The dynamic chemistry of molecular Borromean rings and Solomon knots

Chemistry - A European Journal

Volumn 16, Issue 42, 2010, Pages 12570-12581

  Meyer, Cari D ^a   Forgan, Ross S ^b   Chichak, Kelly S ^a   Peters, Andrea J ^a   Tangchaivang, Nicholas ^a   Cave, Gareth W V ^c   Khan, Saeed I ^a   Cantrill, Stuart J ^a   Stoddart, J Fraser ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c NOTTINGHAM TRENT UNIVERSITY   (United Kingdom)

Author keywords

coordination compounds; dynamic covalent chemistry; Schiff bases; self assembly; template directed synthesis

Indexed keywords

BIPYRIDYL; COORDINATION COMPOUNDS; CRYSTALLIZATION CONDITIONS; DYNAMIC COVALENT CHEMISTRY; DYNAMIC EQUILIBRIA; DYNAMIC SOLUTIONS; H NMR SPECTROSCOPY; MACROCYCLES; METAL CENTERS; REACTION CONDITIONS; ROOM TEMPERATURE; SCHIFF BASIS; SOLID-STATE STRUCTURES; SYNTHETIC CONDITIONS; SYNTHETIC PROTOCOLS; TEMPLATE-DIRECTED SYNTHESIS; TEMPLATED; TEMPLATION;

CHELATION; COMPLEXATION; CRYSTALLIZATION; FUNCTIONAL GROUPS; MANGANESE; METAL IONS; METALS; MINERALOGY; NETWORK ARCHITECTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SELF ASSEMBLY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY; ZINC;

COORDINATION REACTIONS;

EID: 78349265801     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001806     Document Type: Article

References (158)

1. E. Wasserman, J. Am. Chem. Soc. 1960, 82, 4433 - 4434
2. E. Wasserman, Bell Lab. Rec. 1960, 394.
3. A [2]catenane is a compound containing molecules comprised of two mutually interlocked rings. When the molecules also serve as a ligand for a metal ion, the compound is referred to as a [2]catenate, and the ligand, a [2]catenand, see:, C. O. Dietrich-Buchecker, J.-P. Sauvage, J.-M. Kern, J. Am. Chem. Soc. 1984, 106, 3043 - 3045. Note that the digit inside the square brackets refers to the number of interlocked rings in the molecule.
4. H. L. Frisch, E. Wasserman, J. Am. Chem. Soc. 1961, 83, 3789 - 3795
5. S. J. Tauber, J. Res. Natl. Bur. Stand. Sect. A 1963, 67 A, 591 - 599
6. J. Simon, Proc. Symp. Appl. Math. 1992, 45, 97 - 130
7. N. van Gulick, New J. Chem. 1993, 17, 619 - 625
8. C. Liang, K. Mislow, J. Math. Chem. 1994, 16, 27 - 35
9. J. S. Siegel, Science 2004, 304, 1256 - 1258
10. E. E. Fenlon, Eur. J. Org. Chem. 2008, 5023 - 5035
11. D. B. Amabilino, L. Pérez-García, Chem. Soc. Rev. 2009, 38, 1562 - 1571.
12. V. I. Sokolov, Russ. Chem. Rev. 1973, 42, 452 - 463
13. D. M. Walba, Tetrahedron 1985, 41, 3161 - 3212
14. K. Mislow, Top. Stereochem. 1999, 22, 1 - 82.
15. For an overview of interlocked molecules, see
16. D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725 - 2828
17. Molecular Catenanes, Rotaxanes and Knots (Eds.:, J.-P. Sauvage, C. Dietrich-Buchecker,), Wiley-VCH, Weinheim, 1999
18. F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643 - 1663
19. M. Fujita, Acc. Chem. Res. 1999, 32, 53 - 61
20. J. P. Collin, C. Dietrich-Buchecker, P. Gaviña, M. C. Jiminez-Molero, J.-P. Sauvage, Acc. Chem. Res. 2001, 34, 477 - 487
21. G. Kaiser, T. Jarrosson, S. Otto, Y.-F. Ng, A. D. Bond, J. K. M. Sanders, Angew. Chem. 2004, 116, 1993 - 1996
22. Angew. Chem. Int. Ed. 2004, 43, 1959 - 1962
23. L. Wang, M. O. Vysotsky, A. Bogdan, M. Bolte, V. Böhmer, Science 2004, 304, 1312 - 1314
24. C. A. Schalley, T. Weilandt, J. Brüggermann, F. Vögtle, Top. Curr. Chem. 2004, 232-242, 141 - 200
25. M. S. Vickers, P. D. Beer, Chem. Soc. Rev. 2007, 36, 211 - 225
26. M. A. Olson, Y. Y. Botros, J. F. Stoddart, Pure Appl. Chem. 2010, 82, 1569 - 1574.
27. Note that the strength of a mechanical bond equates with the strength of the weakest covalent or coordinative bond in the molecule. See
28. J. F. Stoddart, H. M. Colquhoun, Tetrahedron 2008, 64, 8231 - 8263
29. J. F. Stoddart, Chem. Soc. Rev. 2009, 38, 1802 - 1820.
30. D. H. Busch, N. A. Stephenson, Coord. Chem. Rev. 1990, 100, 119 - 154
31. S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469 - 475
32. R. Cacciapaglia, L. Mandolini, Chem. Soc. Rev. 1993, 22, 221 - 231
33. R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389 - 398
34. Angew. Chem. Int. Ed. Engl. 1994, 33, 375 - 384
35. J. P. Schneider, J. W. Kelly, Chem. Rev. 1995, 95, 2169 - 2187
36. F. M. Raymo, J. F. Stoddart, Pure Appl. Chem. 1996, 68, 313 - 322
37. M. Fujita, Chem. Soc. Rev. 1998, 27, 417 - 425
38. G. A. Breault, C. A. Hunter, P. C. Mayers, Tetrahedron 1999, 55, 5265 - 5293
39. Templated Organic Synthesis (Eds.:, F. Diederich, P. J. Stang,), Wiley-VCH, Weinheim, 2000
40. T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200, 5 - 52
41. J. F. Stoddart, H.-R. Tseng, Proc. Natl. Acad. Sci. USA 2002, 99, 4797 - 4800
42. M.-J. Blanco, J.-C. Chambron, M. C. Jiménez, J.-P. Sauvage, Top. Stereochem. 2002, 23, 125 - 173
43. D. H. Busch, Top. Curr. Chem. 2005, 249, 1 - 65
44. F. Arićo, J. D. Badjić, S. J. Cantrill, A. H. Flood, K. C.-F. Leung, Y. Liu, J. F. Stoddart, Top. Curr. Chem. 2005, 249, 203 - 259
45. S. J. Cantrill, R. H. Grubbs, D. Lanari, K. C.-F Leung, A. Nelson, K. G. Poulin-Kerstien, S. P. Smidt, J. F. Stoddart, D. A. Tirrell, Org. Lett. 2005, 7, 4213 - 4216
46. B. H. Northrop, F. Arićo, N. Tangchaivang, J. D. Badjić, J. F. Stoddart, Org. Lett. 2006, 8, 3899 - 3902
47. A. R. Williams, B. H. Northrop, T. Chang, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2006, 118, 6817 - 6821
48. Angew. Chem. Int. Ed. 2006, 45, 6665 - 6669
49. C. D. Meyer, C. S. Joiner, J. F. Stoddart, Chem. Soc. Rev. 2007, 36, 1705 - 1723
50. K. E. Griffiths, J. F. Stoddart, Pure Appl. Chem. 2008, 80, 485 - 506
51. J. D. Crowley, S. M. Goldup, A.-L. Lee, D. A. Leigh, R. T. McBurney, Chem. Soc. Rev. 2009, 38, 1530 - 1541.
52. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995, Chapter 2
53. Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.:, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle,), Pergamon, Oxford, 1996
54. M. A. Garcia-Garibay, Curr. Opin. Solid State Mater. Sci. 1998, 3, 399 - 406
55. A. N. M. M. Rahman, R. Bishop, D. C. Craig, M. L. Scudder, Eur. J. Org. Chem. 2003, 72 - 81
56. L. R. Nassimbeni, Acc. Chem. Res. 2003, 36, 631 - 637
57. A. Angeloni, P. C. Crawford, A. G. Orpen, T. J. Podesta, B. J. Shore, Chem. Eur. J. 2004, 10, 3783 - 3791
58. P. Metrangolo, H. Neukirch, T. Pilati, G. Resnati, Acc. Chem. Res. 2005, 38, 386 - 395
59. J. F. Stoddart, Nat. Chem. 2009, 1, 14 - 15.
60. B. Hasenknopf, J.-M. Lehn, N. Boumediene, A. Dupont-Gervais, A. Van Dorsselaer, B. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956 - 10962
61. D. M. Bassani, J.-M. Lehn, S. Serroni, F. Puntoriero, S. Campagna, Chem. Eur. J. 2003, 9, 5936 - 5946
62. R. W. Saalfrank, C. Deutscher, H. Maid, A. M. Ako, S. Sperner, T. Nakajima, W. Bauer, F. Hampel, B. A. Heß, N. J. R. van Eikema Hommes, R. Puchta, F. W. Heinmann, Chem. Eur. J. 2004, 10, 1899 - 1905
63. J. R. Nitschke, Acc. Chem. Res. 2007, 40, 103 - 112.
64. S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938 - 993
65. Angew. Chem. Int. Ed. 2002, 41, 898 - 952
66. R. L. E. Furlan, S. Otto, J. K. M. Sanders, Proc. Natl. Acad. Sci. USA 2002, 99, 4801 - 4804
67. P. T. Corbett, J. Leclaire, L. Vial, K. R. West, J.-L. Wietor, J. K. M. Sanders, S. Otto, Chem. Rev. 2006, 106, 3652 - 3711
68. J.-M. Lehn, Chem. Soc. Rev. 2007, 36, 151 - 160
69. P. C. Haussmann, J. F. Stoddart, Chem. Rec. 2009, 9, 136 - 154.
70. V. Balzani, A. Credi, F. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484 - 3530
71. Angew. Chem. Int. Ed. 2000, 39, 3348 - 3391
72. A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Res. 2001, 34, 433 - 444
73. E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72 - 196
74. Angew. Chem. Int. Ed. 2007, 46, 72 - 191
75. B. Champin, P. Mobian, J.-P. Sauvage, Chem. Soc. Rev. 2007, 36, 358 - 366
76. V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld, Wiley, New York, 2008
77. R. Klajn, J. F. Stoddart, B. A. Grzybowski, Chem. Soc. Rev. 2010, 39, 2203 - 2237.
78. D. B. Amabilino, P. R. Ashton, A. S. Reder, N. Spencer, J. F. Stoddart, Angew. Chem. 1994, 106, 1316 - 1319
79. Angew. Chem. Int. Ed. Engl. 1994, 33, 1286 - 1290
80. D. B. Amabilino, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, J. Y. Lee, S. Menzer, J. F Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 4295 - 4307.
81. D. B. Amabilino, P. R. Ashton, S. E. Boyd, J. Y. Lee, S. Menzer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1997, 109, 2160 - 2162
82. Angew. Chem. Int. Ed. Engl. 1997, 36, 2070 - 2072.
83. L. R. Rose, Seeing Solomon's Knot, Lois Rose, Los Angeles, 2005.
84. D. Rolfsen, Knots and Links, Publish or Perish, Berkeley, 1976
85. C. C. Adams, The Knot Book, Freeman, New York, 1994
86. D. Andrae, New J. Chem. 2006, 30, 873 - 882.
87. J.-F. Nierengarten, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1994, 116, 375 - 376
88. F. Ibukuro, M. Fujita, K. Yamaguchi, J.-P. Sauvage, J. Am. Chem. Soc. 1999, 121, 11014 - 11015
89. C. P. McArdle, J. J. Vittal, R. J. Puddephatt, Angew. Chem. 2000, 112, 3977 - 3980
90. Angew. Chem. Int. Ed. 2000, 39, 3819 - 3822
91. C. Peinador, V. Blanco, J. M. Quintela, J. Am. Chem. Soc. 2009, 131, 920 - 921
92. T. K. Ronson, J. Fisher, L. P. Harding, P. J. Rizkallah, J. E. Warren, M. J. Hardie, Nat. Chem. 2009, 1, 212 - 216.
93. SKs, which are 41 2 links, can be thought of as [2]catenanes, which are 21 2 links, wherein the two rings crossover at four nodes rather than two, to give the doubly interlocked structure.
94. P. Cromwell, E. Beltrami, M. Rampichini, Math. Intelligencer 1998, 20, 53 - 62
95. other examples are highlighted in greater detail on the world wide web, see:.
96. C. A. Schalley, Angew. Chem. 2004, 116, 4499 - 4501
97. Angew. Chem. Int. Ed. 2004, 43, 4399 - 4401
98. S. J. Cantrill, K. S. Chichak, A. J. Peters, J. F. Stoddart, Acc. Chem. Res. 2005, 38, 1 - 9.
99. C. Liang, K. Mislow, J. Math. Chem. 1995, 18, 1 - 24.
100. A. Ruzmaikin, P. Akhmetiev, Phys. Plasmas 1994, 1, 331 - 336
101. S. M. Austin, G. F. Bertsch, Sci. Am. 1995, 272, 90 - 95
102. B. V. Danilin, T. Rogde, J. S. Vaagen, I. J. Thompson, M. V. Zhukov, Phys. Rev. C 2004, 69, 024609 /1- 10.
103. C. Mao, W. Sun, N. C. Seeman, Nature 1997, 386, 137 - 138
104. N. C. Seeman, Angew. Chem. 1998, 110, 3408 - 3428
105. Angew. Chem. Int. Ed. 1998, 37, 3220 - 3238.
106. For an examination of previously unnoticed BR topologies in framework materials, see
107. L. Carlucci, G. Ciani, D. M. Proserpio, CrystEngComm 2003, 5, 269 - 279; for further examples, see
108. L. Dobrzańska, H. G. Raubenheimer, L. J. Barbour, Chem. Commun. 2005, 5050 - 5052
109. R. Liantonio, P. Metrangolo, F. Meyer, T. Pilati, W. Navarrini, G. Resnati, Chem. Commun. 2006, 1819 - 1821
110. X.-Q. Lu, M. Pan, J.-R. He, Y.-P. Cai B.-S. Kang, C.-Y. Su, CrystEngComm 2006, 8, 847 - 849
111. J. Li, L. Song, S. Du, Inorg. Chem. Commun. 2007, 10, 358 - 361
112. X.-L. Zhang, C.-P. Guo, Q.-Y. Yang, W. Wang, W.-S. Liu, B.-S. Kang, C.-Y. Su, Chem. Commun. 2007, 4242 - 4244
113. X.-L. Zhang, C.-P. Guo, Q.-Y. Yang, T.-B. Lu, Y.-X. Tong, C.-Y. Su, Chem. Mater. 2007, 19, 4630 - 4632
114. Q.-Y. Yang, S.-R. Zheng, R. Yang, M. Pan, R. Cao, C.-Y. Su, CrystEngComm 2009, 11, 680 - 685
115. P. Byrne, G. O. Lloyd, N. Clarke, J. W. Steed, Angew. Chem. 2008, 120, 5845 - 5848
116. Angew. Chem. Int. Ed. 2008, 47, 5761 - 5764
117. J.-J. Jang, L. Li, T. Yang, D.-B. Kuang, W. Wang, C.-Y. Su, Chem. Commun. 2009, 2387 - 2389
118. Y.-B. Men, J. Sun, Z.-T. Huang, Q.-Y. Zheng, Angew. Chem. 2009, 121, 2917 - 2920
119. Angew. Chem. Int. Ed. 2009, 48, 2873 - 2876
120. Q.-X. Yao, X.-H. Jin, Z.-F. Ju, H.-X. Zhang, J. Zhang, CrystEngComm 2009, 11, 1502 - 1504
121. N. N. Adarsh, P. Dastidar, Cryst. Growth Des. 2010, 10, 483 - 487.
122. S.-H. Chiu, A. R. Pease, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2002, 114, 280 - 284
123. Angew. Chem. Int. Ed. 2002, 41, 270 - 274
124. M. Schmittel, A. Ganz, D. Fenske, Org. Lett. 2002, 4, 2289 - 2292
125. J. C. Loren, M. Yoshizawa, R. F. Haldimann, A. Linden, J. S. Siegel, Angew. Chem. 2003, 115, 5880 - 5883
126. Angew. Chem. Int. Ed. 2003, 42, 5702 - 5705
127. Y. Liu, Tetrahedron Lett. 2007, 48, 3871 - 3874
128. R. S. Forgan, J. M. Spruell, J.-C. Olsen, C. L. Stern, J. F. Stoddart, J. Mex. Chem. Soc. 2009, 53, 134 - 138
129. R. S. Forgan, D. C. Friedman, C. L. Stern, C. J. Bruns, J. F. Stoddart, Chem. Commun. 2010, 46, 5861 - 5863.
130. We use the term "ring-in-ring" complex to describe only assemblies in which the macrocycles are arranged in an approximately perpendicular fashion. These compounds are considerably rarer than the more familiar "macrocycle-within-macrocycle" architectures.
131. T. J. Hubin, A. G. Kolchinski, A. L. Vance, D. H. Busch, Adv. Supramol. Chem. 1999, 6, 237 - 357.
132. K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart, Science 2004, 304, 1308 - 1312.
133. K. S. Chichak, A. J. Peters, S. J. Cantrill, J. F. Stoddart, J. Org. Chem. 2005, 70, 7956 - 7962.
134. C. D. Pentecost, K. S. Chichak, A. J. Peters, G. W. V. Cave, S. J. Cantrill, J. F. Stoddart, Angew. Chem. 2007, 119, 222 - 226
135. Angew. Chem. Int. Ed. 2007, 46, 218 - 222.
136. [31]
137. A. J. Peters, K. S. Chichak, S. J. Cantrill, J. F. Stoddart, Chem. Commun. 2005, 3394 - 3396.
138. IIBR · 12TFA, their weakly diffracting nature precluded structural characterization by single-crystal X-ray diffraction analysis.
139. IIBR · 12TFA) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
140. 2=0.4472 for 403 parameters.
141. 2=0.3285 for 1506 parameters. Owing to the low parameter/observation ratio 75 restraints had to be imposed on the molecule.
142. 12+ cavity, 85%, far exceeds the ideal value of 55% proposed by Rebek et al. The 55% solution was formulated for dynamic host-guest complexes in solution, rather than solid-state assemblies, which may explain the difference in packing coefficients. See:, S. Mecozzi, J. Rebek, Jr., Chem. Eur. J. 1998, 4, 1016 - 1022. All cavity and packing volumes were determined computationally by using the software packages MCAVITY and X-Seed, see
143. L. J. Barbour, MCAVITY'Molecular Cavity Calculator, 2003 and
144. L. J. Barbour, J. Supramol. Chem. 2001, 1, 189 - 191.
145. P. Manikandan, K. R. J. Thomas, P. T. Manoharan, J. Chem. Soc. Dalton Trans. 2000, 2779 - 2785
146. J. M. Holland, X. Liu, J. P. Zhao, F. E. Mabbs, C. A. Kilner, M. Thornton-Pett, M. A. Halcrow, J. Chem. Soc. Dalton Trans. 2000, 3316 - 3324
147. D. S. Marlin, M. M. Olmstead, P. K. Mascharak, Inorg. Chem. 2001, 40, 7003 - 7008.
148. Other solvents have led to the successful formation of BRs, including MeOH and EtOH (ref. [27]), yet not as efficiently as iPrOH. This solvent effect on the yield and purity is likely to result from the solubility differences of the product in these solvents. BRs are soluble in EtOH and MeOH, but are not soluble in iPrOH, and therefore, precipitate upon formation, kinetically trapping the BR product.
149. We have modified the synthesis of molecular BRs to embrace undergraduate laboratory practical classes and have used the establishment of this teaching tool to have undergraduate students prepare molecular BRs on a gram scale. See:, C. D. Pentecost, N. Tangchaivang, S. J. Cantrill, K. S. Chichak, A. J. Peters, J. F. Stoddart, J. Chem. Educ. 2007, 84, 855 - 859.
150. The kinetically controlled self-assembly of two different donor-acceptor pseudorotaxanes on crystallization has been reported. See:, B. H. Northrop, S. J. Khan, J. F. Stoddart, Org. Lett. 2006, 8, 2159 - 2162.
151. -1, see
152. P. R. Ashton, S. J. Cantrill, J. A. Preece, J. F. Stoddart, Z.-H. Wang, A. J. P. White, D. J. Williams, Org. Lett. 1999, 1, 1917 - 1920
153. S. J. Cantrill, J. A. Preece, J. F. Stoddart, Z.-H. Wang, A. J. P. White, D. J. Williams, Tetrahedron 2000, 56, 6675 - 6681.
154. 2=0.3067 for 487 parameters.
155. J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley-VCH, Weinheim, 1981.
156. 1H NMR spectrum: we continue to suspect that it exists, at least in the gas phase!
157. 2 symmetric conformations freeze out, giving rise to a larger number of signals.
158. ⊥ tensor pattern characteristic of similar tetragonally elongated copper complexes.