Reduction of a redox-active ligand drives switching in a Cu(I) pseudorotaxane by a bimolecular mechanism

Journal of the American Chemical Society

Volumn 131, Issue 3, 2009, Pages 1305-1313

  McNitt, Kristy A ^a   Parimal, Kumar ^a   Share, Andrew I ^a   Fahrenbach, Albert C ^a   Witlicki, Edward H ^a   Pink, Maren ^a   Bediako, D Kwabena ^b   Plaisier, Christina L ^b   Le, Nga ^b   Heeringa, Lee P ^b   Griend, Douglas A Vander ^b   Flood, Amar H ^a  

^a INDIANA UNIVERSITY   (United States)

^b CALVIN COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRIDINES; BINUCLEATING LIGANDS; COOPERATIVITY; DIGITAL SIMULATION; DISPROPORTIONATION; DRIVING FORCES; EC MECHANISM; ENHANCED STABILITY; FORMATION CONSTANTS; LOW ENERGIES; MACROCYCLE; METAL TO LIGAND CHARGE TRANSFERS; MOLECULAR MACHINES; ONE-ELECTRON REDUCTIONS; PHENANTHROLINE; PSEUDOROTAXANES; QUANTITATIVE ANALYSIS; RED SHIFT; REDOX-ACTIVE LIGAND; REVERSIBLE SWITCHING; SCAN RATES; SELF-ASSEMBLED; TETRAZINE; UV-VIS-NIR; UV-VIS-NIR SPECTRA;

CYCLIC VOLTAMMETRY; DRIVES; INFRARED DEVICES; LIGANDS; SPECTROELECTROCHEMISTRY; STOICHIOMETRY; SULFUR COMPOUNDS; ULTRAVIOLET SPECTROSCOPY;

X RAY CRYSTALLOGRAPHY;

1,10 PHENANTHROLINE; 3,6 BIS(5 METHYL 2 PYRIDINE) 1,2,4,5 TETRAZINE; COPPER; MACROCYCLIC COMPOUND; PSEUDOROTAXANE; TAXANE DERIVATIVE; TETRAZINE DERIVATIVE; UNCLASSIFIED DRUG; LIGAND; ROTAXANE;

ARTICLE; COULOMETRY; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; MOLECULAR MECHANICS; OXIDATION REDUCTION REACTION; QUANTITATIVE ANALYSIS; REDUCTION; STOICHIOMETRY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; THERMODYNAMICS; TITRIMETRY; ULTRAVIOLET RADIATION; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; KINETICS;

COPPER; CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; KINETICS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; ROTAXANES; SPECTROPHOTOMETRY, INFRARED;

EID: 61749101323     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8085593     Document Type: Article

References (145)

1. (a) Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines - A Journey into the Nano World; Wiley-VCH: Weinheim, 2003.
2. (b) Barboiu, M.; Vaughan, G.; Kyritsakas, N.; Lehn, J. M. Chem.-Eur. J. 2003, 9, 763-769.
3. (c) Flood, A. H.; Ramirez, R. J. A.; Deng, W. Q.; Muller, R. P.; Goddard, W. A.; Stoddart, J. F. Aust. J. Chem. 2004, 57, 301-322.
4. (d) Sobransingh, D.; Kaifer, A. E. Org. Lett. 2006, 8, 3247-3250.
5. (e) Champin, B.; Mobian, P.; Sauvage, J.- P. Chem. Soc. Rev. 2007, 36, 358-366.
6. (f) Lee, J. W.; Hwang, I.; Jeon, W. S.; Ko, Y. H.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Chem. Asian J. 2008, 3, 1277-1283.
7. (g) Fioravanti, G.; Haraszkiewicz, N.; Kay, E. R.; Mendoza, S. M.; Bruno, C.; Marcaccio, M.; Wiering, P. G.; Paolucci, F.; Rudolf, P.; Brouwer, A. M.; Leigh, D. A. J. Am. Chem. Soc. 2008, 730, 2593-2601.
8. Nijhuis, C. A.; Ravoo, B. J.; Huskens, J.; Reinhoudt, D. N. Coord. Chem. Rev. 2007, 257, 1761-1780.
9. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191.
10. (a) Ozin, G. A.; Manners, I.; Fournier-Bidoz, S.; Arsenault, A. Adv. Mater. 2005, 77, 3011-3018.
11. (b) Kinbara, K.; Aida, T. Chem. Rev. 2005, 705, 1377-1400.
12. (c) Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Chem. Rev. 2005, 705, 1281-1376.
13. (d) Khuong, T. A. V.; Nunez, J. E.; Godinez, C. E.; Garcia-Garibay, M. A. Acc. Chem. Res. 2006, 39, 413-422.
14. (e) Shirai, Y.; Morin, J. F.; Sasaki, T.; Guerrero, J. M.; Tour, J. M. Chem. Soc. Rev. 2006, 35, 1043-1055.
15. (f) Paxton, W. F.; Sundararajan, S.; Mallouk, T. E.; Sen, A. Angew. Chem., Int. Ed. 2006, 45, 5420-5429.
16. (g) Hess, H. Science 2006, 372, 860-861.
17. (h) Bath, J.; Turberfield, A. J. Nat. Nanotechnol. 2007, 2, 275-284.
18. (i) Feringa, B. L. J. Org. Chem. 2007, 72, 6635-6652.
19. (j) Hiraoka, S.; Okuno, E.; Tanaka, T.; Shiro, M.; Shionoya, M. J. Am. Chem. Soc. 2008, 730, 9089-9098.
20. (k) Hsueh, S. Y.; Cheng, K. W.; Lai, C. C.; Chiu, S. H. Angew. Chem., Int. Ed. 2008, 47, 4436-4439.
21. (l) Tomasulo, M.; Sortino, S.; Raymo, F. M. J. Org. Chem. 2008, 73, 118-126.
22. (a) Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172-1175.
23. (b) Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. R. Science 2004, 306, 2055-2056.
24. (c) Green, J. E.; Choi, J. W.; Boukai, A.; Bunimovich, Y.; Johnston-Halperin, E.; Delonno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shin, Y. S.; Tseng, H.-R.; Stoddart, J. F.; Heath, J. R. Nature 2007, 445, 414-417.
25. (a) Jimenez-Molero, M. C.; Dietrich-Buchecker, C.; Sauvage, J. P. Chem.-Eur. J. 2002, 8, 1456-1466.
26. (b) Jimenez-Molero, M. C.; Dietrich-Buchecker, C.; Sauvage, J. P. Chem. Commun. 2003, 1613-1616.
27. (a) Huang, T. J.; Brough, B.; Ho, C. M.; Liu, Y.; Flood, A. H.; Bonvallet, P. A.; Tseng, H.-R.; Stoddart, J. F.; Baller, M.; Magonov, S. Appl. Phys. Lett. 2004, 85, 5391-5393.
28. (b) Liu, Y.; Flood, A. H.; Bonvallett, P. A.; Vignon, S. A.; Northrop, B. H.; Tseng, H.-R.; Jeppesen, J. O.; Huang, T. J.; Brough, B.; Baller, M.; Magonov, S.; Solares, S. D.; Goddard, W. A.; Ho, C. M.; Stoddart, J. F. J. Am. Chem. Soc. 2005, 127, 9745-9759.
29. (c) Wu, J. S.; Leting, K. C. F.; Benitez, D.; Han, J. Y.; Cantrill, S. J.; Fang, L.; Stoddart, J. F. Angew. Chem., Int. Ed. 2008, 47, 7470-7474.
30. Katz, E.; Sheeney-Haj-Ichia, L.; Willner, I. Angew. Chem., Int. Ed. 2004, 43, 3292-3300.
31. (a) Geiger, W. E. Pros. Inors. Chem. 1985, 33, 275-352.
32. (b) Evans, D. H. Chem. Rev. 1990, 90, 739-751.
33. (a) Miller, S. R.; Gustowski, D. A.; Chen, Z. H.; Gokel, G. W.; Echegoyen, L.; Kaifer, A. E. Anal. Chem. 1988, 60, 2021-2024.
34. (b) Boulas, P. L.; Gomez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247.
35. Molecular Catenanes, Rotaxanes and Knots; Wiley-VCH: Weinheim,1999.
36. (a) Li, Y. J.; Li, H.; Li, Y. L.; Liu, H. B.; Wang, S.; He, X. R.; Wang, N.; Zhu, D. B. Org. Lett. 2005, 7, 4835-4838.
37. (b) Mobian, P.; Collin, J. P.; Sauvage, J.-P. Tetrahedron Lett. 2006, 47, 4907-4909.
38. (c) Cabrera, D. G.; Koivisto, B. D.; Leigh, D. A. Chem Commun 2007, 4218-4220.
39. (d) Braunschweig, A. B.; Dichtel, W. R.; Miljanic, O. S.; Olson, M. A.; Spruell, J. M.; Khan, S. I.; Heath, J. R.; Stoddart, J. F. Chem. Asian J. 2007, 2, 634-647.
40. (e) Miljanic, O. S.; Stoddart, J. F. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 12966-12970.
41. (f) Nygaard, S.; Laursen, B. W.; Hansen, T. S.; Bond, A. D.; Flood, A. H.; Jeppesen, J. O. Angew. Chem., Int. Ed. 2007, 46, 6093-6097.
42. (g) Liu, Y.; Klivansky, L. M.; Khan, S. I.; Zhang, X. Y. Org. Lett. 2007, 9, 2577-2580.
43. (h) Chiu, C. W.; Lai, C. C.; Chiu, S. H. J. Am. Chem. Soc. 2007, 129, 3500-3501.
44. (i) Fioravanti, G.; Haraszkiewicz, N.; Kay, E. R.; Mendoza, S. M.; Bruno, C.; Marcaccio, M.; Wiering, P. G.; Paolucci, F.; Rudolf, P.; Brouwer, A. M.; Leigh, D. A. J. Am. Chem. Soc. 2008, 130, 2593-2601.
45. (j) Mullen, K. M.; Gunter, M. J. J. Org. Chem. 2008, 73, 3336-3350.
46. (k) Koshkakaryan, G.; Parimal, K.; He, J.; Zhang, X.; Abliz, Z.; Flood, A. H.; Liu, Y. Chem. Eur. J. 2008,14, 10211-10218.
47. Bissell, R. A.; Cordova, E.; Kaifer, A. E.; Stoddart, J. F. Nature 1994, 369, 133-137.
48. Livoreil, A.; Dietrich-Buchecker, C. O.; Sauvage, J. P. J. Am. Chem. Soc. 1994, 116, 9399-9400.
49. Berna, J.; Leigh, D. A.; Lubomska, M.; Mendoza, S. M.; Perez, E. M.; Rudolf, P.; Teobaldi, G.; Zerbetto, F. Nat. Mater. 2005, 4, 704-710.
50. (a) Nguyen, T. D.; Tseng, H.-R.; Celestre, P. C.; Flood, A. H.; Liu, Y.; Stoddart, J. F.; Zink, J. I. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 10029-10034.
51. (b) Nygaard, S.; Liu, Y.; Stein, P. C.; Flood, A. H.; Jeppesen, J. O. Adv. Funct. Mater. 2007, 17, 751-762.
52. (c) Angelos, S.; Yang, Y. W.; Patel, K.; Stoddart, J. F.; Zink, J. I. Angew. Chem., Int. Ed. 2008, 47, 2222-2226.
53. Allgeier, A. M.; Mirkin, C. A. Angew. Chem., Int. Ed. 1998, 37, 894-908.
54. (a) Amendola, V.; Fabbrizzi, L.; Mangano, C.; Pallavicini, P. Acc. Chem. Res. 2001, 34, 488-493.
55. (b) Fabbrizzi, L.; Foti, F.; Licchelli, M.; Maccarini, P. M.; Sacchi, D.; Zema, M. Chems Eur. J. 2002, 8,4965-4972.
56. (c) Amendola, V.; Colasson, B.; Fabbrizzi, L.; Douton, M. J. R. ChemsEur. J. 2007, 13, 4988-4997.
57. (a) Gisselbrecht, J. P.; Gross, M.; Lehn, J. M.; Sauvage, J. P.; Ziessel, R.; Piccinnileopardi, C.; Arrieta, J. M.; Germain, G.; Vanmeerssche, M. Nou. J. Chim. 1984, 8, 659-667.
58. (b) Collin, J. P.; Gavina, P.; Sauvage, J. P. New J. Chem. 1997, 21, 525-528.
59. (c) Poleschak, I.; Kern, J. M.; Sauvage, J. P. Chem. Commun. 2004, 474-476.
60. (d) Collin, J. P.; Durola, F.; Mobian, P.; Sauvage, J. P. Eur. J. Inorg. Chem. 2007, 242, 0-2425.
61. (e) Prikhod'ko, A. I.; Durola, F.; Sauvage, J. P. J. Am. Chem. Soc. 2008, 130, 448.
62. (a) Yeh, A.; Scott, N.; Taube, H. Inorg. Chem. 1982, 21, 2542-2545.
63. (b) Gaudiello, J. G.; Wright, T. C.; Jones, R. A.; Bard, A. J. J. Am. Chem. Soc. 1985, 107, 888-897.
64. (c) Sano, M.; Taube, H. J. Am. Chem. Soc. 1991, 113, 2327-2328.
65. (d) Potts, K. T.; Keshavarzk, M.; Tham, F. S.; Raiford, K. A. G.; Arana, C.; Abruna,H.D. Inorg. Chem. 1993, 32, 5477-5484.
66. (e) Zelikovich, L.; Libman, J.; Shanzer, A. Nature 1995, 374, 790-792.
67. (f) Zahn, S.; Canary, J. W. Angew. Chem., Int. Ed. 1998, 37, 305-307.
68. (g) Belle, C.; Pierre, J. L.; Saint-Aman, E. New J. Chem. 1998, 22, 1399-1402.
69. (h) Li, Y. J.; Huffman, J. C.; Flood, A. H. Chem. Commun. 2007, 2692-2694.
70. (i) Johansson, O.; Lomoth, R. Inorg. Chem. 2008, 47, 5531-5533.
71. (a) Desantis, G.; Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Perotti, A. J. Chem. Soc., Dalton Trans. 1992, 3283-3284.
72. (b) Liu, X. G.;Eisenberg, A. H.; Stern, C. L.; Mirkin, C. A. Inorg. Chem. 2001, 40, 2940-2941.
73. (c) Weinberger, D. A.; Higgins, T. B.; Mirkin, C. A.; Stern, C. L.; Liable-Sands, L. M.; Rheingold, A. L. J. Am. Chem. Soc. 2001, 123, 2503-2516.
74. Amendola, V.; Fabbrizzi, L.; Mangano, C.; Pallavicini, P.; Perotti, A.; Taglietti, A. J. Chem. Soc., Dalton Trans. 2000, 185-189.
75. He, Z. C.; Colbran, S. B.; Craig, D. C. Chems. Eur. J. 2003, 9, 116-129.
76. Oklejas, V.; Uibel, R. H.; Horton, R.; Harris, J. M. Anal. Chem. 2008, 80, 1891-1901.
77. Maret, W. Biochemistry 2004, 43, 3301-3309.
78. Georgiou, G. Cell 2002, 111, 607-610.
79. (a) Reduction has been used to affect reactivity; see:
80. (b) Lorkovic, I. M.; Wrighton, M. S.; Davis, W. M. J. Am. Chem. Soc. 1994, 116, 6220-6228.
81. (a) Gross, R.; Kaim, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 614-615.
82. (b) Gross, R.; Kaim, W. Inorg. Chem. 1986, 25, 498-506.
83. Ward, M. D.; McCleverty, J. A. J. Chem. Soc., Dalton Trans. 2002, 275-288.
84. Kaim, W. Coord. Chem. Rev. 1987, 76, 187-235.
85. (a) Case, F. H.; Koft, E. J. Am. Chem. Soc. 1959, 87, 905-906.
86. (b) Dallacker, F. Monatsh. Chem. 1960, 97, 294-304.
87. (c) Butte, W. A.; Case, F. H. J. Org. Chem. 1961, 26, 4690-4692.
88. (d) Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318-319.
89. (e) Zajac, W. W.; Siuda, J. F.; Nolan, M. J.; Santosus, T. M. J. Org. Chem. 1971, 36, 3539-3541.
90. (f) Lim, C. L.; Pyo, S. H.; Kim, T. Y.; Yim, E. S.; Han, B. H. Bull. Korean Chem. Soc. 1995, 76, 374-377.
91. (g) Brown, D.; Muranjan, S.; Jang, Y. C.; Thummel, R. Org. Lett. 2002, 4, 1253-1256.
92. (a) Kohlmann, S.; Ernst, S.; Kaim, W. Angew. Chem., Int. Ed. Engl. 1985, 24, 684-685.
93. (b) Kaim, W.; Ernst, S.; Kohlmann, S.; Welkerling, P. Chem. Phys. Lett. 1985, 778, 431-434.
94. (c) Jaradat, Q.; Barqawi, K.; Akasheh, T. S. Inorg. Chim. Acta 1986, 776, 63-73.
95. (d) Kaim, W.; Ernst, S.; Kohlmann, S. Polyhedron 1986, 5, 445-449.
96. (e) Kaim, W.; Kohlmann, S. Inorg. Chem. 1987, 26, 68-77.
97. (f) Kaim, W.; Kohlmann, S. Inorg. Chem. 1987, 26, 1469-1470.
98. (g) Johnson, J. E. B.; de Groff, C.; Ruminski, R. R. Inorg. Chim. Acta 1991, 787, 73-80.
99. (h) Poppe, J.; Moscherosch, M.; Kaim, W. Inorg. Chem. 1993, 32, 2640-2643.
100. (i) Roche, S.; Yellowlees, L. J.; Thomas, J. A. Chem. Commun. 1998, 1429-1430.
101. (j) Glockle, M.; Kaim, W.; Katz, N. E.; Posse, M. G.; Cutin, E. H.; Fiedler, J. Inorg. Chem. 1999, 38, 3270-3274.
102. (k) Chellamma, S.; Lieberman, M. Inorg. Chem. 2001, 40, 3177-3180.
103. (l) Scheiring, T.; Fiedler, J.; Kaim, W. Organometallics 2001, 20, 1437-1441.
104. (m) Gordon, K. C.; Burrell, A. K.; Simpson, T. J.; Page, S. E.; Kelso, G.; Polson, M. I. J.; Flood, A. Eur. J. Inorg. Chem. 2002, 55, 4-563.
105. (n) Ye, S. F.; Kaim, W.; Sarkar, B.; Schwederski, B.; Lissner, F.; Schleid, T.; Duboc-Toia, C.; Fiedler, J. Inorg. Chem. Commun. 2003, 6, 1196-1200.
106. (o) Sarkar, B.; Kaim, W.; Schleid, T.; Hartenbach, I.; Fiedler, J. Zeit. Anorg. Allge. Chem. 2003, 629, 1353-1357.
107. (p) Sarkar, B.; Frantz, S.; Kaim, W.; Duboc, C. Dalton Trans. 2004, 3727-3731.
108. (a) Campos-Fernandez, C. S.; Clerac, R.; Dunbar, K. R. Angew. Chem., Int. Ed. 1999, 38, 3477-3479.
109. (b) Bu, X.-H.; Morishita, H.; Tanaka, K.; Biradha, K.; Furusho, S.; Shionoya, M. Chem. Commun. 2000, 971-972.
110. (c) Campos-Fernandez, C. S.; Clerac, R.; Koomen, J. M.; Russell, D. H.; Dunbar, K. R. J. Am. Chem. Soc. 2001, 723, 773-774.
111. (d) Constable, E. C.; Housecroft, C. E.; Kariuki, B. M.; Kelly, N.; Smith, C. B. Inorg. Chem. Commun. 2002, 5, 199-202.
112. (e) Constable, E. C.; Housecroft, C. E.; Kariuki, B. A.; Kelly, N.; Smith, C. B. Comptes Rendus Chimie 2002, 5, 425-430.
113. (f) Schottel, B. L.; Bacsa, J.; Dunbar, K. R. Chem. Commun. 2005, 46-47l.
114. (g) Campos- Fernandez, C. S.; Schottel, B. L.; Chifotides, H. T.; Bera, J. K.; Bacsa, J.; Koomen, J. M.; Russell, D. H.; Dunbar, K. R. J. Am. Chem. Soc. 2005, 727, 12909-12923.
115. (h) Schottel, B. L.; Chifotides, H. T.; Shatruk, M.; Chouai, A.; Perez, L. M.; Bacsa, J.; Dunbar, K. R. J. Am. Chem. Soc. 2006, 728, 5895-5912.
116. (a) Schwach, M.; Hausen, H. D.; Kaim, W. Inorg. Chem. 1999, 38, 2242-2243.
117. (b) Remenyi, C.; Reviakine, R.; Kaupp, M. J. Phys. Chem. A 2006, 770, 4021-4033.
118. (a) Kaim, W.; Kohlmann, S. Inorg. Chem. 1990, 29, 2909-2914.
119. (b) Kaim, W.; Kohlmann, S. Inorg. Chem. 1986, 25, 3306-3310.
120. (c) Garcia Posse, M. E.; Vergara, M. M.; Fagalde, F.; Mellace, M. G.; Katz, N. E. J. Argn. Chem. Soc. 2004, 92, 101-107.
121. Jordan, B. J.; Pollier, M. A.; Miller, L. A.; Tiernan, C.; Clavier, G.; Audebert, P.; Rotello, V. M. Org. Lett. 2007, 9, 2835-2838.
122. (a) Sleiman, H.; Baxter, P.; Lehn, J.-M.; Rissanen, K. J. Chem. Soc., Chem. Commun. 1995, 715-716.
123. (b) Sleiman, H.; Baxter, P. N. W.; Lehn, J.-M.; Airola, K.; Rissanen, K. Inorg. Chem. 1997, 36, 4734-4742.
124. (c) Baxter, P. N. W.; Sleiman, H.; Lehn, J.-M.; Rissanen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1294-1296.
125. (a) Baxter, P. N. W.; Hanan, G. S.; Lehn, J.-M. Chem. Commun. 1996, 2019-2020.
126. (b) Baxter, P. N. W.; Lehn, J.-M.; Fischer, J.; Youinou, M. T. Angew. Chem., Int. Ed. Engl. 1994, 33, 2284-2287.
127. (c) Baxter, P.; Lehn, J.-M.; Decian, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 69-72.
128. (d) Sleiman, H.; Baxter, P. N. W.; Lehn, J.-M.; Airola, K.; Rissanen, K. Inorg. Chem. 1997, 36, 4734-4742.
129. (e) Baxter, P. N. W.; Khoury, R. G.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem.-Eur. J. 2000, 6, 4140-U48.
130. Jimenez-Molero, M. C.; Dietrich-Buchecker, C.; Sauvage, J.-P. Chem.-Eur. J. 2002, 8, 1456-1466.
131. Youinou, M. T.; Rahmouni, N.; Fischer, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 37, 733-735.
132. Schwach, M.; Hausen, H.-D.; Kaim, W. Inorg. Chem. 1999, 38, 224-2243.
133. Abdel-Rahman, M. O.; Kira, M. A.; Tolba, M. N. Tetrahedron Lett. 1968, 3871-3872.
134. Ichinaga, A. K.; Kirchhoff, J. R.; McMillin, D. R.; Dietrich-Buchecker, C. O.; Marnot, P. A.; Sauvage, J.-P. Inorg. Chem. 1987, 26, 4290-4292.
135. Glockle, M.; Kaim, W.; Katz, N. E.; Posse, M. G.; Cutin, E. H.; Fiedler, J. Inorg. Chem. 1999, 38, 3270-3274.
136. (a) Vander Griend, D. A.; Bediako, D. K.; DeVries, M. J.; DeJong, N. A.; Heeringa, L. P. Inorg. Chem. 2008, 47, 656-662.
137. (b) Li, Y.; Vander Griend, D. A.; Flood, A. H. Supramol. Chem. 2008, in press.
138. Alderighi, L.; Gans, P.; Ienco, A.; Peters, D.; Sabatini, A.; Vacca, A. Coord. Chem. Rev. 1999, 184, 311-318.
139. Badjic, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723-732.
140. Spectroelectrochemistry: Theory and Practice; Gale, R. J., Ed.; Plenum Press: New York, 1988.
141. Kaim, W.; Berger, S.; Greulich, S.; Reinhardt, R.; Fiedler, J. J. Organomet. Chem. 1999, 582, 153-159.
142. Muller, P. Pure Appl. Chem. 1994, 86, 1077-1184.
143. The IUPAC identifies more than one definition of disproportionation. The use of supramolecular disproportionation is to distinguish the reaction from the more common relation to changes in oxidation state.
144. -1, were required.
145. -, was not able to reproduce the experimental CVs.