, 2, 137.
41. Lever, A. B. P.; Dodsworth, E. S. In Inorganic Electronic Structure and Spectroscopy, Volume II, Applications and Case Studies; Solomon, E. I., Lever, A. B. P., Eds.; J. Wiley and Sons Inc.: New York, 1999; Chapter 4.
42. Clarke, R. J. H.; Dines, T. J. Angew. Chem., Int. Ed. Engl. 1986, 25, 131.
43. (a) Clark, R. J. H.; Turtle, P. C.; Strommen, D. P.; Streusand, B.; Kincaid, J. R.; Nakamoto, K. Inorg. Chem. 1977, 16, 84.
44. (b) Ma'nuel, D. J.; Strommen, D. P.; Bhuiyan, A.; Sykora, M.; Kincaid, J. R. J. Raman Spectrosc. 1997, 28, 933.
45. (c) Flood, A.; Girling, R. B.; Gordon, K. C.; Hester, R. E.; Moore, J. N.; Polson, M. I. J. J. Raman Spectrosc. 2002, 32, 434.
46. Tsuboi, M.; Hirakawa, A. Y. Science 1975, 188, 359.
47. A complete listing of the vibrational data for the radical anion species is given in Table S2 in Supporting Information.
48. Flood, A. H. Ph.D. Thesis, University of Otago, Dunedin, New Zealand, 2001.
49. Page, S. E.; Gordon, K. C.; Burrell, A. K. Inorg. Chem. 1998, 37, 4452.
50. Czernuszewicz, R. S.; Spiro, T. G. In Inorganic Electronic Structure and Spectroscopy. Volume 1, Methodology; Solomon, E. I., Lever, A. B. P., Eds.; J. Wiley and Sons Inc.: New York, 1999: Chapter 7.
51. Thormon, D. A.; Watkin, G. M. J. Coord. Chem. 1992, 25, 299.
52. Campos-Vallette, M. M.; Clavijo, R. E.; Mendizabel, F.; Zamudio, W.; Baraona, R.; Diaz, G. Vib. Spectrosc. 1996, 12, 37.
53. Yam, V. W.-W.; Lo, K. K.-W. J. Chem. Soc., Dalton Trans. 1995, 499.
54. Junk, T.; Catallo, W. J.; Elguero, J. Tetrahedron Lett. 1997, 38, 6309.
55. (a) Dickeson, J. E.; Summers, L. A. Aust. J. Chem. 1970, 23, 1023.
56. (b) Gillard, R. D.; Hill, R. E. E.; Maskill, R. J. Chem. Soc. A 1970, 1447.
57. Waterland, M. R.; Simpson, T. J.; Gordon, K. C.; Burrell, A. K. J. Chem. Soc., Dalton Trans. 1998, 185.
58. Sheldrick, G. M. SHELXL 95, Institut für Anorganische Chemie der Universität Göttingen, 1993.
59. Johnson, C. K. ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory: Oak Ridge, TN, 1976.
60. House, H. O.; Feng, E.; Peet, N. P. J. Org. Chem. 1971, 36, 2371.
61. (a) McCreery, R. L. Raman Spectroscopy for Chemical Analysis: Wiley Chemical Analysis Series, Vol. 157; Winefordner, J., Ed.; John Wiley: New York, 2000.
62. (b) The ASTM subcommitte on Raman spectroscopy has adopted eight materials as Raman shift standards (ASTM E 1840). The band wavenumbers for these standards are available at http://chemistry.ohio-state.edu/~rmccreer/shift.html.
63. 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.; Stralmann, 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.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98. Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
64. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakizewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D.4; Gaussian. Inc.: Pittsburgh, PA, 1995.
65. Schaftenaar, G.; Noordik, J. H. J. Comput-Aided Mol. Des. 2000, 14, 123.