Generalized Mulliken-Hush analysis of electronic coupling interactions in compressed π-stacked porphyrin-bridge-quinone systems

Journal of the American Chemical Society

Volumn 127, Issue 32, 2005, Pages 11303-11310

  Zheng, Jieru ^a   Kang, Youn K ^b   Therien, Michael J ^b   Beratan, David N ^a  

^a DUKE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ELECTRONIC EQUIPMENT; ELECTRONS; KETONES; MATHEMATICAL MODELS; SEPARATION;

CHARGE RECOMBINATION REACTIONS; COUPLING MATRIX ELEMENTS; ELECTRONIC COUPLING; MULLIKEN-HUSH ANALYSIS;

AROMATIC COMPOUNDS;

PHENYL GROUP; PORPHYRIN; QUINONE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; ENERGY;

BENZOQUINONES; ELECTRON TRANSPORT; MOLECULAR STRUCTURE; PORPHYRINS;

EID: 23844454911     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050984y     Document Type: Article

References (65)

1. Electron Transfer in Chemistry; Balzani, V., Piotrowiak, P., Rodgers, M. A. J., Mattay, J., Astruc, D., Gray, H. B., Fukuzumi, S., Mallouk, T. E., Haas, Y., de Silva, A. P., Gould, I. R., Eds.; Wiley-VCH: Weinheim, Germany, 2001; I-V.
2. Molecular Electronics: Science and Technology, Jortner, J., Ratner, M., Eds.; Blackwell Press: Oxford, U.K., 1997.
3. May, V.; Kühn, O. Charge and Energy Transfer Dynamics in Molecular Systems; Wiley-VCH: Berlin, 2000.
4. Electron Transfer-Front Isolated Molecules to Biomolecules; Jortner, J., Bixon, M., Eds.; Advances in Chemical Physics Series 106-107; Wiley: New York, 1999.
5. Gray, H. B.; Winkler, J. R. Q. Rev. Biophys. 2003, 36, 341.
6. Bioelectronics; Willner, E., Katz, E., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
7. Long-Range Charge Transfer in DNA (I and II); Schuster, G. B., Ed.; Topics in Current Chemistry Series; Springer-Verlag: Berlin, New York, 2004; Vois. 236 and 237.
8. Endres, R. G.; Cox, D. L.; Singh, R. R. P. Rev. Mod. Phys. 2004, 76, 195.
9. Purugganan, M. D.; Kumar, C. V.; Turro, N. J.; Barton, J. K. Science 1988, 241, 1645.
10. Murphy, C. J.; Arkin, M. R.; Jenkins, Y.; Ghatlia, N. D.; Bossmann, S. H.; Turro, N. J.; Barton, J. K. Science 1993, 262, 1025.
11. Arkin, M. R.; Stemp, E. D. A.; Holmlin, R. E.; Barton, J. K.; Hörmann, A.; Olson, E. J. C.; Barbara, P. F. Science 1996, 273, 475.
12. Kelley, S. O.; Jackson, N. M.; Hill, M. G.; Barton, J. K. Angew. Chem., Int. Ed. 1999, 38, 941.
13. Wan, C. Z.; Fiebig, T.; Kelley, S. O.; Treadway, C. R.; Barton, J. K.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 6014.
14. Lewis, F. D.; Wu, T.; Zhang, Y.; Letsinger, R. L.; Greenfield, S. R.; Wasielewski, M. R. Science 1997, 277, 673.
15. Lewis, F. D.; Liu, X.; Miller, S. E.; Wasielewski, M. R. J. Am. Chem. Soc. 1999, 121, 9746.
16. Lewis, F. D.; Liu, X.; Liu, J.; Miller, S. E.; Hayes, R. T.; Wasielewski, M. R. Nature 2000, 406, 51.
17. Lewis, F. D.; Wu, T.; Liu, X.; Letsinger, R. L.; Greenfield, S. R.; Miller, S. E.; Wasielewski, M. R. J. Am. Chem. Soc. 2000, 122, 2889.
18. Lewis, F. D.; Kalgutkar, R. S.; Wu, Y.; Liu, X.; Liu, J.; Hayes, R. T.; Miller, S. E.; Wasielewski, M. R. J. Am. Chem. Soc. 2000, 122, 12346.
19. Meade, T. J.; Kayyem, J. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 352.
20. Meggers, E.; Kusch, D.; Spichty, M.; Wille, U.; Giese, B. Angew. Chem., Int. Ed. 1998, 37, 460.
21. Meggers, E.; Michel-Beyerle, M. E.; Giese, B. J. Am. Chem. Soc. 1998, 120, 12950.
22. Fukui, K.; Tanaka, K. Angew. Chem., Int. Ed. 1998, 37, 158.
23. Iovine, P. M.; Kellett, M. A.; Redmore, N. P.; Therien, M. J. J. Am. Chem. Soc. 2000, 122, 8717.
24. Iovine, P. M.; Veglia, G.; Furst, G.; Therien, M. J. J. Am. Chem. Soc. 2001, 123, 5668.
25. Kang, Y. K.; Rubtsov, I. V.; Iovine, P. M.; Chen, J.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 8275.
26. Yaliniki, S. N.; Roitbera, A. E.; Gonzalez, C.; Mujica, V.; Ratner, M. A. J. Chem. Phys. 1999, 111, 6997.
27. Brandbyge, M.; Mozos, J.-L.; Ordejon, P.; Taylor, J.; Stokbro, K. Phys. Rev. B 2002, 65, 165401.
28. Nitzan, A.; Galperin, M.; Ingold, G. L.; Grabert, H. J. Chem. Phys. 2002, 117, 10837.
29. Heath, J. R.; Rainer, M. A. Phys. Today 2003, 56, 43.
30. Nitzan, A.; Ratner, M. A. Science 2003, 300, 1384.
31. Nitzan, A. Annu. Rev. Phys. Chem. 2001, 52, 681.
32. Dreuw, A.; Worth, G. A.; Cederbaum, L. S.; Head-Gordon, M. J. Phys. Chem. 2004, 108, 19049.
33. Cave, R. J.; Newton, M. D. Chem. Phys. Lett. 1996, 249, 15.
34. Cave, R. J.; Newton, M. D. J. Chem. Phys. 1997, 106, 9213.
35. Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 1.
36. Hush, N. S. Prog. Inorg. Chem. 1967, 8, 391.
37. Hush, N. S. Electrochim. Acta 1968, 13, 1005.
38. Reimers, J. R.; Hush, N. S. J. Phys. Chem. 1991, 95, 9773.
39. Rust, M.; Lappe, J.; Cave, R. J. J. Phys. Chem. A 2002, 106, 3930.
40. Creutz, C.; Newton, M. D.; Sutin, N. J. Photochem. Photobiol., A 1994. 82, 47.
41. There ure two LE states for porphyrin structure (polarized X and Y). The reported electronic coupling data in this article were the average result of those two states.
42. (a) Zerner, M. C.; Loew, G. H.; Kirchner, R. F.; MuellerWesterhoff, U. T. J. Am. Chem. Soc. 1980, 102, 589.
43. (b) Thompson, M. A. (mark@arguslab.com). ArgusLah 4.0; Planaria Software LLC: Seattle, WA, 2004 (http://www.arguslab.com).
44. Newton, M. D. J. Phys. Chem. 1991, 95, 30.
45. Newton, M. D.; Ohta, K.; Zhong, E. J. Phys. Chem. 1991, 95, 2317.
46. Newton, M. D. Chem. Rev. 1991, 91, 767.
47. Cave, R. J.; Newton, M. D.; Kumar, K.; Zimmt, M. B. J. Phys. Chem. 1995, 99, 17501.
48. Ungar, L. W.; Newton, M. D.; Voth, G. A. J. Phys. Chem. B 1999, 103, 7367.
49. Lee, M.; Shephard, M. J.; Risser, S. M.; Priyadarshy, S.; Paddon-Row, M. N.; Beratan, D. N. J. Phys. Chem. A 2000, 104, 7593.
50. House, H. O.; Koepsell, D. G.; Campbell, W. J. J. Org. Chem. 1972, 37, 1003.
51. Clough, R. L.; Rung, W. J.; Marsh, R. E.; Roberts, J. D. J. Org. Chem. 1976, 41, 3603.
52. HyperChem4.5; Hypercube, Inc.: Gainesville, FL, 1995.
53. 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.; 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.; Rega, N.; Salvador, P.; Dannenberg, J. J.; 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.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11.3: Gaussian, Inc.: Pittsburgh, PA, 2002.
54. The "exptl distance" column in Table 1 is based on the NMR data of molecule 2a (the same structure as 2a-Zn except without Zn); the "1low" in Tables 1 and 2 is based on the calculated structure using CHARMm, which is published in ref 24; the distance information of 1,8-diphenyl-naphthalene is from X-ray data of refs 49 and 50.
55. For la-Zn, we included all single excitations from the highest 26 occupied molecular orbitals (MOs) to the lowest 26 virtual MOs: IOr 2a-Zn we included all single excitations from the highest 34 occupied MOs to the lowest 34 virtual MOs; for 3a-Zn we included all single excitations from the highest 42 occupied MOs to the lowest 42 virtual MOs, and for 4a-Zn we included all single excitations from the highest 50 occupied MOs to the lowest 50 virtual MOs. The number was chosen based on analysis of the convergence of the electronic coupling. These excitations include CI excitations of bridge (π) to bridge (π*) and donor (π) Io bridge (π*). as well as the porphyrin and quinone local excitations.
56. It may seem that the D A distances for the PM3-based (2-3)a-Zn structures are smaller than those for the DFT-based structures. However, that is because the axis through the centers of the phenyl and quinonyl rings is not perpendicular to the porphyrin plane, not because of tighter stacking of the rings. This can be proven by the fact that the D-A center-to-center distance of PM3-based structures is always about I Å larger than that in DFT-based structures.
57. Tavernier, H. L.; Payer, M. D. J. Phys. Chem. B 2000, 104, 11541.
58. Voityuk, A. A.; Rosch, N.; Bixon, M.; Jortner, J. J. Phys. Chem. B 2000, 104, 9740.
59. Tong, G. S. M.; Kurnikov, I. V.; Beratan, D. N. J. Phys. Chem. B 2002, 104, 2381.
60. LeBard, D. N.; Lilichenko, M.; Matyushov, D. V.; Berlin, Y. A.; Ratner, M. A. J. Phys. Chem. B 2003, 107, 14509.
61. Siriwong, K.; Voityuk, A. A.; Newton, M. D.; Rösch, N. J. Phys. Chem. B 2003, 107, 2595.
62. Gupta, S.; Matyushov, D. V. J. Phys. Chem. A 2004, 108, 2087.
63. Matyushov, D. V. J. Chem. Phys. 2004, 16, 7532.
64. Troisi, A.; Ratner, M. A.; Zimmt, M. B. J. Am. Chem. Soc. 2004, 126, 2215.
65. Lewis, F. D.; Liu, J.; Weigel, W.; Rettig, W.; Kurnikov, I. V.; Beratan, D. N. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 12536.