Amphiphilic bistable rotaxanes

Chemistry - A European Journal

Volumn 9, Issue 13, 2003, Pages 2982-3007

  Jeppesen, Jan O ^a,b   Nielsen, Kent A ^a,b   Perkins, Julie ^a   Vignon, Scott A ^a   Di Fabio, Alberto ^c   Ballardini, Roberto ^c,d   Gandolfi, M Teresa ^c   Venturi, Margherita ^c   Balzani, Vincenzo ^c   Becher, Jan ^b   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c UNIVERSITY OF BOLOGNA   (Italy)

^d CNR   (Italy)

Author keywords

Electrochemistry; Molecular devises; Rotaxanes self assembly; Tetrathiafulvalenes

Indexed keywords

ALKYLATION; HYDROPHILICITY; HYDROPHOBICITY; ISOMERS; ULTRAVIOLET SPECTROSCOPY;

HYDROPHOBIC STOPPERS;

AROMATIC HYDROCARBONS;

AMPHOPHILE; CYCLOPHANE DERIVATIVE; NAPHTHALENE DERIVATIVE; ROTAXANE; TETRATHIAFULVALENE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ELECTROCHEMICAL ANALYSIS; HYDROPHILICITY; HYDROPHOBICITY; ISOMER; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0043027831     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204589     Document Type: Article

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101. 4+. See: R. Castro, K. R. Nixon, J. D. Evenseck, A. E. Kaifer, J. Org. Chem. 1996, 61, 7298-7303.
102. V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936.
103. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
104. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
105. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
106. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
107. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
108. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
109. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992-1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
110. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
111. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
112. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
113. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
114. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
115. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
116. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A.
117. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
118. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
119. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
120. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
121. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
122. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
123. 4+ have been reported (vide infra), very few rotaxanes (see: ref. [19a,e,o,r]) employing these particular components have been described to date in the literature. For examples of catenanes, rotaxanes, and pseudorotaxanes containing TTF or TTF derivatives, see: a) P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley, Synlett 1992, 923-926; b) T. Jorgensen, J. Becher, J.-C. Chambron, J.-P. Sauvage, Tetrahedron Lett. 1994, 35, 4339-4342; c) Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719-2723; Angew. Chem. Int. Ed. Engl. 1995, 34, 2524-2528; d) Z.-T. Li, J. Becher, Chem. Commun. 1996, 639-640; e) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk, N. Svenstrup, Chem. Eur. J. 1996, 2, 624-633; f) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, N. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992 -1996; g) Z.-T. Li, J. Becher, Synlett 1997, 557-560; h) M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175-1187; i) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Hamers, G. Mattersteig, N. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 357-361; Angew. Chem. Int. Ed. 1998, 37, 333-337; j) M. B. Nielsen, N. Thorup, J. Becher, J. Chem. Soc. Perkin Trans. 1 1998, 1305-1308; k) A. Credi, M. Montalti, V. Balzani, S. J. Langford, F. M. Raymo, J. F. Stoddart, New J. Chem. 1998, 22, 1061-1065; l) M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem. 1999, 985-994; m) J. Lau, M. B. Nielsen, N. Thorup, M. P. Cava, J. Becher, Eur. J. Org. Chem. 1999, 3335-3341; n) V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65, 1924-1936; o) D. Jensen, M. B. Nielsen, J. Lau, K. B. Jensen, R. Zubarev, E. Levillain, J. Becher, J. Mater. Chem. 2000, 10, 2249-2258; p) R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem. 2001, 25, 293-298; q) M. R. Bryce, G. Cooke, W. Devonport, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2001, 42, 4223-4226; r) H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533; Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
124. J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Angew. Chem. 2001, 113, 1256-1261; Angew. Chem. Int. Ed. 2001, 40, 1216-1221.
125. J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Angew. Chem. 2001, 113, 1256-1261; Angew. Chem. Int. Ed. 2001, 40, 1216-1221.
126. Recently some of us developed an efficient synthesis of the parent pyrrolo[3,4-d]tetrathiafulvalene unit using a simple and nonclassical pyrrole synthesis, see: a) J. O. Jeppesen, K. Takimiya, F. Jensen, J. Becher, Org. Lett. 1999, 1, 1291-1294; b) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2000, 65, 5794-5805.
127. Recently some of us developed an efficient synthesis of the parent pyrrolo[3,4-d]tetrathiafulvalene unit using a simple and nonclassical pyrrole synthesis, see: a) J. O. Jeppesen, K. Takimiya, F. Jensen, J. Becher, Org. Lett. 1999, 1, 1291-1294; b) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2000, 65, 5794-5805.
128. J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Org. Lett. 2000, 2, 3547-3550.
129. K. B. Simonsen, N. Svenstrup, J. Lau, O. Simonsen, P. Mørk, G. J. Kristensen, J. Becher, Synthesis 1996, 407-418.
130. Although the preparation of 6 has been described before in the literature (see: ref. [21b]), it was synthesized by a different route and only on a very small scale.
131. Unreacted dumbbell can be recovered and reused.
132. It is well established that organic reactions with a negative volume of activation (ΔV‡) are favored by high pressure, see: F.-G. Klärner, F. Wurche, J. Prakt. Chem. 2000, 342, 609-636.
133. The FAB mass spectrum of the isolated mixture revealed only peaks with a substantially lower mass than the molecular weight of the desired dumbbell.
134. 4 as a way of accessing thiolates has only been introduced recently into the growing field of TTF chemistry, see: a) J. O. Jeppesen, K. Takimiya, N. Thorup J. Becher, Synthesis 1999, 803-810; b) J. O. Jeppesen, K. Takimiya, J. Becher, Org. Lett. 2000, 2, 2471-2473.
135. 4 as a way of accessing thiolates has only been introduced recently into the growing field of TTF chemistry, see: a) J. O. Jeppesen, K. Takimiya, N. Thorup J. Becher, Synthesis 1999, 803-810; b) J. O. Jeppesen, K. Takimiya, J. Becher, Org. Lett. 2000, 2, 2471-2473.
136. 4+ is well documented (see: refs. [15, 18, 19]) and leads to the formation of pseudorotaxanes. Pseudorotaxanes are obtained under thermodynamic control upon mixing of their acyclic and cyclic components in solution, and the occurrence of the threading process is evidenced by the 1H NMR and absorption spectra, see: a) ref. [10]; b) ref. [19f]; c) ref. [19k]; d) P. R. Ashton, R. Ballardini, V. Balzani, S. E. Boyd, A. Credi, M. T. Gandolfi, M. Gómez-López, S. Iqbal, D. Philp, J. A. Preece, L. Prodi, H. G. Ricketts, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Chem. Eur. J. 1997, 3, 152-170.
137. 4+ is well documented (see: refs. [15, 18, 19]) and leads to the formation of pseudorotaxanes. Pseudorotaxanes are obtained under thermodynamic control upon mixing of their acyclic and cyclic components in solution, and the occurrence of the threading process is evidenced by the 1H NMR and absorption spectra, see: a) ref. [10]; b) ref. [19f]; c) ref. [19k]; d) P. R. Ashton, R. Ballardini, V. Balzani, S. E. Boyd, A. Credi, M. T. Gandolfi, M. Gómez-López, S. Iqbal, D. Philp, J. A. Preece, L. Prodi, H. G. Ricketts, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Chem. Eur. J. 1997, 3, 152-170.
138. 4+ is well documented (see: refs. [15, 18, 19]) and leads to the formation of pseudorotaxanes. Pseudorotaxanes are obtained under thermodynamic control upon mixing of their acyclic and cyclic components in solution, and the occurrence of the threading process is evidenced by the 1H NMR and absorption spectra, see: a) ref. [10]; b) ref. [19f]; c) ref. [19k]; d) P. R. Ashton, R. Ballardini, V. Balzani, S. E. Boyd, A. Credi, M. T. Gandolfi, M. Gómez-López, S. Iqbal, D. Philp, J. A. Preece, L. Prodi, H. G. Ricketts, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Chem. Eur. J. 1997, 3, 152-170.
139. 4+ is well documented (see: refs. [15, 18, 19]) and leads to the formation of pseudorotaxanes. Pseudorotaxanes are obtained under thermodynamic control upon mixing of their acyclic and cyclic components in solution, and the occurrence of the threading process is evidenced by the 1H NMR and absorption spectra, see: a) ref. [10]; b) ref. [19f]; c) ref. [19k]; d) P. R. Ashton, R. Ballardini, V. Balzani, S. E. Boyd, A. Credi, M. T. Gandolfi, M. Gómez-López, S. Iqbal, D. Philp, J. A. Preece, L. Prodi, H. G. Ricketts, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Chem. Eur. J. 1997, 3, 152-170.
140. The synthesis of compound 27 will be reported elsewhere.
141. a) P. R. Ashton, R. Ballardini, V. Balzani, A, Credi, M. T. Gandolfi, D. J.-F. Marquis, L. Pérez-Garcia, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11171-11197;
142. b) M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, M. T. Gandolfi, O. Kocian, L. Prodi, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1997, 119, 302-310;
143. c) R. Ballardini, V. Balzani, W. Dehaen, A. E. Dell'Erba, F. M. Raymo, J. F. Stoddart, M. Venturi, Eur. J. Org. Chem. 2000, 591-602.
144. a) R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. J. Langford, S. Menzer, L. Prodi, J. F. Stoddart, M. Venturi, D. J. Williams, Angew. Chem. 1996, 108, 1056-1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 978-981;
145. a) R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. J. Langford, S. Menzer, L. Prodi, J. F. Stoddart, M. Venturi, D. J. Williams, Angew. Chem. 1996, 108, 1056-1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 978-981;
146. b) P. R. Ashton, R. Ballardini, V. Balzani, M. C. T. Fyfe, M. T. Gandolfi, M. V Martínez-Díaz, M. Morosini, C. Schiavo, K. Shibata, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 2332-2341;
147. c) P. R. Ashton, V. Balzani, J. Becher, A. Credi, M. C. T. Fyfe, G. Mattersteig, S. Menzer, M. B. Nielsen, F. M. Raymo, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 3951-3957.
148. R. Ballardini, V. Balzani, J. Becher, A. Di Fabio, M. T. Gandolfi, G. Mattersteig, M. B. Nielsen, F. M. Raymo, S. J. Rowan, J. F. Stoddart, A. J. P. Williams, D. J. Williams, J. Org. Chem. 2000, 65, 4120-4126.
149. J. O. Jeppesen, J. Becher, J. F. Stoddart, Org. Lett. 2002, 4, 557-560.
150. See Supporting Information for further details.
151. a, in which R is the gas constant and T is the absolute temperature.
152. D. J. Leggett, Computational Methods for Determination of Formation Constants, Plenum, London and New York, 1985, Chapter 1.
153. A. Mirzoian, A. E. Kaifer, J. Org. Chem. 1995, 60, 8093-8095.
154. a) R. Wolf, M. Asakawa, P. R. Ashton, M. Gómez-López, C. Hamers, S. Menzer, I. W. Parsons, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, Angew. Chem. 1998, 110, 1018-1022; Angew. Chem. Int. Ed. 1998, 37, 975-979;
155. a) R. Wolf, M. Asakawa, P. R. Ashton, M. Gómez-López, C. Hamers, S. Menzer, I. W. Parsons, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, Angew. Chem. 1998, 110, 1018-1022; Angew. Chem. Int. Ed. 1998, 37, 975-979;
156. b) V. Balzani, A. Ceroni, A. Credi, M. Gómez-López, C. Hamers, J. F. Stoddart, R. Wolf, New J. Chem. 2001, 25, 25-31.
157. -1).
158. 4+ equilibration takes 24 h (see dynamic investigations).
159. 4+.
160. 2O resonance (6=2.72-2.85 ppm) close to the singlet resonating at δ = 2.70 ppm.
161. 4+ is very strong at this temperature.
162. 4+ the DNP-H-4/8 protons resonate at very high field (δ = 2.0-3.0 ppm), see: a) M. Asakawa, P. R. Ashton, V. Balzani, C. L. Brown, A, Credi, O. A. Matthews, S. P. Newton, F. M. Raymo, A. N. Shipway, N. Spencer, A. Quick, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1999, 5, 860-875; b) ref. [29d].
163. 4+ the DNP-H-4/8 protons resonate at very high field (δ = 2.0-3.0 ppm), see: a) M. Asakawa, P. R. Ashton, V. Balzani, C. L. Brown, A, Credi, O. A. Matthews, S. P. Newton, F. M. Raymo, A. N. Shipway, N. Spencer, A. Quick, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1999, 5, 860-875; b) ref. [29d].
164. B is the Boltzmann constant.
165. ex) were measured using the spin saturation transfer method, see: a) B. E. Mann, J. Magn. Reson. 1977, 25, 91-94; b) M. Feigel, H. Kessler, D. Leibfritz, J. Am. Chem. Soc. 1979, 101, 1943-1950.
166. ex) were measured using the spin saturation transfer method, see: a) B. E. Mann, J. Magn. Reson. 1977, 25, 91-94; b) M. Feigel, H. Kessler, D. Leibfritz, J. Am. Chem. Soc. 1979, 101, 1943-1950.
167. Temperatures were calibrated using a neat MeOH sample. See: A. L. Van Geet, Anal. Chem. 1970, 42, 679-680.
168. H.-R. Tseng, S. A. Vignon, P. C. Celestre, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 2003, 9, 543-556.
169. 2O signal, which appears at δ = 2.76-2.80 ppm.
170. K. J. Laidler, Chemical Kinetics, Harper Collins, New York, 1987.
171. 4+ and t the time, see: ref. [52].
172. 4+ in the [2]rotaxane.
173. 4+, respectively.
174. a) M. Asakawa, C. L. Brown, S. Menzer, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 2614-2627;
175. b) K. N. Houk, S. Menzer, S. P. Newton, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 1479-1487;
176. c) F. M. Raymo, M. D. Bartberger, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 2001, 123, 9264-9267.
177. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, Pergamon, New York, 1988.
178. S. F. Nelsen, L.-J. Chen, M. T. Ramm, G. T. Voy, D. R. Powell, M. A. Aceola, T. R. Seehafer, J. J. Sabelko, J. R. Pladziewicz, J. Org. Chem. 1996, 61, 1405-1412.
179. E. P. Parry, R. A. Osteryoung, Anal. Chem. 1965, 37, 1634-1637.
180. J. B. Flanagan, S. Margel, A. J. Bard, F. C. Anson, J. Am. Chem. Soc. 1978, 100, 4248-4253.