Photoinduced processes in some mechanically interlocked supramolecules as studied by time-resolved electron paramagnetic resonance

Journal of Physical Chemistry C

Volumn 115, Issue 50, 2011, Pages 24555-24563

  Jakob, Manuela ^a   Berg, Alexander ^a   Levanon, Haim ^a   Schuster, David I ^b   Megiatto Jr , Jackson D ^b,c  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b NEW YORK UNIVERSITY   (United States)

^c ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATENANES; CHARGE-SEPARATED STATE; CONFORMATIONAL MOBILITY; DONOR-ACCEPTORS; EXPERIMENTAL CONDITIONS; INTERLOCKED MOLECULES; ISOTROPIC SOLVENTS; MOLECULAR ENTITIES; PHOTOEXCITED STATE; PHOTOINDUCED INTRAMOLECULAR ELECTRON TRANSFERS; PHOTOINDUCED PROCESS; RADICAL ION PAIRS; ROTAXANES; SUPRAMOLECULES; TIME-RESOLVED ELECTRON PARAMAGNETIC RESONANCES; TRANSFER PROCESS;

ENERGY TRANSFER; FREE RADICAL REACTIONS; NEMATIC LIQUID CRYSTALS; PORPHYRINS; SEPARATION; ZINC COMPOUNDS;

PARAMAGNETISM;

EID: 84857264396     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp2073655     Document Type: Article

References (85)

1. Noy, D. Photosynth. Res. 2008, 95, 23.
2. Nocera, D. G. Inorg. Chem. 2009, 48, 10001.
3. Renger, G. Curr. Sci. 2010, 98, 1305.
4. Benniston, A. C.; Harriman, A. Mater. Today 2008, 11, 26.
5. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2009, 12, 1890.
6. Ricks, A. B.; Solomon, G. C.; Colvin, M. T.; Scott, A. M.; Chen, K.; Ratner, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2010, 132, 15427.
7. Gagliardi, C. J.; Westlake, B. C.; Kent, C. A.; Paul, J. J.; Papanikolas, J. M.; Meyer, T. J. Coord. Chem. Rev. 2010, 254, 2459.
8. Gray, H. B.; Winkler, J. R. Biochim. Biophys. Acta, Bioenerg. 2010, 1797.
9. Taniguchi, M.; Lindsey, J. S. Tetrahedron 2010, 66, 5549.
10. Albinsson, B.; Martensson, J. Phys. Chem. Chem. Phys. 2010, 12, 7338.
11. Kalyanasundaram, M. G. Curr. Opin. Biotechnol. 2010, 21, 298.
12. McConnell, I.; Li, G.; Brudvig, G. W. Chem. Biol. 2010, 17, 434.
13. Duerr, H.; Bossmann, S. Acc. Chem. Res. 2001, 34, 905.
14. Sauvage, J. P.; Collin, J., P.; Faiz, J. A.; Frey, J.; Heitz, V.; Tock, C. J. Porphyrins Phthalocyanines 2008, 12, 881.
15. Benniston, A. C.; Harriman, A. Angew. Chem., Int. Ed. 1993, 32, 1459.
16. Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611.
17. Brouwer, A. M.; Fazio, S. M.; Frochot, C.; Gatti, F. G.; Leigh, D. A.; Wong, J. K. Y.; Wurpel, G. W. H. Pure Appl. Chem. 2003, 75, 1055.
18. Willner, I.; Basnar, B.; Willner, B. Adv. Funct. Mater. 2007, 17, 702.
19. Stoddart, J. F. Chem. Soc. Rev. 2009, 38, 1802.
20. Bravo, J. A.; Raymo, F. M.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Eur. J. Org. Chem. 1998, 2565.
21. Kay, E. Rotaxanes and Catenanes. The University of Edinburgh. Available at http://www.catenane.net/home/rotcatintro.html (accessed August 2011).
22. Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology; Sauvage, J.-P., Dietrich-Buchecker, C., Ed.; Wiley-VCH: Weinheim, 1999.
23. Mateo-Alonso, A.; Ehli, C.; Rahman, G. M. A.; Guldi, D. M.; Fioravanti, G.; Marcaccio, M.; Paolucci, F.; Prato, M. Angew. Chem., Int. Ed. 2007, 46, 3521.
24. Stowell, M. H. B.; McPhillips, T. M. Science 1997, 276, 812.
25. Darrouzet, E.; Valkova-Valchanova, M.; Moser, C. C.; Dutton, P. L.; Daldal, F. Proc. Natl. Acad. Sci. 2000, 97, 4567.
26. El-Khouly, M. E.; Ito, O.; Smith, P. M.; D'Souza, F. J. Photo-chem. Photobiol., C 2004, 5, 79.
27. Sandanayaka, A. S. D.; Watanabe, N.; Ikeshita, K. I.; Araki, Y.; Kihara, N.; Furusho, Y.; Ito, O.; Takata, T. J. Phys. Chem. B 2005, 109, 2516.
28. Balzani, V.; Credi, A.; Venturi, M. Chem. Soc. Rev. 2009, 38, 1542.
29. Megiatto, J. D. J.; Schuster, D. I. Interlocked Artificial Photo-synthetic Model Systems Composed of Electron Donor and [60]Fullerene Units. In Fullerenes: Principles and Applications, 2 ed.; Langa, F., Nierengarten, J. F., Eds.; The Royal Society of Chemistry: Cambridge, 2011; p 354.
30. Jurow, M.; Schuckman, A. E.; Batteas, J. D.; Drain, C. M. Coord. Chem. Rev. 2010, 254, 2297.
31. Ohkubo, K.; Fukuzumi, S. J. Porphyrins Phthalocyanines 2008, 12, 993.
32. Balzani, V.; Credi, A.; Venturi, M. ChemSusChem 2008, 1, 26.
33. Seitz, W.; Kahnt, A.; Guldi, D. M.; Torres, T. J. Porphyrins Phthalocyanines 2009, 13, 1034.
34. Sauvage, J.-P. Acc. Chem. Res. 1990, 23, 319.
35. Linke, M.; Chambron, J.-C.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1997, 119, 11329.
36. Jakob, E.; Berg, A.; Rubin, R.; Levanon, H.; Li, K.; Schuster, D. I. J. Phys. Chem. A 2009, 113, 5846.
37. Jakob, M.; Berg, A.; Levanon, H.; Schuster, D. I.; Megiatto, J. D. J. J. Phys. Chem. A 2011, 115, 5044.
38. Flamigni, L.; Armaroli, N.; Barigelletti, F.; Chambron, J.-C.; Sauvage, J.-P.; Solladie, N. New J. Chem. 1999, 23, 1151.
39. Lockard, J. V.; Kabehie, S.; Zink, J. I.; Smolentsev, G.; Soldatov, A.; Chen, L. X. J. Phys. Chem. B 2010, 114, 14521.
40. Megiatto, J. D. J.; Spencer, R.; Schuster, D. I. Org. Lett. 2009, 11, 4152.
41. Megiatto, J. D. J.; Schuster, D. I.; Abwandner, S.; de Miguel, G.; Guldi, D. J. Am. Chem. Soc. 2010, 132, 3847.
42. Levanon, H.; Hasharoni, K. Prog. React. Kinet. 1995, 20, 309.
43. Levanon, H. Adv. Photosynth. 1996, 3, 211.
44. Savitsky, A.; Möbius, K. Photosynth. Res. 2009, 102, 311.
45. Allen, J. P.; Cordova, J. M.; Jolley, C. C.; Murray, T. A.; Schneider, J. W.; Woodbury, N. W.; Williams, J. C.; Niklas, J.; Klihm, G.; Reus, M.; Lubitz, W. Photosynth. Res. 2009, 99, 1.
46. Ponomarenko, N. S.; Poluektov, O. G.; Bylina, E. J.; Norris, J. R. Biochim. Biophys. Acta, Bioenerg. 2010, 1797, 1617.
47. Megiatto, J. D. J.; Schuster, D. I. Synthesis of Electron Donor-[60]Fullerene Multi-Ring Interlocked Systems. In Handbook of Carbon Nano Materials; D'Souza, F., Kadish, K. M., Eds.; World Scientific: Singapore, 2011; Vol. 1: Synthesis and Supramolecular Systems; pp 207.
48. Jakob, M.; Berg, A.; Stavitski, E.; Chernick, E. T.; Weiss, E. A.; Wasielewski, M. R.; Levanon, H. Chem. Phys. 2006, 324, 63.
49. Regev, A.; Galili, T.; Levanon, H. J. Chem. Phys. 1991, 95, 7907.
50. Gonen, O.; Levanon, H. J. Phys. Chem. 1984, 88, 4223.
51. Blank, A.; Levanon,H. Concepts Magn. Reson., Part A 2005, 25A, 18.
52. Salikhov, K. M.; Molin, Y. N.; Sagdeev, R. Z.; Buchachenko, A. L. Spin Polarization and Magnetic Effects in Radical Reactions; Elsevier: Amsterdam, 1984.
53. Hore, P. J. Analysis of Polarized EPR Spectra. In Advanced EPR: Applications in Biology and Biochemistry; Hoff, A. J., Ed.; Elsevier: Amsterdam, 1989; p 405.
54. Norris, J. R.; Morris, A. L.; Thurnauer, M. C.; Tang, J. J. Chem. Phys. 1990, 92, 4239.
55. Furrer, R.; Fujara, F.; Lange, C.; Stehlik, D.; Vieth, H. M.; Vollmann, W. Chem. Phys. Lett. 1980, 75, 332.
56. Kavarnos, G. J. Fundamentals of Photoinduced Electron Transfer; VCH Publishers, Inc: New York, 1993.
57. Bialkowski, S. E. Parameters for Common Solvents Used in Photothermal and Photoacoustic Spectrometry. Utah State University, Logan, UT. Available at http://www.chem.usu.edu/∼sbialkow/Research/Tablevalues.html (accessed August 2011).
58. Merck, E. Merck Ltd. Catalog: Nematic Liquid Crystal Mixtures, 1989.
59. Ruthkosky, M.; Kelly, C. A.; Castellano, F. N.; Meyer, G. J. Coord. Chem. Rev. 1998, 171, 309.
60. Optical Spectra. Oregon Medical Laser Center, Portland, OR. Available at http://omlc.ogi.edu/spectra/PhotochemCAD/html/ZnTPP. html (accessed August 2011).
61. Moravsky, A. P.; Fursikov, P. V.; Kachapina, L. M.; Khramov, A. V.; Kiryakov, N. V. UV-VIS Photometric Analysis of Fullerenes C60 and C70 in Toluene and Hexane Solutions. In Recent Advances in the Chemistry and Physics of Fullerenes; Kadish, K. M., Ruoff, R. S., Eds.; The Electrochemical Society Inc.: Pennington, NJ, 1995; Vol. 2, p 156.
62. Galili, T.; Regev, A.; Levanon, H.; Schuster, D. I.; Guldi, D. M. J. Phys. Chem. A 2004, 108, 10632.
63. Parker, W. L.; Crosby, G. A. J. Phys. Chem. 1989, 93, 5692.
64. Kirchhoff, J. R.; Gamache, R. E.; Blaskie, M. W.; Del Paggio, A. A.; Lengel, R. K.; McMillin, D. R. Inorg. Chem. 1983, 22, 2380.
65. Gonen, O.; Levanon, H. J. Phys. Chem. 1985, 89, 1637.
66. Scherz, A.; Levanon, H. J. Phys. Chem. 1980, 84, 324.
67. Levanon, H.; Meiklyar, V.; Michaeli, A.; Michaeli, S.; Regev, A. J. Phys. Chem. 1992, 96, 6128.
68. Regev, A.; Gamliel, D.; Meiklyar, V.; Michaeli, S.; Levanon, H. J. Phys. Chem. 1993, 97, 3671.
69. Levanon, H.; Norris, J. R. Chem. Rev. 1978, 78, 185.
70. Closs, G. L.; Forbes, M. D. E.; Norris, J. R. J. Phys. Chem. 1987, 91, 3592.
71. Hasharoni, K.; Levanon, H.; Greenfield, S. R.; Gosztola, D. J.; Svec, W. A.; Wasielewski, M. R. J. Am. Chem. Soc. 1996, 118, 10228.
72. Berg, A.; Shuali, Z.; Asano-Someda, M.; Levanon, H.; Fuhs, M.; Möbius, K.; Wang, R.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 7433.
73. Li, K.; Schuster, D. I.; Guldi, D.; Herranz, M. A.; Echegoyen, L. J. Am. Chem. Soc. 2004, 126, 3388.
74. Felton, R. H. Redox Reactions of Metalloporphyrins. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 5, p 53.
75. Gordon, K. C. J.; McGarvey, J. J. Inorg. Chem. 1991, 30, 2986.
76. Molin, Y. N.; Salikhov, K. M.; Zamaraev, K. I. Spin Exchange, Principles and Applications in Chemistry and Biology; Springer: New York, 1980.
77. Okamura, M. Y.; Isaacson, R. A.; Feher, G. Biochim. Biophys. Acta 1979, 546, 394.
78. Hoffmann, S. K.; Hilczer, W.; Goslar., J. Appl. Magn. Reson. 1994, 7, 289.
79. Mazzoni, M.; Conti, F.; Corvaja, C. Appl. Magn. Reson. 2000, 18, 351.
80. Flamigni, L. Pure Appl. Chem. 2001, 73, 241.
81. Schanze, K. S.; Walters, K. A. Photoinduced Electron Transfer in Metal-Organic Dyads. In Organic and Inorganic Photochemistry; Marcel Dekker: New York, 1998; Vol. 2: Molecular and Supra-molecular Photochemistry; p 75.
82. Schuster, D. I.; Li, K.; Guldi, D. M. C. R. Chim. 2006, 9, 892.
83. Rozenshtein, V.; Berg, A.; Levanon, H.; Krueger, U.; Stehlik, D.; Kandrashkin, Y.; van der Est, A. Isr. J. Chem. 2003, 43, 373.
84. Yagi, M.; Kaneshima, T.; Torii, M.; Matsuo, K.; Higuchi, J. Chem. Phys. Lett. 1992, 197, 457.
85. Megiatto, J. D. J.; Schuster, D. I.; de Miguel, G.; Wolfrum, S.; Guldi, D. M. J. Am. Chem. Soc. 2011 submitted.