Ultrafast long-distance excitation energy transport in donor-bridge- acceptor systems

Journal of Physical Chemistry A

Volumn 117, Issue 5, 2013, Pages 918-928

  Duvanel, Guillaume ^a   Grilj, Jakob ^a   Vauthey, Eric ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DONOR-BRIDGE-ACCEPTOR SYSTEMS; EXCITED-STATE DYNAMICS; FREE BASE; INTERNAL CONVERSIONS; PICOSECOND TIME SCALE; SINGLET EXCITED STATE; SORET BANDS; SPECTROSCOPIC DATA; TETRAPHENYL PORPHYRINS; TIME-RESOLVED; TIME-SCALES; ULTRA-FAST; ULTRAFAST SPECTROSCOPY; ZINC TETRAPHENYLPORPHYRIN;

ENERGY TRANSFER; PORPHYRINS;

EXCITED STATES;

ALKYNE; ETHER DERIVATIVE; METALLOPORPHYRIN; PHENYLENEETHYNYLENE; PORPHYRIN; TETRAPHENYLPORPHYRIN; TETRAPHENYLPORPHYRIN ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENERGY TRANSFER; QUANTUM THEORY;

ALKYNES; ENERGY TRANSFER; ETHERS; METALLOPORPHYRINS; MOLECULAR STRUCTURE; PORPHYRINS; QUANTUM THEORY;

EID: 84873419783     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp311540x     Document Type: Article

References (78)

1. Davila, J.; Harriman, A.; Milgrom, L. R. A Light Harvesting Array of Synthetic Porphyrins Chem. Phys. Lett. 1987, 136, 427-430
2. Gust, D.; Moore, T. A.; Moore, A. L.; Gao, F.; Luttrull, D.; DeGraziano, J. M.; Ma, X. C.; Makings, L. R.; Lee, S.-J.; Trier, T. T. Long-Lived Photoinitiated Charge Separation in Carotene Diporphyrin Triad Molecules J. Am. Chem. Soc. 1991, 113, 3638-3649
3. Li, F.; Yang, S. I.; Ciringh, Y.; Seth, J.; Martin, C. H., III; Singh, D. L.; Kim, D.; Birge, R. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Design, Synthesis and Photodynamics of Light Harvesting Arrays Comprised of a Porphyrin and One, Two or Eight Boron-Dipyrrin Accessory Pigments J. Am. Chem. Soc. 1998, 120, 10001-10017
4. Brodard, P.; Matzinger, S.; Vauthey, E.; Mongin, O.; Papamicaël, C.; Gossauer, A. Investigations of Electronic Energy Transfer Dynamics in Multiporphyrin Arrays J. Phys. Chem. A 1999, 103, 5858-5870
5. Yeow, E. K. L.; Ghiggino, K. P.; Reek, J. N. H.; Crossley, M. J.; Bosman, A. W.; Schenning, A. P. H. J.; Meijer, E. W. The Dynamics of Electronic Energy Transfer in Novel Multiporphyrin Functionalized Dendrimers: A Time-Resolved Fluorescence Anisotropy Study J. Phys. Chem. B 2000, 104, 2596-2606
6. Holten, D.; Bocian, D. F.; Lindsey, J. S. Probing Electronic Communication in Covalently Linked Multiporphyrin Arrays. A Guide to the Rational Design of Molecular Photonics Devices Acc. Chem. Res. 2002, 35, 57
7. Morandeira, A.; Vauthey, E.; Schuwey, A.; Gossauer, A. Ultrafast Excited State Dynamics of Tri- and Hexaporphyrin Arrays J. Phys. Chem. A 2004, 108, 5741-5751
8. 3-Acceptor Triad J. Am. Chem. Soc. 2005, 127, 17504-17515
9. Wasielewski, M. R. Energy, Charge, and Spin Transport in Molecules and Self-Assembled Nanostructures Inspired by Photosynthesis J. Org. Chem. 2006, 71, 5051-5066
10. Kodis, G.; Terazono, Y.; Liddell, P. A.; Andréasson, J.; Garg, V.; Hambourger, M.; Moore, T. A.; Moore, A. L.; Gust, D. Energy and Photoinduced Electron Transfer in a Wheel-Shaped Artificial Photosynthetic Antenna-Reaction Center Complex J. Am. Chem. Soc. 2006, 128, 1818
11. Bhosale, S.; Sisson, A. L.; Talukdar, P.; Fürstenberg, A.; Banerji, N.; Vauthey, E.; Bollot, G.; Mareda, J.; Röger, C.; Würthner, F. Photoproduction of Proton Gradients with π-Stacked Fluorophore Scaffolds in Lipid Bilayers Science 2006, 313, 84-86
12. Kelley, R. F.; Goldsmith, R. H.; Wasielewski, M. R. Ultrafast Energy Transfer within Cyclic Self-Assembled Chlorophyll Tetramers J. Am. Chem. Soc. 2007, 129, 6384-6385
13. Mongin, O.; Pla-Quintana, A.; Terenziani, F.; Drouin, D.; Le Droumaget, C.; Caminade, A.-M.; Majoral, J.-P.; Blanchard-Desce, M. Organic Nanodots for Multiphotonics: Synthesis and Photophysical Studies New J. Chem. 2007, 31, 1354-1367
14. Gust, D.; Moore, T. A.; Moore, A. L. Solar Fuels via Artificial Photosynthesis Acc. Chem. Res. 2009, 42, 1890-1898
15. Aratani, N.; Kim, D.; Osuka, A. Discrete Cyclic Porphyrin Arrays as Artificial Light-Harvesting Antenna Acc. Chem. Res. 2009, 42, 1922-1934
16. O'Sullivan, M. C.; Sprafke, J. K.; Kondratuk, D. V.; Rinfray, C.; Claridge, T. D. W.; Saywell, A.; Blunt, M. O.; O'Shea, J. N.; Beton, P. H.; Malfois, M. Vernier Templating and Synthesis of a 12-Porphyrin Nano-Ring Nature 2011, 469, 72-75
17. Sakai, N.; Lista, M.; Kel, O.; Sakurai, S.-i.; Emery, D.; Mareda, J.; Vauthey, E.; Matile, S. Self-Organizing Surface-Initiated Polymerization: Facile Access to Complex Functional Systems J. Am. Chem. Soc. 2011, 133, 15224-15227
18. Grimm, B.; Schornbaum, J.; Jasch, H.; Trukhina, O.; Wessendorf, F.; Hirsch, A.; Torres, T.; Guldi, D. M. Step-by-Step Self-Assembled Hybrids that Feature Control over Energy and Charge Transfer Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 15565-15571
19. Oevering, H.; Paddon-Row, M. N.; Heppener, M.; Oliver, A. M.; Cotsaris, E.; Verhoeven, J. W.; Hush, N. S. Long-Range Photoinduced Through-Bond Electron Transfer and Radiative Recombination via Rigid Non-Conjugated Bridges: Distance and Solvent Dependence J. Am. Chem. Soc. 1987, 109, 3258-3269
20. Closs, G. L.; Johnson, M. D.; Miller, J. R.; Piotrowiak, P. A Connection between Intramolecular Long-Range Electron, Hole and Triplet Energy Transfer J. Am. Chem. Soc. 1989, 111, 3751-3753
21. Ratner, M. A. Bridge Assisted Electron Transfer: Effective Electronic Coupling J. Phys. Chem. 1990, 94, 4877-4883
22. Kroon, J.; Oliver, A. M.; Paddon-Row, M. N.; Verhoeven, J. W. Observation of a Remarkable Dependence of the Rate of Singlet-Singlet Energy Transfer on the Configuration of the Hydrocarbon Bridge in Bichromophoric Systems J. Am. Chem. Soc. 1990, 112, 4868-4873
23. Scholes, G. D.; Ghiggino, K. P.; Oliver, A. M.; Paddon-Row, M. N. Intramolecular Electronic Energy Transfer between Rigidly Linked Naphthalene and Anthracene Chromophores J. Phys. Chem. 1993, 97, 11871-11876
24. KilsaÌŠ, K.; Kajanus, J.; MaÌŠrtensson, J.; Albinsson, B. Mediated Electronic Coupling: Singlet Energy Transfer in Porphyrin Dimers Enhanced by the Bridging Chromophore J. Phys. Chem. B 1999, 103, 7329-7339
25. Piet, J. J.; Taylor, P. N.; Wegewijs, B. R.; Anderson, H. L.; Osuka, A.; Warman, J. M. Photoexcitations of Covalently Bridged Zinc Porphyrin Oligomers: Frenkel versus Wannier-Mott Type Excitons J. Phys. Chem. B 2001, 105, 97-104
26. Albinsson, B.; MaÌŠrtensson, J. Long-Range Electron and Excitation Energy Transfer in Donor-Bridge-Acceptor Systems J. Photochem. Photobiol., C 2008, 9, 138-155
27. Chaignon, F.; Falkenstrom, M.; Karlsson, S.; Blart, E.; Odobel, F.; Hammarström, L. Very Large Acceleration of the Photoinduced Electron Transfer in a Ru(bpy)3-Naphthalene Bisimide Dyad Bridged on the Naphthyl Core Chem. Commun. 2007, 64-66
28. Wiberg, J.; Guo, L.; Petterson, K.; Nilsson, D.; Ljungdahl, T.; MaÌŠrtensson, J.; Albinsson, B. Charge Recombination versus Charge Separation in Donor-Bridge-Acceptor Systems J. Am. Chem. Soc. 2007, 129, 155-163
29. Wenger, O. S. How Donor-Bridge-Acceptor Energetics Influence Electron Tunneling Dynamics and Their Distance Dependences Acc. Chem. Res. 2011, 44, 25-35
30. Winters, M. U.; Pettersson, K.; Martensson, J.; Albinsson, B. Competition between Superexchange Mediated and Sequential Electron Transfer in a Bridged Donor-Acceptor System Chem.-Eur. J. 2005, 11, 562-573
31. Weiss, E. A.; Tauber, M. J.; Kelley, R. F.; Ahrens, M. J.; Ratner, M. A.; Wasielewski, M. R. Conformationally Gated Switching between Superexchange and Hopping within Oligo-p-phenylene-Based Molecular Wires J. Am. Chem. Soc. 2005, 127, 11842-11850
32. Paulson, B. P.; Miller, J. R.; Gan, W.-X.; Closs, G. Superexchange and Sequential Mechanisms in Charge Transfer with a Mediating State between the Donor and Acceptor J. Am. Chem. Soc. 2005, 127, 4860-4868
33. Duvanel, G.; Grilj, J.; Schuwey, A.; Gossauer, A.; Vauthey, E. Ultrafast Excited-State Dynamics of Phenyleneethynylene Oligomers in Solution Photochem. Photobiol. Sci. 2007, 6, 956-963
34. Gurzadyan, G. G.; Tran-Thi, T.-H.; Gustavsson, T. Time-Resolved Fluorescence Spectroscopy of High-Lying Electronic States of Zn-Tetraphenylporphyrin J. Chem. Phys. 1998, 108, 385-388
35. Liu, H. Z.; Baskin, J. S.; Steiger, B.; Wan, C. Z.; Anson, F. C.; Zewail, A. H. Femtosecond Dynamics of Metalloporphyrins: Electron Transfer and Energy Redistribution Chem. Phys. Lett. 1998, 293, 1-8
36. Liu, X.; Tripathy, U.; Bhosale, S. V.; Langford, S. J.; Steer, R. P. Photophysics of Soret-Excited Tetrapyrroles in Solution. II. Effects of Perdeuteration, Substituent Nature and Position, and Macrocycle Structure and Conformation in Zinc(II) Porphyrins J. Phys. Chem. A 2008, 112, 8986-8998
37. 2-States of Porphyrin Trimers J. Phys. Chem. A 2001, 105, 4822-4833
38. Muller, P.-A.; Högemann, C.; Allonas, X.; Jacques, P.; Vauthey, E. Deuterium Isotope Effect on the Charge Recombination Dynamics of Contact Ion Pairs Formed by Electron Transfer Quenching in Acetonitrile Chem. Phys. Lett. 2000, 326, 321-327
39. Morandeira, A.; Fürstenberg, A.; Gumy, J.-C.; Vauthey, E. Fluorescence Quenching in Electron Donating Solvents. 1. Influence of the Solute-Solvent Interactions on the Dynamics J. Phys. Chem. A 2003, 107, 5375-5383
40. Morandeira, A.; Engeli, L.; Vauthey, E. Ultrafast Charge Recombination of Photogenerated Ion Pairs to an Electronic Excited State J. Phys. Chem. A 2002, 106, 4833-4837
41. Duvanel, G.; Grilj, J.; Chaumeil, H.; Jacques, P.; Vauthey, E. Ultrafast Excited-State Dynamics of a Series of Zwitterionic Pyridinium Phenoxides with Increasing Sterical Hindering Photochem. Photobiol. Sci. 2010, 9, 908-915
42. Duvanel, G.; Banerji, N.; Vauthey, E. Excited-State Dynamics of Donor-Acceptor Bridged Systems Containing a Boron-Dipyrromethene Chromophore: Interplay between Charge Separation and Reorientational Motion J. Phys. Chem. A 2007, 111, 5361-5369
43. Banerji, N.; Duvanel, G.; Perez-Velasco, A.; Maity, S.; Sakai, N.; Matile, S.; Vauthey, E. Excited-State Dynamics of Hybrid Multichromophoric Systems: Toward an Excitation Wavelength Control of the Charge Separation Pathways J. Phys. Chem. A 2009, 113, 8202-8212
44. Perdew, J. P. Density-Functional Approximation for the Correlation Energy of the Inhomogeneous Electron Gas Phys. Rev. B 1986, 33, 8822-8824
45. Schäfer, A.; Horn, H.; Ahlrichs, R. Fully Optimized Contracted Gaussian Basis Sets for Atoms Li to K J. Chem. Phys. 1992, 97, 2571-2577
46. Bauernschmitt, R.; Ahlrichs, R. Treatment of Electronic Excitations within the Adiabatic Approximation of Time Dependent Density Functional Theory Chem. Phys. Lett. 1996, 256, 454-464
47. Ahlrichs, R.; Bär, M.; Häser, M. Electronic Structure Calculations on Workstation Computers: The Program System Turbomole Chem. Phys. Lett. 1989, 162, 165-169
48. Gouterman, M. Spectra of Porphyrins J. Mol. Spectrosc. 1961, 6, 138-163
49. Magyar, R. J.; Tretiak, S.; Gao, Y.; Wang, H.-L.; Shreve, A. P. A Joint Theoretical and Experimental Study of Phenylene-Acetylene Molecular Wires Chem. Phys. Lett. 2005, 401, 149-156
50. Sluch, M. I.; Godt, A.; Bunz, U. H. F.; Berg, M. A. Excited-State Dynamics of Oligo(p-phenyleneethynylene): Quadratic Coupling and Torsional Motions J. Am. Chem. Soc. 2001, 123, 6447-6448
51. Liu, L. T.; Yaron, D. J.; Sluch, M. I.; Berg, M. A. Modelling the Effect of Torsional Disorder on the Spectra of Poly- and Oligo-(p -phenyleneethylenes) J. Phys. Chem. B 2006, 110, 18844-18852
52. Dreuw, A.; Head-Gordon, M. Failure of Time-Dependent Density Functional Theory for Long-Range Charge-Transfer Excited States: The Zincbacteriochlorin- Bacteriochlorin and Bacteriochlorophyll-Spheroidene Complexes J. Am. Chem. Soc. 2004, 126, 4007-4016
53. Karolczak, J.; Kowalska, D.; Lukaszewicz, A.; Maciejewski, A.; Steer, R. P. Photophysical Studies of Porphyrins and Metalloporphyrins: Accurate Measurements of Fluorescence Spectra and Fluorescence Quantum Yields for Soret Band Excitation of Zinc Tetraphenylporphyrin J. Phys. Chem. A 2004, 108, 4570-4575
54. Ohno, O.; Kaizu, Y.; Kobayashi, H. Luminescence of some Metalloporphins Including the Complexes of the IIIb Metal Group J. Chem. Phys. 1985, 82, 1779-1787
55. Quimby, D. J.; Longo, F. R. Luminescence Studies on several Tetraarylporphins and their Zinc Derivatives J. Am. Chem. Soc. 1975, 97, 5111-5117
56. Cho, H. S.; Song, N. W.; Kim, Y. H.; Jeoung, S. C.; Hahn, S.; Kim, D.; Kim, S. K.; Yoshida, N.; Osuka, A. Ultrafast Energy Relaxation Dynamics of Directly Linked Porphyrin Arrays J. Phys. Chem. A 2000, 104, 3287-3298
57. Villamaina, D.; Bhosale, S.; Langford, S. J.; Vauthey, E. Excited-State Dynamics of Porphyrin-Naphthalenediimide-Porphyrin Triads Phys. Chem. Chem. Phys. 2013, 15, 1177-1187
58. Petterson, K.; Kyrychenko, A.; Rönnow, E.; Ljungdahl, T.; MaÌŠrtensson, J.; Albinsson, B. Singlet Energy Transfer in Porphyrin-Based Donor-Bridge-Acceptor Systems: Interaction between Bridge Length and Bridge Energy J. Phys. Chem. A 2006, 110, 310-318
59. Edholm, O.; Blomberg, C. Stretched Exponentials and Barrier Distributions Chem. Phys. 1999, 252, 221-225
60. Wlodarczyk, J.; Kierdaszuk, B. Interpretation of Fluorescence Decays Using a Power-like Model Biophys. J. 2003, 85, 589-598
61. Baskin, J. S.; Yu, H.-Z.; Zewail, A. H. Ultrafast Dynamics of Porphyrins in the Condensed Phase: I. Free Base Tetraphenylporphyrin J. Phys. Chem. A 2002, 106, 9837-9844
62. Birks, J. B. Photophysics of Aromatic Molecules; Wiley: New York, 1970
63. Hui, M.-H.; Ware, W. R.; Exciplex Photophysics, V. The Kinetics of Fluorescence Quenchin of Anthracene by N, N -Dimethylaniline in Cyclohexane J. Am. Chem. Soc. 1976, 98, 4718-4727
64. Banerji, N.; Bhosale, S. V.; Petkova, I.; Langford, S. J.; Vauthey, E. Ultrafast Excited-State Dynamics of Strongly Coupled Porphyrin/Core-Substituted- Naphthalenediimide Dyads Phys. Chem. Chem. Phys. 2011, 13, 1019-1029
65. Rodriguez, J.; Kirmaier, C.; Holten, D. Optical Properties of Metalloporphyrin Excited States J. Am. Chem. Soc. 1989, 111, 6500-6506
66. van Stokkum, I. H. M.; Larsen, D. S.; van Grondelle, R. Global and Target Analysis of Time-Resolved Spectra Biochim. Biophys. Acta, Bioenerg. 2004, 1657, 82-104
67. Yu, H.-Z.; Baskin, J. S.; Zewail, A. H. Ultrafast Dynamics of Porphyrins in the Condensed Phase: II. Zinc Tetraphenylporphyrin J. Phys. Chem. A 2002, 106, 9845-9854
68. Elsaesser, T.; Kaiser, W. Vibrational and Vibronic Relaxation of Large Polyatomic Molecules in Liquids Annu. Rev. Phys. Chem. 1991, 42, 83-107
69. Kovalenko, S. A.; Schanz, R.; Hennig, H.; Ernsting, N. P. Cooling Dynamics of an Optically Excited Molecular Probe in Solution from Femtosecond Broadband Transient Absorption Spectroscopy J. Chem. Phys. 2001, 115, 3256-3274
70. Pigliucci, A.; Duvanel, G.; Lawson Daku, M. L.; Vauthey, E. Investigation of the Influence of Solute-Solvent Interactions on the Vibrational Energy Relaxation Dynamics of Large Molecules in Liquids J. Phys. Chem. A 2007, 111, 6135-6145
71. Förster, T. Energy Migration and Fluorescence Naturwissenschaften 1946, 33, 166-175
72. Dexter, D. L. A Theory of Sensitized Luminescence in Solids J. Chem. Phys. 1953, 21, 836-850
73. Pullerits, T.; Hess, S.; Herek, J. L.; Sundström, V. Temperature Dependence of Excitation Transfer in LH2 of Rhodobacter Sphaeroides J. Phys. Chem. B 1997, 101, 10560-10567
74. van Amerongen, H.; Valkunas, L.; van Grondelle, R. Photosynthetic Excitons; World Scientific: Singapore, 2000
75. MaÌŠrtensson, J. Calculation of the Förster Orientation Factor for Donor-Acceptor Systems with One Chromophore of Threefold or Higher Symmetry: Zinc Porphyrin Chem. Phys. Lett. 1994, 229, 449-456
76. Hsiao, J. S.; Krueger, B. P.; Wagner, R. W.; Johnson, T. E.; Delaney, J. K.; Mauzerall, D. C.; Fleming, G. R.; Lindsey, J. S.; Bocian, D. F.; Donohoe, R. J. Soluble Synthetic Multiporphyrin Arrays. 2. Photodynamics of Energy Transfer Processes J. Am. Chem. Soc. 1996, 118, 11181-11193
77. Pettersson, K.; Wiberg, J.; Ljungdahl, T.; MaÌŠrtensson, J.; Albinsson, B. Interplay between Barrier Width and Height in Electron Tunneling: Photoinduced Electron Transfer in Porphyrin-Based Donor-Bridge-Acceptor Systems J. Phys. Chem. A 2006, 110, 319-326
78. Scholes, G. D.; Jordanides, X. J.; Fleming, G. R. Adapting the Förster Theory of Energy Transfer for Modeling Dynamics in Aggregated Molecular Assemblies J. Phys. Chem. B 2001, 105, 1640-1651