Controllable donor-acceptor neutral [2]rotaxanes

Chemistry - A European Journal

Volumn 10, Issue 24, 2004, Pages 6375-6392

  Iijima, Takahiro ^a   Vignon, Scott A ^a   Tseng, Hsian Rong ^a   Jarrosson, Thibaut ^b   Sanders, Jeremy K M ^b   Marchioni, Filippo ^c   Venturi, Margherita ^c   Apostoli, Emanuela ^c   Balzani, Vincenzo ^c   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Bistable switches; Molecular devices; Rotaxanes; Self assembly; Template synthesis

Indexed keywords

ACTIVATION ANALYSIS; ELECTROCHEMISTRY; ELECTRONS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYIMIDES; POSITIVE IONS; REDUCTION;

DEGENERATIVE COUNTERPARTS; ELECTRON DONORS; MOLECULAR INTERACTIONS; ROTAXANES;

AROMATIC COMPOUNDS;

CARBENE; IMIDE; LITHIUM ION; MACROCYCLIC COMPOUND; METHANE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; ROTAXANE;

ABSORPTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; COMPARATIVE STUDY; CORRELATION ANALYSIS; DYNAMICS; ELECTRIC POTENTIAL; ELECTROCHEMISTRY; ELECTRON; ENERGY; EXPERIMENT; ISOMER; MECHANICS; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS; THERMODYNAMICS; TITRIMETRY;

EID: 19944416209     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400651     Document Type: Article

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68. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
69. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
70. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
71. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
72. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
73. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
74. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
75. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
76. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
77. The clipping approach to rotaxane assembly relies on the macrocyclization of the subunits of a wheel-like component around the axle-like subunit of the dumbbell-shaped component. For recent examples, see: a) V. Balzani, A. Credi, S. J. Langford, L. Prodi, J. F. Stoddart, M. Venturi, Supramol. Chem. 2001, 13, 303-311; b) F. G. Gatti, D. A. Leigh, S. A. Nepogodiev, A. M. Z. Slawin, S. J. Teat, J. K. Y. Wong, J. Am. Chem. Soc. 2001, 123, 5983-5989; c) G. Doddi, G. Ercolani, S. Franconeri, P. Mencarelli, J. Org. Chem. 2001, 66, 4950-4953; e) D. A. Leigh, P. J. Lusby, S. J. Teat, A. J. Wilson, J. K. Y. Wong, Angew. Chem. 2001, 113, 1586-1591; Angew. Chem. Int. Ed. 2001, 40, 1538-1543; d) P. T. Glink, A. I. Oliva, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 1922-1927; Angew. Chem. Int. Ed. 2001, 40, 1870-1875; e) M. Horn, J. Ihringer, P. T. Glink, J. F. Stoddart, Chem. Eur. J. 2003, 9, 4046-4054; f) A. F. M. Kilbinger, S. J. Cantrill, A. W. Waltman, M. W. Day, R. H. Grubbs, Angew. Chem. 2003, 115, 3403-3407; Angew. Chem. Int. Ed. 2003, 42, 3281-3285.
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82. The slippage methodology was exploited early on when rotaxanes were prepared in a statistical manner. For example see : a) I. T. Harrison, J. Chem. Soc. Chem. Commun. 1972, 231-232; b) G. Schill, W. Beckmann, N. Schweikert, H. Fritz, Chem. Ber. 1986, 119, 2647-2655;
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