Electron transfer in a supramolecular complex of zinc chlorin carboxylate anion with Li+@C60 affording the long-lived charge-separated state

Journal of Physical Chemistry C

Volumn 117, Issue 41, 2013, Pages 21166-21177

  Kawashima, Yuki ^a   Ohkubo, Kei ^a   Kentaro, Mase ^a   Fukuzumi, Shunichi ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BACK ELECTRON TRANSFER; CHARGE-SEPARATED STATE; ELECTRONIC COUPLING; REORGANIZATION ENERGIES; SINGLET EXCITED STATE; SUPRAMOLECULAR COMPLEXES; TEMPERATURE DEPENDENCE; TRANSIENT ABSORPTION;

AROMATIC COMPOUNDS; CARBOXYLATION; ELECTRON TRANSITIONS; EXCITED STATES; RATE CONSTANTS; SUPRAMOLECULAR CHEMISTRY; ZINC;

LITHIUM;

EID: 84885986847     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp407976b     Document Type: Article

References (123)

1. The Photosynthetic Reaction Center; Deisenhofer, J., Norris, J. R., Eds.; Academic Press: San Diego, 1993.
2. Molecular Level Artificial Photosynthetic Materials; Meyer, G. J., Ed.; Wiley: New York, 1997.
3. Frey, J.; Kodis, G.; Straight, S. D.; Moore, T. A.; Moore, A. L.; Gust, D. Photonic Modulation of Electron Transfer with Switchable Phase Inversion J. Phys. Chem. A 2013, 117, 607-615
4. Gust, D.; Moore, T. A.; Moore, A. L. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley: Weinheim, 2001; Vol. 3, pp 272-336.
5. Terazono, Y.; Kodis, G.; Liddell, P. A.; Garg, V.; Moore, T. A.; Moore, A. L.; Gust, D. Multiantenna Artificial Photosynthetic Reaction Center Complex J. Phys. Chem. B 2009, 113, 7147-7155
6. Gust, D.; Moore, T. A.; Moore, A. L. Solar Fuels via Artificial Photosynthesis Acc. Chem. Res. 2009, 42, 1890-1898
7. Ricks, A. B.; Brown, K. E.; Wenninger, M.; Karlen, S. D.; Berlin, Y. A.; Co, D. T.; Wasielewski, M. R. Exponential Distance Dependence of Photoinitiated Stepwise Electron Transfer in Donor-Bridge-Acceptor Molecules: Implications for Wirelike Behavior J. Am. Chem. Soc. 2012, 134, 4581-4581
8. Gunderson, V. L.; Smeigh, A. L.; Kim, C. H.; Co, D. T.; Wasielewski, M. R. Electron Transfer within Self-Assembling Cyclic Tetramers Using Chlorophyll-Based Donor-Acceptor Building Blocks J. Am. Chem. Soc. 2012, 134, 4363-4372
9. Lewis, F. D.; Letsinger, R. L.; Wasielewski, M. R. Dynamics of Photoinduced Charge Transfer and Hole Transport in Synthetic DNA Hairpins Acc. Chem. Res. 2001, 34, 159-170
10. Wasielewski, M. R. Self-Assembly Strategies for Integrating Light Harvesting and Charge Separation in Artificial Photosynthetic Systems Acc. Chem. Res. 2009, 42, 1910-1921
11. Balzani, V. Dendrimers Based on Photoactive Metal Complexes. Recent Advances Coord. Chem. Rev. 2001, 219-221, 545-572
12. Faiz, J. A.; Heitz, V.; Sauvage, J.-P. Design and Synthesis of Porphyrin-Containing Catenanes and Rotaxanes Chem. Soc. Rev. 2009, 38, 422-442
13. Diederich, F.; Gómez-López, M. Supramolecular Fullerene Chemistry Chem. Soc. Rev. 1999, 28, 263-277
14. Chambron, J.-C.; Collin, J.-P.; Dalbavie, J.-O.; Dietrich-Buchecker, C. O.; Heitz, V.; Odobel, F.; Solladié, N.; Sauvage, J.-P. Rotaxanes and Other Transition Metal-Assembled Porphyrin Arrays for Long-Range Photoinduced Charge Separation Coord. Chem. Rev. 1998, 178-180, 1299-1312
15. Fukuzumi, S. New Perspective of Electron Transfer Chemistry Org. Biomol. Chem. 2003, 1, 609-620
16. Fukuzumi, S. Development of Bioinspired Artificial Photosynthetic Systems Phys. Chem. Chem. Phys. 2008, 10, 2283-2297
17. Fukuzumi, S. Bioinspired Electron-Transfer Systems and Applications Bull. Chem. Soc. Jpn. 2006, 79, 177-195
18. Fukuzumi, S.; Kojima, T. Photofunctional Nanomaterials Composed of Multiporphyrins and Carbon-Based π-Electron Acceptors J. Mater. Chem. 2008, 18, 1427-1439
19. Fukuzumi, S.; Honda, T.; Ohkubo, K.; Kojima, T. Charge Separation in Metallomacrocycle Complexes Linked with Electron Acceptors by Axial Coordination Dalton Trans. 2009, 3880-3889
20. Boyle, M. M.; Forgan, R. S.; Friedman, D. C.; Gassensmith, J. J.; Smaldone, R. A.; Stoddart, J. F.; Sauvage, J.-P. Donor-Acceptor Molecular Figures-of-Eight Chem. Commun. 2011, 47, 11870-11872
21. Linke, M.; Chambron, J.-C.; Heitz, V.; Sauvage, J.-P.; Encinas, S.; Barigelletti, F.; Flamigni, L. Multiporphyrinic Rotaxanes: Control of Intramolecular Electron Transfer Rate by Steering the Mutual Arrangement of the Chromophores J. Am. Chem. Soc. 2000, 122, 11834-11844
22. Dixon, I. M.; Collin, J.-P.; Sauvage, J.-P.; Barigelletti, F.; Flamigni, L. Charge Separation in a Molecular Triad Consisting of an Iridium(III)-Bis- terpy Central Core and Porphyrins as Terminal Electron Donor and Acceptor Groups Angew. Chem., Int. Ed. 2000, 112, 1292-1295
23. Kamat, P. V. Meeting the Clean Energy Demand: Nanostructure Architectures for Solar Energy Conversion J. Phys. Chem. C 2007, 111, 2834-2860
24. 2 with Coordinating Ligands to Immobilize Sensitizers and Dyads via Metal-Ligand Coordination for Enhanced Photocurrent Generation J. Am. Chem. Soc. 2009, 131, 14646-14647
25. Imahori, H.; Umeyama, T.; Ito, S. Large π-Aromatic Molecules as Potential Sensitizers for Highly Efficient Dye-Sensitized Solar Cells Acc. Chem. Res. 2009, 42, 1809-1818
26. Imahori, H.; Tamaki, K.; Guldi, D. M.; Luo, C.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. Modulating Charge Separation and Charge Recombination Dynamics in Porphyrin-Fullerene Linked Dyads and Triads: Marcus-Normal versus Inverted Region J. Am. Chem. Soc. 2001, 123, 2607-2617
27. Wijesinghe, C. A.; El-Khouly, M. E.; Subbaiyan, N. K.; Supur, M.; Zandler, M. E.; Ohkubo, K.; Fukuzumi, S.; D'Souza, F. Photochemical Charge Separation in Closely Positioned Donor-Boron Dipyrrin-Fullerene Triads Chem.-Eur. J. 2011, 17, 3147-3156
28. Ohkubo, K.; Sintic, P. J.; Tkachenko, N. V.; Lemmetyinen, H.; E, W.; Ou, Z.; Shao, J.; Kadish, K. M.; Crossley, M. J.; Fukuzumi, S. Photoinduced Electron-Transfer Dynamics and Long-Lived CS States of Donor-Acceptor Linked Dyads and a Triad Containing a Gold Porphyrin in Nonpolar Solvents Chem. Phys. 2006, 326, 3-14
29. Céspedes-Guirao, F. J.; Ohkubo, K.; Fukuzumi, S.; Sastre-Santos, A.; Fernández-Lázaro, F. Synthesis and Photoinduced Electron Transfer of Phthalocyanine-Perylenebisimide Pentameric Arrays J. Org. Chem. 2009, 74, 5871-5880
30. Murakami, M.; Ohkubo, K.; Hasobe, T.; Sgobba, V.; Guldi, D. M.; Wessendorf, F.; Hirsch, A.; Fukuzumi, S. Implementation of Redox Gradients in Hydrogen Bonded Complexes Containing N,N -Dimethylaniline, Flavin and Fullerene Derivatives J. Mater. Chem. 2010, 20, 1457-1466
31. Jiménez, á. J.; Spänig, F.; Rodríguez-Morgade, M. S.; Ohkubo, K.; Fukuzumi, S.; Guldi, D. M.; Torres, T. A Tightly Coupled Bis(Zinc(II) Phthalocyanine)-Perylenediimide Ensemble to Yield Long-Lived Radical Ion Pair States Org. Lett. 2007, 9, 2481-2487
32. Martín-Gomis, L.; Ohkubo, K.; Fernández-Lázaro, F.; Fukuzumi, S.; Sastre-Santos, á. Multistep Electron Transfer Systems Based on Silicon Phthalocyanine, [60]Fullerene and Trinitrofluorenon Chem. Commun. 2010, 46, 3944-3946
33. Guldi, D. M.; Sgobba, V. Carbon Nanostructures for Solar Energy Conversion Schemes Chem. Commun. 2011, 47, 606-610
34. Guldi, D. M.; Rahman, G. M. A.; Sgobba, V.; Ehli, C. Multifunctional Molecular Carbon Materials-From Fullerenes to Carbon Nanotubes Chem. Soc. Rev. 2006, 35, 471-487
35. Bottari, G.; de la Torre, G.; Guldi, D. M.; Torres, T. Covalent and Noncovalent Phthalocyanine-Carbon Nanostructure Systems: Synthesis, Photoinduced Electron Transfer, and Application to Molecular Photovoltaics Chem. Rev. 2010, 110, 6768-6816
36. 60 Systems: Toward Molecular Solar Energy Conversion Materials? Acc. Chem. Res. 2007, 40, 1015-1024
37. Fukuzumi, S.; Kotani, H.; Ohkubo, K.; Ogo, S.; Tkachenko, N. V.; Lemmetyinen, H. Electron-Transfer State of 9-Mesityl-10-methylacridinium Ion with a Much Longer Lifetime and Higher Energy Than That of the Natural Photosynthetic Reaction Center J. Am. Chem. Soc. 2004, 126, 1600-1601
38. Ohkubo, K.; Kotani, H.; Fukuzumi, S. Misleading Effects of Impurities Derived from the Extremely Long-Lived Electron-Transfer State of 9-Mesityl-10-methylacridinium Ion Chem. Commun. 2005, 4520-4522
39. Fukuzumi, S.; Kotani, H.; Ohkubo, K. Response: Why Had Long-Lived Electron-Transfer States of Donor-Substituted 10-Methylacridinium Ions Been Overlooked? Formation of the Dimer Radical Cations Detected in the Near-IR Region Phys. Chem. Chem. Phys. 2008, 10, 5159-5162
40. 60 Dyads J. Am. Chem. Soc. 2001, 123, 10676-10683 (full author list is shown in the Supporting Information)
41. Ohkubo, K.; Imahori, H.; Shao, J.; Ou, Z.; Kadish, K. M.; Chen, Y.; Zheng, G.; Pandey, R. K.; Fujitsuka, M.; Ito, O. Small Reorganization Energy of Intramolecular Electron Transfer in Fullerene-Based Dyads with Short Linkage J. Phys. Chem. A 2002, 106, 10991-10998 (full author list is shown in the Supporting Infomation)
42. D'Souza, F.; Maligaspe, E.; Ohkubo, K.; Zandler, M. E.; Subbaiyan, N. K.; Fukuzumi, S. Photosynthetic Reaction Center Mimicry: Low Reorganization Energy Driven Charge Stabilization in Self-Assembled Cofacial Zinc Phthalocyanine Dimer-Fullerene Conjugate J. Am. Chem. Soc. 2009, 131, 8787-8797
43. Murakami, M.; Ohkubo, K.; Fukuzumi, S. Inter- and Intramolecular Photoinduced Electron Transfer of Flavin Derivatives with Extremely Small Reorganization Energies Chem.-Eur. J. 2010, 16, 7820-7832
44. Murakami, M.; Ohkubo, K.; Nanjo, T.; Souma, K.; Suzuki, N.; Fukuzumi, S. Photoinduced Electron Transfer in Photorobust Coumarins Linked with Electron Donors Affording Long Lifetimes of Triplet Charge-Separated States ChemPhysChem 2010, 11, 2594-2605
45. Martín-Gomis, L.; Ohkubo, K.; Fernández-Lázaro, F.; Fukuzumi, S.; Sastre-Santos, á. Adiabatic Photoinduced Electron Transfer and Back Electron Transfer in a Series of Axially Substituted Silicon Phthalocyanine Triads J. Phys. Chem. C 2008, 112, 17694-17701
46. Fukuzumi, S.; Imahori, H.; Okamoto, K.; Yamada, H.; Fujitsuka, M.; Ito, O.; Guldi, D. M. Uphill Photooxidation of NADH Analogues by Hexyl Viologen Catalyzed by Zinc Porphyrin-Linked Fullerenes J. Phys. Chem. A 2002, 106, 1903-1908
47. 60 Dyad Org. Lett. 2003, 5, 2719-2721
48. Fukuzumi, S.; Ohkubo, K.; E, W.; Ou, Z.; Shao, J.; Kadish, K. M.; Hutchison, J. A.; Ghiggino, K. P.; Sintic, P. J.; Crossley, M. J. Metal-Centered Photoinduced Electron Transfer Reduction of a Gold(III) Porphyrin Cation Linked with a Zinc Porphyrin to Produce a Long-Lived Charge-Separated State in Nonpolar Solvents J. Am. Chem. Soc. 2003, 125, 14984-14985
49. 60 Dyad by One-Step Photoinduced Electron Transfer Angew. Chem., Int. Ed. 2004, 43, 853-856 (full author list is shown in the Supporting Information)
50. Echegoyen, L.; Diederich, F.; Echegoyen, L. E. In Fullerenes, Chemistry, Physics, and Technology; Kadish, K. M.; Ruoff, R. S., Eds.; Wiley-Interscience: New York, 2000; pp 1-51.
51. Guldi, D. M.; Fukuzumi, S. In Fullerenes: From Synthesis to Optoelectronic Properties; Guldi, D. M.; Martin, N., Eds.; Kluwer: Dordrecht, 2003; pp 237-265.
52. Sgobba, V.; Rahman, G. M. A.; Guldi, D. M. In Carbon Nanotubes in Electron Donor-Acceptor Nanocomposites, Chemistry of Carbon Nanotubes; Basiuk, V. A., Ed.; American Scientific Publishers: Stevenson Ranch, CA, 2006.
53. Fukuzumi, S.; Guldi, D. M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 270-337.
54. Connolly, J. S.; Bolton, J. R. In Photoinduced Electron Transfer; Fox, M. A.; Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part D, pp 303-393.
55. Wasielewski, M. R. In Photoinduced Electron Transfer; Fox, M. A.; Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part A, pp 161-206.
56. Bixon, M.; Fajer, J.; Feher, G.; Freed, J. H.; Gamliel, D.; Hoff, A. J.; Levanon, H.; Möbius, K.; Nechushtai, R.; Norris, J. R. Primary Events in Photosynthesis Problems, Speculations, Controversies, and Future Trends Isr. J. Chem. 1992, 32, 369-518 (full author list is shown in the Supporting Information)
57. Kurreck, H.; Huber, M. Model Reactions for Photosynthesis-Photoinduced Charge and Energy Transfer between Covalently Linked Porphyrin and Quinone Units Angew. Chem., Int. Ed. 1995, 34, 849-866
58. Gust, D.; Moore, T. A. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8, pp 153-190.
59. Elliott, K. J.; Harriman, A.; Le Pleux, L.; Pellegrin, Y.; Blart, E.; Mayer, C. R.; Odobel, F. A Porphyrin-Polyoxometallate Bio-Inspired Mimic for Artificial Photosynthesis Phys. Chem. Chem. Phys. 2009, 11, 8767-8773
60. Benniston, A. C.; Harriman, A. Artificial Photosynthesis Mater. Today 2008, 11, 26-34
61. Odobel, F.; Séverac, M.; Pellegrin, Y.; Blart, E.; Fosse, C.; Cannizzo, C.; Mayer, C. R.; Elliott, K. J.; Harriman, A. Coupled Sensitizer-Catalyst Dyads: Electron-Transfer Reactions in a Perylene- Polyoxometalate Conjugate Chem.-Eur. J. 2009, 15, 3130-3138
62. Fukuzumi, S.; Saito, K.; Ohkubo, K.; Troiani, V.; Qiu, H.; Gadde, S.; D'Souza, F.; Solladié, N. Multiple Photosynthetic Reaction Centres Using Zinc Porphyrinic Oligopeptide-Fulleropyrrolidine Supramolecular Complexes Phys. Chem. Chem. Phys. 2011, 13, 17019-1702
63. Verhoeven, J. W. In Electron Transfer-From Isolated Molecules to Biomolecules; Jortner, J.; Bixon, M., Eds.; John Wiley & Sons: New York, 1999; Part 1, pp 603-644.
64. Tokuji, S.; Yorimitsu, H.; Osuka, A. Preferential Formation of Cyclic Trimers by Palladium-Catalyzed Oxidative Coupling Reactions of 2,18-Diethynylporphyrins Angew. Chem., Int. Ed. 2012, 51, 12357-12361
65. Yoon, M.-C.; Lee, S.; Tokuji, S.; Yorimitsu, H.; Osuka, A.; Kim, D. Homoconjugation in Diporphyrins: Excitonic Behaviors in Singly and Doubly Linked Zn(II)porphyrin Dimers Chem. Sci. 2013, 4, 1756-1746
66. Kim, K. S.; Lim, J. M.; Osuka, A.; Kim, D. Various Strategies for Highly-Efficient Two-Photon Absorption in Porphyrin Arrays J. Photochem. Photobiol., C 2008, 9, 13-28
67. Sun, L.; Hammarström, L.; Åkermark, B.; Styring, S. Towards Artificial Photosynthesis Ruthenium-Manganese Chemistry for Energy Production Chem. Soc. Rev. 2001, 30, 36-49
68. Imahori, H.; Tamaki, K.; Araki, Y.; Sekiguchi, Y.; Ito, O.; Sakata, Y.; Fukuzumi, S. Stepwise Charge Separation and Charge Recombination in Ferrocene- meso, meso -Linked Porphyrin Dimer-Fullerene Triad J. Am. Chem. Soc. 2002, 124, 5165-5174
69. Imahori, H.; Sekiguchi, Y.; Kashiwagi, Y.; Sato, T.; Araki, Y.; Ito, O.; Yamada, H.; Fukuzumi, S. Long-Lived Charge-Separated State Generated in a Ferrocene- meso, meso -Linked Porphyrin Trimer-Fullerene Pentad with a High Quantum Yield Chem.-Eur. J. 2004, 10, 3184-3196
70. Imahori, H.; Guldi, D. M.; Tamaki, K.; Yoshida, Y.; Luo, C.; Sakata, Y.; Fukuzumi, S. Charge Separation in a Novel Artificial Photosynthetic Reaction Center Lives 380 ms J. Am. Chem. Soc. 2001, 123, 6617-6628
71. Guldi, D. M.; Imahori, H.; Tamaki, K.; Kashiwagi, Y.; Yamada, H.; Sakata, Y.; Fukuzumi, S. A Molecular Tetrad Allowing Efficient Energy Storage for 1.6 s at 163 K J. Phys. Chem. A 2004, 108, 541-548
72. Marcus, R. A. Chemical and Electrochemical Electron-Transfer Theory Annu. Rev. Phys. Chem. 1964, 15, 155-196
73. Marcus, R. A. Electron Transfer Reactions in Chemistry: Theory and Experiment (Nobel Lecture) Angew. Chem., Int. Ed. 1993, 32, 1111-1121
74. Sugiyama, Y.; Takahashi, S.; Ishimori, K.; Morishima, I. Pressure Effects on Electron Transfer Rates in Zinc/Ruthenium Modified Myoglobins J. Am. Chem. Soc. 1997, 119, 9582-9583
75. Cave, R. J.; Newton, M. D.; Kumar, K.; Zimmt, M. B. Theoretical Study of Solvent Effects on the Electronic Coupling Matrix Element in Rigidly Linked Donor-Acceptor Systems J. Phys. Chem. 1995, 99, 17501-17504
76. Fernando, S. R. L.; Kozlov, G. V.; Ogawa, M. Y. Distance Dependence of Electron Transfer along Artificial β-Strands at 298 and 77 K Inorg. Chem. 1998, 37, 1900-1905
77. Isied, S. S.; Vassilian, A.; Wishart, J. F.; Creutz, C.; Schwarz, H. A.; Sutin, N. The Distance Dependence of Intramolecular Electron-Transfer Rates: Importance of the Nuclear Factor J. Am. Chem. Soc. 1988, 110, 635-637
78. 5 Labeled with Ruthenium(II) Polypyridine Complexes: Rate Measurements in the Marcus Inverted Region J. Am. Chem. Soc. 1993, 115, 6820-6824
79. D'Souza, F.; Deviprasad, G. R.; Zandler, M. E.; Hoang, V. T.; Klykov, A.; VanStipdonk, M.; Perera, A.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O. Spectroscopic, Electrochemical, and Photochemical Studies of Self-Assembled via Axial Coordination Zinc Porphyrin-Fulleropyrrolidine Dyads J. Phys. Chem. A 2002, 106, 3243-3252
80. D'Souza, F.; Sandanayaka, A. S. D.; Ito, O. SWNT-Based Supramolecular Nanoarchitectures with Photosensitizing Donor and Acceptor Molecules J. Phys. Chem. Lett. 2010, 1, 2586-2593
81. D'Souza, F.; Ito, O. Supramolecular Donor-acceptor Hybrids of Porphyrins/Phthalocyanines with Fullerenes/Carbon Nanotubes: Electron Transfer, Sensing, Switching, and Catalytic Applications Chem. Commun. 2009, 4913-4928
82. D'Souza, F.; Ito, O. Spectroscopic, Electrochemical, and Photochemical Studies of Self-Assembled via Axial Coordination Zinc Porphyrin- Fulleropyrrolidine Dyads J. Phys. Chem. A 2002, 106, 3243-3252
83. El-Khouly, M. E.; Rogers, L. M.; Zandler, M. E.; Suresh, G.; Fujitsuka, M.; Ito, O.; D'Souza, F. Studies on Intra-Supramolecular and Intermolecular Electron-Transfer Processes between Zinc Naphthalocyanine and Imidazole-Appended Fullerene ChemPhysChem 2003, 4, 474-481
84. Flamigni, L.; Johnston, M. R.; Giribabu, L. Photoinduced Electron Transfer in Bisporphyrin-Diimide Complexes Chem.-Eur. J. 2002, 8, 3938-3947
85. Xiao, S.; El-Khouly, M. E.; Li, Y.; Gan, Z.; Liu, H.; Jiang, L.; Araki, Y.; Ito, O.; Zhu, D. Dyads and Triads Containing Perylenetetracarboxylic Diimide and Porphyrin Efficient Photoinduced Electron Transfer Elicited via Both Excited Singlet States J. Phys. Chem. B 2005, 109, 3658-3667
86. Grimm, B.; Schornbaum, J.; Cardona, C. M.; van Paauwe, J. D.; Boyd, P. D. W.; Guldi, D. M. Enhanced Binding Strengths of Acyclic Porphyrin Hosts with Endohedral Metallofullerenes Chem. Sci. 2011, 1530-1537
87. Ohkubo, K.; Fukuzumi, S. Long-Lived Charge-Separated States of Simple Electron Donor-Acceptor Dyads Using Porphyrins and Phthalocyanines J. Porphyrins Phthalocyanines 2008, 12, 993-1004
88. Fukuzumi, S.; Saito, K.; Ohkubo, K.; Khoury, T.; Kashiwagi, Y.; Absalom, M. A.; Gadde, S.; D'Souza, F.; Araki, Y.; Ito, O. Multiple Photosynthetic Reaction Centres Composed of Supramolecular Assemblies of Zinc Porphyrin Dendrimers with a Fullerene Acceptor Chem. Commun. 2011, 47, 7980-7982 (full author list is shown in the Supporting Information)
89. D'Souza, F.; Subbaiyan, N. K.; Xie, Y.; Hill, J. P.; Ariga, K.; Ohkubo, K.; Fukuzumi, S. Anion-Complexation-Induced Stabilization of Charge Separation J. Am. Chem. Soc. 2009, 131, 16138-16146
90. Sessler, J. L.; Karnas, E.; Kim, S. K.; Ou, Z.; Zhang, M.; Kadish, K. M.; Ohkubo, K.; Fukuzumi, S. "Umpolung" Photoinduced Charge Separation in an Anion-Bound Supramolecular Complex J. Am. Chem. Soc. 2008, 130, 15256-15257
91. Kojima, T.; Honda, T.; Ohkubo, K.; Shiro, M.; Kusukawa, T.; Fukuda, T.; Kobayashi, N.; Fukuzumi, S. A Discrete Supramolecular Conglomerate Composed of Two Saddle-Distorted Zinc(II)-Phthalocyanine Complexes and a Doubly Protonated Porphyrin with Saddle Distortion Undergoing Efficient Photoinduced Electron Transfer Angew. Chem., Int. Ed. 2008, 47, 6712-6716
92. Fukuzumi, S.; Ohkubo, K.; D'Souza, F.; Sessler, J. L. Supramolecular Electron Transfer by Anion Binding Chem. Commun. 2012, 48, 9801-9815
93. Fukuzumi, S.; Ohkubo, K. Assemblies of Artificial Photosynthetic Reaction Centres J. Mater. Chem. 2012, 22, 4575-4587
94. Honda, T.; Nakanishi, T.; Ohkubo, K.; Kojima, T.; Fukuzumi, S. Structure and Photoinduced Electron Transfer Dynamics of a Series of Hydrogen-Bonded Supramolecular Complexes Composed of Electron Donors and a Saddle-Distorted Diprotonated Porphyrin J. Am. Chem. Soc. 2010, 132, 10155-10163
95. 60 J. Am. Chem. Soc. 2011, 133, 15938-15941
96. 60 with Sulfonated meso -Tetraphenylporphyrins and Long-Lived Photoinduced Charge Separation Chem. Commun. 2012, 48, 4314-4316
97. 60 J. Phys. Chem. A 2012, 116, 8942-8948
98. 60 and Cyclic Porphyrin Dimers Chem. Sci. 2013, 4, 1451-1461
99. 60-Sulphonated Porphyrin Supramolecular Nanoclusters Chem. Commun. 2013, 49, 4474-4476
100. Kawashima, Y.; Ohkubo, K.; Fukuzumi, S. Small Reorganization Energies of Photoinduced Electron Transfer between Spherical Fullerenes J. Phys. Chem. A 2013, 117, 6737-6743
101. Bill, N. L.; Ishida, M.; Bähring, S.; Lim, J. M.; Lee, S.; Davis, C. M.; Lynch, V. M.; Nielsen, K. A.; Jeppesen, J. O.; Ohkubo, K. Porphyrins Fused with Strongly Electron Donating 1,3-Dithole-2-ylidene Moieties. Redox Control by Metal Cation Complexation and Anion Binding J. Am. Chem. Soc. 2013, 135, 10852-10862 (full author list is shown in the Supporting Information)
102. 60 Superatoms Nat. Chem. 2010, 2, 678-683 (full author list is shown in the Supporting Information)
103. 60 with Encapsulated Lithium Cation Angew. Chem., Int. Ed. 2012, 51, 3377-3381
104. - Org. Lett. 2012, 14, 3784-3787
105. Ueno, H.; Nakamura, Y.; Ikuma, N.; Kokubo, K.; Oshima, T. Synthesis of a Lithium-Encapsulated Fullerenol and the Effect of the Internal Lithium Cation on Its Aggregation Behavior Nano Res. 2012, 5, 558-564
106. Wasielenski, M. R.; Svec, W. A. Synthesis of Covalently Linked Dimeric Derivatives of Chlorophyll a, Pyrochlorophyll a, Chlorophyll b, and Bacteriochlorophyll a J. Org. Chem. 1980, 45, 1969-1974
107. Zheng, G.; Li, H.; Zhang, M.; L-Katz, S.; Chance, B.; Glickson, J. D. Low-Density Lipoprotein Reconstituted by Pyropheophorbide Cholesteryl Oleate as Target-Specific Photosensitizer Bioconjugate Chem. 2002, 13, 392-396
108. Arian, D.; Cló, E.; Gothelf, K. V.; Mokhir, A. A Nucleic Acid Dependent Chemical Photocatalysis in Live Human Cells Chem.-Eur. J. 2010, 16, 288-295
109. Ishigure, S.; Mitsui, T.; Ito, S.; Kondo, Y.; Kawabe, S.; Kondo, M.; Dewa, T.; Mino, H.; Itoh, S.; Nango, M. Peroxide Decoloration of CI Acid Orange 7 Catalyzed by Manganese Chlorophyll Derivatives at the Surfaces of Micelles and Lipid Bilayers Langmuir 2010, 26, 7774-7782
110. Paolesse, R.; Pandey, R. K.; Forsyth, T. P.; Jaquinod, L.; Gerzevske, K. R.; Nurco, D. J.; Sengo, M. O.; Licoccia, S.; Boschi, T.; Smith, K. M. Stepwise Syntheses of Bisporphyrins, Bischlorins, and Biscorroles, and of Porphyrin-Chlorin and Porphyrin-Corrole Heterodimers J. Am. Chem. Soc. 1996, 118, 3869-3882
111. Armarego, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals, 6 th ed; Pergamon Press: Oxford, 2009.
112. Mase, K.; Ohkubo, K.; Fukuzumi, S. Efficient Two-Electron Reduction of Dioxygen to Hydrogen Peroxide with One-Electron Reductants with a Small Overpotential Catalyzed by a Cobalt Chlorin Complex J. Am. Chem. Soc. 2013, 135, 2800-2808
113. Tamiaki, H.; Kunieda, M. Regioisomerically Controlled Self-Aggregation of Zinc 3-Hydroxymethyl-13-Formyl-Chlorin/Porphyrin and Their 3,13-Inverted Pigments J. Org. Chem. 2007, 72, 2443-2451
114. Huber, V.; Sengupta, S.; Würthner, F. Structure-Property Relationships for Self-Assembled Zinc Chlorin Light-Harvesting Dye Aggregates Chem.-Eur. J. 2008, 14, 7791-7807
115. Mann, C. K.; Barnes, K. K. In Electrochemical Reactions in Non-aqueous Systems; Mercel Dekker: New York, 1970.
116. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009, (full author list is shown in the Supporting Infomation).
117. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
118. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlfation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
119. 70 with a Monoporphyrin in Presence of Silver Nanoparticles Spectrochim. Acta, Part A 2012, 89, 284-293
120. D'Souza, F.; Chitta, R.; Gadde, S.; Islam, D.-M. S.; Schumacher, A. L.; Zandler, M. E.; Araki, Y.; Ito, O. Design and Studies on Supramolecular Ferrocene-Porphyrin-Fullerene Constructs for Generating Long-Lived Charge Separated States J. Phys. Chem. B 2006, 110, 25240-25250
121. Kadish, K. M.; Chen, P.; Enakieva, Y. Y.; Nefedov, S. E.; Gorbunova, Y. G.; Tsivadze, A. Y.; Bessmertnykh-Lemeune, A.; Stern, C.; Guilard, R. Electrochemical and Spectroscopic Studies of Poly(diethoxyphosphoryl)porphyrins J. Electroanal. Chem. 2011, 656, 61-71
122. Hasobe, T.; Imahori, H.; Kamat, P. V.; Ahn, T. K.; Kim, S. K.; Kim, D.; Fujimoto, A.; Hirakawa, T.; Fukuzumi, S. Photovoltaic Cells Using Composite Nanoclusters of Porphyrins and Fullerenes with Gold Nanoparticles J. Am. Chem. Soc. 2005, 127, 1216-1228
123. Hasobe, T.; Saito, K.; Kamat, P. V.; Troiani, V.; Qiu, H.; Solladie, N.; Kim, K. S.; Park, J. K.; Kim, D.; D'Souza, F. Organic Solar Cells. Supramolecular Composites of Porphyrins and Fullerenes Organized by Polypeptide Structures as Light Harvesters J. Mater. Chem. 2007, 17, 4160-4170 (full author list is shown in the Supporting Information)