Dynamic photophysical properties of conformationally distorted nickel porphyrins. 1. Nickel(II) dodecaphenylporphyrin

Journal of Physical Chemistry

Volumn 100, Issue 29, 1996, Pages 11984-11993

  Drain, Charles Michael ^a,c   Kirmaier, Christine ^a   Medforth, Craig J ^b   Nurco, Daniel J ^b   Smith, Kevin M ^b   Holten, Dewey ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON ENERGY LEVELS; MOLECULAR DYNAMICS; PHOTOCHEMICAL REACTIONS; PHYSICAL CHEMISTRY; PROTEINS; SPECTROSCOPIC ANALYSIS;

NICKEL DODECAPHENYLPORPHYRINS; PHOTOPHYSICAL PROPERTIES; STERIC CONSTRAINTS; TETRAPYRROLE COFACTORS;

NICKEL COMPOUNDS;

EID: 0030198139     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp960735j     Document Type: Article

References (74)

1. Tetrapyrroles adopt a number of conformations, the most common types being the planar, saddled, and ruffled structures: Scheidt, W. R.; Lee, Y. J. Struct. Bonding (Berlin) 1987, 64, 1. When in the planar conformation the opposite N-Ni-N angle is ∼180° and the C-N-N-C dihedral is ∼0°. The saddle conformation is characterized by a tilting of alternate pyrrole ring planes above and below the mean plane of the core while the meso carbons remain nearly in the plane (N-Ni-N < 180 and C-N-N-C remains ∼0°) The ruffled conformation is characterized by a twisting of alternate pyrrole ring planes such that the β-pyrrole carbons and meso carbons lie above and below the mean plane of the core (N-Ni-N remains ∼180° and C-N-N-C > 0°).
2. Harning, T. L.; Fujita, E.; Fajer, J. J. Am. Chem Soc. 1986, 108, 323.
3. (b) Barkigia, K. M.; Chantranupong, L.; Smith. K. M.; Fajer, J. J. Am.Chem. Soc. 1988, 110, 7566.
4. (a) Ladner, R. L.; Heidner, E. J.; Perutz, M. F. J. Mol. Biol. 1977, 114, 385.
5. (b) Geno, M. K.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1238.
6. (c) Deisenhofer, J.; Michel, H. Science 1989, 245, 1463.
7. (d) Huber, R. Eur. J. Biochem. 1990, 187, 283.
8. (e) Furenlid, L. R.; Renner, M. W.; Fajer, J. J. Am. Chem. Soc. 1990, 112, 8987.
9. (f) Alden, R. G.; Ondrias, M. R.; Shelnutt, J. A. J. Am. Chem. Soc. 1990, 112, 691.
10. Gunsalus, R. P.; Wolfe, R. S. Biochem. Biophys. Res. Commun. 1977, 76, 790.
11. (a) Eschenmoser, A. Ann. N.Y. Acad. Sci. 1986, 471, 108.
12. (b) Shelnutt, J. A. J. Phys. Chem. 1989, 93, 6283.
13. (a) Drain, C. M.; Sable, D.; Corden, B. B. Inorg. Chem. 1988, 27, 2396.
14. (b) Drain, C. M.; Sable, D.; Corden, B. B. Inorg. Chem. 1990, 29, 1428.
15. Ravikanth, M.; Chandashekar, T. K. Struct. Bond. 1995, 82, 105.
16. (a) Barkigia, K. M.; Berber, M. D.; Fajer, J.; Medforth, C. J.; Renner, M. W.; and Smith, K. M. J. Am. Chem. Soc. 1990, 112, 8851.
17. (b) Medforth, C. J.; Senge, M. O.; Smith, K. M.; Sparks, L. D.; Shelnutt, J. A. J. Am. Chem. Soc. 1992, 114, 9859.
18. (c) Sparks, D. L.; Medforth, C. J.; Park, M.-S.; Chamberlain, J. R.; Ondrias, M. R.; Senge, M. O.; Smith, K. M.; Shelnutt, J. A. J. Am. Chem. Soc. 1993, 115, 581.
19. Abbreviations used: TPP, 5,10,15,20-tetraphenylporphyrin; OEP, 2,3,7,8,12,13,17,18-octaethylporphyrin; DPP, 2,3,5,7,8,10,12,13,15,17,18,20-dodecaphenylporphyrin; PPDME, 2,18-dimethylpropionate-3,18-divinyl-3,7,12,17-tetramethylporphyrin; T(tert-butyl)P, 5,10,15,20-tetra-tert-butylporphyrin; OETPP, 5,10,15,20-tetraphenyl-2,3,7,8,12,13,17,18-octaethylporphyrin.
20. (a) Takeda, J.; Ohya, T.; Sato, M. Chem. Phys. Lett. 1990, 31, 5583.
21. (b) Tsuchiya, S. Chem. Phys. Lett. 1991, 183, 384.
22. (c) Rivikanth, M.; Reddy, D.; Chandrashekar, T. K. J. Photochem. Photobiol. A: Chem. 1993, 72, 51.
23. (d) Charlesworth, P.; Truscott, T. G.; Kessel, D.; Medforth, C. J.; Smith, K. M. J. Chem. Soc., Faraday Trans. 1994, 90, 1073.
24. (a) Gentemann, S.; Medforth, C. J.; Forsyth, T. P.; Nurco, D. J.; Smith, K. M.; Fajer, J.; Holten, D. J. Am. Chem. Soc. 1994, 116, 7376.
25. (b) Gentemann, S.; Medforth, C. J.; Ema, T.; Nelson, N. Y.; Smith, K. M.; Fajer, J.; Holten, D. Chem. Phys. Lett. 1995, 245, 441.
26. (a) Renner, M. W.; Cheng, R.-J.; Chang, C. K.; Fajer, J. J. Phys. Chem. 1990, 94, 8508.
27. (b) Regev, A.; Galili, T.; Medforth, C. J.; Smith, K. M.; Barkigia, K. M.; Fajer, J.; Levanon, H. J. Phys. Chem. 1994, 98, 2520.
28. (c) Drain, C. M.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 2313.
29. (d) Renner, M. W.; Barkigia, K. M.; Zhang, Y.; Medforth, C. J.; Smith, K. M.; Fajer, J. J. Am Chem. Soc. 1994, 116, 8582.
30. (a) Nurco, D. J.; Medforth, C. J.; Forsyth, T. P.; Olmstead, M. M.; Smith, K. M., manuscript in preparation.
31. (b) Caemelbech, E. V.; Forsyth, T. P.; Hobbs, J. D.; Kadish, K. M.; Ma, J.; Medforth, C. J.; Nurco, D. J.; Shelnutt, J. A.; Showalter, M.; Simpson, M. C.; Smith, K. M.; Song, X.; D'Souza, F.; Taylor, K. K., manuscript in preparation.
32. (a) Alden, R. G.; Crawford, B. A.; Doolen, R.; Ondrias, M. R.; Shelnutt, J. A. J. Am. Chem. Soc. 1989, 111, 2070.
33. (b) Brennan, T. D.; Scheidt, W. R.; Shelnutt, J. A. J. Am. Chem. Soc. 1988, 110, 3919.
34. (b) Prendergast, K.; Spiro, T. G. J. Am. Chem. Soc. 1992, 114, 3793.
35. (c) Cullen, D. L.; Meyer, E. F. J. Am. Chem. Soc. 1974, 96, 2095.
36. (d) Meyer, E. F. Acta Crystallogr. 1972, B28, 2162.
37. (a) Shelnutt, J. A.; Medforth, C. J.; Berber, M. D.; Barkigia, K. M.; Smith, K. M. J. Am. Chem. Soc. 1991, 113, 4077.
38. (b) Stichternath, A.; Scheitzer-Stenner, R.; Dreybrodt, W.; Mak, R. S.; Li, X.; Sparks, L. D.; Shelnutt, J. A.; Medforth, C. J.; Smith, K. M. J. Phys. Chem. 1993, 97, 8701.
39. (c) Barkigia, K. M.; Renner, M. W.; Furenlid, L. R.; Medforth, C. J.; Smith, K. M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 3627.
40. (d) Sparks, L. D.; Anderson, K. K.; Medforth, C. J.; Smith, K. M.; Shelnutt, J. A. Inorg. Chem. 1994, 33, 2297.
41. (e) Hobbs, J. D.; Majumder, S. A.; Luo, L.; Sickelsmith, G. A.; Quirke, J. M. E.; Medforth, C. J.; Smith, K. M.; Shelnutt, I. A. J. Am. Chem. Soc. 1994, 116, 3261.
42. (f) Jentzen, W.; Simpson, M. C.; Hobbs, J. D.; Song, X.; Ema, T.; Nelson, N. Y.; Medforth, C. J.; Smith, K. M.; Veyrat, M.; Mazzarti, M.; Ramasseul, R; Marchon, J.-C.; Takeuchi, T.; Goddard, W. A., III; Shelnutt, J. A. J. Am. Chem. Soc. 1995, 117, 11085.
43. (a) CRC Handbook of Chemistry and Physics, 71st ed.; Lide, D. R., Ed.; CRC Press: Boston, 1990.
44. (b) Pauling, L. The Nature of the Chemical Bond and the Structure of Molecules, 3rd ed.,; Cornell University Press: Ithaca, NY, 1960.
45. (a) Antipas, A.; Gouterman, M. J. Am. Chem. Soc. 1983, 105, 4896.
46. (b) Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 3, pp 1-165.
47. (a) Findsen, E. W.; Shelnutt, J. A.; Ondrias, M. R. J. Phys. Chem. 1988, 92, 307.
48. (b) Crawford, B. A.; Ondrias, M. R.; Shelnutt, J. A. J. Phys. Chem. 1990, 94, 6649.
49. (c) Courtney, S. H.; Jedju, T. M.; Freidman, J. M.; Alden, R. G.; Ondrias, M. R. Chem. Phys. Lett. 1989, 164, 39.
50. (a) Rodriguez, J.; Holten, D. J. Chem. Phys. 1989, 91, 3525.
51. (b) Rodriguez, J.; Kirmaier, C.; Holten, D. J. Am. Chem. Soc. 1989, 111, 6500.
52. (c) Rodriguez, J.; Kirmaier, C.; Holten, D. J. Chem. Phys. 1991, 94, 6020.
53. Kobayashi, T.; Straub, K. D.; Rentzepis, P. M. Photochem. Photobiol. 1979, 29, 925.
54. (a) Chirvonyi, V. S.; Dzhagarov, B. M.; Timinskii, Y. V.; Gurinovich, G. P. Chem. Phys. Lett. 1980, 70, 79.
55. (b) Chirvonyi, V. S.; Dzhagarov, B. M.; Shul'ga, M.; Gurinovich, G. P. Dokl Akad. Nauk. SSSR 1981, 259, 144.
56. (c) Kim, D.; Kirmaier, C.; Holten, D. Chem. Phys. 1983, 75, 305.
57. (d) Kim, D. H.; Holten, D. Chem. Phys. Lett. 1983, 98, 584.
58. (a) Chikisev, A. Y.; Kamalov, V. F.; Korteev N. I.; Kvach, V. V.; Shkvrinov, A. P.; Toluetaev, B. N. Chem. Phys. Lett. 1988, 144, 90.
59. (b) Apanasevich, P. A.; Kvach, V. V.; Orlovich, V. A. J. Roman Spectrosc. 1989, 20, 125.
60. (c) Sato, S.; Kitiagawa, T. Appl. Phys. 1994, B59, 415.
61. (a) Bilsel, O.; Rodriguez, J.; Holten, D. J. Phys. Chem. 1990, 94, 5945.
62. (b) Rodriguez, J.; Holten, D. J. Chem. Phys. 1990, 92, 5944.
63. (c) Bilsel, O.; Milam, S. N.; Girolami, G. S.; Suslick, K. S.; Holten, D. J. Phys. Chem. 1993, 97, 7216.
64. (a) Seilmeier, A.; Scherer, P. O. J.; Kaiser, W. Chem. Phys. Lett. 1984, 105, 140.
65. (b) Hill, J. R.; Chronister, E. L.; Chang, T.-C.; Kim, H.; Postlewaite, J.-C.; Dlott, D. D. J. Chem. Phys. 1988, 88, 949.
66. (c) Sukowski, U.; Seilmeier, A.; Elaesser, T.; Fischer, S. F. J. Chem. Phys. 1990, 93, 4094.
67. (d) Sension, R. J.; Szarka, A. Z.; Hochstrasser, R. M. J. Chem. Phys. 1992, 97, 5239.
68. Kadish, K. M.; Franzen, M. M.; Han, B. C.; Araullo-McAdams, C.; Sazou, D. J. Am. Chem. Soc. 1991, 113, 512.
69. 1(π,π*) spectrum of NiDPP occurs about 5 nm to shorter wavelengths than the position of the ground-state Soret band (Figures 3 and 4A), and (iii) the amplitude of the bleaching is about 40% of that expected based on the amplitudes of the bleachings in the Q bands.
70. Drain, C. M.; Nurco, D. J.; Medforth, C. J.; Smith, K. M.; Holten, D., manuscript in preparation.
71. 1(π,π*) decay.
72. Since similar spectra of the ligand-field excited state have been observed for NiTPP, NiOEP, NiPPDME, and all the other nickel porphyrins investigated previously, specific effects involving the peripheral groups appear to be relatively unimportant. Since similar results have been found for all of these molecules using several different excitation wavelengths, it is unlikely that the red-shifts derive from excitation of some fraction of slightly distorted molecules that may be present in solution.
73. Drain, C. M.; Nurco, D. J.; Ema, T.; Nelson, N. Y.; Medforth, C. J.; Smith, K. M.; Simpson, C.; Shelnutt, J. A.; Holten, D., manuscript in preparation.
74. x2-y2) should not have substantially different inherent decay times, and other short-lived excited states such as metal ↔ ring charge-transfer states should be at considerably higher energy.