Synthetic molecular machine based on reversible end-to-interior and end-to-end loop formation triggered by electrochemical stimuli

Chemistry - An Asian Journal

Volumn 3, Issue 8-9, 2008, Pages 1277-1283

  Lee, Jae Wook ^a,c   Hwang, Ilha ^a   Jeon, Woo Sung ^a   Ko, Young Ho ^a   Sakamoto, Shigeru ^b   Yamaguchi, Kentaro ^b   Kim, Oon ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^c Dong A University   (South Korea)

Author keywords

Charge transfer; Electrochemistry; Molecular machines; Pseudorotaxanes; Supramolecular chemistry

Indexed keywords

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY;

ELECTROCHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY;

EID: 54849440779     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800054     Document Type: Article

References (121)

1. For reviews, see: a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530;
2. Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
3. b) E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72-196;
4. Angew. Chem. Int. Ed. 2007, 46, 72-191;
5. c) W. R. Browne, B. L. Ferringa, Nat. Nanotechnol. 2006, 1, 25-35.
6. Molecular machines special issues: a) Acc. Chem. Res. 2001, 34, 409-522;
7. b) Adv. Funct. Mater. 2007, 17, 671-840.
8. For representative examples, see: a) P. L. Anelli, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1991, 113, 5131-5133;
9. b) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133-137;
10. c) A. S. Lane, D. A. Leigh; A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093;
11. A. Murphy, J. Am. Chem. Soc. 1997, 119, 11092-11093;
12. d) P. R. Ashton, R. Ballardini, V. Balzani, I. Baxter, A. Credi, M. C. T. Fyfe, M. T. Gandolfi; M. Gómez-López, M.-V. Martí-nez- Díaz, A. Piersanti, N. Spencer, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 11932-11942;
13. M. Gómez-López, M.-V. Martínez-Díaz, A. Piersanti, N. Spencer, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 11932-11942;
14. e) A. M. Brouwer, C. Frochot, F. G. Gatti, D. A. Leigh, L. Mottier, F. Paolucci, S. Roffia, G. W. H. Wurpel, Science 2001, 291, 2124-2128;
15. f) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533;
16. Angew. Chem. Int. Ed. 2003, 42, 1491-1495;
17. g) G. Bottari, F. Dehez, D. A. Leigh, P. J. Nash, E. M. Pérez, J. K. Y. Wong, F. Zerbetto, Angew. Chem. 2003, 115, 6066-6069;
18. Angew. Chem. Int. Ed. 2003, 42, 5886-5889;
19. h) C. M. Keaveney, D. A. Leigh, Angew. Chem. 2004, 116, 1242-1244;
20. Angew. Chem. Int. Ed. 2004, 43, 1222-1224;
21. i) J. Berná, D. A. Leigh, M. Lubomska, S. M. Mendoza, E. M. Pérez, P. Rudolf, G. Teobaldi, F. Zerbetto, Nat. Mater. 2005, 4, 704-710;
22. j) V. Balzani, M. Clemente-León, A. Credi, B. Ferrer, M. Venturi, A. H. Flood, J. F. Stoddart, Proc. Natl. Acad. Sci. USA 2006, 103,1178-1183.
23. For representative examples, see: a) T. R. Kelly, H. De Silva, R. A. Silva, Nature 1999, 401, 150-152;
24. b) N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada, B. L. Feringa, Nature 1999, 401,152-155;
25. c) H. Jian, J. M. Tour, J. Org. Chem. 2003, 68, 5091-5103;
26. d) D. A. Leigh, J. K. Y. Wong, F. Dehez, F. Zerbetto, Nature 2003, 424, 174-179;
27. e) J. V. Hernández, E. R. Kay, D. A. Leigh, Science 2004, 306, 1532-1537;
28. f) X. Zheng, M. E. Mulcahy, D. Horinek, F. Galeotti, T. F. Magnera, J. Michl, J. Am. Chem. Soc. 2004, 126, 4540-4542;
29. g) S. P. Fletcher, F. Dumur, M. M. Pollard, B. L. Feringa, Science 2005, 310, 80-82;
30. h) D. Pijper, R. A. van Delden, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2005, 127, 17612-17613.
31. a) M. C. Jiménez, C. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 2000, 112, 3422-3425;
32. Angew. Chem. Int. Ed. 2000, 39, 3284-3287;
33. b) M. C. Jiménez-Molero, C. Dietrich-Buchecker, J.-P. Sauvage, Chem. Eur. J. 2002, 8, 1456-1466;
34. c) M. C. Jiménez-Molero, C. Dietrich-Buchecker, J.-P. Sauvage, Chem. Commun. 2003, 1613-1616;
35. d) Y. Liu, A. H. Flood, P. A. Bonvallet, S. A. Vignon, B. H. Northrop, H.-R. Tseng, J. O. Jeppesen, T. J. Huang, B. Brough, M. Baller, S. Magonov, S. D. Solares, W. A. Goddard, C.-M. Ho, J. F. Stoddart, J. Am. Chem. Soc. 2005, 127, 9745-9759.
36. a) T. Muraoka, K. Kinbara, Y. Kobayashi, T. Aida, J. Am. Chem. Soc. 2003, 125, 5612-5613;
37. b) T. Muraoka, K. Kinbara, T. Aida, Nature 2006, 440, 512-515.
38. a) J. D. Badjić, V. Balzani, A. Credi, S. Silvi, J. F. Stoddart, Science 2004, 303, 1845-1849;
39. b) J. D. Badjic, C. M. Ronconi, J. F. Stoddart, V. Balzani, S. Silvi, A. Credi, J. Am. Chem. Soc. 2006, 128, 1489-1499.
40. a) L. Finzi, J. Gelles, Science 1995, 267, 378-380;
41. b) S. H. Yoshimura, H. Maruyama, F. Ishikawa, R. Ohki, K. Takeyasu, Genes Cells 2004, 9, 205-218;
42. c) Y. Zhang, C. L. Smith, A. Saha, S. W. Grill, S. Mihardja, S. B. Smith, B. R. Cairns, C. L. Peterson, C. Bustamante, Mol. Cell 2006, 24, 559-568.
43. a) F. Krieger, B. Fierz, O. Bieri, M. Drewello, T. Kiefhaber, J. Mol. Biol. 2003, 332, 265-274;
44. b) R. R. Hudgins, F. Huang, G. Gramlich, W. M. Nau, J. Am. Chem. Soc. 2002, 124, 556-564;
45. c) L. J. Lapidus, W. A. Eaton, J. Hofrichter, Proc. Natl. Acad. Sci. USA 2000, 97, 7220-7225;
46. d) B. Fierz, T. Kiefhabar, J. Am. Chem. Soc. 2007, 129, 672-679.
47. a) S. Shinkai, M. Ishihara, K. Ueda, O. Manabe, J. Chem. Soc. Perkin Trans. 2 1985, 511-518;
48. b) P. R. Ashton, R. Ballardini, V. Balzani, S. E. Boyd, A. Credi, M. T. Gandolfi, M. Gómez-López, S. Iqbal, D. Philp, J. A. Preece, L. Prodi, H. G. Ricketts, J. F. Stoddart, M. S. Tolley, M. Venturi, M. Venturi, A. J. P. White, D. J. Williams, Chem. Eur. J. 1997, 3, 152-170;
49. c) Y. Liu, A. H. Flood, J. F. Stoddart, J. Am. Chem. Soc. 2004, 126, 9150-9151.
50. W. S. Jeon, A. Y. Ziganshina, J. W. Lee, Y. H. Ko, J.-K. Kang, C. Lee, K. Kim, Angew. Chem. 2003, 115, 4231-4234;
51. Angew. Chem. Int. Ed. 2003, 42, 4097-4100.
52. a) W. A. Freeman, W. L. Mock, N.-Y. Shih, J. Am. Chem. Soc. 1981, 103, 7367-7368;
53. b) J. Kim, I.-S. Jung, S.-Y. Kim, E. Lee, J.-K. Kang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2000, 122, 540-541;
54. c) A. Day, A. P. Arnold, R. J. Blanch, B. Snushall, J. Org. Chem. 2001, 66, 8094-8100;
55. d) S. Liu, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2005, 127, 16798-16799.
56. a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333-11334;
57. b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451-452;
58. c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899-4900;
59. d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 671-675;
60. Angew. Chem. Int. Ed. 1999, 38, 637-641;
61. e) E. Lee, J. Heo, K. Kim, Angew. Chem. 2000, 112, 2811-2813;
62. Angew. Chem. Int. Ed. 2000, 39, 2699-2701;
63. f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413-416;
64. Angew. Chem. Int. Ed. 2001, 40, 399-402;
65. g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 769-771;
66. Angew. Chem. Int. Ed. 2001, 40, 746-749;
67. h) D. Tuncel, J. H. G. Steinke, Chem. Commun. 2001, 253-254;
68. i) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498-508;
69. j) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140-2147;
70. k) K. Kim, Chem. Soc. Rev. 2002, 31, 96-107;
71. l) S. Choi, J. W. Lee, Y. H. Ko, K. Kim, Macromolecules 2002, 35, 3526-3531;
72. m) Y. Tan, S. Choi, J. W. Lee, Y. H. Ko, K. Kim, Macromolecules 2002, 35, 7161-7165;
73. n) K.-M. Park, E. Lee, S.-G. Roh, J. Kim, K. Kim, Bull. Korean Chem. Soc. 2004, 25, 1711-1713;
74. o) S.-Y. Kim, J. W. Lee, S. C. Han, K. Kim, Bull. Korean Chem. Soc. 2005, 26, 1265-1268;
75. p) V. Sindelar, K. Moon, A. E. Kaifer, Org. Lett. 2004, 6, 2665-2668;
76. q) H.-J. Buschmann, L. Mutihac, E. Schollmeyer, J. Inclusion Phenom. Macrocyclic Chem. 2005, 53, 85-88;
77. r) J. W. Lee, G. T. Lim, J. Korean Chem. Soc. 2005, 49, 112-116;
78. s) M. V. Rekharsky, H. Yamamura, M. Kawai, I. Osaka, R. Arakawa, A. Sato, Y. H. Ko, N. Selvapalam, K. Kim, Y. Inoue, Org. Lett. 2006, 8, 815-818;
79. t) Z.-B. Wang, H.-F. Zhu, M. Zhao, Y.-Z. Li, T. Okamura, W.-Y. Sun, H.-L. Chen, N. Ueyama, Cryst. Growth Des. 2006, 6, 1420-1427;
80. u) D. Tuncel, N. Cindir, Ü. Koldemir, J. Inclusion Phenom. Macrocyclic Chem. 2006, 55, 373-380;
81. v) F.-J. Huo, C.-X. Yin, P. Yang, J. Inclusion Phenom. Macrocyclic Chem. 2006, 56, 193-196;
82. w) Z.-S. Hou, Y.-B. Tan, K. Kim, Q.-F. Zhou, Polymer 2006, 47, 742-750;
83. x) Y. Liu, C.-F. Ke, H.-Y. Zhang, W.-J. Wu, J. Shi, J. Org. Chem. 2007, 72, 280-283;
84. y) R. Eelkema, K. Maeda, B. Odell, H. L. Anderson, J. Am. Chem. Soc. 2007, 129, 12384-12385;
85. z) M. Zhao, Z.-B. Wang, Y.-Z. Li, H.-L. Chen, Inorg. Chem. Commun. 2007, 10, 101-104.
86. a) S. I. Jun, J. W. Lee, S. Sakamoto, K. Yamaguchi, K. Kim, Tetrahedron Lett. 2000, 41, 471-475;
87. b) J. W. Lee, K. Kim, K. Kim, Chem. Commun. 2001, 1042-1043;
88. c) K. Kim, W. S. Jeon, J.-K. Kang, J. W. Lee, S. Y. Jeon, T. Kim, K. Kim, Angew. Chem. 2003, 115, 2395-2398;
89. Angew. Chem. Int. Ed. 2003, 42, 2293-2296;
90. d) V. Sindelar, S. Silvi, A. E. Kaifer, Chem. Commun. 2006, 2185-2187;
91. e) T. Ooya, D. Inoue, H. S. Choi, Y. Kobayashi, S. Loethen, D. H. Thompson, Y. H. Ko, K. Kim, N. Yui, Org. Lett. 2006, 8, 3159-3162;
92. f) D. Sobransingh, A. E. Kaifer, Org. Lett. 2006, 8, 3247-3250;
93. g) D. Tuncel, H. B. Tiftik, B. Salih, J. Mater. Chem. 2006, 16, 3291-3296;
94. h) V. Sindelar, S. Silvi, S. E. Parker, D. Sobransingh, A. E. Kaifer, Adv. Funct. Mater. 2007, 17, 694-701;
95. i) D. Tuncel, Ö. Özsar, H. B. Tiftik, B. Salih, Chem. Commun. 2007, 1369-1371;
96. j) S. Chakrabarti, P. Mukhopadhyay, S. Lin, L. Isaacs, Org. Lett. 2007, 9, 2349-2352;
97. k) Y. Liu, X.-Y. Li, H.-Y. Zhang, C.-J. Li, F. Ding, J. Org. Chem. 2007, 72, 3640-3645.
98. H.-J. Kim, J. Heo, W. S. Jeon, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 1574-1577;
99. Angew. Chem. Int. Ed. 2001, 40, 1526-1529.
100. a) J. W. Lee, S. Samal, N. Selvapalam, H.-J. Kim, K. Kim, Acc. Chem. Res. 2003, 36, 621-630;
101. b) J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs, Angew. Chem. 2005, 117, 4922-4949;
102. Angew. Chem. Int. Ed. 2005, 44, 4844-4870;
103. c) Y. H. Ko, E. Kim, I. Hwang, K. Kim, Chem. Commun. 2007, 1305-1315.
104. a) Y. H. Ko, K. Kim, J.-K. Kang, H. Chun, J. W. Lee, S. Sakamoto, K. Yamaguchi, J. C. Fettinger, K. Kim, J. Am. Chem. Soc. 2004, 126, 1932-1933;
105. b) Y. J. Jeon, P. K. Bharadwaj, S. W. Choi, J. W. Lee, K. Kim, Angew. Chem. 2002, 114, 4654-4656;
106. Angew. Chem. Int. Ed. 2002, 41, 4474-4476;
107. c) W. Wang, A. E. Kaifer, Angew. Chem. 2006, 118, 7200-7204;
108. Angew. Chem. Int. Ed. 2006, 45, 7042-7046;
109. d) S.-Y. Kim, Y. H. Ko, J. W. Lee, S. Sakamoto, K. Yamaguchi, K. Kim, Chem. Asian J. 2007, 2, 747-754;
110. e) J. W. Lee, S. C. Han, J. H. Kim, Y. H. Ko, K. Kim, Bull. Korean Chem. Soc. 2007, 28, 1837-1840;
111. f) J. W. Lee, K. Kim, S. Choi, Y. H. Ko, S. Sakamoto, K. Yamaguchi, K. Kim, Chem. Commun. 2002, 2692-2693;
112. g) K. Kim, D. Kim, J. W. Lee, Y. H. Ko, K. Kim, Chem. Commun. 2004, 848-849;
113. h) M. E. Bush, N. D. Bouley, A. R. Urbach, J. Am. Chem. Soc. 2005, 127, 14511-14517;
114. i) V. Sindelar, M. A. Cejas, F. M. Raymo, W. Chen, S. E. Parker, A. E. Kaifer, Chem. Eur. J. 2005, 11, 7054-7059;
115. j) Y. H. Ko, K. Kim, E. Kim, K. Kim, Supramol. Chem. 2007, 19, 287-293;
116. k) J.-K. Kang, I. Hwang, Y. H. Ko, W. S. Jeon, H.-J. Kim, K. Kim, Supramol. Chem. 2008, 20, 149-155.
117. W. S. Jeon, E. Kim, Y. H. Ko, I. Hwang, J. W. Lee, S.-Y. Kim, H.-J. Kim, K. Kim, Angew. Chem. 2005, 117, 89-93;
118. Angew. Chem. Int. Ed. 2005, 44, 87-91.
119. W. S. Jeon, H.-J. Kim, C. Lee, K. Kim, Chem. Commun. 2002, 1828-1829.
120. 0) has not been established, decomplexation of 4 does not seem to occur at least on the cyclic voltammetric time scale for the following reasons: a) Essentially the same cyclic voltammograms are obtained for 4 and no growth of the peaks corresponding to 3 is observed in the successive full scans, b) The anodic peak for 4 at -0.8 V is sharp, presumably owing to adsorption of the fully reduced species, but clearly different from the corresponding anodic peak for 3 in terms of both potential and current (Figure 3), c) When the scan potential is reversed at -1.0 V, the reoxidation peak occurs at the same potential (-0.45 V) as before (Figure S4 in the Supporting Information).
121. The formation of intermolecular viologen radical cation dimers such as a 2:2 complex with a face-to-face dimer structure cannot be ruled out. However, the intermolecular dimerization should be entropically much more unfavorable; therefore it is less likely to happen at the concentration of the ligand (0.25 mM) employed in this study.