Reversible copper(II)/(I) electrochemical potential switching driven by visible light-induced coordinated ring rotation

Journal of the American Chemical Society

Volumn 134, Issue 25, 2012, Pages 10543-10553

  Nishikawa, Michihiro ^a   Nomoto, Kuniharu ^a   Kume, Shoko ^a   Nishihara, Hiroshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BI-STABLE STATE; COPPER CENTERS; COPPER COMPLEXES; CYCLIC VOLTAMMOGRAMS; DIIMINES; ELECTROCHEMICAL MEASUREMENTS; ELECTROCHEMICAL POTENTIAL; ELECTRON TRANSFER; ELECTRONIC SIGNALS; HEAT-DRIVEN; INITIAL STATE; KEY FEATURE; LIGHT ENERGY; METAL-TO-LIGAND CHARGE TRANSFER; MOLECULAR SIGNALING; PARTIAL OXIDATIONS; POTENTIAL SHIFT; PYRIDYL; PYRIMIDINE DERIVATIVES; REDOX MEDIATORS; REDOX POTENTIALS; ROTATIONAL ISOMERIC STATE; ROTATIONAL MOTION; STABLE ISOMERS; VARIABLE TEMPERATURE; VISIBLE LIGHT;

AROMATIC COMPOUNDS; CHARGE TRANSFER; COPPER; ISOMERS; LIGANDS; LIGHT; METAL COMPLEXES; RATE CONSTANTS; REDOX REACTIONS; ROTATION;

COPPER COMPOUNDS;

CUPRIC ION; CUPROUS ION; PYRIMIDINE DERIVATIVE;

ARTICLE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ISOMERIZATION; LIGHT; OXIDATION REDUCTION REACTION; THERMODYNAMICS;

EID: 84863490551     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3028873     Document Type: Article

References (93)

1. Kubatkin, S.; Danilov, A.; Hjort, M.; Cornil, J.; Brédas, J.-L.; Stuhr-Hansen, N.; Hedegård, P.; Bjørnholm, T. Nature 2003, 425, 698-701
2. Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yaish, Y.; Petta, J. R.; Rinkoski, M.; Sthena, J. P.; Abruña, H. D.; McEuen, P. L.; Ralph, D. C. Nature 2002, 417, 722-725
3. Moth-Poulsen, K.; Bjørnholm, T. Nat. Nanotechnol. 2009, 4, 551-556
4. Joachim, C.; Gimzewski, J. K.; Aviram, A. Nature 2000, 408, 541-548
5. de Silva, A. P. Nature 2008, 454, 417-418
6. Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. R. Science 2004, 306, 2055-2056
7. Green, J. E.; Wook Choi, J.; Boukai, A.; Bunimovich, Y.; Johnston-Halperin, E.; DeIonno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shik Shin, Y.; Tseng, H.-R.; Stoddart, J. F.; Heath, J. R. Nature 2007, 445, 414-417
8. Simão, C.; Mas-Torrent, M.; Crivillers, N.; Lloveras, V.; Artés, J. M.; Gorostiza, P.; Veciana, J.; Rovira, C. Nat. Chem. 2011, 3, 359-364
9. Sato, O.; Iyoda, T.; Fujishima, A.; Hashimoto, K. Science 1996, 272, 704-705
10. Venkataramani, S.; Jana, U.; Dommaschk, M.; Sönnichsen, F. D.; Tuczek, F.; Herges, R. Science 2011, 331, 445-448
11. Imahori, H.; Guldi, D. M.; Tamaki, K.; Yoshida, Yu.; Luo, C.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6617-6628
12. Meyer, T. J. Acc. Chem. Res. 1989, 22, 163-170
13. Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Nature 2002, 420, 759-760
14. Kobatake, S.; Takami, S.; Muto, H.; Ishikawa, T.; Irie, M. Nature 2007, 446, 778-781
15. Gorostiza, P.; Isacoff, E. Y. Science 2008, 322, 395-399
16. Beharry, A. A.; Sadovski, O.; Woolley, G. A. J. Am. Chem. Soc. 2011, 133, 19684-19687
17. Uchida, K.; Yamanoi, Y.; Yonezawa, T.; Nishihara, H. J. Am. Chem. Soc. 2011, 133, 9239-9241
18. Kume, S.; Nishihara, H. Dalton Trans. 2008, 3260-3271
19. Muratsugu, S.; Kume, S.; Nishihara, H. J. Am. Chem. Soc. 2008, 130, 7204-7205
20. Sakamoto, R.; Murata, M.; Nishihara, H. Angew. Chem., Int. Ed. 2006, 45, 4793-4795
21. Nishihara, H. Coord. Chem. Rev. 2005, 249, 1468-1475
22. Kurihara, M.; Hirooka, A.; Kume, S.; Sugimoto, M.; Nishihara, H. J. Am. Chem. Soc. 2002, 124, 8800-8801
23. Fraysse, S.; Coudret, C.; Launay, J.-P. Eur. J. Inorg. Chem. 2000, 1581-1590
24. Tanaka, Y.; Inagaki, A.; Akita, M. Chem. Commun. 2007, 1169-1171
25. Muraoka, T.; Kinbara, K.; Aida, T. Nature 2006, 440, 512-515
26. Ruangsupapichat, N.; Pollard, M. M.; Harutyunyan, S. R.; Feringa, B. L. Nat. Chem. 2011, 3, 53-60
27. Fletcher, S. P.; Dumur, F.; Pollard, M. M.; Feringa, B. L. Science 2005, 310, 80-82
28. Hernández, J. V.; Kay, E. R.; Leigh, D. A. Science 2004, 306, 1532-1537
29. Serreli, V.; Lee, C.-F.; Kay, E. R.; Leigh, D. A. Nature 2007, 445, 523-527
30. Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines, 2 nd ed.; Wiley-VCH: Weinheim, 2008.
31. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191
32. Browne, W. R.; Feringa, B. L. Nat. Nanotechnol. 2006, 1, 25-35
33. Brouwer, A. M.; Frochot, C.; Gatti, F. G.; Leigh, D. A.; Mottier, L.; Paolucci, F.; Roffia, S.; Wurpel, G. W. H. Science 2001, 291, 2124-2128
34. Mobian, P.; Kern, J.-M.; Sauvage, J.-P. Angew. Chem., Int. Ed. 2004, 43, 2392-2395
35. Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashima, N. J. Am. Chem. Soc. 1997, 119, 7605-7606
36. Armaroli, N.; Balzani, V.; Collin, J.-P.; Gavina, P.; Sauvage, J.-P.; Ventura, B. J. Am. Chem. Soc. 1999, 121, 4397-4408
37. Collin, J.-P.; Dietrich-Buchecker, C.; Gaviña, P.; Jiménez-Molero, M. C.; Sauvage, J.-P. Acc. Chem. Res. 2001, 34, 477-487
38. Zahn, S.; Canary, J. W. J. Am. Chem. Soc. 2002, 124, 9204-9211
39. Dau, H.; Zaharieva, I. Acc. Chem. Res. 2009, 42, 1861-1870
40. Vale, R. D.; Milligan, R. A. Science 2000, 288, 88-95
41. Junge, W.; Sielaff, H.; Engelbrecht, S. Nature 2009, 459, 364-370
42. Vives, G.; Carella, A.; Launay, J.-P.; Rapenne, G. Coord. Chem. Rev. 2008, 252, 1451-1459
43. Ruthkosky, M.; Kelly, C. A.; Castellano, F. N.; Meyer, G. J. Coord. Chem. Rev. 1998, 171, 309-322
44. Ruthkosky, M.; Castellano, F. N.; Meyer, G. J. Inorg. Chem. 1996, 35, 6406-6412
45. Miller, M. T.; Gantzel, P. K.; Karpishin, T. B. Inorg. Chem. 1998, 37, 2285-2290
46. Itoh, S.; Funahashi, S.; Koshino, N.; Takagi, H. D. Inorg. Chim. Acta 2001, 324, 252-265
47. Armaroli, N.; Accorsi, G.; Cardinali, F.; Listorti, A. Top. Curr. Chem. 2007, 280, 69-115
48. Lavie-Cambot, A.; Cantuel, M.; Leydet, Y.; Jonusauskas, G.; Bassani, D. M.; McClenaghan, N. D. Coord. Chem. Rev. 2008, 252, 2572-2584
49. McMillin, D. R.; McNett, K. M. Chem. Rev. 1998, 98, 1201-1219
50. Everly, R. M.; Ziessel, R.; Suffert, J.; McMillin, D. R. Inorg. Chem. 1991, 30, 559-561
51. Cunningham, C. T.; Cunningham, K. L. H.; Michalec, J. F.; McMillin, D. R. Inorg. Chem. 1999, 38, 4388-4392
52. Iwamura, M.; Watanabe, H.; Ishii, K.; Takeuchi, S.; Tahara, T. J. Am. Chem. Soc. 2011, 133, 7728-7736
53. Desvergnes-Breuil, V.; Hebbe, V.; Dietrich-Buchecker, C.; Sauvage, J.-P.; Lacour, J. Inorg. Chem. 2003, 42, 255-257
54. Meyer, M.; Albrecht-Gary, A. M.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Inorg. Chem. 1999, 38, 2279-2287
55. Rorabacher, D. B. Chem. Rev. 2004, 104, 651-697
56. Le Poul, N.; Campion, M.; Douziech, B.; Rondelez, Y.; Le Clainche, L.; Reinaud, O.; Le Mest, Y. J. Am. Chem. Soc. 2007, 129, 8801-8810
57. Solomon, E. I.; Szilagyi, R. K.; George, S. D.; Basumallick, L. Chem. Rev. 2004, 104, 419-458
58. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076
59. Farver, O.; Pecht, I. Coord. Chem. Rev. 2011, 255, 757-773
60. Bessho, T.; Constable, E. C.; Grätzel, M.; Redondo, A. H.; Housecroft, C. E.; Kylberg, W.; Nazeeruddin, M. K.; Neuburger, M.; Schaffner, S. Chem. Commun. 2008, 32, 3717-3719
61. Zhang, Q.; Zhou, Q.; Cheng, Y.; Wang, L.; Ma, D.; Jing, X.; Wang, F. Adv. Funct. Mater. 2006, 16, 1203-1208
62. Smith, C. S.; Branham, C. W.; Marquardt, B. J.; Mann, K. R. J. Am. Chem. Soc. 2010, 132, 14079-14085
63. Hsu, C.-W.; Lin, C.-C.; Chung, M.-W.; Chi, Y.; Lee, G.-H.; Chou, P.-T.; Chang, C.-H.; Chen, P.-Y. J. Am. Chem. Soc. 2011, 133, 12085-12099
64. Tran, D.; Ryu, C. K.; Ford, P. C. Inorg. Chem. 1994, 33, 5957-5959
65. Campagna, S.; Puntoriero, F.; Nastasi, F.; Bergamini, G.; Balzani, V. Top. Curr. Chem. 2007, 280, 117-214
66. Kume, S.; Murata, M.; Ozeki, T.; Nishihara, H. J. Am. Chem. Soc. 2005, 127, 490-491
67. Umeki, S.; Kume, S.; Nishihara, H. Chem. Lett. 2010, 39, 204-205
68. Nomoto, K.; Kume, S.; Nishihara, H. J. Am. Chem. Soc. 2009, 131, 3830-3831
69. Kume, S.; Nomoto, K.; Kusamoto, T.; Nishihara, H. J. Am. Chem. Soc. 2009, 131, 14198-14199
70. Kume, S.; Nishihara, H. Chem. Commun. 2011, 47, 415-417
71. Kume, S.; Nishihara, H. Dalton Trans. 2011, 40, 2299-2305
72. Nishikawa, M.; Nomoto, K.; Kume, S.; Inoue, K.; Sakai, M.; Fujii, M.; Nishihara, H. J. Am. Chem. Soc. 2010, 132, 9579-9581
73. Photoresponsive coordinated ligand rotational isomerization, such as based on a rhenium=carbon double bond, has been reported. McCormick, F. B.; Kiel, W. A.; Gladysz, J. A. Organometallics 1982, 1, 405-408
74. Schmittel, M.; Michel, C.; Wiegrefe, A.; Kalsani, V. Synthesis 2001, 10, 1561-1567
75. Schmittel, M.; Ganz, A. Chem. Commun. 1997, 999-1000
76. Schmittel, M.; Michel, C.; Liu, S.-X.; Schildbach, D.; Fenske, D. Eur. J. Inorg. Chem. 2001, 1155-1166
77. Pallenberg, A. J.; Koenig, K. S.; Barnhart, D. M. Inorg. Chem. 1995, 34, 2833-2840
78. Hsieh, H.-Y.; Lin, C.-H.; Tu, G.-M.; Chi, Y.; Lee, G.-H. Inorg. Chim. Acta 2009, 362, 4734-4739
79. Medwid, J. B.; Paul, R.; Baker, J. S.; Brockman, J. A.; Du, M. T.; Hallett, W. A.; Hanifin, J. W.; Hardy, R. A.; Tarrant, M. E.; Torley, L. W.; Wrenn, S. J. Med. Chem. 1990, 33, 1230-1241
80. Lafferty, J. J.; Case, F. H. J. Org. Chem. 1967, 32, 1591-1596
81. Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176-2179
82. Bard, A. J.; Faulkner, L. R. Electrochemical Methods, Fundamentals and Applications, 2 nd ed.; Wiley: New York, 2001.
83. Jacq, J. J. Electroanal. Chem. 1971, 29, 149-180
84. Carano, M.; Echegoyen, L. Chem.-Eur. J. 2003, 9, 1974-1981
85. Lerke, S. A.; Evans, D. H.; Feldberg, S. W. J. Electroanal. Chem. 1990, 296, 299-315
86. 2, which is enough positive to oxidize the copper(I) complexes. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910
87. The redox potential in the excited state was estimated according to a well-established method. Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; von Zelewsky, A. Coord. Chem. Rev. 1988, 84, 85-277
88. Fery-Forgues, S.; Delavaux-Nicot, B. J. Photochem. Photobiol. A 2000, 132, 137-159
89. Merrill, C. L.; Wilson, L. J.; Thamann, T. J.; Loehr, T. M.; Ferris, N. S.; Woodruff, W. H. J. Chem. Soc., Dalton Trans. 1984, 2207-2221
90. Tabbi, G.; Cassino, C.; Cavigiolio, G.; Colangelo, D.; Ghiglia, A.; Viano, I.; Osella, D. J. Med. Chem. 2002, 45, 5786-5796
91. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435
92. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
93. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838