Photophysical and structural properties of saddle-shaped free base porphyrins: Evidence for an "orthogonal" dipole moment

Journal of Physical Chemistry B

Volumn 105, Issue 32, 2001, Pages 7818-7829

  Sazanovich, Igor V ^a   Galievsky, Victor A ^a   Van Hoek, Arie ^b   Schaafsma, Tjeerd J ^b   Malinovskii, Vladimir L ^c   Holten, Dewey ^d   Chirvony, Vladimir S ^a  

^a B I STEPANOV INSTITUTE OF PHYSICS   (Belarus)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c A V BOGATSKY PHYSICO CHEMICAL INSTITUTE   (Ukraine)

^d WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

ABSORPTION; ADDITION REACTIONS; CHEMICAL BONDS; CHROMOPHORES; CONFORMATIONS; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; FLUORESCENCE; GROUND STATE; MOLECULAR DYNAMICS; NITROGEN; SPECTRUM ANALYSIS;

PORPHYRINS;

EID: 0035899708     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp010274o     Document Type: Article

References (55)

1. (a) Tronrud, D.E.; Schmid, M.F.; Matthews, B.W. J. Mol. Biol. 1986, 188, 443-454.
2. (b) Martinez, S.E.; Smith, J.L.; Huang, D.; Szczepaniak, A.; Cramer, W.A. In Research in Photosynthesis; Murata, N., Ed.; Proceedings of the IXth International Congress on Photosynthesis; Kluwer Academic: Dordrecht, The Netherlands, 1992; Vol. 2, p 495.
3. (c) Ermler, V.; Fritch, G.; Buchanan, S.K.; Michel, H. Structure 1994, 2, 925.
4. (d) Deisenhofer, J.; Epp, O.; Sinning, I.; Michel, H. J. Mol. Biol. 1995, 246, 429.
5. (e) Crane, B.R.; Siegel, L.M.; Getzoff, E.D. Science 1995, 270, 59.
6. (f) Freer, A.; Prince, S.; Sauer, K.; Papaz, M.; Hawthornthwaite-Lawless, A.; McDermott, G.; Cogdell, R.; Isaacs, N.W. Structure 1996, 4, 449.
7. (g) McDermott, G.; Prince, S.M.; Freer, A.A.; Hawthornthwaite-Lawless, A.M.; Papiz, M.Z.; Cogdell, R.J.; Isaacs, N.W. Structure 1996, 4, 243-251.
8. (a) Medforth, C.J.; Senge, M.O.; Smith, K.M.; Sparks, L.D.; Shelnutt, J.A. J. Am. Chem. Soc. 1992, 114, 9859-9869.
9. (b) Nurco, D.J.; Medforth, C.J.; Forsyth, T.P.; Olmstead, M.M.; Smith, K.M. J. Am. Chem. Soc. 1996, 118, 10 918.
10. (c) Barkigia, K.M.; Nurco, D.J.; Renner, M.W.; Melamed, D.; Smith, K.M.; Fajer, J. J. Phys. Chem. B. 1998, 102, 322.
11. (d) Senge, M.O.; Z. Naturforsch 1999, 54b, 821.
12. Senge, M.O.; Kalish, W.W. Inorg. Chem. 1997, 36, 6103.
13. (a) Barkigia, K.M.; Berber, M.D.; Fajer, J.; Medforth, C.J.; Renner, M.W.; Smith, K.M. J. Am. Chem. Soc. 1990, 112, 8851.
14. (b) Barkigia, K.M.; Renner, M.W.; Furenlid, L.R.; Medforth, C.J.; Smith, K.M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 3627-3635.
15. (c) Regev, A.; Galili, T.; Medforth, C.J.; Smith, K.M.; Barkigia, K.M.; Fajer, J.; Levanon, H. J. Phys. Chem. 1994, 98, 2520-2526.
16. (a) Sparks, L.D.; Medforth, C.J.; Park, M.-S.; Chamberlian, J.R.; Ondrias, M.R.; Senge, M.O.; Smith, K.M.; Shelnutt, J.A. J. Am. Chem. Soc. 1993, 115, 581-592.
17. Jentzen, W.; Simpson, M.C.; Hobbs, J.D.; Song, X.; Ema, T.; Nelson, N.Y.; Medforth, C.J.; Smith, K.M.; Veyrat, M.; Maxxanti, M.; Ramasseul, R.; Marchon, J.-C.; Takeuchi, T.; Gaddard, W.A.; Shelnutt, J.A. J. Am. Chem. Soc. 1995, 117, 11 085-11 097.
18. (a) Takeda, J.; Ohya, T.; Sato, M. Chem. Phys. Lett. 1991, 183, 384-386.
19. (b) Charlesworth, P.; Truscott, T.G.; Kessel, D.; Medforth, C.J.; Smith, K.M. J. Chem. Soc., Faraday Trans. 1994, 90, 1073-1076.
20. (c) Maiti, N.C.; Ravikanth, M. J. Chem. Soc., Faraday Trans. 1996, 92, 1095-1100.
21. (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, 7363-7368.
22. (b) Gentemann, S.; Medforth, C.J.; Ema, T.; Nelson, N.Y.; Smith, K.M.; Fajer, J.; Holten, D. Chem. Phys. Lett. 1995, 245, 441-447.
23. (c) Gentemann, S.; Nelson, N.Y.; Jaquinod, L.; Nurco, D.J.; Leung, S.H.; Medforth, C.J.; Smith, K.M.; Fajer, J.; Holten, D. J. Phys. Chem. B 1997, 101, 1247-1254.
24. (d) Retsek, J.L.; Gentemann, S.; Medforth, C.J.; Smith, K.M.; Chirvony, V.S.; Fajer, J.; Holten, D. J. Phys. Chem. B 2000, 104, 6690-6693.
25. (e) Retsek, J.L.; Medforth, C.J.; Nurco, D.J.; Gentemann, S.; Chirvony; V.S.; Smith, K.M.; Holten, D. J. Phys. Chem., submitted.
26. (a) Drain, C.M.; Kirmaier, C.; Medforth, C.J.; Nurco, D.J.; Smith, K.M.; Holten, D. J. Phys. Chem. 1996, 100, 11 984-11 993.
27. (b) Drain, C.M.; Gentemann, S.; Roberts, J.A.; Nelson, N.Y.; Medforth, C.J.; Jia, S.; Simpson, M.C.; Smith, K.M.; Fajer, J.; Shelnutt, J.A.; Holten., D. J. Am. Chem. Soc. 1998, 120, 3781-3791.
28. Chirvony, V.S.; van Hoek, A.; Galievsky, V.A.; Sazanovich, I.V.; Schaafsma, T.J.; Holten, D. J. Phys. Chem. 2000, 104, 9909-9917.
29. (a) Barkigia, K.M.; Chantranupong, L.; Smith, K.M.; Fajer, J. J. Am. Chem. Soc. 1988, 110, 7566.
30. (b) Shelnutt, J.A.; Song, X.Z.; Ma, J.-G.; Jia, S.L.; Jentzen, W.; Medforth, C.J. Chem. Soc. Rev. 1998, 27, 31.
31. (a) Franzen, S.; Lambry, B.; Bohn, B.; Poyart, C.; Martin, J.-L. Nature Struct. Biol. 1994, 1, 230-233.
32. (b) Springer, B.A.,; Sligar, S.G.; Olson, J.S.; Phillips, G.N. Chem. Rev. 1994, 94, 699-714.
33. Little, R.G.; Anton, J.A.; Loach, P.A.; Ibers, J.A. J. Heterocycl. Chem. 1975, 12, 343.
34. Bruggeman, Y.E.; Boogert, A.; Van Hoek, A.; Jones, P.T.; Winter, G.; Schots, A.; Hilhorst, R. FEBS Lett. 1996, 388, 242.
35. Van Hoek, A.; Visser, A.J.W.G. Analytical Instrumentation 1985, 14, 359.
36. Vos, K.; Van Hoek, A.; Visser, A.J.W.G. Eur. J. Biochem. 1987, 165, 55.
37. Stewart, J.J.P. J. Comput. Chem. 1991, 12, 320.
38. HyperChem, Molecular Visualization and Simulation, Hypercube, Inc.
39. (a) Ridley, J.; Zemer, M.C. Theor. Chim. Acta 1973, 32, 111.
40. (b) Ridley, J.; Zerner, M.C. Theor. Chim. Acta 1976, 42, 223.
41. (c) Zerner, M.C.; Loew, G.H.; Kirchner, R.F.; Mueller-Westerhoff, U.T. J. Am. Chem. Soc. 1980, 102, 589.
42. N (see ref 19b) was used to characterize the solvent polarity. Similar trends are found using the dielectric constant.
43. (b) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; Mir: Moscow, 1991; Chapter 7, pp 524-530.
44. 0), will depend on the detection wavelength and the time-response and overall time scale of the measurements.
45. (b) Akimoto, S.; Yamazaki, T.; Yamazaki, I.; Osuka, A. Chem. Phys. Lett. 1999, 309, 177.
46. (c) Galievsky, V.A.; Dobkowski, J.; Waluk, J.; Chirvony, V.S., to be published.
47. Ethyl groups are mildly electron donating in character while phenyl groups substituents are weakly electron withdrawing.
48. (a) Takeda, J.; Sato, M. Chem. Lett. 1995, 971.
49. (b) Li, M.; Xiao, Z.; Xiong, H.; Lu, Z. Spectrochim. Acta, Part A, 1997, 53, 1691.
50. Parusel, A.B.J.; Wondimagegn, T.; Gosh, A. J. Am. Chem. Soc. 2000, 122, 6371.
51. Siebrand, W. J. Chem. Phys. 1967, 46, 440-447.
52. 2OETPP.
53. Chirvony, V.S.; van Hoek, A.; Schaafsma, T.J.; Pershukevich, P.P.; Filatov, I.V.; Avilov, I.V.; Shishporenok, I.V.; Terekhov, S.N.; Malinovskii, V.L. J. Phys. Chem. B 1998, 102, 9714.
54. Minkin, V.I.; Osipov, O.A.; Zhdanov, Yu.A. Dipol'nyie Momenty (Dipole moments); Khimiia: Leningrad, 1968; Chapter 3 (in Russian).
55. We note that the standard explanation of a drop in energy and contribution of charge-transfer states to nonradiative decay does not play a significant role (if any) in these free-base porphyrins. In particular, the only possible charge-transfer states involve the macrocycle and the peripheral meso-phenyl rings, and our calculations suggest that these states are not sufficiently low in energy for our compounds as well as for the related planar porphyrins. Such additional states did not appear also in case of a rotation of the phenyl substituents toward their coplanarity with the "porphyrin plane".