In search of molecular ratchets

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 17, 1997, Pages 1866-1868

  Kelly, T Ross ^a   Tellitu, Imanol ^a   Sestelo, José Pérez ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

Helical structures; Molecular devices; Nanostructures; Triptycenes

Indexed keywords

EID: 0030765853     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199718661     Document Type: Article

References (14)

1. a) For the report of a molecular brake from this laboratory see T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. Garcia, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657-3658.
2. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
3. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
4. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
5. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
6. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
7. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
8. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
9. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
10. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
11. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
12. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
13. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.
14. For leading references to other studies see b) T. C. Bedard, J. S. Moore, ibid. 1995, 117, 10662-10671; c) J. Rebek, Jr., Acc. Chem. Res. 1984, 17, 258-264; d) K. Mislow, Chemtracts: Org. Chem. 1989, 2, 151-174; e) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 2t, 175-182; f) D. H. Evans, A. Fitch, J. Am. Chem. Soc. 1984, 106, 3039-3041; g) R. Ballardini, V. Balzini, A. Credi, M. T. Ganfolfi, 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 ; h) K. V. Kilway, J.S. Siegel, J. Am. Chem. Soc. 1991, 113, 2332-2333; i) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686-1688; j) M. Jorgenson, K. Lerstrup, P. Frederiksen, T. Bjornholm, P. Sommer-Larsen, K. Schaumburg, K. Brunfeldt, K. Bechgaard, J. Org. Chem. 1993,58,2785-2790; k) R. M. Metzger, C. A. Panetta, New: J. Chem. 1991, 15, 209-221; 1) A. C. Benniston, A. Harriman, Angew. Chem. 1993, 105, 1553-1555; Angew. Chem. Int. Ed. Engl. 1993, 32, 1459-1461.