Synthetic strategies for the construction of threaded and interlocked molecules

Current Organic Synthesis

Volumn 7, Issue 1, 2010, Pages 24-43

  Gaviña, Pablo ^a   Tatay, Sergio ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Catenanes; Pseudorotaxanes; Rotaxanes; Self assembly; Template synthesis

Indexed keywords

EID: 77950801872     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017910790820346     Document Type: Article

References (174)

1. Harada, A. Cyclodextrin-based molecular machines. Acc. Chem. Res. 2001, 34, 456.
2. Collin, J. P.; Dietrich-Buchecker, C. O.; Gaviña, P.; Jimenez-Molero, M. C.; Sauvage, J. P. Shuttles and Muscles: Linear Molecular Machines Based on Transition Metals. Acc. Chem. Res. 2001, 34, 477.
3. Balzani, V.; Credi, A.; Silvi, S.; Venturi, M. Artificial nanomachines based on interlocked molecular species: recent advances. Chem. Soc. Rev. 2006, 35, 1135.
4. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Synthetic molecular motors and mechanical machines. Angew. Chem. Int. Ed. 2007, 46, 72.
5. Saha, S.; Stoddart, J. F. Photo-driven molecular devices. Chem. Soc. Rev. 2007, 36, 77.
6. Willner, I.; Basnar, B.; Willner, B. From molecular machines to microscale motility of objects: Application as "smart materials", sensors, and nanodevices. Adv. Funct. Mater. 2007, 17, 702.
7. Aricó, F.; Badjic, J. D.; Cantrill, S. J.; Flood, A. H.; Leung, K. C.; Liu, Y.; Stoddart, J. F. Templated synthesis of interlocked molecules. Top. Curr. Chem. 2005, 249, 203.
8. Molecular Catenanes, Rotaxanes, and Knots: A Journey through the World of Molecular Topology; Sauvage, J.-P.; Dietrich-Buchecker, C. Eds.; Wiley-VCH: Weinheim, Germany, 1999.
9. Encyclopedia of Supramolecular Chemistry; J. L. Atwood, J. W. Steeds, Eds.; Marcel Dekker: New York, 2004.
10. Hubin, T. J.; Busch, D. H. Template routes to interlocked molecular structures and orderly molecular entanglements. Coord. Chem. Rev. 2000, 200-202, 5.
11. Wasserman, E. The preparation of interlocking rings: a catenane. J. Am. Chem. Soc. 1960, 82, 4433.
12. Frisch, H. L.; Wasserman, E. Chemical topology. J. Am. Chem. Soc. 1961, 83, 3789.
13. Harrison, I. T.; Harrison, S. Synthesis of a stable complex of a macrocycle and a threaded chain. J. Am. Chem. Soc. 1967, 89, 5723.
14. Schill, G.; Zöllenkorpf, H. Rotaxan-Verbindungen. Just. Lieb. Ann. Chem. 1969, 721, 53.
15. Agam, G.; Graiver, D.; Zilkha, A. Studies on formation of topological isomers by statistical-methods. J. Am. Chem. Soc. 1976, 98, 5206.
16. Agam, G.; Zilkha, A. Synthesis of a catenane by a statistical double-stage method. J. Am. Chem. Soc. 1976, 98, 5214.
17. Wolovsky, R. Interlocked ring system obtained by metathesis reaction of cyclododecene -mass spectral evidence. J. Am. Chem. Soc. 1970, 92, 2132.
18. Ben-Efraim, D. A.; Batich, C.; Wasserman, E. Mass spectral evidence for catenanes formed via a Moebius-strip approach. J. Am. Chem. Soc. 1970, 92, 2133.
19. Schill, G.; Lüttringhaus, A. Preparation of Catena Compounds by Directed Synthesis. Angew. Chem., Int. Ed. 1964, 3, 546.
20. Hiratani, K.; Suga, J.; Nagawa, Y.; Houjou, H.; Tokuhisa, H.; Numata, M.; Watanabe, K. A new synthetic method for rotaxanes via tandem Claisen rearrangement, diesterification, and aminolysis. Tetrahedron Lett. 2002, 43, 5747.
21. Hirose, K.; Nishihara, K.; Harada, N.; Nakamura, Y.; Masuda, D.; Araki, M.; Tobe, Y. Highly selective and high-yielding rotaxane synthesis via aminolysis of prerotaxanes consisting of a ring component and a stopper unit. Org. Lett. 2007, 9, 2969.
22. Asakawa, M.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Blohradsky, M.; Gandolfi, M. T.; Kocian, O.; Prodi, L.; Raymo, F. M.; Stoddart, J.; Venturi, M. The slipping approach to self-assembling [n]rotaxanes. J. Am. Chem. Soc. 1997, 119, 302.
23. Gibson, H. W.; Lee, S. H.; Engen, P. T.; Lecavalier, P.; Sze, J.; Shen, Y. X.; Bheda, M. New triarylmethyl derivatives: blocking groups for rotaxanes and polyrotaxanes. J. Org. Chem. 1993, 58, 3748.
24. Cárdenas, D. J.; Gaviña, P.; Sauvage, J.-P. Construction of interlocking and threaded rings using two different transition metals as templating and connecting centers: catenanes and rotaxanes incorporating ru(terpy)2-units in their framework. J. Am. Chem. Soc. 1997, 119, 2656.
25. Weck, M.; Mohr, B.; Sauvage, J.-P.; Grubbs, R. H. Synthesis of catenane structures via ring-closing metathesis. J. Org. Chem. 1999, 64, 5463.
26. Dichtel, W. R.; Miljanic, O. S.; Spruell, J. M.; Heath, J. R.; Stoddart, J. F. Efficient templated synthesis of donor-acceptor rotaxanes using click chemistry. J. Am. Chem. Soc. 2006, 128, 10388.
27. Dietrich-Buchecker, C. O.; Sauvage, J.-P. Synthese de composes polyethers macrocycliques derives de la phenanthroline-1,10 diphenyl-2,9. Tetrahedron Lett. 1983, 24, 5091.
28. Dietrich-Buchecker, C. O.; Sauvage, J.-P. Interlocking of molecular threads -from the statistical approach to the templated synthesis of catenands. Chem. Rev. 1987, 87, 795.
29. Mohr, B.; Sauvage, J.-P.; Grubbs, R. H.; Weck, M. High-yield synthesis of [2] catenanes by intramolecular ring-closing metathesis. Angew. Chem., Int. Ed. Eng. 1997, 36, 1308.
30. Dietrich-Buchecker, C. O.; Sauvage, J.-P.; Kern, J.-M. Templated synthesis of interlocked macrocyclic ligands: The catenands. J. Am. Chem. Soc. 1984, 106, 3043.
31. Wu, C.; Lecavalier, P. R.; Shen, Y. X.; Gibson, H. W. Synthesis of a rotaxane via the template method. Chem. Mater. 1991, 3, 569.
32. Kern, J.-M.; Sauvage, J.-P.; Bidan, G.; Billon, M.; Divisia-Blohorn, B. Electroactive films with a polyrotaxane organic backbone. Adv. Mater. 1996, 8, 580.
33. Billon, M.; Divisia-Blohorn, B.; Kern, J.-M.; Sauvage, J.-P. Electroactive polymer films of silver complexes with intertwined and interlocked ligands: The AgI-Ag0 redox couple as a topological probe. J. Mater. Chem. 1997, 7, 1169.
34. Zhu, S. S.; Carroll, P. J.; Swager, T. M. Conducting polymetallorotaxanes: a supramolecular approach to transition metal ion sensors. J. Am. Chem. Soc. 1996, 118, 8713.
35. Dietrich-Buchecker, C. O.; Sauvage, J.-P. Lithium templated synthesis of catenanes: efficient synthesis of doubly interlocked [2]-catenanes. Chem. Commun. 1999, 615.
36. Sauvage, J.-P.; Ward, M. A bis(terpyridine)ruthenium(II) catenate. Inorg. Chem. 1991, 30, 3869.
37. Mobian, P.; Kern, J.-M.; Sauvage, J.-P. A [2]catenane constructed around a Ru(dilmine)32+ complex used as a template. J. Am. Chem. Soc. 2003, 125, 2016.
38. Chambron, J.-C.; Collin, J.-P.; Heitz, V.; Jouvenot, D.; Kern, J.-M.; Mobian, P.; Pomeranc, D.; Sauvage, J.-P. Rotaxanes and catenanes built around octa-hedral transition metals. Eur. J. Org. Chem. 2004, 1627.
39. Leigh, D. A.; Lusby, P. J.; Teat, S. J.; Wilson, A. J.; Wong, J. K. Y. Benzylic imine catenates: readily accessible octahedral analogues of the sauvage catenates. Angew. Chem., Int. Ed. 2001, 40, 1538.
40. Hamann, C.; Kern, J. M.; Sauvage, J. P. Zinc(II)-templated synthesis of a [2]-catenane consisting of a 2,2':6',2″-terpyridine-incorporating cycle and a 1,10-phenanthroline-containing ring. Inorg. Chem. 2003, 42, 1877.
41. Hamann, C.; Kern, J. M.; Sauvage, J. P. Palladium(II)-directed formation of pseudo-rotaxanes: the 3+1 approach to threaded species using square-planar geometries. Dalton Trans. 2003, 3770.
42. Fuller, A. M.; Leigh, D. A.; Lusby, P. J.; Oswald, I. D. H.; Parsons, S.; Walker, D. B. A 3D interlocked structure from a 2D template: Structural requirements for the assembly of a square-planar metal-coordinated [2]rotaxane. Angew. Chem. Int. Ed. 2004, 43, 3914.
43. Fuller, A. M. L.; Leigh, D. A.; Lusby, P. J.; Slawin, A. M. Z.; Walker, D. B. Selecting topology and connectivity through metal-directed macrocyclization reactions: A square planar palladium [2]catenate and two noninterlocked isomers. J. Am. Chem. Soc. 2005, 127, 12612.
44. Furusho, Y.; Matsuyama, T.; Takata, T.; Moriuchi, T.; Hirao, T. Synthesis of novel interlocked systems utilizing a palladium complex with 2,6-pyridinedicarboxamide-based tridentate macrocyclic ligand. Tetrahedron Lett. 2004, 45, 9593.
45. Goldup, S. M.; Leigh, D. A.; Lusby, P. J.; McBurney, R. T.; Slawin, A. M. Gold(I)-template catenane and rotaxane synthesis13. Angew. Chem. Int. Ed. 2008, 47, 6999.
46. Leigh, D. A.; Lusby, P. J.; McBurney, R. T.; Morelli, A.; Slawin, A.; Thomson, A. R.; Walker, D. B. Getting Harder: Cobalt(III)-Template synthesis of catenanes and rotaxanes. J. Am. Chem. Soc. 2009, 131, 3762.
47. Crowley, J. D.; Goldup, S. M.; Lee, A.; Leigh, D. A.; McBurney, R. T. Active metal template synthesis of rotaxanes, catenanes and molecular shuttles. Chem. Soc. Rev. 2009, 38, 1530.
48. Aucagne, V.; Hanni, K. D.; Leigh, D. A.; Lusby, P. J.; Walker, D. B. Catalytic click rotaxanes: A substoichiometric metal-template pathway to mechanically interlocked architectures. J. Am. Chem. Soc. 2006, 128, 2186.
49. Saito, S.; Takahashi, E.; Nakazono, K. Synthesis of [2]rotaxanes by the catalytic reactions of a macrocyclic copper complex. Org. Lett. 2006, 8, 5133.
50. Crowley, J. D.; Hanni, K. D.; Lee, A. L.; Leigh, D. A. [2]rotaxanes through palladium active-template oxidative heck cross-couplings. J. Am. Chem. Soc. 2007, 129, 12092.
51. Berná, J.; Crowley, J. D.; Goldup, S. M.; Hänni, K. D.; Lee, A.-L.; Leigh, D. A. A Catalytic palladium active-metal template pathway to [2]Rotaxanes. Angew. Chem. Int. Ed. 2007, 46, 5709.
52. Berná, J.; Goldup, S. M.; Lee, A.-L.; Leigh, D. A.; Symes, M. D.; Teobaldi, G.; Zerbetto, F. Cadiot-Chodkiewicz active template synthesis of rotaxanes and switchable molecular shuttles with weak intercomponent interactions. Angew. Chem. Int. Ed. 2008, 47, 4392.
53. Goldup, S. M.; Leigh, D. A.; Lusby, P. J.; McBurney, R. T.; Slawin, A. M. Z. Active template synthesis of rotaxanes and molecular shuttles with switchable dynamics by four-component pdii-promoted michael additions. Angew. Chem. Int. Ed. 2008, 47, 3381.
54. Sato, Y.; Yamasaki, R.; Saito, S. Synthesis of [2]Catenanes by oxidative intramolecular diyne coupling mediated by macrocyclic Copper(I) complexes. Angew. Chem. Int. Ed. 2009, 48, 504.
55. Allwood, B. L.; Spencer, N.; Shahriarizavareh, H.; Stoddart, J. F.; Williams, D. J. Complexation of paraquat by a bisparaphenylene-34-crown-10 derivative. J. Chem. Soc. Chem. Commun. 1987, 1064.
56. Ashton, P. R.; Odell, B.; Reddington, M. V.; Slawin, A. M. Z.; Stoddart, J. F.; Williams, D. J. Isostructural, alternately-charged receptor stacks -the inclusion complexes of hydroquinone and catechol dimethyl ethers with cyclobis(Paraquat-Para-Phenylene). Angew. Chem. Int. Ed. Eng. 1988, 27, 1550.
57. Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. A [2]Catenane made to order. Angew. Chem., Int. Ed. Eng. 1989, 28, 1396.
58. Ashton, P. R.; Grognuz, M.; Slawin, A. M. Z.; Stoddart, J. F.; Williams, D. J. The template-directed synthesis of a [2]Rotaxane. Tetrahedron Lett. 1991, 32, 6235.
59. Allwood, B. L.; Shahriari-Zavareh, H.; Stoddart, J. F.; Williams, D. J. Complexation of paraquat and diquat by a bismetaphenylene-32-Crown-10 derivative. J. Chem. Soc. Chem. Commun. 1987, 1058.
60. Allwood, B. L.; Spencer, N.; Shahriari-Zavareh, H.; Stoddart, J. F.; Williams, D. J. Complexation of diquat by a bisparaphenylene-34-Crown-10 derivative. J. Chem. Soc. Chem. Commun. 1987, 1061.
61. Nygaard, S.; Laursen, B. W.; Hansen, T. S.; Bond, A. D.; Flood, A. H.; Jeppesen, J. O. Preparation of cyclobis(paraquat-p-phenylene)-based [2]Rotaxanes without flexible glycol chains. Angew. Chem. Int. Ed. 2007, 46, 6093.
62. Amabilino, D. B.; Stoddart, J. F. Interlocked and intertwined structures and superstructures. Chem. Rev. 1995, 95, 2725.
63. Lestini, E.; Nikitin, K.; Müller-Bunz, H.; Fitzmaurice, D. Introducing negative charges into Bis-p-phenylene crown ethers: a study of bipyridinium-based [2]Pseudorotaxanes and [2]Rotaxanes. Chem. Eur. J. 2008, 14, 1095.
64. Cordova, E.; Bissell, R. A.; Kaifer, A. E. Synthesis and electrochemical properties of redox-active [2]rotaxanes based on the inclusion complexation of 1,4-phenylenediamine and benzidine by cyclobis(paraquat-p-phenylene). J. Org. Chem. 1995, 60, 1033.
65. Ikeda, T.; Aprahamian, I.; Stoddart, J. F. Blue-colored donor-acceptor [2]rotaxane. Org. Lett. 2007, 9, 1481.
66. Ikeda, T.; Higuchi, M.; Sato, A.; Kurth, D. G. Thiophene donor-acceptor [2]rotaxanes. Org. Lett. 2008, 10, 2215.
67. Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O. A.; Montalti, M.; Spencer, N.; Stoddart, J. F.; Venturi, M. Electro-chemically induced molecular motions in pseudorotaxanes: a case of dual-mode (oxidative and reductive) dethreading. Chem. Eur. J. 1997, 3, 1992.
68. Li, Z. T.; Becher, J. Configurationally selective self-assembly of a cis-[3]pseudocatenane incorporating three tetrathiafulvalene units. Chem. Commun. 1996, 639.
69. Asakawa, M.; Ashton, P. R.; Balzani, V.; Boyd, S. E.; Credi, A.; Mattersteig, G.; Menzer, S.; Montalti, M.; Raymo, F. M.; Ruffilli, C.; Stoddart, J. F.; Venturi, M.; Williams, D. J. Molecular meccano, 49. pseudorotaxanes and catenanes containing a redox-active unit derived from tetrathiafulvalene. Eur. J. Org. Chem. 1999, 985.
70. Laursen, B. W.; Nygaard, S.; Jeppesen, J. O.; Stoddart, J. F. Counterion-induced translational isomerism in a bistable [2]Rotaxane. Org. Lett. 2004, 6, 4167.
71. Jeppesen, J. O.; Perkins, J.; Becher, J.; Stoddart, J. F. Slow shuttling in an amphiphilic bistable [2]rotaxane incorporating a tetrathiafulvalene unit. Angew. Chem. Int. Ed. 2001, 40, 1216.
72. Lukyanenko, N. G.; Lyapunov, A. Y.; Kirichenko, T. I.; Botoshansky, M. M.; Simonov, Y. A.; Fonari, M. S. A high yielding template-directed synthesis of the first fluorenone-containing [2]catenane. Tetrahedron Lett. 2005, 46, 2109.
73. Balzani, V.; Clemente-Leon, M.; Credi, A.; Ferrer, B.; Venturi, M.; Flood, A. H.; Stoddart, J. F. Autonomous artificial nanomotor powered by sunlight. Proc. Natl. Acad. Sci. USA 2006, 103, 1178.
74. Ashton, P. R.; Ballardini, R.; Balzani, V.; Gandolfi, M. T.; Marquis, D. J. F.; Perez-Garcia, L.; Prodi, L.; Stoddart, J. F.; Venturi, M. The self assembly of controllable [2]catenanes. J. Chem. Soc. Chem. Commun. 1994, 177.
75. Hamilton, D. G.; Sanders, J. K. M. Co2(CO)6-induced deformation of alkynes as a reversible modulator of supramolecular interactions: controlling the synthesis of catenanes. Chem. Commun. 1998, 1749.
76. Korybut-Daszkiewicz, B.; Wieckowska, A.; Bilewicz, R.; Domagala, S.; Wozniak, K. Novel [2]Catenane structures introducing communication between transition metal centers via interactions. J. Am. Chem. Soc. 2001, 123, 9356.
77. Ashton, P. R.; Boyd, S. E.; Brindle, A.; Langford, S. J.; Menzer, S.; Perez-Garcia, L.; Preece, J. A.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Molecular meccano Part 50 Diazapyrenium-containing catenanes and rotaxanes. New J. Chem. 1999, 23, 587.
78. Vignon, S. A.; Jarrosson, T.; Iijima, T.; Tseng, H. R.; Sanders, J. K. M.; Stoddart, J. Switchable neutral bistable rotaxanes. J. Am. Chem. Soc. 2004, 126, 9884.
79. Schalley, C. A.; Weilandt, T.; Brüggemann, J.; Vögtle, F. Hydrogen-bond-mediated template synthesis of rotaxanes, catenanes, and knotanes. Top. Curr. Chem. 2004, 248, 141.
80. Hunter, C. A. Synthesis and structure elucidation of a new [2]-catenane. J. Am. Chem. Soc. 1992, 114, 5303.
81. Vögtle, F.; Meier, S.; Hoss, R. One-step synthesis of a fourfold functionalized catenane. Angew. Chem., Int. Ed. Eng. 1992, 31, 1619.
82. Vögtle, F.; Handel, M.; Meier, S.; Ottenshildebrandt, S.; Ott, F.; Schmidt, T. Template synthesis of the first amide-based rotaxanes. Lieb. Ann. 1995, 739.
83. Johnston, A. G.; Leigh, D. A.; Pritchard, R. J.; Deegan, M. D. Facile synthesis and solid-state structure of a benzylic amide [2]Catenane. Angew. Chem. Int. Ed. Eng. 1995, 34, 1209.
84. Gatti, F. G.; Leigh, D. A.; Nepogodiev, S. A.; Slawin, A. M. Z.; Teat, S. J.; Wong, J. K. Y. Stiff, and sticky in the right places: the dramatic influence of preorganizing guest binding sites on the hydrogen bond-directed assembly of rotaxanes. J. Am. Chem. Soc. 2001, 123, 5983.
85. Johnston, A.; Leigh, D.; Nezhat, L.; Smart, J.; Deegan, M. Structurally diverse and dynamically versatile benzylic amide [2]catenanes assembled directly from commercially available precursors. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212.
86. Ottens-Hildebrandt, S.; Nieger, M.; Rissanen, K.; Rouvinen, J.; Meier, S.; Harder, G.; Vögtle, F. Amide-based furanocatenanes: Regioselective template synthesis and crystal structure. J. Chem. Soc. Chem. Commun. 1995, 777.
87. Dünnwald, T.; Jäger, R.; Vögtle, F. Synthesis of rotaxane assemblies. Chem. Eur. J. 1997, 3, 2043.
88. Altieri, A.; Bottari, G.; Dehez, F.; Leigh, D. A.; Wong, J. K. Y.; Zerbetto, F. Remarkable positional discrimination in bistable light- and heat-switchable hydrogen-bonded molecular shuttles. Angew. Chem. Int. Ed. 2003, 42, 2296.
89. Da Ros, T.; Guldi, D. M.; Morales, A. F.; Leigh, D. A.; Prato, M.; Turco, R. Hydrogen bond-assembled fullerene molecular shuttle. Org. Lett. 2003, 5, 689.
90. Leigh, D. A.; Murphy, A.; Smart, J.; Slawin, A. Glycylglycine rotaxanes- the hydrogen bond directed assembly of synthetic peptide rotaxanes. Angew. Chem. Int. Ed. Engl. 1997, 36, 728.
91. Clegg, W.; Gimenez-Saiz, C.; Leigh, D. A.; Murphy, A.; Slawin, A.; Teat, S. J. 'Smart' rotaxanes: Shape memory and control in tertiary amide peptido[2]rotaxanes. J. Am. Chem. Soc. 1999, 121, 4124.
92. Leigh, D. A.; Perez, E. M. Shuttling through reversible covalent chemistry. Chem. Commun. 2004, 10, 2262.
93. Fischer, C.; Nieger, M.; Mogck, O.; Böhmer, V.; Ungaro, R.; Vögtle, F. Calixarenes as stoppers in rotaxanes. Eur. J. Org. Chem. 1998, 155.
94. Seel, C.; Parham, A.; Safarowsky, O.; Hubner, G.; Vögtle, F. How selective threading of amides through macrocylic lactam wheels leads to rotaxane synthesis. J. Org. Chem. 1999, 64, 7236.
95. Jeong, K. S.; Choi, J. S.; Chang, S. Y.; Chang, H. Y. Self-assembly of rotax- ane-like complexes with macrocycles containing reversible coordinate bonds. Angew. Chem. Int. Ed. Engl. 2000, 39, 1692.
96. Huang, Y. L.; Hung, W. C.; Lai, C. C.; Liu, Y. H.; Peng, S. M.; Chiu, S. H. Using acetate anions to induce translational isomerization in a neutral urea- based molecular switch. Angew. Chem. Int. Ed. Engl. 2007, 46, 6629.
97. Pedersen, C. J. Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 1967, 89, 7017.
98. Cram, D. J.; Cram, J. M. Design of complexes between synthetic hosts and organic guests. Acc. Chem. Res. 1978, 11, 8.
99. Sutherland, I. O. Tilden Lecture. Molecular recognition by synthetic receptors. Chem. Soc. Rev. 1986, 15, 63.
100. Kolchinski, A. G.; Busch, D. H.; Alcock, N. W. Gaining control over molecular threading-benefits of 2nd coordination sites and aqueous-organic interfaces in rotaxane synthesis. J. Chem. Soc. Chem. Commun. 1995, 1289.
101. Ashton, P. R.; Campbell, P. J.; Glink, P. T.; Philp, D.; Spencer, N.; Stoddart, J. F.; Chrystal, E. J. T.; Menzer, S.; Williams, D. J.; Tasker, P. A. Dialky-lammonium Ion/Crown ether complexes: the forerunners of a new family of interlocked molecules. Angew. Chem. Int. Ed. Eng. 1995, 34, 1865.
102. Ashton, P. R.; Glink, P. T.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Self-assembling [2]- and [3]rotaxanes from secondary dialky-lammonium salts and crown ethers. Chem. Eur. J. 1996, 2, 729.
103. Cantrill, S. J.; Pease, A. R.; Stoddart, J. F. A molecular meccano kit. J. Chem. Soc. Dalton Trans. 2000, 3715.
104. Loeb, S. J.; Wisner, J. A. A new motif for the self-assembly of [2]pseudorotaxanes; 1,2-bis(pyridinium)ethane axles and [24]crown-8 ether wheels. Angew. Chem. Int. Ed. 1998, 37, 2838.
105. Loeb, S. J.; Wisner, J. A. 1,2-bis(4,4 '-dipyridinium)ethane: a versatile dication for the formation of [2]rotaxanes with dibenzo-24-crown-8 ether. Chem. Commun. 1998, 2757.
106. Loeb, S. J. Rotaxanes as ligands: From molecules to materials. Chem. Soc. Rev. 2007, 36, 226.
107. Chiu, C. W.; Lai, C. C.; Chiu, S. H. Threading-followed-by-swelling: A new protocol for rotaxane synthesis. J. Am. Chem. Soc. 2007, 129, 3500.
108. Watanabe, N.; Yagi, T.; Kihara, N.; Takata, T. Highly efficient synthesis of [3]- and [5]-rotaxanes consisting of crown ether and a sec-ammonium salt. Chem. Commun. 2002, 2720.
109. Loeb, S. J.; Tiburcio, J.; Vella, S. J. [2]Pseudorotaxane formation with N-benzylanilinium axles and 24-crown-8 ether wheels. Org. Lett. 2005, 7, 4923.
110. Castillo, D.; Astudillo, P.; Mares, J.; González, F. J.; Vela, A.; Tiburcio, J. Chemically controlled self-assembly of [2]pseudorotaxanes based on 1,2-bis(benzimidazolium)ethane cations and 24-crown-8 macrocycles. Org. Biomol. Chem. 2007, 5, 2252.
111. Li, L. W.; Clarkson, G. J. New bis(benzimidazole) cations for threading through dibenzo-24-crown-8. Org. Lett. 2007, 9, 497.
112. Noujeim, N.; Leclercq, L.; Schmitzer, A. R. N,N'-Disubstituted methylenedi-imidazolium salts: a versatile guest for various macrocycles. J. Org. Chem. 2008, 73, 3784.
113. Gimeno, N.; Vilar, R. Anions as templates in coordination and supramolecular chemistry. Coord. Chem. Rev. 2006, 250, 3161.
114. Lankshear, M. D.; Beer, P. D. Strategic anion templation. Coord. Chem. Rev. 2006, 250, 3142.
115. Hubner, G. M.; Glaser, J.; Seel, C.; Vögtle, F. High-yielding rotaxane synthesis with an anion template. Angew. Chem. Int. Ed. 1999, 38, 383.
116. Ghosh, P.; Mermagen, O.; Schalley, C. A. Novel template effect for the preparation of [2]rotaxanes with functionalised centre pieces. Chem. Commun. 2002, 2628.
117. Arunkumar, E.; Forbes, C. C.; Noll, B. C.; Smith, B. D. Squaraine-derived rotaxanes: sterically protected fluorescent near-ir dyes. J. Am. Chem. Soc. 2005, 127, 3288.
118. Vickers, M. S.; Beer, P. D. Anion templated assembly of mechanically interlocked structures. Chem. Soc. Rev. 2007, 36, 211.
119. Lankshear, M. D.; Beer, P. D. Interweaving anion templation. Acc. Chem. Res. 2007, 40, 657.
120. Wisner, J. A.; Beer, P. D.; Drew, M. G. B. A demonstration of anion templation and selectivity in pseudorotaxane formation. Angew. Chem. Int. Ed. 2001, 40, 3606.
121. Wisner, J. A.; Beer, P. D.; Berry, N. G.; Tomapatanaget, B. Anion recognition as a method for templating pseudorotaxane formation. Proc. Natl. Acad. Sci. USA 2002, 99, 4983.
122. Sambrook, M. R.; Beer, P. D.; Wisner, J. A.; Paul, R. L.; Cowley, A. R.; Szemes, F.; Drew, M. G. B. Anion-templated assembly of pseudorotaxanes: Importance of anion template, strength of ion-pair thread association, and macrocycle ring size. J. Am. Chem. Soc. 2005, 127, 2292.
123. Wisner, J. A.; Beer, P. D.; Drew, M. G. B.; Sambrook, M. R. Anion-templated rotaxane formation. J. Am. Chem. Soc. 2002, 124, 12469.
124. Sambrook, M. R.; Beer, P. D.; Wisner, J. A.; Paul, R. L.; Cowley, A. R. Anion-templated assembly of a [2]catenane. J. Am. Chem. Soc. 2004, 126, 15364.
125. Ng, K. Y.; Cowley, A. R.; Beer, P. D. Anion templated double cyclization assembly of a chloride selective [2]catenane. Chem. Commun. 2006, 3676.
126. Chmielewski, M. J.; Zhao, L.; Brown, A.; Curiel, D.; Sambrook, M. R.; Thompson, A. L.; Santos, S. M.; Felix, V.; Davis, J. J.; Beer, P. D. Sulfate anion templation of a neutral pseudorotaxane assembly using an indolocarbazole threading component. Chem. Commun. 2008, 3154.
127. Huang, B.; Santos, S. M.; Felix, V.; Beer, P. D. Sulfate anion-templated assembly of a [2]catenane. Chem. Commun. 2008, 4610.
128. Barrell, M. J.; Leigh, D. A.; Lusby, P. J.; Slawin, A. M. Z. An Ion-Pair Template for Rotaxane Formation and its Exploitation in an Orthogonal Interaction Anion-Switchable Molecular Shuttle. Angew. Chem. Int. Ed. 2008, 47, 8036.
129. Blight, B. A.; Van Noortwyk, K. A.; Wisner, J. A.; Jennings, M. C. [2]Pseudorotaxanes through second-sphere coordination. Angew. Chem. Int. Ed. 2005, 44, 1499.
130. Blight, B. A.; Wei, X.; Wisner, J. A.; Jennings, M. C. [2]pseudorotaxane and [2]rotaxane molecular shuttles: Self-assembly through second-sphere coordination of thiocyanate ligands. Inorg. Chem. 2007, 46, 8445.
131. Muller, P. Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994). Pure Appl. Chem. 1994, 66, 1177.
132. Dill, K. A. Dominant forces in protein folding. Biochemistry 1990, 29, 7133.
133. Andrew M. Davis, S. J. T. Hydrogen bonding, hydrophobic interactions, and failure of the rigid receptor hypothesis. Angew. Chem.; Int. Ed. 1999, 38, 736.
134. Ball, P. Water as an active constituent in cell biology. Chem. Rev. 2008, 108, 74.
135. Cramer, F.; Saenger, W.; Spatz, H. Inclusion compounds. XIX. the formation of inclusion compounds of -cyclodextrin in aqueous solutions. thermodynamics and kinetics. J. Am. Chem. Soc. 1967, 89, 14.
136. Ogino, H. Relatively high-yield syntheses of rotaxanes -syntheses and properties of compounds consisting of cyclodextrins threaded by, -diaminoalkanes coordinated to Cobalt(III) complexes. J. Am. Chem. Soc. 1981, 103, 1303.
137. Rao, T. V. S.; Lawrence, D. S. Self-assembly of a threaded molecular loop. J. Am. Chem. Soc. 1990, 112, 3614.
138. Wylie, R. S.; Macartney, D. H. Self-assembling metal rotaxane complexes of.alpha.-cyclodextrin. J. Am. Chem. Soc. 1992, 114, 3136.
139. Harada, A.; Li, J.; Kamachi, M. The molecular necklace: a rotaxane containing many threaded [alpha]-cyclodextrins. Nature 1992, 356, 325.
140. Wenz, G.; Keller, B. Threading cyclodextrin rings on polymer chains. Angew. Chem. Int. Ed. Engl. 1992, 31, 197.
141. Armspach, D.; Ashton, P.; Moore, C. P.; Spencer, N.; Stoddart, J. F.; Wear, T. J.; Williams, D. J. The self-assembly of catenated cyclodextrins. Angew. Chem. Int. Ed. Eng. 1993, 32, 854.
142. Wenz, G.; Han, B. H.; Müller, A. Cyclodextrin rotaxanes and polyrotaxanes. Chem. Rev. 2006, 106, 782.
143. Nepogodiev, S. A.; Stoddart, J. F. Cyclodextrin-based catenanes and rotaxanes. Chem. Rev. 1998, 98, 1959.
144. Sugiyama, J.; Tomita, I. Novel approach to stabilize unstable molecular wires by simultaneous rotaxane formation. Synthesis of inclusion complexes of oligocarbynes with cyclic host molecules. Eur. J. Org. Chem. 2007, 4651.
145. Stanier, C. A.; O'Connell, M. J.; Clegg, W.; Anderson, H. L. Synthesis of fluorescent stilbene and tolan rotaxanes by Suzuki coupling. Chem. Commun. 2001, 493.
146. Liu, Y.; Zhao, Y.; Zhang, H.; Li, X.; Liang, P.; Zhang, X.; Xu, J. Supramolecular polypseudorotaxane with conjugated polyazomethine prepared directly from two inclusion complexes of ß-cyclodextrin with tolidine and phthaldehyde. Macromolecules 2004, 37, 6362.
147. Maniam, S.; Cieslinski, M. M.; Lincoln, S. F.; Onagi, H.; Steel, P. J.; Willis, A. C.; Easton, C. J. Molecular fibers and wires in solid-state and solution self-assemblies of cyclodextrin [2]rotaxanes. Org. Lett. 2008, 10, 1885.
148. van den Boogaard, M.; Bonnet, G.; van't Hof, P.; Wang, Y.; Brochon, C.; van Hutten, P.; Lapp, A.; Hadziioannou, G. Synthesis of Insulated Single-Chain Semiconducting Polymers Based on Polythiophene, Polyfluorene, and -Cyclodextrin. Chem. Mater. 2004, 16, 4383.
149. Zhao, Y.; Dichtel, W. R.; Trabolsi, A.; Saha, S.; Aprahamian, I.; Stoddart, J. F. A Redox-Switchable -Cyclodextrin-Based [2]Rotaxane. J. Am. Chem. Soc. 2008, 130, 11294.
150. Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. The Cucurbit [n]uril Family. Angew. Chem. Int. Ed. 2005, 44, 4844.
151. Freeman, W. A.; Mock, W. L.; Shih, N. Y. Cucurbituril. J. Am. Chem. Soc. 1981, 103, 7367.
152. Mock, W. L.; Shih, N. Y. Structure and selectivity in host-guest complexes of cucurbituril. J. Org. Chem. 1986, 51, 4440.
153. Mock, W. L.; Pierpont, J. A cucurbituril-based molecular switch. J. Chem. Soc. Chem. Commun. 1990, 1509.
154. Jeon, Y.; Whang, D.; Kim, J.; Kim, K. A Simple construction of a rotaxane and a pseudorotaxne: synthesis and X-Ray strucutres of a cucurbituril threaded and substitutes spermine. Chem. Lett. 1996, 503.
155. Whang, D.; Jeon, Y.; Heo, J.; Kim, K. Self-assembly of a polyrotaxane containing a cyclic bead in every structural unit in the solid state: cucurbituril molecules threaded on a one-dimensional coordination polymer. J. Am. Chem. Soc. 1996, 118, 11333.
156. Kim, K. Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies. Chem. Soc. Rev. 2002, 31, 96.
157. Whang, D.; Park, K.; Heo, J.; Ashton, P.; Kim, K. Molecular necklace: quantitative self-assembly of a cyclic oligorotaxane from nine molecules. J. Am. Chem. Soc. 1998, 120, 4899.
158. Park, K.; Kim, S.; Heo, J.; Whang, D.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Designed self-assembly of molecular necklaces. J. Am. Chem. Soc. 2002, 124, 2140.
159. Kim, J.; Jung, I.; Kim, S.; Lee, E.; Kang, J. K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. New Cucurbituril homologues:syntheses, isolation, characterization, and X-ray crystal structures of cucurbit[n]uril (n = 5, 7, and 8). J. Am. Chem. Soc. 2000, 122, 540.
160. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.; Kim, K. Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. Acc. Chem. Res. 2003, 36, 621.
161. Ooya, T.; Inoue, D.; Choi, H. S.; Kobayashi, Y.; Loethen, S.; Thompson, D. H.; Ko, Y. H.; Kim, K.; Yui, N. pH-responsive movement of cucurbit[7]uril in a diblock polypseudorotaxane containing dimethyl beta-cyclodextrin and cucurbit[7]uril. Org. Lett. 2006, 8, 3159.
162. Tuncel, D.; Tiftik, H. B.; Salih, B. PH-Responsive polypseudorotaxane synthesized through cucurbit[6]uril catalyzed 1,3-dipolar cycloaddition. J. Mater. Chem. 2006, 16, 3291.
163. Sobransingh, D.; Kaifer, A. E. Electrochemically switchable cucurbit[7]uril-based pseudorotaxanes. Org. Lett. 2006, 8, 3247.
164. Sindelar, V.; Silvi, S.; Kaifer, A. E. Switching a molecular shuttle on and off: simple, pH-controlled pseudorotaxanes based on cucurbit[7]uril. Chem. Commun. 2006, 2185.
165. Eelkema, R.; Maeda, K.; Odell, B.; Anderson, H. L. Radical cation stabilization in a cucurbituril oligoaniline rotaxane. J. Am. Chem. Soc. 2007, 129, 12384.
166. Liu, Y.; Li, X. Y.; Zhang, H. Y.; Li, C. J.; Ding, F. Cyclodextrin-driven movement of Cucurbit[7]uril. J. Org. Chem. 2007, 72, 3640.
167. Yuan, L.; Wang, R.; Macartney, D. H. Binding modes of cucurbit[6]uril and Cucurbit[7]uril with a tetracationic Bis(viologen) guest. J. Org. Chem. 2007, 72, 4539.
168. Fujita, M. Self-assembly of [2]catenanes containing metals in their back-bones. Acc. Chem. Res. 1999, 32, 53.
169. Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Quantitative self-assembly of a [2]catenane from two preformed molecular rings. Nature 1994, 367, 720.
170. Fujita, M.; Aoyagi, M.; Ibukuro, F.; Ogura, K.; Yamaguchi, K. Made-to-order assembling of [2]catenanes from palladium(II)-linked rectangular molecular boxes. J. Am. Chem. Soc. 1998, 120, 611.
171. Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. A molecular lock. J. Am. Chem. Soc. 1995, 117, 4175.
172. Hori, A.; Kataoka, H.; Okano, T.; Sakamoto, S.; Yamaguchi, K.; Fujita, M. Selective cross-catenation of Pd(II) and Pt(II) coordination rings. Chem. Commun. 2003, 9, 182.
173. Miljanic, O. S.; Stoddart, J. F. Dynamic donor acceptor [2]catenanes. Proc. Natl. Acad. Sci. USA 2007, 104, 12966.
174. West, K. R.; Ludlow, R. F.; Corbett, P. T.; Besenius, P.; Mansfeld, F. M.; Cormack, P. A. G.; Sherrington, D. C.; Goodman, J. M.; Stuart, M. C. A.; Otto, S. Dynamic combinatorial discovery of a [2]-catenane and its guest-induced conversion into a molecular square host. J. Am. Chem. Soc. 2008, 130, 10834.