Theoretical investigation of the electronic coupling element in bis-ruthenium porphyrin dimers

Molecular Simulation

Volumn 32, Issue 9, 2006, Pages 677-693

  Pheasant, S ^a,b   Kouzelos, J A ^a   Van Ryswyk, H ^a   Cave, R J ^a  

^a HARVEY MUDD COLLEGE   (United States)

^b RICE UNIVERSITY   (United States)

Author keywords

Compounds; Creutz Taube ion; Electronic coupling element; Ruthenium porphyrin dimers

Indexed keywords

COUPLINGS; DIMERS; ELECTRIC CONNECTORS; MOLECULAR STRUCTURE; OPTIMIZATION; PORPHYRINS; RUTHENIUM;

CREUTZ TAUBE ION; ELECTRONIC COUPLING ELEMENT; RUTHENIUM PORPHYRIN DIMERS;

ELECTRON TRANSITIONS;

EID: 33750207369     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020600863717     Document Type: Article

References (101)

1. S.S. Skourtis, D.N. Beratan. Theories of structure-function relationships for bridge-mediated electron transfer reactions. Electron Transfer-from Isolated Molecules to Biomolecules, Pt 1, pp. 377-452 (1999).
2. M.D. Newton, R.J. Cave. Molecular control of electorn and hole transfer processes: theory and applications. In Molecular Electronics, J. Jortner, M. Ratner (Eds.), Blackwell, Maiden, MA (1997).
3. R.A. Marcus. On the theory of electron transfer reactions VI. Unified treatment for homgeneous and electrode reactions.J. Chem. Phys., 43, 679 (1965).
4. N.S. Hush. Adiabtic theory of outer sphere electron transfer reactions in solution. Trans. Faraday Soc., 57, 557 (1961).
5. V.G. Levich. Present state of the theory of oxidation-reduction reactions in solution (Bulk and Electrode Reactions). Adv. Electrochem. Electrochem. Eng., 4, 249 (1966).
6. R.R. Dogonadze, A.M. Kuznetsov, M.A. Vorotyntsev. On the theory of nonradiative transitions in polar media. Phys. Status Solidi B, 54 (1972) 125, 425.
7. N.R. Kestner, J. Logan, J. Jortner. Thermal electron transfer reactions in polar solvents. J. Phys. Chem., 78, 2148 (1974).
8. M. Bixon, J. Jortner. Electron transfer - from isolated molecules to biomolecules. Electron Transfer-from Isolated Molecules to Biomolecules, Pt 1, pp. 35-202 (1999).
9. H. Sumi, R.A. Marcus. Dynamical effects in electron transfer reactions. J. Chem. Phys., 84, 4894 (1986).
10. J. Jortner, M. Bixon. Intramolecular vibrational excitations accompanying solvent-controlled electron transfer reactions. J. Chem. Phys., 88, 167 (1988).
11. R.A. Marcus, N. Sutin. Electron transfers in chemistry and biology. Biochim. Biophys. Acta. 811, 265 (1985).
12. M.D. Newton. Quantum chemical probes of electron transfer kinetics. Chem. Rev., 91, 767 (1991).
13. M.D. Newton, N. Sutin. Electron transfer reaction in condensed phases. Annu. Rev. Phys. Chem., 35, 437 (1985).
14. M.D. Newton. Quantum chemical probes of electron-transfer kinetics - the nature of donor-acceptor interactions. Chem. Rev., 91, 767 (1991).
15. D.N. Beratan, J.J. Hopfield. Calculation of electron tunneling matrix elements in rigid systems: mixed-valence dithiospirocuclohutane molecules. J. Am. Chem. Soc., 106, 1584 (1984).
16. D.N. Beratan, J.N. Onuchic. Electron-transfer - from model compounds to proteins. Adv. Chem. Ser., 71 (1991).
17. S. Larsson. Electron-exchange reactions in aqueous solution. J. Phys. Chem., 88, 1321 (1984).
18. S. Larsson. Electron transfer in proteins. Biochim. Biophys. Acta Bioenerg., 1365, 294 (1998).
19. S. Larsson. Energy saving electron pathways in proteins. J. Biol. Inorg. Chem., 5, 560 (2000).
20. S. Larsson, M. Braga. Calculation of the electronic factor. J. Photochem. Photobiol. A. Chem., 82, 61 (1994).
21. 2Chains, n = 3-16. J. Phys. Chem., 97, 4050 (1993).
22. L.A. Curtiss, C.A. Naleway, J.R. Miller. Superexchange pathway calculation of electronic coupling through cyclohexane spacers. J. Phys. Chem., 99, 1182 (1995).
23. R.J. Cave, D.V. Baxter, W.A. Goddard, J.D. Baldeschwieler. Theoretical-studies of electron-transfer in metal dimers - Xy + - ]X + Y, Where X. Y = Be, Mg. Ca, Zn, Cd. J. Chem. Phys., 87, 926 (1987).
24. E.W. Castner, D. Kennedy, R.J. Cave. Solvent as electron donor: donor/acceptor electronic coupling is a dynamical variable. J. Phys. Chem. A, 104, 2869 (2000).
25. R.J. Cave, S.J. Klippenstein, R.A. Marcus. A Semiclassical model for orientation effects in electron-transfer reactions. J Chem. Phys., 84, 3089 (1986).
26. R.J. Cave, P. Siders, R.A. Marcus. Mutual orientation effects on electron-transfer between porphyrins. J. Phys. Chem., 90, 1436 (1986).
27. P.D. Siders, R.J. Cave, R.A. Marcus. A model for orientation effects in electron-transfer reactions. J. Chem. Phys., 81, 5613 (1984).
28. D.N. Beratan, J.N. Onuchic, J.J. Hopfield. Electron-tunneling through covalent and noncovalent pathways in proteins. J. Chem. Phys., 86, 4488 (1987).
29. E. Cukier, S. Daniels, E. Vinson, R.J. Cave. Are hydrogen bonds unique among weak interactions in their ability to mediate electronic coupling? J. Phys. Chem. A, 106, 11240 (2002).
30. E. Cukier, R.J. Cave. A comparison of through-space and through-bond coupling for tunneling in alkane chains. Chem. Phys. Lett., 402, 186 (2005).
31. N.E. Miller, M.C. Wander, R.J. Cave. A theoretical study of the electronic coupling element for electron transfer in water. J. Phys. Chem. A, 103, 1084 (1999).
32. M.R. Wasielewski. Photoinduced electron-transfer in supramolecular systems for artificial photosynthesis. Chem. Rev., 92, 435 (1992).
33. J.P. Collman, C.E. Barnes, T.J. Collins, P.J. Brothers, J. Gallucci, J.A. Ibers. Binuclear ruthenium(II) porphyrins: reinvestigation of their preparation, characterization, and interactions with molecular oxygen. J. Am. Chem. Soc., 7030 (1981).
34. D. Gust, T.A. Moore, P.A. Liddell, G.A. Nemeth, L.R. Makings, A.L. Moore, D. Barrett, P.J. Pessiki, R.V. Bensasson, M. Rougee, C. Chachaty, F.C. Deschryver, M. Vanderauweraer, A.R. Holzwarth, J.S. Connolly. Charge separation in carotenoporphyrin - quinone triads - synthetic, conformational, and fluorescence lifetime studies. J. Am. Chem. Soc., 109, 846 (1987).
35. D. Gust, T.A. Moore, L.R. Makings, P.A. Liddell, G.A. Nemeth, A.L. Moore. Photodriven electron-transfer in triad molecules - a 2-step charge recombination reaction. J. Am. Chem. Soc., 108, 8028 (1986).
36. L.Y. Zhang, R.A. Friesner, R.B. Murphy. Ab initio quantum chemical calculation of electron transfer matrix elements for large molecules. J. Chem. Phys., 107, 450 (1997).
37. J.P. Collman, J.T. McDevitt, C.R. Leidner, G.T. Yee, J.B. Torrance, W.A. Little. Synthetic, electrochemical, optical, and conductivity studies of coordination polymers of iron, ruthenium, and osmium octaethylporphyrin. J. Am. Chem. Soc., 109, 4606 (1987).
38. J.P. Collman, J.T. McDevitt, G.T. Yee, C.R. Leidner, L.G. McCullough, W.A. Little, J.B. Torrance. Conductive polymers derived from iron, ruthenium, and osmium metalloporphyrins: the shish-kebab approach. Proc. Natl. Acatl. Sci. USA, 83, 4581 (1986).
39. H.L. Anderson, Building molecular wires from the colours of life: conjugated porphyrin oligomers. Chem. Commun. (Camb.), 2323 (1999).
40. N. Aratani, A. Osuka, Y.H. Kim, D.H. Jeong, D. Kim. Extremely long, discrete meso-meso-coupled porphyrin arrays. Angew. Chem. Int. Ed., 39, 1458 (2000).
41. L. Baldini, C.A. Hunter. Self-assembly of porphyrin arrays. Adv. Inorg. Chem., 213 (2002).
42. R.A. Haycock, C.A. Hunter, D.A. James, U. Michelsen, L.R. Sutton. Self-assembly of oligomeric porphyrin rings. Org. Lett., 2435 (2000).
43. G.A.T. Mines, B.C. Tzeng, K.J. Stevenson, J. Li, J.T. Hupp. Microporous supratnolecular coordination compounds as chemosensory photonic lattices. Angew. Chem., 41, 154 (2002).
44. K.F.S. Czaplewski, J.T. Hupp, R.Q. Snurr. Molecular squares as molecular sieves: size-selective transport through porousmembrane-supported thin-film materials. Adv. mater., 1895 (2001).
45. R.T. Kumar, I. Diskin-Posner, I. Goldberg. Solid-Mate supramolecular chemistry of porphyrins. Ligand-bridged tetraphenylmetalloporphyrin dimers. J. Inclusion Phenom. Macrocycl. Chem., 219 (2000).
46. N. Aratani, A. Osuka. A new strategy for construction of covalently linked giant porphyrin arrays with one. two, and three dimensionally arranged architectures. Bull. Chem. Soc. Jpn., 1361 (2001).
47. J.J. Piet, P.N. Taylor, B.R. Wegewijs, H.L. Anderson, A. Osuka, J.M. Warman. Photoexcitations of covalently bridged zinc porphyrin oligomers: Frenkel versus Wannier-Mott type excitons. J. Phys. Chem. B, 97 (2001).
48. T.-B. Tsao, G.-H. Lee, C.-Y. Yeh, S.-M. Peng. Supramolecular assembly of linear trinickel complexes incorporating metalloporphyrins: a novel one-dimensional polymer and oligomer. Dalton Trans., 1465 (2003).
49. R.S. Loewe, R.K. Lammi, J.R. Diers, C. Kirmaier, D.F. Bocian, D. Holten, J.S. Lindsey. Design and synthesis of light-harvesting rods for intrinsic rectification of the migration of excited-state energy and ground-state holes. J. Mater, Chem., 1530 (2002).
50. T.S. Balaban, R. Goddard, M. Linke-Schaetzel, J.-M. Lehn. 2-Aminopyrimidine directed self-assembly of zinc porphyrins containing bulky 3,5-Di-tert-butylphenyl groups. J. Am. Chem. Soc., 4233 (2003).
51. M.L. Merlau, M. del Pilar Mejia, S.T. Nguyen, J.T. Hupp. Artificial enzymes formed via directed assembly of molecular square-encapsulated epoxidation catalysts. Angew. Chem., 40, 4369 (2001).
52. T. Kawatsu, D.N. Beratan, T. Kakitani. Conformationally averaged score functions for electronic propagation in proteins. J. Phys. Chem. B. 110 (2006) in press.
53. K. Funatsu, T. Imamura, A. Ichimura, Y. Sasaki. Novel cofacial ruthenium(II) porphyrin dimers and tetramers. Inorg. Chem., 37, 4986 (1998).
54. B.S. Brunschwig, C. Creutz, N. Sutin. Electroabsorption spectroscopy of charge transfer states of transition metal complexes. Coord. Chem. Rev., 177, 61 (1998).
55. J.R. Reimers, Z.-L. Cai, N.S. Hush. A priori evaluation of the solvent contribution to the reorganization energy accompanying intramolecular electron transfer: predicting the nature of the Creutz-Taube ion. Chem. Phys., 319, 39 (2005).
56. 3)(5)](5 +), using DFT. J. Am. Chem. Soc., 121, 11418 (1999).
57. A.D. Becke. Density-functional theory thermochemistry, 3. The role of exact exchange. J. Chem. Phys., 98, 5648 (1993).
58. P.J. Hay, W.R. Wadt. Ab initio effective core potentials for molecular calculations - potentials for the transition metal atoms Sc to Hg. J. Chem. Phys., 82, 270 (1985).
59. T.H.J. Dunning, P.J. Hay. Gaussian basis sets for molecular calculations. In Methods of Electronic Structure Theory. H.F. Schaefer (Ed.), pp. 1-50, Plenum, New York (1977).
60. G.M. Brown, F.R. Hopf, T.J. Meyer, D.G. Whitten. Effect of extraplanar ligands on the redox properties and the site of oxidation in iron, ruthenium, and osmium porphyrin complexes. J. Am. Chem. Soc., 97, 5385 (1975).
61. C. Liang, M.D. Newton. Ab Initio studies of electron transfer: pathway analysis of effective transfer integrals. J. Phys. Chem., 96, 2855 (1992).
62. C. Liang, M.D. Newton. Ab Initio studies of electron transfer 2. Pathway analysis for homologous organic spacers. J. Phys. Chem., 97, 3199 (1992).
63. L.A. Curtiss, J.R. Miller. Distance dependence of electronic coupling through trans alkyl chains: effects of electron correlation. J. Phys. Chem. A, 102, 160 (1998).
64. C.X. Liang, M.D. Newton. Ab initio studies of electron-transfer - pathway analysis of effective transfer integrals. J. Phys. Chem., 96, 2855 (1992).
65. J. Logan, M.D. Newton. Ab Initio study of electronic coupling in the aqueous Fe + 2-Fe + 3 electron exchange process. J. Chem. Phys., 4086 (1983).
66. I.V. Kurnikov, D.N. Beratan. Ab initio based effective hamiltonians for long-range electron transfer: Hartree-Fock analysis. J. Chem. Phys., 105, 9561 (1996).
67. A.A. Stuchebrukhov. Tunneling currents in long-distance electron transfer reactions. III. Many-electron formulation. J. Chem. Phys., 108, 8499 (1998).
68. A.A. Stuchebrukhov. Tunneling currents in long-distance electron transfer reactions. IV. Many-electron formulation. Nonorthogonal atomic basis sets and Mulliken population analysis. J. Chem. Phys., 108, 8510 (1998).
69. R.J. Cave, M.D. Newton. Generalization of the Mulliken-Hush treatment for the calculation of electron transfer matrix elements. Chem. Phys. Lett., 249, 15 (1996).
70. R.J. Cave, M.D. Newton. Calculation of electronic coupling matrix elements for ground and excited state electron transfer reactions: comparison of the generalized Mulliken-Hush and block diagonalization methods. J. Chem. Phys., 106, 9213 (1997).
71. A. Voiytuk, N. Rosch. Fragment charge difference method for estimating donor-acceptor electronic coupling: application to DNA pi-stacks. J. Chem. Phys., 117, 5607 (2002).
72. J. Lappe, R.J. Cave, M.D. Newton, I. Rostov, A theoretical investigation of charge transfer in several substituted acridinium ions. J. Phys. Chem. B, 109, 6610 (2005).
73. R. Parr, W. Yang. Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York (1989).
74. D.P. Chong, O.V. Gritsenko, E.J. Baerends. Interpretation of the Kohn-Sham orbital energies as approximate vertical ionization potentials. J. Chem. Phys., 116, 1760 (2002).
75. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.J.A. Montgomery, R.E. Stratmann, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J.Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Gaussian, Inc., Pittsburgh, PA (2001).
76. M.J.T. Frisch, G.W. Schlegel, H.B. Scuseria, G.E. Robb, M.A. Cheeseman, J.R. Montgomery Jr., J.A. Vreven, T. Kudin, K.N. Burant, J.C. Millam, J.M. Iyengar, S.S. Tomasi, J. Barone, V. Mennucci, B. Cossi, M. Scalmani, G. Rega, N. Petersson, G.A. Nakatsuji, H. Hada, M. Ehara, M. Toyota, K. Fukuda, R. Hasegawa, J. Ishida, M. Nakajima, T. Honda, Y. Kitao, O. Nakai, H. Kiene, M. Li, X. Knox, J.E. Hratchian, H.P. Cross, J.B. Bakken, V. Adamo, C. Jaramillo, J. Gomperts, R. Stratmann, R.E. Yazyev, O. Austin, A.J. Cammi, R. Pomelli, C. Ochterski, J.W. Ayala, P.Y. Morokuma, K. Voth, G.A. Salvador, P. Dannenberg, J.J. Zakrzewski, V.G. Dapprich, S. Daniels, A.D. Strain, M.C. Farkas, O. Malick, D.K. Rabuck, A.D. Raghavachari, K. Foresman, J.B. Ortiz, J.V. Cui, Q. Baboul, A.G. Clifford, S. Cioslowski, J. Stefanov, B.B. Liu, G. Liashenko, A. Piskorz, P. Komaromi, I. Martin, R.L. Fox, D.J. Keith, T. Al-Lahain, M.A. Peng, C.Y. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople. Gaussian 03, Gaussian Inc., Wallingford, CT (2004).
77. Cerius 2, 3.5 and 3.7, Molecular Simulations Inc., La Jolla, CA (1997).
78. M.C. Zerner. ZINDO, 3.7. Molecular Simulations Inc., San Diego, CA, 1991 (1991).
79. W. Koch, M.C. Holthausen. A Chemist's Guide to Density Functional Theory. Wliey-VCH, New York. NY (2001).
80. B.S. Brunschwig, C. Creutz, N. Sutin. Optical transitions of symmetrical mixed-valence systems in the class II-III Regime. Chem. Soc. Rev. 31, 168 (2002).
81. G.M. Brown, F.R. Hopf, J.A. Ferguson, T.J. Meyer, D.G. Whitten. Mettaloporphyrin redox chemistry. The effect of extra planar ligands on the site of oxidation in ruthenium porphyrins. J. Am. Chem. Soc., 95, 5939 (1973).
82. A. Dreuw, J.L. Weisman, M. Head-Gordon. Long-range chrage-transfer excited states in time-dependent density functional theory require non-local exchange. J. Chem. Phys., 119, 2943 (2003).
83. Z.-L. Cai, K. Sendt, J.R. Reimers. Failure of density-functional theory and time-dependent density-functional theory for large extended pi systems. J. Chem. Phys., 117, 5543 (2002).
84. S. van Gisbergen, V. Osinga, O.V. Gritsenko, R. vanLeeuwen, J.G. Snijders, E.J. Baerends. Improved density functional theory results for frequency-dependent polarizabilities. by the use of an exchange-correlation potential with correct asymptotic behavior. J. Chem. Phys., 105, 3142 (1996).
85. B. Champagne, E.A. Perpete, S.J.A. v. E.J. Gisbergen, J.G. Baerends, C. Snijders, K.A. Soubra-Ghaoui, B Robins. Assessment of conventional density functional theory schemes for computing the polarizabilities and hyperpolarizabilities of conjugated oligomers: an ab initio investigation of polyacetylene chains. J. Chem. Phys., 109, 10489 (1998).
86. A.A. Stuchebrukhov. Tunneling currents in electron transfer reaction in proteins. 2. Calculation of electronic superexchange matrix element and tunneling currents using nonorthogonal basis sets. J. Chem., Phys., 105, 10819 (1996).
87. A.A. Stuchebrukhov. Tunneling currents in proteins: nonorthogonal atomic basis sets and Mulliken population analysis. J. Chem. Phys., 107, 6495 (1997).
88. A.A. Stuchebrukhov. Toward ah initio theory of long-distance electron tunneling in proteins: tunneling currents approach. Adv. Chem. Phys., 118, 1 (2001).
89. G.S.M. Tong, I.V. Kurnikov, D.N. Beratan. Tunneling energy effects on GC oxidation in DNA. J. Phys. Chem. B, 106, 2381 (2002).
90. M.V. Basilevsky, G.E. Chudinov, M.D. Newton. The multiconfigurational adiabatic electron-transfer theory and its invariance under transformations of charge-density basis functions. Chem. Phys., 179, 263 (1994).
91. M.V. Basilevsky, G.E. Chudinov, I.V. Rostov, Y.P. Liu, M.D. Newton. Quantum-chemical evaluation of energy quantities governing electron transfer kinetics: applications to intramolecular processes. J. Mol. Struct. (Theochem), 371, 191 (1996).
92. M.V. Basilevsky, I.V. Rostov, M.D. Newton. A two-dimensional Born-Oppenheimer treatment of intramolecular electron transfer reactions. J. Electroanal. Chem., 450, 69 (1998).
93. M.V. Basilevsky, I.V. Rostov, M.D. Newton. A frequency-resolved cavity model (FRCM) for treating equilibrium and nonequilibrium solvation energies. Chem. Phys., 232, 189 (1998).
94. M.V. Basilevsky, I.V. Rostov, M.D. Newton. A two-dimensional Born-Oppenheimer treatment of intramolecular electron transfer reactions. J. Electroanal. Chem., 450, 69 (1998).
95. H.M. McConnell. Intramolecular charge transfer in aromatic free radicals. J. Chem. Phys., 35, 508 (1961).
96. D.N. Beratan. Electron-tunneling through rigid molecular Bridges-Bicyclo[2.2.2]Octane. J. Am. Chem. Soc., 108, 4321 (1986).
97. J.F. Stanton, RJ. Bartlett. The equation of motion coupled-cluster method. A systematic biorthogonal approach to molecular excitation energies, transition probabilities, and excited state properties. J. Chem. Phys., 98, 7029 (1993).
98. M. Nooijen. Similarity transformed equation of motion coupledcluster study of excited states of selected azabenzenes. Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 55, 539 (1999).
99. I. Daizadeh, E.S. Medvedev, A.A. Stuchebrukhov. Effect of protein dynamics on biological electron transfer. Proc. Natl. Acad. Sci. USA, 94, 3703 (1997).
100. S.S. Skourtis, I.A. Balabin, T. Kawatsu, D.N. Beratan. Protein dynamics and electron transfer: electronic decoherence and noncondon effects. Proc. Natl. Acad. Sci. USA, 102, 3552 (2005).
101. G. Jones II, L.N. Lu, H. Pu, C.W. Farahat, C. Oh, S.R. Greenfield, D.J. Gosztola, M.R. Wasielewski. Intramolecular electron transfer across amino acid spacers in the picosecond time regime. Charge transfer interaction through peptide bonds. J. Phys. Chem. B, 103, 572 (1999).