Molecular and supramolecular synthesis with dibenzofuran-containing systems

Chemistry - A European Journal

Volumn 3, Issue 7, 1997, Pages 1136-1150

  Asakawa, Masumi ^a   Ashton, Peter R ^a   Brown, Christopher L ^a   Fyfe, Matthew C T ^a   Menzer, Stephan ^b   Pasini, Dario ^a   Scheuer, Cecile ^b   Spencer, Neil ^a   Fraser Stoddart, J ^a   White, Andrew J P ^b   Williams, David J ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Crystal engineering; Dibenzofuran; Molecular quadrilaterals; Supramolecular chemistry; Template synthesis

Indexed keywords

EID: 0030839784     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030720     Document Type: Article

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4. Selected recent examples: a) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473-5475; b) P. Baxter, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72; c) S. Rüttiman, G. Bernardinelli, A. F. Williams, ibid. 1993, 32, 392-394; d) R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, ibid. 1994, 33, 1621-1623; e) J. Yang, J.-L. Marendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665-3668; f) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature (London) 1995, 378, 469-471; g) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489; h) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
5. Selected recent examples: a) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473-5475; b) P. Baxter, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72; c) S. Rüttiman, G. Bernardinelli, A. F. Williams, ibid. 1993, 32, 392-394; d) R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, ibid. 1994, 33, 1621-1623; e) J. Yang, J.-L. Marendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665-3668; f) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature (London) 1995, 378, 469-471; g) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489; h) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
6. Selected recent examples: a) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473-5475; b) P. Baxter, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72; c) S. Rüttiman, G. Bernardinelli, A. F. Williams, ibid. 1993, 32, 392-394; d) R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, ibid. 1994, 33, 1621-1623; e) J. Yang, J.-L. Marendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665-3668; f) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature (London) 1995, 378, 469-471; g) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489; h) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
7. Selected recent examples: a) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473-5475; b) P. Baxter, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72; c) S. Rüttiman, G. Bernardinelli, A. F. Williams, ibid. 1993, 32, 392-394; d) R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, ibid. 1994, 33, 1621-1623; e) J. Yang, J.-L. Marendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665-3668; f) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature (London) 1995, 378, 469-471; g) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489; h) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
8. Selected recent examples: a) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473-5475; b) P. Baxter, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72; c) S. Rüttiman, G. Bernardinelli, A. F. Williams, ibid. 1993, 32, 392-394; d) R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, ibid. 1994, 33, 1621-1623; e) J. Yang, J.-L. Marendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665-3668; f) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature (London) 1995, 378, 469-471; g) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489; h) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
9. Selected recent examples: a) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473-5475; b) P. Baxter, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72; c) S. Rüttiman, G. Bernardinelli, A. F. Williams, ibid. 1993, 32, 392-394; d) R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, ibid. 1994, 33, 1621-1623; e) J. Yang, J.-L. Marendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665-3668; f) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature (London) 1995, 378, 469-471; g) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489; h) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
10. Selected recent examples: a) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473-5475; b) P. Baxter, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72; c) S. Rüttiman, G. Bernardinelli, A. F. Williams, ibid. 1993, 32, 392-394; d) R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, ibid. 1994, 33, 1621-1623; e) J. Yang, J.-L. Marendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665-3668; f) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature (London) 1995, 378, 469-471; g) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489; h) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
11. Selected recent examples: a) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, J. Am. Chem. Soc. 1992, 114, 5473-5475; b) P. Baxter, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72; c) S. Rüttiman, G. Bernardinelli, A. F. Williams, ibid. 1993, 32, 392-394; d) R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, ibid. 1994, 33, 1621-1623; e) J. Yang, J.-L. Marendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665-3668; f) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature (London) 1995, 378, 469-471; g) R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489; h) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
12. Selected examples (not involving X-ray crystal structures): a) M. R. Ghadiri, J. R. Granja, R. A. Milligan, D. E. McRee, N. Khazanovich, Nature (London) 1993, 366, 324-327; b) F. M. Menger, S. J. Lee, J. Am. Chem. Soc. 1994, 116, 5987-5988; c) M. Kotera, J.-M. Lehn, J.-P. Vigneron, J. Chem. Soc. Chem. Commun. 1994, 197-199; d) N. Kimizuka, S. Fujikawa, H. Kuwahara, T. Kunitake, A. Marsh, J.-M. Lehn, ibid. 1995, 2103-2104.
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15. Selected examples (not involving X-ray crystal structures): a) M. R. Ghadiri, J. R. Granja, R. A. Milligan, D. E. McRee, N. Khazanovich, Nature (London) 1993, 366, 324-327; b) F. M. Menger, S. J. Lee, J. Am. Chem. Soc. 1994, 116, 5987-5988; c) M. Kotera, J.-M. Lehn, J.-P. Vigneron, J. Chem. Soc. Chem. Commun. 1994, 197-199; d) N. Kimizuka, S. Fujikawa, H. Kuwahara, T. Kunitake, A. Marsh, J.-M. Lehn, ibid. 1995, 2103-2104.
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62. For solid-state supramolecular synthesis employing both hydrogen bonding and aryl-aryl stacking interactions, see: a) J. C. Beeson, L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, J. T. Rademacher, A. W. Czarnik, J. Am. Chem. Soc. 1994, 116, 4621-4622; b) Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, H. Masuda, ibid. 1996, 118, 5562-5571. For crystal engineering utilizing both dative bonds and hydrogen bonding, see: c) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1981, 849-850; d) S. B. Copp, S. Subramanian, M. J. Zaworotko, J. Am. Chem. Soc. 1992, 114, 8719-8720; e) M. M. Chowdry, D. M. P. Mingos, A. J. P. White, D. J. Williams. Chem. Commun. 1996, 899-900. For solid-state supramolecular synthesis employing both hydrogen bonding and heteroatom-halogen interactions, see: f) ref. [12c]; g) D. S. Reddy, Y. E. Ovchinmkov, O. V. Shishkin, Y. T. Struchkov, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4085-4089. For solid state supramolecular synthesis of polymeric networks using both coordinate covalent bonds and π-π stacking interactions, see: h) J. Harrowfield, J. Chem. Soc. Dalton Trans. 1996, 3165-3171; i) A. C. Deveson, S. L. Heath, C. J. Harding, A. K. Powell, ibid. 1996, 3173-3178.
63. For solid-state supramolecular synthesis employing both hydrogen bonding and aryl-aryl stacking interactions, see: a) J. C. Beeson, L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, J. T. Rademacher, A. W. Czarnik, J. Am. Chem. Soc. 1994, 116, 4621-4622; b) Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, H. Masuda, ibid. 1996, 118, 5562-5571. For crystal engineering utilizing both dative bonds and hydrogen bonding, see: c) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1981, 849-850; d) S. B. Copp, S. Subramanian, M. J. Zaworotko, J. Am. Chem. Soc. 1992, 114, 8719-8720; e) M. M. Chowdry, D. M. P. Mingos, A. J. P. White, D. J. Williams. Chem. Commun. 1996, 899-900. For solid-state supramolecular synthesis employing both hydrogen bonding and heteroatom-halogen interactions, see: f) ref. [12c]; g) D. S. Reddy, Y. E. Ovchinmkov, O. V. Shishkin, Y. T. Struchkov, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4085-4089. For solid state supramolecular synthesis of polymeric networks using both coordinate covalent bonds and π-π stacking interactions, see: h) J. Harrowfield, J. Chem. Soc. Dalton Trans. 1996, 3165-3171; i) A. C. Deveson, S. L. Heath, C. J. Harding, A. K. Powell, ibid. 1996, 3173-3178.
64. For solid-state supramolecular synthesis employing both hydrogen bonding and aryl-aryl stacking interactions, see: a) J. C. Beeson, L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, J. T. Rademacher, A. W. Czarnik, J. Am. Chem. Soc. 1994, 116, 4621-4622; b) Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, H. Masuda, ibid. 1996, 118, 5562-5571. For crystal engineering utilizing both dative bonds and hydrogen bonding, see: c) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1981, 849-850; d) S. B. Copp, S. Subramanian, M. J. Zaworotko, J. Am. Chem. Soc. 1992, 114, 8719-8720; e) M. M. Chowdry, D. M. P. Mingos, A. J. P. White, D. J. Williams. Chem. Commun. 1996, 899-900. For solid-state supramolecular synthesis employing both hydrogen bonding and heteroatom-halogen interactions, see: f) ref. [12c]; g) D. S. Reddy, Y. E. Ovchinmkov, O. V. Shishkin, Y. T. Struchkov, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4085-4089. For solid state supramolecular synthesis of polymeric networks using both coordinate covalent bonds and π-π stacking interactions, see: h) J. Harrowfield, J. Chem. Soc. Dalton Trans. 1996, 3165-3171; i) A. C. Deveson, S. L. Heath, C. J. Harding, A. K. Powell, ibid. 1996, 3173-3178.
65. For solid-state supramolecular synthesis employing both hydrogen bonding and aryl-aryl stacking interactions, see: a) J. C. Beeson, L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, J. T. Rademacher, A. W. Czarnik, J. Am. Chem. Soc. 1994, 116, 4621-4622; b) Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, H. Masuda, ibid. 1996, 118, 5562-5571. For crystal engineering utilizing both dative bonds and hydrogen bonding, see: c) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1981, 849-850; d) S. B. Copp, S. Subramanian, M. J. Zaworotko, J. Am. Chem. Soc. 1992, 114, 8719-8720; e) M. M. Chowdry, D. M. P. Mingos, A. J. P. White, D. J. Williams. Chem. Commun. 1996, 899-900. For solid-state supramolecular synthesis employing both hydrogen bonding and heteroatom-halogen interactions, see: f) ref. [12c]; g) D. S. Reddy, Y. E. Ovchinmkov, O. V. Shishkin, Y. T. Struchkov, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4085-4089. For solid state supramolecular synthesis of polymeric networks using both coordinate covalent bonds and π-π stacking interactions, see: h) J. Harrowfield, J. Chem. Soc. Dalton Trans. 1996, 3165-3171; i) A. C. Deveson, S. L. Heath, C. J. Harding, A. K. Powell, ibid. 1996, 3173-3178.
66. For solid-state supramolecular synthesis employing both hydrogen bonding and aryl-aryl stacking interactions, see: a) J. C. Beeson, L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, J. T. Rademacher, A. W. Czarnik, J. Am. Chem. Soc. 1994, 116, 4621-4622; b) Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, H. Masuda, ibid. 1996, 118, 5562-5571. For crystal engineering utilizing both dative bonds and hydrogen bonding, see: c) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1981, 849-850; d) S. B. Copp, S. Subramanian, M. J. Zaworotko, J. Am. Chem. Soc. 1992, 114, 8719-8720; e) M. M. Chowdry, D. M. P. Mingos, A. J. P. White, D. J. Williams. Chem. Commun. 1996, 899-900. For solid-state supramolecular synthesis employing both hydrogen bonding and heteroatom-halogen interactions, see: f) ref. [12c]; g) D. S. Reddy, Y. E. Ovchinmkov, O. V. Shishkin, Y. T. Struchkov, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4085-4089. For solid state supramolecular synthesis of polymeric networks using both coordinate covalent bonds and π-π stacking interactions, see: h) J. Harrowfield, J. Chem. Soc. Dalton Trans. 1996, 3165-3171; i) A. C. Deveson, S. L. Heath, C. J. Harding, A. K. Powell, ibid. 1996, 3173-3178.
67. For solid-state supramolecular synthesis employing both hydrogen bonding and aryl-aryl stacking interactions, see: a) J. C. Beeson, L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, J. T. Rademacher, A. W. Czarnik, J. Am. Chem. Soc. 1994, 116, 4621-4622; b) Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, H. Masuda, ibid. 1996, 118, 5562-5571. For crystal engineering utilizing both dative bonds and hydrogen bonding, see: c) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1981, 849-850; d) S. B. Copp, S. Subramanian, M. J. Zaworotko, J. Am. Chem. Soc. 1992, 114, 8719-8720; e) M. M. Chowdry, D. M. P. Mingos, A. J. P. White, D. J. Williams. Chem. Commun. 1996, 899-900. For solid-state supramolecular synthesis employing both hydrogen bonding and heteroatom-halogen interactions, see: f) ref. [12c]; g) D. S. Reddy, Y. E. Ovchinmkov, O. V. Shishkin, Y. T. Struchkov, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4085-4089. For solid state supramolecular synthesis of polymeric networks using both coordinate covalent bonds and π-π stacking interactions, see: h) J. Harrowfield, J. Chem. Soc. Dalton Trans. 1996, 3165-3171; i) A. C. Deveson, S. L. Heath, C. J. Harding, A. K. Powell, ibid. 1996, 3173-3178.
68. For solid-state supramolecular synthesis employing both hydrogen bonding and aryl-aryl stacking interactions, see: a) J. C. Beeson, L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, J. T. Rademacher, A. W. Czarnik, J. Am. Chem. Soc. 1994, 116, 4621-4622; b) Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, H. Masuda, ibid. 1996, 118, 5562-5571. For crystal engineering utilizing both dative bonds and hydrogen bonding, see: c) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1981, 849-850; d) S. B. Copp, S. Subramanian, M. J. Zaworotko, J. Am. Chem. Soc. 1992, 114, 8719-8720; e) M. M. Chowdry, D. M. P. Mingos, A. J. P. White, D. J. Williams. Chem. Commun. 1996, 899-900. For solid-state supramolecular synthesis employing both hydrogen bonding and heteroatom-halogen interactions, see: f) ref. [12c]; g) D. S. Reddy, Y. E. Ovchinmkov, O. V. Shishkin, Y. T. Struchkov, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4085-4089. For solid state supramolecular synthesis of polymeric networks using both coordinate covalent bonds and π-π stacking interactions, see: h) J. Harrowfield, J. Chem. Soc. Dalton Trans. 1996, 3165-3171; i) A. C. Deveson, S. L. Heath, C. J. Harding, A. K. Powell, ibid. 1996, 3173-3178.
69. For solid-state supramolecular synthesis employing both hydrogen bonding and aryl-aryl stacking interactions, see: a) J. C. Beeson, L. J. Fitzgerald, J. C. Gallucci, R. E. Gerkin, J. T. Rademacher, A. W. Czarnik, J. Am. Chem. Soc. 1994, 116, 4621-4622; b) Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, H. Masuda, ibid. 1996, 118, 5562-5571. For crystal engineering utilizing both dative bonds and hydrogen bonding, see: c) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1981, 849-850; d) S. B. Copp, S. Subramanian, M. J. Zaworotko, J. Am. Chem. Soc. 1992, 114, 8719-8720; e) M. M. Chowdry, D. M. P. Mingos, A. J. P. White, D. J. Williams. Chem. Commun. 1996, 899-900. For solid-state supramolecular synthesis employing both hydrogen bonding and heteroatom-halogen interactions, see: f) ref. [12c]; g) D. S. Reddy, Y. E. Ovchinmkov, O. V. Shishkin, Y. T. Struchkov, G. R. Desiraju, J. Am. Chem. Soc. 1996, 118, 4085-4089. For solid state supramolecular synthesis of polymeric networks using both coordinate covalent bonds and π-π stacking interactions, see: h) J. Harrowfield, J. Chem. Soc. Dalton Trans. 1996, 3165-3171; i) A. C. Deveson, S. L. Heath, C. J. Harding, A. K. Powell, ibid. 1996, 3173-3178.
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78. The dibenzofuran unit has been utilized previously in supramolecular chemistry. For instance, this unit has been incorporated into molecular tweezers that form complexes with 1,3,5-trinitrobenzene. See: a) M. Harmata, C. L. Barnes, J. Am. Chem. Soc. 1990, 112, 5655-5657; b) M. Harmata, C. L. Barnes, S. R. Karra, S. Elahmad, ibid. 1994, 116, 8392-8393. Furthermore, it has been used to hold peptide subunits together in order to nucleate an antiparallel β-sheet structure. See: c) H. Díaz, J. R. Espina, J. W. Kelly, J. Am. Chem. Soc. 1992, 114, 8316-8318; d) H. Díaz, K. Y. Tsang, D. Choo, J. R. Espina, J. W. Kelly, ibid. 1993, 115, 3790-3791; e) H. Díaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545. For the incorporation of the dibenzofuran subunit into cavitands with rigidly preorganized clefts, see: f) D. J. Cram, J. M. Cram, Container Molecules and their Guests, The Royal Society of Chemistry, Cambridge, 1994, pp. 102-106 and references cited therein.
79. The dibenzofuran unit has been utilized previously in supramolecular chemistry. For instance, this unit has been incorporated into molecular tweezers that form complexes with 1,3,5-trinitrobenzene. See: a) M. Harmata, C. L. Barnes, J. Am. Chem. Soc. 1990, 112, 5655-5657; b) M. Harmata, C. L. Barnes, S. R. Karra, S. Elahmad, ibid. 1994, 116, 8392-8393. Furthermore, it has been used to hold peptide subunits together in order to nucleate an antiparallel β-sheet structure. See: c) H. Díaz, J. R. Espina, J. W. Kelly, J. Am. Chem. Soc. 1992, 114, 8316-8318; d) H. Díaz, K. Y. Tsang, D. Choo, J. R. Espina, J. W. Kelly, ibid. 1993, 115, 3790-3791; e) H. Díaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545. For the incorporation of the dibenzofuran subunit into cavitands with rigidly preorganized clefts, see: f) D. J. Cram, J. M. Cram, Container Molecules and their Guests, The Royal Society of Chemistry, Cambridge, 1994, pp. 102-106 and references cited therein.
80. The dibenzofuran unit has been utilized previously in supramolecular chemistry. For instance, this unit has been incorporated into molecular tweezers that form complexes with 1,3,5-trinitrobenzene. See: a) M. Harmata, C. L. Barnes, J. Am. Chem. Soc. 1990, 112, 5655-5657; b) M. Harmata, C. L. Barnes, S. R. Karra, S. Elahmad, ibid. 1994, 116, 8392-8393. Furthermore, it has been used to hold peptide subunits together in order to nucleate an antiparallel β-sheet structure. See: c) H. Díaz, J. R. Espina, J. W. Kelly, J. Am. Chem. Soc. 1992, 114, 8316-8318; d) H. Díaz, K. Y. Tsang, D. Choo, J. R. Espina, J. W. Kelly, ibid. 1993, 115, 3790-3791; e) H. Díaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545. For the incorporation of the dibenzofuran subunit into cavitands with rigidly preorganized clefts, see: f) D. J. Cram, J. M. Cram, Container Molecules and their Guests, The Royal Society of Chemistry, Cambridge, 1994, pp. 102-106 and references cited therein.
81. The dibenzofuran unit has been utilized previously in supramolecular chemistry. For instance, this unit has been incorporated into molecular tweezers that form complexes with 1,3,5-trinitrobenzene. See: a) M. Harmata, C. L. Barnes, J. Am. Chem. Soc. 1990, 112, 5655-5657; b) M. Harmata, C. L. Barnes, S. R. Karra, S. Elahmad, ibid. 1994, 116, 8392-8393. Furthermore, it has been used to hold peptide subunits together in order to nucleate an antiparallel β-sheet structure. See: c) H. Díaz, J. R. Espina, J. W. Kelly, J. Am. Chem. Soc. 1992, 114, 8316-8318; d) H. Díaz, K. Y. Tsang, D. Choo, J. R. Espina, J. W. Kelly, ibid. 1993, 115, 3790-3791; e) H. Díaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545. For the incorporation of the dibenzofuran subunit into cavitands with rigidly preorganized clefts, see: f) D. J. Cram, J. M. Cram, Container Molecules and their Guests, The Royal Society of Chemistry, Cambridge, 1994, pp. 102-106 and references cited therein.
82. The dibenzofuran unit has been utilized previously in supramolecular chemistry. For instance, this unit has been incorporated into molecular tweezers that form complexes with 1,3,5-trinitrobenzene. See: a) M. Harmata, C. L. Barnes, J. Am. Chem. Soc. 1990, 112, 5655-5657; b) M. Harmata, C. L. Barnes, S. R. Karra, S. Elahmad, ibid. 1994, 116, 8392-8393. Furthermore, it has been used to hold peptide subunits together in order to nucleate an antiparallel β-sheet structure. See: c) H. Díaz, J. R. Espina, J. W. Kelly, J. Am. Chem. Soc. 1992, 114, 8316-8318; d) H. Díaz, K. Y. Tsang, D. Choo, J. R. Espina, J. W. Kelly, ibid. 1993, 115, 3790-3791; e) H. Díaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545. For the incorporation of the dibenzofuran subunit into cavitands with rigidly preorganized clefts, see: f) D. J. Cram, J. M. Cram, Container Molecules and their Guests, The Royal Society of Chemistry, Cambridge, 1994, pp. 102-106 and references cited therein.
83. The dibenzofuran unit has been utilized previously in supramolecular chemistry. For instance, this unit has been incorporated into molecular tweezers that form complexes with 1,3,5-trinitrobenzene. See: a) M. Harmata, C. L. Barnes, J. Am. Chem. Soc. 1990, 112, 5655-5657; b) M. Harmata, C. L. Barnes, S. R. Karra, S. Elahmad, ibid. 1994, 116, 8392-8393. Furthermore, it has been used to hold peptide subunits together in order to nucleate an antiparallel β-sheet structure. See: c) H. Díaz, J. R. Espina, J. W. Kelly, J. Am. Chem. Soc. 1992, 114, 8316-8318; d) H. Díaz, K. Y. Tsang, D. Choo, J. R. Espina, J. W. Kelly, ibid. 1993, 115, 3790-3791; e) H. Díaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545. For the incorporation of the dibenzofuran subunit into cavitands with rigidly preorganized clefts, see: f) D. J. Cram, J. M. Cram, Container Molecules and their Guests, The Royal Society of Chemistry, Cambridge, 1994, pp. 102-106 and references cited therein.
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101. BPP 34 C 10 was synthesized by the one-pot reaction of hydroquinone with tetraethylene glycol bistosylate: a) R. C. Helgeson, T. L. Tarnowski, J. M. Timko, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 6411-6418; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen. ibid. 1995, 117, 852-874. See also: c) Y. Delaviz, H. W. Gibson, Polym. Commun. 1991, 32, 103-105; d) Y. Delaviz, Y. X. Shen, H. W. Gibson, Polymer 1992, 33, 212-213.
102. BPP 34 C 10 was synthesized by the one-pot reaction of hydroquinone with tetraethylene glycol bistosylate: a) R. C. Helgeson, T. L. Tarnowski, J. M. Timko, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 6411-6418; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen. ibid. 1995, 117, 852-874. See also: c) Y. Delaviz, H. W. Gibson, Polym. Commun. 1991, 32, 103-105; d) Y. Delaviz, Y. X. Shen, H. W. Gibson, Polymer 1992, 33, 212-213.
103. BPP 34 C 10 was synthesized by the one-pot reaction of hydroquinone with tetraethylene glycol bistosylate: a) R. C. Helgeson, T. L. Tarnowski, J. M. Timko, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 6411-6418; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen. ibid. 1995, 117, 852-874. See also: c) Y. Delaviz, H. W. Gibson, Polym. Commun. 1991, 32, 103-105; d) Y. Delaviz, Y. X. Shen, H. W. Gibson, Polymer 1992, 33, 212-213.
104. BPP 34 C 10 was synthesized by the one-pot reaction of hydroquinone with tetraethylene glycol bistosylate: a) R. C. Helgeson, T. L. Tarnowski, J. M. Timko, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 6411-6418; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen. ibid. 1995, 117, 852-874. See also: c) Y. Delaviz, H. W. Gibson, Polym. Commun. 1991, 32, 103-105; d) Y. Delaviz, Y. X. Shen, H. W. Gibson, Polymer 1992, 33, 212-213.
105. For other examples of heterocycle-containing catenaries, see: a) P. R. Ashton, M. A. Blower, S. Iqbal, C. H. McLean, J. F. Stoddart, M. S. Tolley, D. J. Williams, Synlett 1994, 1059-1062; b) P. R. Ashton, M. A. Blower, C. H. McLean, J. F. Stoddart, M. S. Tolley, ibid. 1994, 1063-1066; c) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344-1352; d) S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; e) A. C. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216; f) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633.
106. For other examples of heterocycle-containing catenaries, see: a) P. R. Ashton, M. A. Blower, S. Iqbal, C. H. McLean, J. F. Stoddart, M. S. Tolley, D. J. Williams, Synlett 1994, 1059-1062; b) P. R. Ashton, M. A. Blower, C. H. McLean, J. F. Stoddart, M. S. Tolley, ibid. 1994, 1063-1066; c) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344-1352; d) S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; e) A. C. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216; f) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633.
107. For other examples of heterocycle-containing catenaries, see: a) P. R. Ashton, M. A. Blower, S. Iqbal, C. H. McLean, J. F. Stoddart, M. S. Tolley, D. J. Williams, Synlett 1994, 1059-1062; b) P. R. Ashton, M. A. Blower, C. H. McLean, J. F. Stoddart, M. S. Tolley, ibid. 1994, 1063-1066; c) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344-1352; d) S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; e) A. C. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216; f) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633.
108. For other examples of heterocycle-containing catenaries, see: a) P. R. Ashton, M. A. Blower, S. Iqbal, C. H. McLean, J. F. Stoddart, M. S. Tolley, D. J. Williams, Synlett 1994, 1059-1062; b) P. R. Ashton, M. A. Blower, C. H. McLean, J. F. Stoddart, M. S. Tolley, ibid. 1994, 1063-1066; c) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344-1352; d) S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; e) A. C. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216; f) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633.
109. For other examples of heterocycle-containing catenaries, see: a) P. R. Ashton, M. A. Blower, S. Iqbal, C. H. McLean, J. F. Stoddart, M. S. Tolley, D. J. Williams, Synlett 1994, 1059-1062; b) P. R. Ashton, M. A. Blower, C. H. McLean, J. F. Stoddart, M. S. Tolley, ibid. 1994, 1063-1066; c) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344-1352; d) S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; e) A. C. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216; f) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633.
110. For other examples of heterocycle-containing catenaries, see: a) P. R. Ashton, M. A. Blower, S. Iqbal, C. H. McLean, J. F. Stoddart, M. S. Tolley, D. J. Williams, Synlett 1994, 1059-1062; b) P. R. Ashton, M. A. Blower, C. H. McLean, J. F. Stoddart, M. S. Tolley, ibid. 1994, 1063-1066; c) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344-1352; d) S. Ottens-Hildebrandt, M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder, F. Vögtle, J. Chem. Soc. Chem. Commun. 1995, 777-778; e) A. C. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216; f) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mork, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633.
111. We have recently prepared a related [2]catenane in which the 2,8-dimethyldibenzofuran units are replaced by m,m′-bitolyl units. See: M. Asakawa, P. R. Ashton, S. E. Boyd, C. L. Brown, S. Menzer, D. Pasini, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, P. G. Wyatt, Chem. Eur. J. 1997, 3, 463-481.
112. C. L. Brown, D. Philp, N. Spencer, J. F. Stoddart, Isr. J. Chem. 1992, 32, 61-67.
113. This π-electron-rich arene has also been used for the template-directed synthesis of other tetracationic cyclophanes. See, for example: a) C. L. Brown, D. Philp, J. F. Stoddart, Synlett 1991, 462-464; b) ref. [27c]; c) ref. [14]; d) P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11171-11197.
114. This π-electron-rich arene has also been used for the template-directed synthesis of other tetracationic cyclophanes. See, for example: a) C. L. Brown, D. Philp, J. F. Stoddart, Synlett 1991, 462-464; b) ref. [27c]; c) ref. [14]; d) P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11171-11197.
115. R. M. Roberts, Serendipity - Accidental Discoveries in Science, Wiley, New York, 1989.
116. a) C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036;
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118. A. C. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1209-1212.
119. K. Weber, G. Kormany (Ciba-Geigy), German Patent 2332089, 1973 [Chem. Abstr. 1974, 80, 134947z].
120. K. Weber, G. Kormany (Ciba-Geigy), German Patent 2332089, 1973 [Chem. Abstr. 1974, 80, 134947z].
121. Catenanes have been synthesized previously in our laboratories. See: a) P. R. Ashton, C. L. Brown, E. J. T. Chrystal, T. T. Goodnow, A. E. Kaifer, K. P. Parry, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1991, 30, 1039-1042;
122. b) D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Córdova, L. A. Godínez, T. T. Goodnow, A. E. Kaifer, S. P. Newton, M. Pietraszkiewicz, D. Philp, F. M. Raymo, A. S. Reder, M. T. Rutland, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 1271-1293.
123. 1 ions, by another group, see: J.-M. Kern, J.-P. Sauvage, J.-L. Weidmann, Tetrahedron 1996, 52, 10921-10934.
124. K. A. Connors, Binding Constants, Wiley, New York, 1987.
125. T. Wang, J. S. Bradshaw, R. M. Izatt, J. Heterocycl. Chem. 1994, 31, 1097-1114.
126. A pseudorotaxane is an interwoven inclusion complex in which a molecular "thread" is encircled by one or more macrorings in such a way that the extremities of the thread are projected away from the center of the ring; not all of these extremities possess bulky "stopper" groups, so that the pseudorotaxane's components are free to dissociate into separate molecular species, that is, as distinct from rotaxanes, there is no mechanical bond present to hold the system together. See: a) P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679; b) D. B. Amabilino, I. W. Parsons, J. F. Stoddart, Trends Polym. Sci. 1994, 2, 146-152; c) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869; d) ref. [21 d]; e) ref. [2 h].
127. A pseudorotaxane is an interwoven inclusion complex in which a molecular "thread" is encircled by one or more macrorings in such a way that the extremities of the thread are projected away from the center of the ring; not all of these extremities possess bulky "stopper" groups, so that the pseudorotaxane's components are free to dissociate into separate molecular species, that is, as distinct from rotaxanes, there is no mechanical bond present to hold the system together. See: a) P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679; b) D. B. Amabilino, I. W. Parsons, J. F. Stoddart, Trends Polym. Sci. 1994, 2, 146-152; c) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869; d) ref. [21 d]; e) ref. [2 h].
128. A pseudorotaxane is an interwoven inclusion complex in which a molecular "thread" is encircled by one or more macrorings in such a way that the extremities of the thread are projected away from the center of the ring; not all of these extremities possess bulky "stopper" groups, so that the pseudorotaxane's components are free to dissociate into separate molecular species, that is, as distinct from rotaxanes, there is no mechanical bond present to hold the system together. See: a) P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677-1679; b) D. B. Amabilino, I. W. Parsons, J. F. Stoddart, Trends Polym. Sci. 1994, 2, 146-152; c) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869; d) ref. [21 d]; e) ref. [2 h].
129. P. R. Ashton, D. Philp, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1991, 1680-1683.
130. 1H NMR timescale, and therefore displays resonances for both complexed and uncomplexed species, see: a) ref. [39c]; b) P. T. Glink, C. Schiavo, J. F. Stoddart, D. J. Williams, Chem. Commun. 1996, 1483-1490; c) ref. [2h].
131. a) H. M. Colquhoun, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1986, 25, 487-507;
132. b) S. J. Loeb in Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, Oxford, 1996, pp. 733-753;
133. c) F. M. Raymo, J. F. Stoddart, Chem. Ber. 1996, 129, 981-990.
134. ex, respectively.
135. ex, respectively.
136. The dynamic processes occurring in catenanes of this type have been discussed previously in several publications. For instance, see: a) ref. [8 f]; b) ref. [21 d]; c) ref. [25]; d) réf. [35 b].
137. This terminology has recently been introduced by Desiraju to indicate identifiable design elements in supramolecular synthesis. See ref. [5 f] for details.
138. a) M. Fujita in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, Oxford, 1996, pp. 254-262;
139. b) W. Hayes, J. F. Stoddart in Large Ring Molecules (Ed.: J. A. Semlyn), Wiley, New York, 1996, pp. 433-471 and references cited therein.
140. For a similar example where a two-component supramolecular macrocycle is formed in the solid state by virtue of [N ⋯ H] hydrogen bonding, see: K. Tanaka, Y. Kitahara, H. Suzuki, H. Osuga, Y. Kawai, Tetrahedron Lett. 1996, 37, 5925-5928.
141. The crossed aryl-aryl stacking of dibenzofuran systems, where two of these units are oriented in an antiparallel manner with respect to one another, has been noted previously: a) O. Dideberg, L. Dupont, J. M. André, Acta Crystallogr. Sect. B 1972, 28, 1002-1007; b) A. Banerjee, ibid. 1973, 29, 2070-2074; c) C. R. Hubbard, A. D. Mighell, I. H. Pomerantz, ibid. 1978, 34, 2381-2384.
142. The crossed aryl-aryl stacking of dibenzofuran systems, where two of these units are oriented in an antiparallel manner with respect to one another, has been noted previously: a) O. Dideberg, L. Dupont, J. M. André, Acta Crystallogr. Sect. B 1972, 28, 1002-1007; b) A. Banerjee, ibid. 1973, 29, 2070-2074; c) C. R. Hubbard, A. D. Mighell, I. H. Pomerantz, ibid. 1978, 34, 2381-2384.
143. The crossed aryl-aryl stacking of dibenzofuran systems, where two of these units are oriented in an antiparallel manner with respect to one another, has been noted previously: a) O. Dideberg, L. Dupont, J. M. André, Acta Crystallogr. Sect. B 1972, 28, 1002-1007; b) A. Banerjee, ibid. 1973, 29, 2070-2074; c) C. R. Hubbard, A. D. Mighell, I. H. Pomerantz, ibid. 1978, 34, 2381-2384.
144. 2O.
145. a) F. M. Raymo, J. F. Stoddart, Trends Polym. Sci. 1996, 4, 208-211;
146. b) M. Asakawa, P. R. Ashton, G. R. Brown, W. Hayes, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams. Adv. Mater. 1996, 8, 37-41;
147. c) P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, M. T. Gandolfi, D. Philp, L. Prodi, F. M. Raymo, M. V. Reddington, N. Spencer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 4931-4951.
148. Analogously, pyrazine perchlorate shows the formation of a linear tape in the solid state: T. Glowiak, L. Sobczyk, E. Grech, Chem. Phys. Lett. 1975, 34, 292-293.
149. For a noteable example where the optical purity of a tecton dictates the type of superstructure formed, see: M.-J. Brienne, J. Gabard, M. Leclerq, J.-M. Lehn, M. Cesario, C. Pascard, M. Chevé, G. Dutruc-Rosset, Tetrahedron Lett. 1994, 35, 8157-8160.
150. For other examples of the formation of nanotubular structures from macrocyclic species in the solid state, see: a) B. Odell, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1988, 27, 1547-1550; b) P. J. Stang, K. Chen, A. M. Arif, J. Am. Chem. Soc. 1995, 117, 8793-8797; c) ref. [14]; d) J. D. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, ibid. 1996, 118, 43-50; e) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591.
151. For other examples of the formation of nanotubular structures from macrocyclic species in the solid state, see: a) B. Odell, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1988, 27, 1547-1550; b) P. J. Stang, K. Chen, A. M. Arif, J. Am. Chem. Soc. 1995, 117, 8793-8797; c) ref. [14]; d) J. D. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, ibid. 1996, 118, 43-50; e) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591.
152. For other examples of the formation of nanotubular structures from macrocyclic species in the solid state, see: a) B. Odell, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1988, 27, 1547-1550; b) P. J. Stang, K. Chen, A. M. Arif, J. Am. Chem. Soc. 1995, 117, 8793-8797; c) ref. [14]; d) J. D. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, ibid. 1996, 118, 43-50; e) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591.
153. For other examples of the formation of nanotubular structures from macrocyclic species in the solid state, see: a) B. Odell, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1988, 27, 1547-1550; b) P. J. Stang, K. Chen, A. M. Arif, J. Am. Chem. Soc. 1995, 117, 8793-8797; c) ref. [14]; d) J. D. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, ibid. 1996, 118, 43-50; e) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591.
154. For other examples of the formation of nanotubular structures from macrocyclic species in the solid state, see: a) B. Odell, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1988, 27, 1547-1550; b) P. J. Stang, K. Chen, A. M. Arif, J. Am. Chem. Soc. 1995, 117, 8793-8797; c) ref. [14]; d) J. D. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, ibid. 1996, 118, 43-50; e) P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591.
155. +, both at the molecular mechanics (Amber*) and semiempirical (PM 3 and AM 1) level, reveal no significant energy differences between the two geometries, suggesting that the observation of only the anti conformation in the solid state (Figure 7) probably arises as a consequence of favorable packing interactions and not as a function of an inherent energy difference between the two conformers.
156. Previously, we have observed only outward bowing of the bipyridinium units in [2]catenanes of this kind. For instance, see: a) ref. [25]; b) D. B. Amabilino, P. R. Ashton, M. S. Tolley, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1993, 32, 1297-1301; c) ref. [28].
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