Recent developments on rotaxane-based shuttles

Current Organic Chemistry

Volumn 13, Issue 5, 2009, Pages 448-481

  Rescifina, Antonio ^a   Zagni, Chiara ^a   Iannazzo, Daniela ^b   Merino, Pedro ^c  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

^c UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 65649125635     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527209787582222     Document Type: Review

References (260)

1. Feynman, R.P. Eng.Sci., 1960, 23, 22.
2. Shinkai, S.; Manabe, O. Top. Curr. Chem., 1984, 121, 76.
3. Balzani, V.; Credi, A.; Raymo, F.M.; Stoddart, J.F. Angew. Chem. Int. Ed., 2000, 39, 3348.
4. (a) Lane, A.S.; Leigh, D.A.; Murphy, A. J. Am. Chem. Soc., 1997, 119, 11092;
5. (b) Ashton, P.R.; Ballardini, R.; Balzani, V.; Baxter, I.; Credi, A.; Fyfe, M.C.T.; Gandolfi, M.T.; Gómez-López, M.; Martínez-Díaz, M.-V.; Piersanti, A.; Spencer, N.; Stoddart, J.F.; Venturi, M.; White, A.J.P.; Williams, D.J. J. Am. Chem. Soc., 1998, 120, 11932;
6. (c) Lee, J.W.; Kim, K. Chem. Commun., 2001, 1042;
7. (d) Elizarov, A.M.; Chiu, H.-S.; Stoddart, J.F. J. Org. Chem., 2002, 67, 9175;
8. (e) Kaiser, G.; Jarrosson, T.; Otto, S.; Ng, Y.-F.; Bond, A.D.; Sanders, J.K.M. Angew. Chem. Int. Ed., 2004, 43, 1959;
9. (f) Liu, Y.; Flood, A.H.; Stoddart, J.F.; J. Am. Chem. Soc., 2004, 126, 9150;
10. (g) Vignon, S.A.; Jarrosson, T.; Iijima, T.; Tseng, H.-R.; Sanders, J.K.M.; Stoddart, J.F. J. Am. Chem. Soc., 2004, 126, 9884.
11. (a) Raehm, L.; Kern, J.M.; Sauvage, J.-P. Chem. Eur. J., 1999, 5, 3310;
12. (b) Bermudez, V.; Capron, N.; Gase, T.; Gatti, F.G.; Kajzar, F.; Leigh, D.A.; Zerbetto, F.; Zhang, S. Nature, 2000, 406, 608;
13. (c) Kern, J.-M.; Raehm, L.; Sauvage, J.-P.; Divisia-Blohorn, B.; Vida, P.-L. Inorg. Chem., 2000, 39, 1555;
14. (d) Ballardini, R.; Balzani, V.; Dehaen, W.; Dell'Erba, A.E.; Raymo, F.M.; Stoddart, J.F.; Venturi, M. Eur. J. Org. Chem., 2000, 65, 591;
15. (e) Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O.A.; Raymo, F.M.; Stoddart, J.F.; Venturi, M.; White, A.J.P.; Williams, D.J.; J. Org. Chem., 2000, 65, 1924;
16. (f) Collin, J.-P.; Kern, J.-M.; Raehm, L.; Sauvage, J.-P. Molecular Switches; Feringa B.L. Ed.; Wiley-VCH: Weinheim, 2000; pp. 249;
17. (g) Altieri, A.; Gatti, F.G.; Kay, E.R.; Leigh, D.A.; Paolucci, F.; Slawin, A.M.; Wong, J.K.Y. J. Am. Chem. Soc., 2003, 125, 8644;
18. (h) Poleschak: I.; Kern, J.-M.; Suavage, J.-P. Chem. Commun., 2004, 474.
19. (a) Ballardini, R.; Balzani, V.; Gandolfi, M.T.; Prodi, L.; Venturi, M.; Philp, D.; Ricketts, H.G.; Stoddart, J.F. Angew. Chem. Int. Ed. Engl., 1993, 32, 1301;
20. (b) Ashton, P.R.; Ballardini, R.; Balzani, V.; Credi, A.; Dress, R.; Ishow, E.; Kocian, O.; Preece, J.A.; Spencer, N.; Stoddart, J.F.; Venturi, M.; Wenger, S. Chem. Eur. J., 2000, 6, 3558;
21. (c) Brower, A.M.; Frochot, C.; Gatti, F.G.; Leigh, D.A.; Mottier, L.; Paolucci, F.; Roffia, S.; Wurpel, G.W.H. Science, 2001, 291, 2124;
22. (d) Collin, J.-P.; Laemmel, A.-C.; Sauvage, J.-P. New J. Chem., 2001, 25, 22;
23. (e) Bottari, G.; Leigh, D. A.; Pérez, E.M. J. Am. Chem. Soc., 2003, 125, 13360;
24. (f) Gatti, F.G.; Len, S.; Wong, J.K.Y.; Bottari, G.; Altieri, A.; Morales, M.A.F.; Teat, S.J.; Frochot, C.; Leigh, D.A.; Brower, A.M.; Zerbetto, F. Proc. Natl. Acad. Sci. USA, 2003, 100, 10;
25. (g) Altieri, A.; Bottari, G.; Dehez, F.; Leigh, D.A.; Wong, J.K.Y.; Zerbetto, F. Angew. Chem. Int. Ed., 2003, 42, 2296;
26. (h) Brower, A.M.; Fazio, S.M.; Frochot, C.; Gatti, F.G.; Leigh, D.A.; Wong, J.K.Y.; Wurpel, G.W.H. J. Pure Appl. Chem., 2003, 75, 1055;
27. (i) Pérez, E.M.; Dryden, D.T.F.; Leigh, D.A.; Teobaldi, G.; Zerbetto, F. J. Am. Chem. Soc., 2004, 126, 12210.
28. (a) Kelly, T.R.; Silva, H.D.; Silva, R.A. Nature, 1999, 401, 150;
29. (b) Koumura, N.; Zijlstra, R.W.; van Delden, R.A.; Harada, H.; Feringa, B.L. Nature, 1999, 401, 152;
30. (c) Yokoyama, Y. Chem. Rev., 2000, 100, 1717;
31. (d) Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev., 2000, 100, 1741;
32. (e) Feringa, B.L.; van Delden, R.A.; Koumura, N.; Geertsema, E.M. Chem. Rev., 2000, 100, 1789;
33. (f) Kelly, T.R.; Acc. Chem. Res., 2001, 34, 514;
34. (g) Shinkai, S.; Ikeda, M.; Sugasaki, A.; Takeuchi, M. Acc. Chem. Res., 2001, 34, 494;
35. (h) Oh, K.; Jeong, K.-S.; Moore, J. S. Nature, 2001, 414, 889;
36. (i) Koumura, N.; Geertsema, E.M.; van Gelder, M.B.; Meetsma, A.; Feringa, B.L. J. Am. Chem. Soc., 2002, 124, 5037;
37. (j) Hawthorne, F.; Zink, J.I.; Skelton, J.M.; Bayer, M.J.; Liu, C.; Livshits, E.; Baer, R.; Neuhauser, D. Science, 2004, 303, 1849;
38. (k) de Jong, J.J.D.; Lucas, L.N.; Kellogg, R.M.; van Esch, J.H.; Feringa, B.L. Science, 2004, 304, 278;
39. (l) Koçer, A.; Walco, M.; Meijberg, W.; Feringa, B.L. Science, 2005, 309, 755;
40. (m) Fletcher, S.P.; Dumur, F.; Pollard, M.M.; Feringa, B.L. Science, 2005, 310, 80;
41. (n) Berná, J.; Leigh, D.A.; Lubomska, M.; Mendoza, S.M.; Pérez, E.M.; Rudolf, P.; Teobaldi, G.; Zerbetto, R. Nat. Mater., 2005, 4, 704.
42. (a) Busch, D.H.; Stephenson, N.A. Coord. Chem. Rev., 1990, 100, 119;
43. (b) Lindsey, J.S. New J. Chem., 1991, 15, 153;
44. (c) Philp, D.; Stoddart, J.F. Synlett, 1991, 445;
45. (d) Hunter, C.A. J. Am. Chem. Soc., 1992, 114, 5303;
46. (e) Anderson, S.; Anderson, H.L.; Sanders, J.K.M. Acc. Chem. Res., 1993, 26, 469;
47. (f) Bisson, A.P.; Carver, F.J.; Hunter, C.A.; Waltho, J.P. J. Am. Chem. Soc., 1994, 116, 10292;
48. (g) Hunter, C.A. Angew. Chem. Int. Ed. Engl., 1995, 34, 1079;
49. (h) Schneider, J.P.; Kelly, J.W. Chem. Rev., 1995, 95, 2169;
50. (i) Philp, D.; Stoddart, J.F. Angew. Chem. Int. Ed. Engl., 1996, 35, 1154;
51. (j) Kolchinski, A.G.; Alcock, N.W.; Roesner, R.A.; Busch, D.H. Chem. Commun., 1998, 1437;
52. (k) Fujita, M. Acc. Chem. Res., 1999, 32, 53;
53. (l) Rebek, J. Jr. Acc. Chem. Res., 1999, 32, 278;
54. (m) Diederich, F.; Stang P. J. Templated Organic Synthesis, Wiley-VCH: Weinheim, 1999;
55. (n) Nakash, M.; Clyde-Watson, Z.; Feeder, N.; Teat, S.J.; Sanders, J.K.M. Chem. Eur. J., 2000, 6, 2112;
56. (o) Sanders, J.K.M. Pure Appl. Chem., 2000, 72, 2265;
57. (p) Bong, D.T.; Clark, T.D.; Granja, J.R.; Ghadiri, M.R. Angew. Chem. Int. Ed., 2001, 40, 988;
58. (q) Prins, L.J.; Reinhoudt, D.N.; Timmerman, P. Angew. Chem. Int. Ed., 2001, 40, 2382;
59. (r) Seidel, S.R.; Stang, P.J. Acc. Chem. Res., 2002, 35, 972;
60. (s) Stoddart, J.F.; Tseng, H.-R. Proc. Natl. Acad. Sci. USA, 2002, 99, 4797;
61. (t) Furlan, R.L.E.; Otto, S.; Sanders, J.K.M. Proc. Natl. Acad. Sci. USA, 2002, 99, 4801;
62. (u) Joester, D.; Walter, E.; Losson, M.; Pugin, R.; Merkle, H.P.; Diederich, F. Angew. Chem. Int. Ed., 2003, 42, 1486;
63. (v) Hogg, L.; Leigh, D.A.; Lusby, P.J.; Morelli, A.; Parsons, S.; Wong, J.K.Y. Angew. Chem. Int. Ed., 2004, 43, 1218;
64. (w) Zheng, X.; Mulcahy, M.E.; Horinek, D.; Galeotti, F.; Magnera, T.F.; Michl, J. J. Am. Chem. Soc., 2004, 126, 4540;
65. (x) Aricó, F.; Badjic, J.D.; Cantrill, S.J.; Flood, A.H.; Leung, K.C.-F.; Liu, Y.; J. Stoddart, F. Top. Curr. Chem., 2005, 249, 203.
66. (a) Carter, F.L.; Siatkowski, R.E.; Wohltjie, H. Molecular Electronic Devices, Elsevier: Amsterdam, 1988;
67. (b) Aviram, A. Molecular Electronics - Science and Technology, Engineering Foundation: New York, 1989;
68. (c) Lazarev, P.I. Molecular Electronics: Materials and Methods, Kluwer: Dordrecht, 1991;
69. (d) Aviram, A. Molecular Electronics - Science and Technology, American Institute of Physics: Washington DC, 1992;
70. (e) Ashwell, G.J. Molecular Electronics, Wiley: New York, 1992;
71. (f) Sienicki, K. Molecular Electronics and Molecular Electronic Devices, CRC Press: Boca Raton FL, 1993;
72. (g) Birge, R.R. Molecular and Biomolecular Electronics, American Chemical Society: Washington DC, 1994;
73. (h) Petty, M.C.; Bryce, M.R.; Bloor D. Introduction to Molecular Electronic Devices, Oxford University Press: New York, 1995;
74. (k) Jortner, J. Ratner M. Molecular Electronics, Blackwell Science: Oxford, 1997;
75. (i) Aviram, A.; Ratner M. Molecular Electronics: Science and Technology, Engineering Foundation: New York, 1998;
76. (j) Chem. Rev., 1999, 99, 1641 (Special Issue on Nanoscale Materials);
77. (k) Acc. Chem. Res., 1999, 32, 387 (Special Issue on Nanoscale Materials);
78. (l) Nalwa, H.S. Handbook of Nanostructured Materials and Nanotechnology, Academic Press: New York, 1999.
79. (a) Urry, D.W. Angew. Chem. Int. Ed. Engl., 1993, 32, 819;
80. (b) Howard, J. Nature, 1997, 389, 561.
81. Bistable catenanes and bistable rotaxanes have been employed as switches in a range of devices and across different environments, see (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;
82. (b) Pease, A.R.; Jeppesen, J.O.; Stoddart, J.F.; Luo, Y.; Collier, C.P.; Heath, J.R. Acc. Chem. Res., 2001, 34, 434;
83. (c) Luo, Y.; Collier, C.P.; Jeppesen, J.O.; Neilsen, K.A.; DeIonno, E.; Ho, G.; Perkins, J.; Tseng, H.-R.; Yamamoto, T.; Stoddart, J.F.; Heath, J.R. ChemPhysChem, 2002, 3, 519;
84. (d) Diehl, M.R.; Steuerman, D.W.; Tseng, H.-R.; Vignon, S.A.; Star, A.; Celestre, P.C.; Stoddart, J.F.; Heath, J.R. ChemPhysChem, 2003, 4, 1335;
85. (e) Tseng, H.-R.; Wu, D.; Fang, N.; Zhang, X.; Stoddart, J.F. ChemPhysChem, 2004, 5, 111;
86. (f) Steuerman, D.W.; Tseng, H.-R.; Peters, A.J.; Flood, A.H.; Jeppesen, J.O.; Nielsen, K.A.; Stoddart, J.F.; Heath, J.R. Angew. Chem. Int. Ed., 2004, 43, 6486;
87. (g) Flood, A.H.; Peters, A.J.; Vignon, S.A.; Steuerman, D.W.; Tseng, H.-R.; Kang, S.; Heath, J. R.; Stoddart, J.F. Chem. Eur. J., 2004, 10, 6558;
88. (h) Flood, A.H.; Stoddart, J.F.; Steuerman, D.W.; Heath, J.R. Science, 2004, 306, 2055;
89. (i) Jang, S.S.; Kim, Y. H.; Goddard, W.A. III; Flood, A.H.; Laursen, B.W.; Tseng, H.-R.; Stoddart, J.F.; Jeppesen, J.O.; Choi, J.W.; Steuerman, D.W.; DeIonno, E.; Heath, J.R.; J. Am. Chem. Soc., 2005, 127, 1563;
90. (j) Jang, S.S.; Jang, Y.H.; Kim, Y.-H.; Goddard, W.A. III; Choi, J.W.; Heath, J.R.; Laursen, B.W.; Flood, A.H.; Stoddart, J.F.; Nørgaard, K.; Bjørnholm, T. J. Am. Chem. Soc., 2005, 127, 14804.
91. (a) Chia, S.; Cao, J.; Stoddart, J.F.; Zink, J.I. Angew. Chem. Int. Ed., 2001, 40, 2447;
92. (b) Kim, K.; Jeon, W.S.; Kang, J.-K.; Lee, J.W.; Jon, S.Y.; Kim, T.; Kim, K. Angew. Chem. Int. Ed., 2003, 42, 2293;
93. (c) Long, B.; Nikitin, K.; Fitzmaurice, D. J. Am. Chem. Soc., 2003, 125, 15490;
94. (d) Hernandez, R.; Tseng, H.-R.; Wong, J.W.; Stoddart, J.F.; Zink, J.I. J. Am. Chem. Soc., 2004, 126, 3370;
95. (e) Lee, I.C.; Frank, C.W.; Yamamoto, T.; Tseng, H.-R.; Flood, A.H.; Stoddart, J.F.; Jeppesen, J.O. Langmuir, 2004, 20, 5809;
96. (f) Katz, E.; Sheeney-Haj-Ichia, L.; Willner, I. Angew. Chem. Int. Ed., 2004, 43, 3292;
97. (g) Lioubashevski, O.; Chegel, V.I.; Patolsky, F.; Katz, E.; Willner, I. J. Am. Chem. Soc., 2004, 126, 7133;
98. (h) Nguyen, T.; Tseng, H.-R.; Celestre, P.C.; Flood, A.H.; Liu, Y.; Zink, J.I.; Stoddart, J. F. Proc. Natl. Acad. Sci. USA, 2005, 102, 10029.
99. (a) Bissell, R.A.; Córdova, E.; Kaifer, A.E.; Stoddart, J.F. Nature, 1994, 369, 133;
100. (b) Anelli, P.-L.; Asakawa, M.; Ashton, P.R.; Bissell, R.A.; Clavier, G.; Górski, R.; Kaifer, A.E.; Langford, S.J.; Mattersteig, G.; Menzer, S.; Philp, D.; Slawin, A.M.Z.; Spencer, N.; Stoddart, J.F.; Tolley, M.S.; Williams, D.J. Chem. Eur. J., 1997, 3, 1136;
101. (c) Jeppesen, J.O.; Nielsen, K.A.; Perkins, J.; Vignon, S.A.; Di Fabio, A.; Ballardini, R.; Gandolfi, M.T.; Venturi, M.; Balzani, V.; Becher, J.; Stoddart, J.F. Chem. Eur. J., 2003, 9, 2982;
102. (d) Jeppesen, J.O.; Vignon, S.A.; Stoddart, J.F. Chem. Eur. J., 2003, 9, 4611;
103. (e) Tseng, H.-R.; Vignon, S.A.; Celestre, P.C.; Perkins, J.; Jeppesen, J.O.; Di Fabio, A.; Ballardini, R.; Gandolfi, M.T.; Venturi, M.; Balzani, V.; Stoddart, J.F. Chem. Eur. J., 2004, 10, 155;
104. (f) Laursen, B.W.; Nygaard, S.; Jeppesen, J.O.; Stoddart, J.F. Org. Lett., 2004, 6, 4167;
105. (g) Iijima, T.; Vignon, S.A.; Tseng, H.-R.; Jarrosson, T.; Sanders, J.K.M.; Marchioni, F.; Venturi, M.; Apostoli, E.; Balzani, V.; Stoddart, J.F. Chem. Eur. J., 2004, 10, 6375;
106. (h) Jeppesen, J.O.; Nygaard, S.; Vignon, S.A.; Stoddart, J.F. Eur. J. Org. Chem., 2005, 196.
107. Fyfe, M.C.T.; Glink, P.T.; Menzer, S.; Stoddart, J.F.; White, A.J.P.; Williams, D.J. Angew. Chem. Int. Ed. Engl., 1997, 36, 2068.
108. Recent examples of photochemically driven molecular machines: (a) 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.
109. (b) van Delden, R.A.; Koumura, N.; Schoevaars, A.; Meetsma, A.; Feringa, B.L. Org. Biomol. Chem., 2003, 1, 33.
110. (c) Perez, E.M.; Dryden, D.T.F.; Leigh, D.A.; Teobaldi, G.; Zerbetto, F. J. Am. Chem. Soc., 2004, 126, 12210.
111. (d) Abraham, W.; Grubert, L.; Grummt, U.W.; Buck, K. Chem. Eur. J., 2004, 10, 3562.
112. (e) Mobian, P.; Kern, J.-M.; Sauvage, J.-P. Angew. Chem., Int. Ed., 2004, 43, 2392.
113. (f) van Delden, R.A.; ter Wiel, M.K.J.; Pollard, M.M.; Vicario, J.; Koumura, N.; Feringa, B.L. Nature, 2005, 437, 1337.
114. (g) Wang, Q.-C.; Qu, D.-H.; Ren, J.; Chen, K.; Tian, H. Angew. Chem. Int. Ed., 2004, 43, 2661.
115. (h) Collin, J.-P.; Jouvenot, D.; Koizumi, M.; Sauvage, J.-P. Eur. J. Inorg. Chem., 2005, 1850.
116. (i) Qu, D.-H.; Wang, Q.-C.; Tian, H. Angew. Chem. Int. Ed., 2005, 44, 5296.
117. (j) Murakami, H.; Kawabuchi, A.; Matsumoto, R.; Ido, T.; Nakashima, N. J. Am. Chem. Soc., 2005, 127, 15891.
118. (k) Murakami, H.; Kawabuchi, A.; Matsumoto, R.; Ido, T.; Nakashima, N. J. Am. Chem. Soc., 2005, 127, 15891.
119. (l) Muraoka, T.; Kinbara, K.; Aida, T. Nature, 2006, 440, 512.
120. (m) Vicario, J.; Walko, M.; Meetsma, A.; Feringa, B.L. J. Am. Chem. Soc., 2006, 128, 5127.
121. (n) Balzani, V.; Clemente-León, M.; Credi, A.; Ferrer, B.; Venturi, M.; Flood, A.H.; Stoddart, J.F. Proc. Natl. Acad. Sci. U.S.A., 2006, 103, 1178.
122. (o) Balzani, V.; Clemente-León, M.; Credi, A.; Semeraro, M.; Venturi, M.; Tseng, H.-R.; Wenger, S.; Saha, S.; Stoddart, J.F. Aust. J. Chem., 2006, 59, 193;
123. (p) Credi, A. Aust. J. Chem., 2006, 59, 157.
124. (q) Saha, S.; Stoddart, J.F. Chem. Soc. Rev., 2007, 36, 77.
125. (a) Anelli, P.-L.; Spencer, N.; Stoddart, J.F. J. Am. Chem. Soc., 1991, 113, 5131.
126. (b) Bissell, R.A.; Córdova, E.; Kaifer, A.E.; Stoddart, J.F. Nature, 1994, 369, 133.
127. (a) Busch, D.H.; Stephenson, N.A. J. Inclusion Phenom. Mol. Recognit. Chem., 1992, 12, 389;
128. (b) Cacciapaglia, R.; Madolini, L. Chem. Soc. Rev., 1994, 106, 389;
129. (c) Hoss, R.; Vögtle, F. Angew. Chem. Int. Ed. Engl., 1994, 33, 375;
130. (d) Raymo, F.M.; Stoddart, J.F.; Pure Appl. Chem., 1996, 68, 313;
131. (e) Hubin, T.J.; Kolchinski, A.G.; Vance, A.L.; Busch, D.L. Adv. Supramol. Chem., 1999, 5, 237.
132. (a) Miljanic, O.S.; Dichtel, W.R.; Aprahamian, I.; Rohde, R.D.; Agnew, H.D.; Heath, J.R.; Stoddart, J.F. QSAR & Combinatorial Science, 2007, 26, 1165.
133. (b) Aprahamian, I.; Miljanic, O.S.; Dichtel, W.R.; Isoda, K.; Yasuda, T.; Kato, T.; Stoddart, J. F. Bull. Chem. Soc. Japan, 2007, 80, 1856.
134. Moses, J.E.; Moorhouse, A.D. Chem. Soc. Rev., 2007, 36, 1249.
135. Chiu, C.-W.; Lai, C.-C.; Chiu, S.-H. J. Am. Chem. Soc., 2007, 129, 3500.
136. Berna, J.; Goldup, S.M.; Lee, A.-L.; Leigh, D.A.; Symes, M.D.; Teobaldi, G.; Zerbetto, F. Angew. Chem. Int. Ed., 2008, 47, 4392.
137. (a) Martínez-Díaz, M.; Spencer, N.; Stoddart, J.F. Angew. Chem. Int. Ed. Engl., 1997, 36, 1904;
138. (b) Badjic, J.D.; Balzani, V.; Credi, A.; Silvi, S.; Stoddart, J.F. Science, 2004, 303, 1845;
139. (c) Badjic, J.D.; Ronconi, C.M.; Flood, A.H.; Stoddart, J.F.; Silvi, S.; Credi, A.; Balzani, V. J. Am. Chem. Soc., 2006, 128, 1489.
140. (a) Consuelo-Jiménez, M.; Dietrich-Buchecker, C.; Sauvage, J.-P. Angew. Chem. Int. Ed., 2000, 39, 3284;
141. (b) Consuelo-Jiménez, M.; Dietrich-Buchecker, C.; Sauvage, J.-P. Chem. Eur. J., 2002, 39, 1456;
142. (c) Dietrich-Buchecker, C.; Consuelo-Jiménez, M.; Sartor, V.; Sauvage, J.-P. Pure Appl. Chem., 2003, 75, 1383.
143. (a) Tseng, H.-R.; Vignon, S.A.; Stoddart, J.F. Angew. Chem. Int. Ed., 2003, 42, 1491;
144. (b) Huang, T.J.; Tseng, H.-R.; Sha, L.; Lu, W.; Brough, B.; Flood, A.H.; Yu, B.-D.; Celestre, P.C.; Chang, J.P.; Stoddart, J.F.; Ho, C.-M. Nano Lett., 2004, 4, 2065;
145. (c) 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;
146. (d) Liu, Y.; Flood, A.H.; Bonvallet, P.A.; Vignon, S.A.; Tseng, H.-R.; Brough, B.; Baller, M.; Magonov, S.; Solares, S.; Goddard, W.A. III; Ho, C.-M.; Stoddart, J.F. J. Am. Chem. Soc., 2005, 127, 127, 9745.
147. Vella, S.J.; Tiburcio, J.; Loeb, S.J. Chem. Commun., 2007, 4752.
148. (a) Loeb, S.J.; Tiburcio, J.; Vella, S.J. Org. Lett., 2005, 7, 4923;
149. (b) Loeb, S.J. Angew. Chem. Int. Ed., 2005, 44, 901.
150. Loeb, S.J.; Tiburcio, J.; Vella, S.J.; Wisner, J.A. Org. Biomol. Chem., 2006, 4, 667.
151. Vella, S.J.; Tiburcio, J.; Loeb, S.J. Org. Lett., 2006, 8, 3421.
152. Kramer, B.P.; Weber, W.; Fussenegger, M. Biotechnol. Bioeng., 2003, 83, 810-820.
153. Zhou, W.; Li, J.; He, X.; Li, C.; Lv, J.; Li, Y.; Wang, S.; Liu, H.; Zhu, D. Chem. Eur. J., 2008, 14, 754.
154. (a) Wang, X.; Bao, X.; McFarland-Mancini, M.; Isaacsohn, I.; Drew, A.F.; Smithrud, D.B. J. Am. Chem. Soc., 2007, 129, 7284;
155. (b) Dvornikovs, V.; House, B.E.; Kaetzel, M.; Dedman, J.R.; Smithrud, D.B. J. Am. Chem. Soc., 2003, 125, 8290;
156. (c) Bao, X.; Isaacsohn, I.; Drew, A.F.; Smithrud, D.B. J. Am. Chem. Soc., 2006, 128, 12229;
157. (d) Katz, E.; Sheeney, H.I.; Willner, I. Angew. Chem. Int. Ed., 2004, 43, 3292;
158. (e) Lam, R.T.S.; Belenguer, A.; Roberts, S.L.; Naumann, C.; Jarrosson, T.; Otto, S.; Sanders, J.K.M. Science, 2005, 308, 667;
159. (f) Smukste, I.; Smithrud, D.B. J. Org. Chem., 2003, 68, 2547;
160. (g) Eguchi, M.; Ooya, T.; Yui, N. J. Controll Release, 2004, 96, 301.
161. (a) Archut, A.; MQller, W.M.; Baumann, S.; Habel, M.; Vçgtle, F. Liebigs Ann./Recl., 1997, 495;
162. (b) Ashton, P.R.; Everitt, S.R.L.; Gomez-Lopez, M.; Jayaraman, N.; Stoddart, J.F. Tetrahedron Lett., 1997, 38, 5691;
163. (c) Coutrot, F.; Busseron, E.; Montero, J.L. Org. Lett., 2008, 10, 753.
164. Coutrot, F.; Busseron, E. Chem. Eur. J., 2008, 14, 4784.
165. Chen, N.-C.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Chem. Eur. J., 2008, 14, 2904.
166. Chen, N.-C.; Huang, P.-Y.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Chem. Commun., 2007, 4122.
167. Crowley, J.D.; Leigh, D.A.; Lusby, P.J.; McBurney, R.T.; Perret-Aebi, L.-E.; Petzold, C.; Slawin, A.M.Z.; Symes, M.D. J. Am. Chem. Soc., 2007, 129, 15085.
168. (a) Fuller, A.-M.; Leigh, D. A.; Lusby, P. J.; Oswald, I. D. H.; Parsons, S.; Walker, D. B. Angew. Chem. Int. Ed., 2004, 43, 3914;
169. (b) Furusho, Y.; Matsuyama, T.; Takata, T.; Moriuchi, T.; Hirao, T. Tetrahedron Lett., 2004, 45, 9593.
170. (c) Fuller, A.-M.L.; Leigh, D.A.; Lusby, P.J.; Slawin, A.M.Z.; Walker, D.B. J. Am. Chem. Soc., 2005, 127, 12612.
171. (d) Leigh, D.A.; Lusby, P.J.; Slawin, A.M.Z.; Walker, D.B. Angew. Chem. Int. Ed., 2005, 44, 4557.
172. (e) Fuller, A.-M.L.; Leigh, D.A.; Lusby, P.J. Angew. Chem. Int. Ed., 2007, 46, 5015.
173. Amabilino, D.B.; Stoddart, J.F. Chem. Rev., 1995, 95, 2725.
174. Wayman, K. A.; Sammakia, T. Org. Lett., 2003, 5, 4105.
175. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett., 1975, 16, 4467.
176. Mitsunobu, O.; Yamada, Y. Bull. Chem. Soc. Jpn., 1967, 40, 2380.
177. Gibson, H.W.; Lee, S.H.; Engen, P.T.; Lecavalier, P.; Sze, J.; Shen, Y.X.; Bheda, M. J. Org. Chem., 1993, 58, 3748.
178. Leff, H.S., Rex, A.F. Maxwell's Demon 2. Entropy, classical and quantum information, computing, Institute of Physics Publishing: Bristol, U.K., 2003.
179. Maxwell, J.C. Theory of Heat; Longmans, Green and Co.: London, U.K., 1871; Chapter 22, p. 308.
180. Bennett, C.H. Int. J. Theor. Phys., 1982, 21, 905.
181. (a) Kay, E.R.; Leigh, D.A. Nature, 2006, 440, 286;
182. (b) Kay, E.R.; Leigh, D.A.; Zerbetto, F. Angew. Chem. Int. Ed., 2007, 46, 72.
183. (c) Astumian, R.D. Phys. Chem. Chem. Phys., 2007, 9, 5067.
184. (a) Astumian, R.D.; Derényi, I. Eur. Biophys. J., 1998, 27, 474.
185. (b) Parmeggiani, A.; Jülicher, F.; Ajdari, A.; Prost, J. Phys. Rev. E, 1999, 60, 2127.
186. (c) Parrondo, J.M.R.; De Cisneros, B.J. Appl. Phys. A, 2002, 75, 179.
187. The other basic class of Brownian ratchet mechanism is an energy ratchet (see ref 46b,c), in which directional transport of a Brownian particle is caused by periodic or random switching (irrespective of the particle position) between two or more potential energy surfaces. For a rotaxane-based two compartment molecular energy ratchet, see Chatterjee, M.N.; Kay, E.R.; Leigh, D.A. J. Am. Chem. Soc., 2006, 128, 4058.
188. Alvarez-Pérez, M.; Goldup, S.M.; Leigh, D.A.; Slawin, A.M.Z. J. Am. Chem. Soc., 2008, 130, 1836.
189. Bottari, G.; Dehez, F.; Leigh, D.A.; Nash, P.J.; Pérez, E.M.; Wong, J.K.Y.; Zerbetto, F. Angew. Chem. Int. Ed., 2003, 42, 5886.
190. (a) Gatti, F.G.; Leigh, D.A.; Nepogodiev, S.A.; Slawin, A.M.Z.; Teat, S.J.; Wong, J.K.Y. J. Am. Chem. Soc., 2001, 123, 5983.
191. (b) Kay, E.R.; Leigh, D.A. Top. Curr. Chem., 2005, 262, 133.
192. (a) Hunter, C.A.; Sanders, J.K.M. J. Am. Chem. Soc., 1990, 112, 5525;
193. (b) Schwartz, M.H. J. Inclusion Phenom. Macrocycl. Chem., 1990, 9, 1;
194. (c) Williams, J.H. Acc. Chem. Res., 1993, 26, 539;
195. (d) Hunter, C.A. Angew. Chem. Int. Ed. Engl., 1993, 32, 1584;
196. (e) Hunter, C.A. J. Mol. Biol., 1993, 230, 1025;
197. (f) Dahl, T. Acta. Chem. Scand., 1994, 48, 95;
198. (g) Cozzi, F.; Siegel, J.S. Pure Appl. Chem., 1995, 67, 683;
199. (h) Claessens, C.G.; Stoddart, J.F. J. Phys. Org. Chem., 1997, 10, 254;
200. (i) Chessari, G.; Hunter, C.A.; Low, C.M.R.; Packer, M.J.; Vinter, J.G.; Zonta, C. Chem. Eur. J., 2002, 8, 2860;
201. (j) Balzani, V.; Clemente-León, M.; Credi, A.; Ferrer, B.; Venturi, M.; Flood, A.H.; Stoddart, J.F. Proc. Natl. Acad. Sci. USA, 2006, 103, 1178.
202. (a) Armaroli, N.; Balzani, V.; Collin, J.-P.; Gaviña, P.; Sauvage, J.-P.; Ventura, B. J. Am. Chem. Soc., 1999, 121, 4397;
203. (b) Collin, J.-P.; Dietrich-Buchecker, C.; Gaviña, P.; Jiminez-Molero, M.C.; Sauvage, J.-P. Acc. Chem. Res., 2001, 34, 477.
204. Zhou, W.; Chen, D.; Li, J.; Xu, J.; Lv, J.; Liu, H.; Li, Y. Org. Lett., 2007, 9, 3929.
205. (a) Raymo, F.M.; Giordani, S. J. Am. Chem. Soc., 2001, 123, 4651;
206. (b) Raymo, F.M.; Alvarado, R.J.; Giordani, S.; Cejas, M.A. J. Am. Chem. Soc., 2003, 125, 2361;
207. (c) Raymo, F.M.; Giordani, S. Org. Lett., 2001, 3, 3475;
208. (d) Raymo, F.M.; Giordani, S. Org. Lett., 2001, 3, 1833;
209. (e) Raymo, F.M.; Giordani, S. J. Org. Chem., 2003, 68, 4158.
210. (a) Guo, X.; Zhang, D.; Zhang, G.; Zhu, D. J. Phys. Chem. B, 2004, 108, 11942;
211. (b) Guo, X.; Zhou, Y.; Zhang, D.; Yin, B.; Liu, Z.; Liu, C.; Lu, Z.; Huang, Y.; Zhu, D. J. Org. Chem., 2004, 69, 8924.
212. Abraham, W.; Buck, K.; Orda-Zgadzaj, M.; Schmidt-Schaäffer, S.; Grummt, U.-W. Chem. Commun., 2007, 3094.
213. Grigor'eva, T.M.; Ivanov, V.L.; Kuzmin, M.G. Zh. Org. Khim., 1981, 17, 423.
214. Hirose, K.; Ishibashi, K.; Shiba. Y.; Doi, Y.; Tobe, Y. Chem. Eur. J., 2008, 14, 981.
215. Hirose, K.; Shiba, Y.; Ishibashi, K.; Doi, Y.; Tobe, Y. Chem. Eur. J., 2008, 14, 3427.
216. (a) Bouas-Laurent, H.; Castellan, A.; Desvergne, J.-P. Pure Appl. Chem., 1980, 52, 2633;
217. (b) Yamashita, I.; Fujii, M.; Kaneda, T.; Misumi, S. Tetrahedron Lett., 1980, 21, 541;
218. (c) Moriwaki, F.; Ueno, A.; Osa, T. Chem. Lett., 1986, 15, 1865;
219. (d) Deng, G.; Sakai, T.; Kawahara, Y.; Shinkai, S. Supramol. Chem., 1993, 2, 71;
220. (e) Desvergne, J.-P.; Lauret, J.; Bouas-Laurent, H. Recl. Trav. Chim. Pays-Bas, 1995, 114, 504;
221. (f) Tucker, J.H.R.; Bouas-Laurent, H.; Marsau, P.; Riley, S.W.; Desvergne, J.-P. Chem. Commun., 1997, 1165.
222. Saha, S.; Flood, A.H.; Stoddart, J.F.; Impellizzeri, S.; Silvi, S.; Venturi, M.; Credi, A. J. Am. Chem. Soc., 2007, 129, 12159.
223. (a) Khalil, B.; Calinaud, P.; Gelas, J.; Ghobsi, M. Carb. Res., 1994, 264, 33;
224. (b) Xie, H.; Wu, S. Supramol. Chem., 2001, 13, 546.
225. Becher, J.; Matthews, O.; Nielsen, K.; Mogens, B.; Raymo, F.M.; Stoddart, J.F. Synlett, 1999, 330.
226. (a) Saha, S.; Johansson, L.E.; Flood, A.H.; Tseng, H.-R.; Zink, J. I.; Stoddart, J.F. Small, 2005, 1, 87;
227. (b) Saha, S.; Johansson, E.; Flood, A.H.; Tseng, H.R.; Zink, J.l.; Stoddart, J.F. Chem. Eur. J., 2005, 11, 6846.
228. (a) Gellman, S.H. Acc. Chem. Res., 1998, 31, 173;
229. (b) Hill, D.J.; Mio, M.J.; Prince, R.B.; Hughes, T.; Moore, J.S. Chem. Rev., 2001, 101, 3893;
230. (c) Schmitt, J.-L.; Stadler, A.-M.; Kyritsakas, N.; Lehn, J.-M. Helv. Chim. Acta, 2003, 86, 1598;
231. (d) Kelley, R.F.; Rybtchinski, B.; Stone, M.T.; Moore, J.S.; Wasielewski, M.R. J. Am. Chem. Soc., 2007, 129, 4114.
232. Fioravanti, G.; Haraszkiewicz, N.; Kay, E.R.; M. Mendoza, S.; Bruno, C.; Marcaccio, M.; Wiering, P.G.; Paolucci, F.; Rudolf, P.; Brouwer, A.M.; Leigh D.A. J. Am. Chem. Soc., 2008, 130, 2593.
233. Leigh, D.A.; Morales, M.A.F.; Pérez, E.M.; Wong, J.K.Y.; Saiz, C.G.; Slawin, A.M.Z.; Carmichael, A.J.; Haddleton, D.M.; Brouwer, A.M.; Buma, W.J.; Wurpel, G.W.H.; León, S.; Zerbetto, F. Angew. Chem. Int. Ed., 2005, 44, 3062.
234. 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.
235. (a) Mendes, P.M.; Flood, A.H.; Stoddart, J.F. Appl. Phys. A, 2005, 80, 1197;
236. (b) 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 and references cited therein.
237. 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.
238. Qu, D.H.; Wang, G.C.; Ren, J.; Tian, H. Org. Lett., 2004, 6, 2085.
239. Guldi D.M.; Prato, M. Acc. Chem. Res., 2000, 33, 695.
240. Echegoyen, L.; Echegoyen, L.E. Acc. Chem. Res., 1998, 31, 593.
241. (a) Da Ros, T.; Guldi, D.M.; Morales, A.F.; Leigh, D.A.; Prato, M.; Turco, R. Org. Lett., 2003, 5, 689;
242. (b) Mateo-Alonso, A.; Prato, A.M. Tetrahedron, 2006, 62, 2003;
243. (c) Mateo-Alonso, A.; Fioravanti, G.; Marcaccio, M.; Paolucci, F.; Jagesar, D.C.; Brouwer, A.M.; Prato, M. Org. Lett., 2006, 8, 5173;
244. (d) Mateo-Alonso, A.; Rahman, G.M.A.; Ehli, C.; Guldi, D.M.; Fioravanti, G.; Marcaccio, M.; Paolucci, F.; Prato, M. Photochem. Photobiol. Sci., 2006, 5, 1173.
245. Mateo-Alonso, A.; Fioravanti, G.; Marcaccio, M.; Paolucci, F.; Aminur Rahman, G.M.; Ehli, C.; Guldi, D.M.; Prato, M. Chem. Commun., 2007, 1945.
246. Hunter, C.A.; Lawson, K.R.; Perkins, J.; Urch, C.J. J. Chem. Soc., Perkin Trans. 2, 2001, 651.
247. Leigh, D.A.; Murphy, A.; Smart, J.P.; Slawin, A.M.Z. Angew. Chem. Int. Ed. Engl., 1997, 36, 728.
248. Lerke, S.A.; Evans, D.H.; Feldberg, S.W. J. Electroanal. Chem., 1990, 296, 299.
249. (a) Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc., 1993, 115, 9798;
250. (b) Prato, M.; Maggini, M. Acc. Chem. Res., 1998, 31, 519.
251. Mateo-Alonso, A.; Ehli, C.; Aminur Rahman, G.M.; Guldi, D.M.; Fioravanti, G.; Marcaccio, M.; Paolucci, F.; Prato, M. Angew. Chem. Int. Ed., 2007, 46, 3521.
252. Durola, F.; Sauvage, J.-P. Angew. Chem. Int. Ed., 2007, 46, 3537.
253. (a) Shipway, A.N.; Willner, I. Acc. Chem. Res., 2001, 34, 421;
254. (b) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M.T.; Venturi, M. Acc. Chem. Res., 2001, 34, 445 and references therein.
255. Yu, H.; Luo, Y.; Beverly, K.; Stoddart, J.F.; Tseng, H.-R.; Heath, J.R. Angew. Chem. Int. Ed., 2003, 42, 5706.
256. Gibson, H.W.; Nagvekar, D.S.; Yamaguchi, M.; Bhattacharjee, S.; Wang, H.; Vergne M.J.; Hercules, D.M. Macromolecules, 2004, 37, 7514 and references therein.
257. Lee, J.W.; Kim, K. Top. Curr. Chem., 2003, 228, 111 and references therein.
258. Yaghi, O.M.; O'Keefe, M.; Ockwing, N.W.; Chae, H.K.; Eddaoudi, M.; Kim, J. Nature, 2003, 423, 705 and references therein.
259. Rowsell, J.L.C.; Yaghi, O.M. Microporous Mesoporous Mater., 2004, 73, 3.
260. Kim, K. Chem. Soc. Rev., 2002, 31, 96.