Photoacid behavior versus proton-coupled electron transfer in phenol-Ru(bpy)32+ dyads

Journal of Physical Chemistry A

Volumn 117, Issue 28, 2013, Pages 5726-5733

  Kuss Petermann, Martin ^a   Wenger, Oliver S ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMICAL INVESTIGATIONS; INTRA-MOLECULAR ELECTRON TRANSFER; KINETIC ISOTOPE EFFECTS; METAL-TO-LIGAND CHARGE TRANSFER; ORDERS OF MAGNITUDE; PROTON-COUPLED ELECTRON TRANSFER; QUENCHING RATE CONSTANT; TRANSIENT ABSORPTION SPECTROSCOPIES;

ACTIVATION ENERGY; ELECTRON TRANSITIONS; EXCITED STATES; ISOTOPES; METAL COMPLEXES; PHENOLS; PHOTOSENSITIZERS; PROTONS; PYRIDINE; QUENCHING; RATE CONSTANTS; RUTHENIUM ALLOYS; RUTHENIUM COMPOUNDS;

FREE RADICAL REACTIONS;

ACID; ORGANOMETALLIC COMPOUND; PHENOL DERIVATIVE; PROTON; TRIS(2,2' BIPYRIDYL)RUTHENIUM(II); TRIS(2,2'-BIPYRIDYL)RUTHENIUM(II);

ARTICLE; CHEMISTRY; CONFORMATION; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; KINETICS; PHOTOCHEMISTRY; SPECTROFLUOROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

ACIDS; ELECTROCHEMICAL TECHNIQUES; ELECTRON TRANSPORT; KINETICS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PHENOLS; PHOTOCHEMICAL PROCESSES; PROTONS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84880567917     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp402567m     Document Type: Article

References (68)

1. Meyer, T. J.; Huynh, M. H. V.; Thorp, H. H. The Possible Role of Proton-Coupled Electron Transfer (PCET) in Water Oxidation by Photosystem II Angew. Chem., Int. Ed. 2007, 46, 5284-5304
2. Meyer, T. J. Chemical Approaches to Artificial Photosynthesis Acc. Chem. Res. 1989, 22, 163-170
3. Bordwell, F. G.; Cheng, J. P. Substituent Effects on the Stabilities of Phenoxyl Radicals and the Acidities of Phenoxyl Radical Cations J. Am. Chem. Soc. 1991, 113, 1736-1743
4. Warren, J. J.; Tronic, T. A.; Mayer, J. M. Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications Chem. Rev. 2010, 110, 6961-7001
5. Mayer, J. M. Proton-Coupled Electron Transfer: A Reaction Chemist's View Annu. Rev. Phys. Chem. 2004, 55, 363-390
6. Roth, J. P.; Yoder, J. C.; Won, T. J.; Mayer, J. M. Application of the Marcus Cross Relation to Hydrogen Atom Transfer Reactions Science 2001, 294, 2524-2526
7. Reece, S. Y.; Nocera, D. G. Proton-Coupled Electron Transfer in Biology: Results from Synergistic Studies in Natural and Model Systems Annu. Rev. Biochem. 2009, 78, 673-699
8. Costentin, C.; Robert, M.; Savéant, J.-M. Concerted Proton-Electron Transfers: Electrochemical and Related Approaches Acc. Chem. Res. 2010, 43, 1019-1029
9. Maki, T.; Araki, Y.; Ishida, Y.; Onomura, O.; Matsumura, Y. Construction of Persistent Phenoxyl Radical with Intramolecular Hydrogen Bonding J. Am. Chem. Soc. 2001, 123, 3371-3372
10. Markle, T. F.; Mayer, J. M. Concerted Proton-Electron Transfer in Pyridylphenols: The Importance of the Hydrogen Bond Angew. Chem., Int. Ed. 2008, 47, 738-740
11. Rhile, I. J.; Markle, T. F.; Nagao, H.; DiPasquale, A. G.; Lam, O. P.; Lockwood, M. A.; Rotter, K.; Mayer, J. M. Concerted Proton-Electron Transfer in the Oxidation of Hydrogen-Bonded Phenols J. Am. Chem. Soc. 2006, 128, 6075-6088
12. Rhile, I. J.; Mayer, J. M. One-Electron Oxidation of a Hydrogen-Bonded Phenol Occurs by Concerted Proton-Coupled Electron Transfer J. Am. Chem. Soc. 2004, 126, 12718-12719
13. Markle, T. F.; Tenderholt, A. L.; Mayer, J. M. Probing Quantum and Dynamic Effects in Concerted Proton-Electron Transfer Reactions of Phenol-Base Compounds J. Phys. Chem. B 2012, 116, 571-584
14. Markle, T. F.; Rhile, I. J.; DiPasquale, A. G.; Mayer, J. M. Probing Concerted Proton-Electron Transfer in Phenol-Imidazoles Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 8185-8190
15. Irebo, T.; Johansson, O.; Hammarström, L. The Rate Ladder of Proton-Coupled Tyrosine Oxidation in Water: A Systematic Dependence on Hydrogen Bonds and Protonation State J. Am. Chem. Soc. 2008, 130, 9194-9195
16. Sjödin, M.; Irebo, T.; Utas, J. E.; Lind, J.; Merenyi, G.; Åkermark, B.; Hammarström, L. Kinetic Effects of Hydrogen Bonds on Proton-Coupled Electron Transfer from Phenols J. Am. Chem. Soc. 2006, 128, 13076-13083
17. Schrauben, J. N.; Cattaneo, M.; Day, T. C.; Tenderholt, A. L.; Mayer, J. M. Mutiple-Site Concerted Proton-Electron Transfer Reactions of Hydrogen-Bonded Phenols are Nonadiabatic and Well Described by Semiclassical Marcus Theory J. Am. Chem. Soc. 2012, 134, 16635-16645
18. Costentin, C.; Robert, M.; Savéant, J. M.; Tard, C. Inserting a Hydrogen-Bond Relay between Proton Exchanging Sites in Proton-Coupled Electron Transfers Angew. Chem., Int. Ed. 2010, 49, 3803-3806
19. Costentin, C.; Robert, M.; Savéant, J. M.; Tard, C. H-Bond Relays in Proton-Coupled Electron Transfers. Oxidation of a Phenol Concerted with Proton Transport to a Distal base Through an OH Relay Phys. Chem. Chem. Phys. 2011, 13, 5353-5358
20. Benisvy, L.; Bittl, R.; Bothe, E.; Garner, C. D.; McMaster, J.; Ross, S.; Teutloff, C.; Neese, F. Phenoxyl Radicals Hydrogen-Bonded to Imidazolium: Analogues of Tyrosyl D of Photosystem II: High-Field EPR and DFT Studies Angew. Chem., Int. Ed. 2005, 44, 5314-5317
21. Pizano, A. A.; Yang, J. L.; Nocera, D. G. Photochemical Tyrosine Oxidation with a Hydrogen-Bonded Proton Acceptor by Bidirectional Proton-Coupled Electron Transfer Chem. Sci. 2012, 3, 2457-2461
22. Zhang, M.-T.; Irebo, T.; Johansson, O.; Hammarström, L. Proton-Coupled Electron Transfer from Tyrosine: A Strong Rate Dependence on Intramolecular Proton Transfer Distance J. Am. Chem. Soc. 2011, 133, 13224-13227
23. Markle, T. F.; Rhile, I. J.; Mayer, J. M. Kinetic Effects of Increased Proton Transfer Distance on Proton-Coupled Oxidations of Phenol-Amines J. Am. Chem. Soc. 2011, 133, 17341-17352
24. Irebo, T.; Reece, S. Y.; Sjödin, M.; Nocera, D. G.; Hammarström, L. Proton-Coupled Electron Transfer of Tyrosine Oxidation: Buffer Dependence and Parallel Mechanisms J. Am. Chem. Soc. 2007, 129, 15462-15464
25. 2+-Tyrosine Complex J. Am. Chem. Soc. 2012, 134, 16247-16254
26. Costentin, C.; Robert, M.; Savéant, J. M. Concerted Proton-Electron Transfer Reactions in Water. Are the Driving Force and Rate Constant Depending on pH When Water Acts as Proton Donor or Acceptor? J. Am. Chem. Soc. 2007, 129, 5870-5879
27. Bonin, J.; Costentin, C.; Louault, C.; Robert, M.; Savéant, J. M. Water (in Water) as an Intrinsically Efficient Proton Acceptor in Concerted Proton Electron Transfers J. Am. Chem. Soc. 2011, 133, 6668-6674
28. Manner, V. W.; DiPasquale, A. G.; Mayer, J. M. Facile Concerted Proton-Electron Transfers in a Ruthenium Terpyridine-4′-carboxylate Complex with a Long Distance between the Redox and Basic Sites J. Am. Chem. Soc. 2008, 130, 7210-7211
29. Manner, V. W.; Mayer, J. M. Concerted Proton-Electron Transfer in a Ruthenium Terpyridyl-Benzoate System with a Large Separation between the Redox and Basic Sites J. Am. Chem. Soc. 2009, 131, 9874-9875
30. Kuss-Petermann, M.; Wolf, H.; Stalke, D.; Wenger, O. S. Influence of Donor-Acceptor Distance Variation on Photoinduced Electron and Proton Transfer in Rhenium(I)-Phenol Dyads J. Am. Chem. Soc. 2012, 134, 12844-12854
31. Warren, J. J.; Menzeleev, A. R.; Kretchmer, J. S.; Miller, T. F.; Gray, H. B.; Mayer, J. M. Long-Range Proton-Coupled Electron-Transfer Reactions of Bis(imidazole) Iron Tetraphenylporphyrins Linked to Benzoates J. Phys. Chem. Lett. 2013, 4, 519-523
32. Edwards, P. P.; Gray, H. B.; Lodge, M. T. J.; Williams, R. J. P. Electron Transfer and Electronic Conduction through an Intervening Medium Angew. Chem., Int. Ed. 2008, 47, 6758-6765
33. Gray, H. B.; Winkler, J. R. Long-Range Electron Transfer Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 3534-3539
34. Eng, M. P.; Albinsson, B. Non-Exponential Distance Dependence of Bridge-Mediated Electronic Coupling Angew. Chem., Int. Ed. 2006, 45, 5626-5629
35. Weiss, E. A.; Ahrens, M. J.; Sinks, L. E.; Gusev, A. V.; Ratner, M. A.; Wasielewski, M. R. Making a Molecular Wire: Charge and Spin Transport through Para-Phenylene Oligomers J. Am. Chem. Soc. 2004, 126, 5577-5584
36. Wenger, O. S. How Donor-Bridge-Acceptor Energetics Influence Electron Tunneling Dynamics and their Distance Dependences Acc. Chem. Res. 2011, 44, 25-35
37. Indelli, M. T.; Chiorboli, C.; Flamigni, L.; De Cola, L.; Scandola, F. Photoinduced Electron Transfer across Oligo- p -Phenylene Bridges. Distance and Conformational Effects in Ru(II)-Rh(III) Dyads Inorg. Chem. 2007, 46, 5630-5641
38. Costentin, C.; Robert, M.; Savéant, J. M. Electrochemical and Homogeneous Proton-Coupled Electron Transfers: Concerted Pathways in the One-Electron Oxidation of a Phenol Coupled with an Intramolecular Amine-Driven Proton Transfer J. Am. Chem. Soc. 2006, 128, 4552-4553
39. Costentin, C.; Robert, M.; Savéant, J. M. Concerted Proton-Electron Transfers in the Oxidation of Phenols Phys. Chem. Chem. Phys. 2010, 12, 11179-11190
40. Biczok, L.; Gupta, N.; Linschitz, H. Coupled Electron-Proton Transfer in Interactions of Triplet C-60 with Hydrogen-Bonded Phenols: Effects of Solvation, Deuteration, and Redox Potentials J. Am. Chem. Soc. 1997, 119, 12601-12609
41. Gagliardi, C. J.; Westlake, B. C.; Kent, C. A.; Paul, J. J.; Papanikolas, J. M.; Meyer, T. J. Integrating Proton Coupled Electron Transfer (PCET) and Excited States Coord. Chem. Rev. 2010, 254, 2459-2471
42. Wenger, O. S. Proton-Coupled Electron Transfer Originating from Excited States of Luminescent Transition-Metal Complexes Chem.-Eur. J. 2011, 17, 11692-11702
43. Concepcion, J. J.; Brennaman, M. K.; Deyton, J. R.; Lebedeva, N. V.; Forbes, M. D. E.; Papanikolas, J. M.; Meyer, T. J. Excited-State Quenching by Proton-Coupled Electron Transfer J. Am. Chem. Soc. 2007, 129, 6968-6969
44. 190 pair of Photosystem II J. Am. Chem. Soc. 2008, 130, 10466-10467
45. Bronner, C.; Wenger, O. S. Proton-Coupled Electron Transfer between 4-Cyanophenol and Photoexcited Rhenium(I) Complexes with Different Protonatable Sites Inorg. Chem. 2012, 51, 8275-8283
46. 2+ by Phenols J. Phys. Chem. Lett. 2012, 3, 70-74
47. Wenger, O. S. Proton-Coupled Electron Transfer with Photoexcited Metal Complexes Acc. Chem. Res. 2013, 10.1021/ar300289x
48. Renger, G.; Renger, T. Photosystem II: The Machinery of Photosynthetic Water Splitting Photosynth. Res. 2008, 98, 53-80
49. Magnuson, A.; Berglund, H.; Korall, P.; Hammarström, L.; Åkermark, B.; Styring, S.; Sun, L. C. Mimicking Electron Transfer Reactions in Photosystem II: Synthesis and Photochemical Characterization of a Ruthenium(II) tris(bipyridyl) Complex with a Covalently linked Tyrosine J. Am. Chem. Soc. 1997, 119, 10720-10725
50. 190 pair of PSII Angew. Chem., Int. Ed. 2005, 44, 1536-1540
51. Sun, L. C.; Burkitt, M.; Tamm, M.; Raymond, M. K.; Abrahamsson, M.; LeGourriérec, D.; Frapart, Y.; Magnuson, A.; Kenéz, P. H.; Brandt, P.; Tran, A.; Hammarström, L.; Styring, S.; Åkermark, B. Hydrogen-Bond Promoted Intramolecular Electron Transfer to Photogenerated Ru(III): A Functional Mimic of Tyrosine(Z) and Histidine 190 in Photosystem II J. Am. Chem. Soc. 1999, 121, 6834-6842
52. Sjödin, M.; Styring, S.; Åkermark, B.; Sun, L. C.; Hammarström, L. Proton-Coupled Electron Transfer from Tyrosine in a Tyrosine-Ruthenium-Tris-Bipyridine Complex: Comparison with Tyrosine(z) Oxidation in Photosystem II J. Am. Chem. Soc. 2000, 122, 3932-3936
53. Johansson, O.; Wolpher, H.; Borgström, M.; Hammarström, L.; Bergquist, J.; Sun, L. C.; Åkermark, B. Intramolecular Charge Separation in a Hydrogen Bonded Tyrosine-Ruthenium(II)-Naphthalene Diimide Triad Chem. Commun. 2004, 194-195
54. Hankache, J.; Niemi, M.; Lemmetyinen, H.; Wenger, O. S. Photoinduced Electron Transfer in Linear Triarylamine-Photosensitizer-Anthraquinone Triads with Ruthenium(II), Osmium(II), and Iridium(III) Inorg. Chem. 2012, 51, 6333-6344
55. Cargill Thompson, A. M. W.; Smailes, M. C. C.; Jeffery, J. C.; Ward, M. D. Ruthenium Tris-(bipyridyl) Complexes with Pendant Protonatable and Deprotonatable Moieties: pH Sensitivity of Electronic Spectral and Luminescence Properties J. Chem. Soc., Dalton Trans. 1997, 737-743
56. 2+ J. Phys. Chem. 1986, 90, 548-550
57. Weller, A. Photoinduced Electron-Transfer in Solution-Exciplex and Radical Ion-Pair Formation Free Enthalpies and their Solvent Dependence Z. Phys. Chem. 1982, 133, 93-98
58. 2+/1+/0/1- J. Chem. Soc., Chem. Commun. 1981, 287-289
59. 2+-Viologen Dyad Chem.-Eur. J. 2002, 8, 102-110
60. Hanss, D.; Wenger, O. S. Conformational Effects on Long-Range Electron Transfer: Comparison of Oligo- p -Phenylene and Oligo- p -Xylene Bridges Eur. J. Inorg. Chem. 2009, 3778-3790
61. Carina, R. F.; Verzegnassi, L.; Bernardinelli, G.; Williams, A. F. Modulation of Iron Reduction Potential by Deprotonation at a Remote Site Chem. Commun. 1998, 2681-2682
62. Jones, H.; Newell, M.; Metcalfe, C.; Spey, S. E.; Adams, H.; Thomas, J. A. Deprotonation of a Ruthenium(II) Complex Incorporating a Bipyrazole Ligand Leading to Optical and Electrochemical Switching Inorg. Chem. Commun. 2001, 4, 475-477
63. 2=4,4′-Dihydroxy-2,2′-bipyridine Inorg. Chem. 2011, 50, 2754-2763
64. Vos, J. G. Excited-State Acid-Base Properties of Inorganic Compounds Polyhedron 1992, 11, 2285-2299
65. Sun, H.; Hoffman, M. Z. Protonation of the Excited-States of Ruthenium(II) Complexes Containing 2,2′-Bipyridine, 2,2′-Bipyrazine, and 2,2′-Bipyrimidine Ligands in Aqueous Solution J. Phys. Chem. 1993, 97, 5014-5018
66. Giordano, P. J.; Bock, C. R.; Wrighton, M. S.; Interrante, L. V.; Williams, R. F. X. Excited-State Proton-Transfer of a Metal-Complex- Determination of Acid Dissociation-Constant for a Metal-to-Ligand Charge-Transfer State of a Ruthenium(II) Complex J. Am. Chem. Soc. 1977, 99, 3187-3189
67. Bare, W. D.; Mack, N. H.; Demas, J. N.; DeGraff, B. A. pH-Dependent Photophysical Behavior of Rhenium Complexes Containing Hydroxypyridine Ligands Appl. Spectrosc. 2004, 58, 1093-1100
68. Biczók, L.; Linschitz, H. Concerted Electron and Proton Movement in Quenching of Triplet C-60 and Tetracene Fluorescence by Hydrogen-Bonded Phenol-Base Pairs J. Phys. Chem. 1995, 99, 1843-1845