Skip to content
Publicly Available Published by De Gruyter January 1, 2009

Template-directed synthesis of donor/acceptor [2]catenanes and [2]rotaxanes

  • Kirsten E. Griffiths and J. Fraser Stoddart

Abstract

The synthesis of mechanically interlocked molecular compounds has advanced by leaps and bounds since the early days of statistical methods and covalent-directing strategies. Template-directed synthesis has emerged as the method of choice for the construction of increasingly complex and functional [2]catenanes and [2]rotaxanes. In particular, mechanically interlocked molecules employing π-donating and π-accepting recognition units have been produced with remarkable efficiencies and show great promise in technologies as diverse as molecular electronics and drug delivery.


Conference

International Symposium on Novel Aromatic Compounds (ISNA-12), International Symposium on Novel Aromatic Compounds, ISNA, Novel Aromatic Compounds, 12th, Awaji Island, Japan, 2007-07-22–2007-07-27


References

1. doi:10.1021/ja01501a082, E. Wasserman. J. Am. Chem. Soc. 82, 4433 (1960).Search in Google Scholar

2. doi:10.1021/ja01479a015, H. L. Frisch, E. Wasserman. J. Am. Chem. Soc. 81, 3789 (1961).Search in Google Scholar

3. (a) doi:10.1021/ja00998a052, I. T. Harrison, S. Harrison. J. Am. Chem. Soc. 89, 5723 (1967);Search in Google Scholar

3. (b) doi:10.1039/p19740000301, I. T. Harrison. J. Chem. Soc., Perkin Trans. 1 301 (1974);Search in Google Scholar

3. (c) I. T. Harrison. J. Chem. Soc., Chem. Comm. 231 (1972).10.1039/c39720000231Search in Google Scholar

4. doi:10.1002/anie.196405461, G. Schill, A. Luttringhaus. Angew. Chem., Int. Ed. Engl. 3, 546 (1964).Search in Google Scholar

5. (a) F. Diederich, P. J. Stang (Eds.). Templated Organic Synthesis, Wiley-VCH, Weinhem (2000);10.1002/9783527613526Search in Google Scholar

5. (b) doi:10.1016/0010-8545(90)85007-F, D. H. Busch, N. A. Stephenson. Coord. Chem. Rev. 100, 119 (1990);Search in Google Scholar

5. (c) doi:10.1021/ar00033a003, S. Anderson, H. L. Anderson, J. K. M. Sanders. Acc. Chem. Res. 26, 469 (1993);Search in Google Scholar

5. (d) doi:10.1016/S0010-8545(99)00242-8, T. J. Hubin, D. H. Busch. Coord. Chem. Rev. 200, 5 (2000);Search in Google Scholar

5. (e) doi:10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E, S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart. Angew. Chem., Int. Ed. 41, 898 (2002);Search in Google Scholar

5. (f) D. H. Busch. Top. Curr. Chem. 249, 1 (2005).Search in Google Scholar

6. (a) J.-M. Lehn. Supramolecular Chemistry, VCH, Weinheim (1995);10.1002/3527607439Search in Google Scholar

6. (b) J.-M. Lehn, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vogtle (Eds.). Comprehensive Supramolecular Chemistry, Pergamon, Oxford (1996);Search in Google Scholar

6. (c) doi:10.1002/anie.199611541, D. Philp, J. F. Stoddart. Angew. Chem., Int. Ed. Engl. 35, 1154 (1996);Search in Google Scholar

6. (d) H.-J. Schneider, A. Yatsimirsky. Principles and Methods in Supramolecular Chemistry, Wiley-VCH, Weinheim (2000);Search in Google Scholar

6. (e) J. W. Steed, J. L. Atwood. Supramolecular Chemistry, Wiley-VCH, Weinheim (2000);Search in Google Scholar

6. (f) doi:10.1126/science.1071063, Special issue on "Supramolecular Chemistry and Self-Assembly": Science 295, 2400-2421 (2002);Search in Google Scholar

6. (g) Y. K. Agrawal, C. R. Sharma. Rev. Anal. Chem. 24, 35 (2005).Search in Google Scholar

7. (a) doi:10.1021/ja071319n, O. S. Miljanic, W. R. Dichtel, S. I. Khan, S. Mortezaei, J. R. Heath, J. F. Stoddart. J. Am. Chem. Soc. 129, 8236 (2007);Search in Google Scholar

7. (b) doi:10.1021/ol061864d, O. S. Miljanic, W. R. Dichtel, S. Mortezaei, J. F. Stoddart. Org. Lett. 8, 4835 (2006).Search in Google Scholar

8. (a) doi:10.1021/ja063127i, W. R. Dichtel, O. S. Miljanic, J. M. Spruell, J. R. Heath, J. F. Stoddart. J. Am. Chem. Soc. 128, 10388 (2006);Search in Google Scholar

8. (b) doi:10.1021/ol070052u, I. Aprahamian, W. R. Dichtel, T. Ikeda, J. R. Heath, J. F. Stoddart. Org. Lett. 9, 1287 (2007).Search in Google Scholar

9. (a) doi:10.1002/asia.200700035, A. B. Braunschweig, W. R. Dichtel, O. S. Miljanic, M. A. Olson, J. M. Spruell, S. I. Khan, J. R. Heath, J. F. Stoddart. Chem. Asian J. 2, 634 (2007);Search in Google Scholar

9. (b) doi:10.1246/bcsj.80.1856, I. Aprahamian, O. S. Miljanic, W. R. Dichtel, K. Isoda, T. Yasuda, T. Kato, J. F. Stoddart. Bull. Chem. Soc. Jpn. 80, 1856 (2007).Search in Google Scholar

10. doi:10.1073/pnas.0704136104, O. S. Miljanic, J. F. Stoddart. Proc. Natl. Acad. Sci. USA 104, 12966 (2007).Search in Google Scholar

11. (a) J.-P. Sauvage, C. Dietrich-Buchecker (Eds.). Molecular Catenanes, Rotaxanes, and Knots: A Journey Through the World of Molecular Topology, Wiley-VCH, Weinheim (1999);10.1002/9783527613724Search in Google Scholar

11. (b) doi:10.1021/cr00040a005, D. B. Amabilino, J. F. Stoddart. Chem. Rev. 95, 2725 (1995);Search in Google Scholar

11. (c) T. J. Hubin, A. G. Kolchinski, A. L. Vance, D. H. Busch. Adv. Supramol. Chem. 6, 237 (1999);10.1016/S1068-7459(99)80017-4Search in Google Scholar

11. (d) doi:10.1039/b003769i, S. J. Cantrill, A. R. Pease, J. F. Stoddart. J. Chem. Soc., Dalton Trans. 3715 (2000);Search in Google Scholar

11. (e) L. Raehm, D. G. Hamilton, J. K. M. Sanders. Synlett 1742 (2002);10.1055/s-2002-34860Search in Google Scholar

11. (f) doi:10.1135/cccc19970527, M. Belohradsky, F. M. Raymo. J. F. Stoddart. Collect. Czech. Chem. Commun. 62, 527 (1997).Search in Google Scholar

12. (a) doi:10.1126/science.1096914, K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart. Science 304, 1308 (2004);Search in Google Scholar

12. (b) doi:10.1021/jo050969b, K. S. Chichak, A. J. Peters, S. J. Cantrill, J. F. Stoddart. J. Org. Chem. 70, 7956 (2005);Search in Google Scholar

12. (c) doi:10.1002/anie.200600817, C. D. Pentecost, A. J. Peters, K. S. Chichak, G. V. W. Cave, S. J. Cantrill, J. F. Stoddart. Angew. Chem., Int. Ed. 45, 4099 (2006);Search in Google Scholar

12. (d) doi:10.1126/science.1099216, J. S. Siegel. Science 304, 1256 (2004);Search in Google Scholar

12. (e) doi:10.1002/anie.200460583, C. A. Schalley. Angew. Chem., Int. Ed. 43, 4399 (2004);Search in Google Scholar

12. (f) doi:10.1021/ar040226x, S. J. Cantrill, K. S. Chichak, A. J. Peters, J. F. Stoddart. Acc. Chem. Res. 38, 1 (2005).Search in Google Scholar

13. (a) doi:10.1021/ja00080a045, J.-F. Niergarten, C. O. Dietrich-Buchecker, J.-P. Sauvage. J. Am. Chem. Soc. 116, 375 (1994);Search in Google Scholar

13. (b) doi:10.1021/ja992391r, F. Ibukuro, M. Fujita, K. Yamaguchi, J.-P. Sauvage. J. Am. Chem. Soc. 121, 11014 (1999);Search in Google Scholar

13. (c) doi:10.1002/1521-3773(20001103)39:21<3819::AID-ANIE3819>3.0.CO;2-6, C. P. McArdle, J. J. Vittal, R. J. Puddephatt. Angew. Chem., Int. Ed. 39, 3819 (2000);Search in Google Scholar

13. (d) doi:10.1002/anie.200603521, C. D. Pentecost, K. S. Chichak, A. J. Peters, G. W. V. Cave, S. J. Cantrill, J. F. Stoddart. Angew. Chem., Int. Ed. 46, 218 (2007).Search in Google Scholar

14. (a) G. Schill. Catenanes, Rotaxanes, and Knots, Academic Press, New York (1971);Search in Google Scholar

14. (b) doi:10.1002/anie.198901891, C. O. Dietrich-Buchecker, J.-P. Sauvage. Angew. Chem., Int. Ed. Engl. 28, 189 (1989);Search in Google Scholar

14. (c) doi:10.1021/ja00077a024, C. O. Dietrich-Buchecker, J. F. Nierengarten, J.-P. Sauvage, N. Armaroli, V. Balzani, L. De Cola. J. Am. Chem. Soc. 115, 11234 (1993);Search in Google Scholar

14. (d) doi:10.1039/a704970f, C. O. Dietrich-Buchecker, G. Rapenne, J.-P. Sauvage. Chem. Commun. 2053 (1997);Search in Google Scholar

14. (e) P. R. Ashton, O. A. Matthews, S. Menzer, F. M. Raymo, N. Spencer, J. F. Stoddart, D. J. Williams. Liebigs Ann./Recl. 2485 (1997);10.1002/jlac.199719971210Search in Google Scholar

14. (f) doi:10.1002/(SICI)1521-3773(20000502)39:9<1616::AID-ANIE1616>3.0.CO;2-Y, O. Safarowsky, M. Nieger, R. Frohlich, F. Vogtle. Angew. Chem., Int. Ed. 39, 1616 (2000);Search in Google Scholar

14. (g) doi:10.1038/35081143, H. Adams, E. Ashworth, G. A. Breault, J. Guo, C. A. Hunter, P. C. Mayers. Nature 411, 763 (2001);Search in Google Scholar

14. (h) doi:10.1002/anie.200460312, O. Lukin, F. Vogtle. Angew. Chem., Int. Ed. 44, 1456 (2005);Search in Google Scholar

14. (i) C. Dietrich-Buchecker, B. X. Colasson, J.P. Sauvage. Top. Curr. Chem. 249, 261 (2005);10.1007/b104331Search in Google Scholar

14. (j) doi:10.1002/anie.200601111, M. Feigel, R. Ladberg, S. Engels, R. Herbst-Irmer, R. Frohlich. Angew. Chem., Int. Ed. 45, 5698 (2006).Search in Google Scholar

15. doi:10.1039/c39910001680, 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. 1680 (1991).Search in Google Scholar

16. doi:10.1021/ar950199y, M. C. T. Fyfe, J. F. Stoddart. Acc. Chem. Res. 30, 393 (1997).Search in Google Scholar

17. doi:10.1016/S0040-4020(99)00282-3, G. A. Breault, C. A. Hunter, D. C. Mayers. Tetrahedron 55, 5265 (1999).Search in Google Scholar

18. doi:10.1007/BF00899187, H. Frisch, I. Martin, H. Mark. Monatsh. Chem. 84, 250 (1953).Search in Google Scholar

19. (a) doi:10.1016/S0040-4039(02)01201-7, K. Hiratani, J. Suga, Y. Nagawa, H. Houjou, H. Tokuhisa, M. Numata, K. Watanabe. Tetrahedron Lett. 43, 5747 (2002);Search in Google Scholar

19. (b) doi:10.1021/ol070999w, K. Hirose, K. Nishihara, N. Harada, Y. Nakamura, D. Masuda, M. Araki, Y. Tobe. Org. Lett. 9, 2969 (2007).Search in Google Scholar

20. (a) doi:10.1002/jlac.19697210109, G. Schill, H. Zollenkopf. Liebigs. Ann. Chem. 721, 53 (1969);Search in Google Scholar

20. (b) doi:10.1002/jlac.19707310114, G. Schill, R. Henschel. Liebigs Ann. Chem. 731, 113 (1970).Search in Google Scholar

21. doi:10.1016/S0040-4039(00)94050-4, C. O. Dietrich-Buchecker, J. P. Sauvage. Tetrahedron Lett. 24, 5095 (1983).Search in Google Scholar

22. (a) doi:10.1021/cr00080a007, C. O. Dietrich-Buchecker, J.-P. Sauvage. Chem. Rev. 87, 795 (1987);Search in Google Scholar

22. (b) doi:10.1021/ar00178a001, J.-P. Sauvage. Acc. Chem. Res. 23, 319 (1990);Search in Google Scholar

22. (c) C. O. Dietrich-Buchecker, J.-P. Sauvage. Bioorg. Chem. Front. 2, 195 (1991);10.1007/978-3-642-76241-3_6Search in Google Scholar

22. (d) doi:10.1007/BFb0111283, J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage. Top. Curr. Chem. 165, 131 (1993).Search in Google Scholar

23. (a) doi:10.1039/c39870001061, B. L. Allwood, N. Spencer, H. Shahriari-Zavareh, J. F. Stoddart, D. J. Williams. J. Chem. Soc., Chem. Commun. 1061 (1987);Search in Google Scholar

23. (b) doi:10.1039/c39870001066, P. R. Ashton, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams. J. Chem. Soc., Chem. Commun. 1066 (1987).Search in Google Scholar

24. doi:10.1002/anie.198815471, B. Odell, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams. Angew. Chem., Int. Ed. Engl. 27, 1547 (1988).Search in Google Scholar

25. doi:10.1039/c39870001064, B. L. Allwood, N. Spencer, H. Sharhriari-Zavareh, J. F. Stoddart, D. J. Williams. J. Chem. Soc., Chem. Commun. 1064 (1987).Search in Google Scholar

26. (a) doi:10.1002/anie.199312971, D. B. Amabilino, P. R. Ashton, M. S. Tolley, J. F. Stoddart, D. J. Williams. Angew. Chem., Int. Ed. Engl. 32, 1297 (1993);Search in Google Scholar

26. (b) doi:10.1039/c39940002479, D. B. Amabilino, P. R. Ashton, G. R. Brown, W. Hayes, J. F. Stoddart, M. S. Tolley, D. J. Williams. J. Chem. Soc., Chem. Commun. 2479 (1994);Search in Google Scholar

26. (c) P. R. Ashton, M. A. Blower, S. Iqbal, C. H. McLean, J. F. Stoddart, M. S. Tolley, D. J. Williams. Synlett 1056 (1994);10.1055/s-1994-34987Search in Google Scholar

26. (d) doi:10.1055/s-1994-25692, P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams. Synthesis 1344 (1994);Search in Google Scholar

26. (e) doi:10.1055/s-1994-34979, P. R. Ashton, M. A. Blower, C. H. McLean, J. F. Stoddart, M. S. Tolley. Synlett 1063 (1994);Search in Google Scholar

26. (f) doi:10.1021/ja00109a011, D. B. Amabilino, P.-L. Anelli, P. R. Ashton, G. R. Brown, E. Cordova, L. A. Godinez, W. Hayes, A. E. Kaifer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams. J. Am. Chem. Soc. 117, 11142 (1995);Search in Google Scholar

26. (g) doi:10.1039/c39950002541, P.-L. Anelli, M. Asakawa, P. R. Ashton, G. R. Brown, W. Hayes, O. Kocian, S. R. Pastor, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams. J. Chem. Soc., Chem. Commun. 2541 (1995);Search in Google Scholar

26. (h) doi:10.1021/ja962937z, M. Asakawa, C. L. Brown, S. Menzer, F. M. Raymo, J. F. Stoddart, D. J. Williams. J. Am. Chem. Soc. 119, 2614 (1997);Search in Google Scholar

26. (i) doi:10.1021/jo961025c, M. Asakawa, P. R. Ashton, S. E. Boyd, C. L. Brown, R. E. Gillard, O. Kocian, F. M. Raymo, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams. J. Org. Chem. 62, 26 (1997);Search in Google Scholar

26. (j) doi:10.1021/ja970640a, R. Ballardini, V. Balzani, A. Credi, C. L. Brown, R. E. Gillard, M. Montalti, D. Philp, J. F. Stoddart, M. Venturi, A. J. P. White, B. J. Williams, D. J. Williams. J. Am. Chem. Soc. 119, 12503 (1997);Search in Google Scholar

26. (k) doi:10.1002/(SICI)1099-0690(199801)1998:1<81::AID-EJOC81>3.0.CO;2-P, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, D. Marquis, L. Perez-Garcia, J. F. Stoddart. Eur. J. Org. Chem. 81 (1998);Search in Google Scholar

26. (l) doi:10.1021/ma970685w, S. Menzer, A. J. P. White, D. J. Williams, M. Belohradsky, C. Hamers, F. M. Raymo, A. N. Shipway, J. F. Stoddart. Macromolecules 31, 295 (1998);Search in Google Scholar

26. (m) doi:10.1002/(SICI)1521-3765(19980210)4:2<299::AID-CHEM299>3.0.CO;2-Z, P. R. Ashton, S. E. Boyd, S. Menzer, D. Pasini, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, P. G. Wyatt. Chem.Eur. J. 4, 299 (1998);Search in Google Scholar

26. (n) doi:10.1002/(SICI)1521-3765(19980310)4:3<449::AID-CHEM449>3.0.CO;2-8, R. Ballardini, V. Balzani, M. T. Gandolfi, R. E. Gillard, J. F. Stoddart, E. Taellini. Chem.Eur. J. 4, 449 (1998);Search in Google Scholar

26. (o) doi:10.1002/(SICI)1521-3765(19980416)4:4<590::AID-CHEM590>3.0.CO;2-C, P. R. Ashton, V. Balzani, A. Credi, O. Kocian, D. Pasini, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams. Chem.Eur. J. 4, 590 (1998);Search in Google Scholar

26. (p) doi:10.1002/(SICI)1521-3765(19990301)5:3<860::AID-CHEM860>3.0.CO;2-K, 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. 5, 860 (1999);Search in Google Scholar

26. (q) doi:10.1002/(SICI)1099-0690(199905)1999:5<995::AID-EJOC995>3.0.CO;2-K, P. R. Ashton, A. M. Heiss, D. Pasini, F. M. Raymo, A. N. Shipway, J. F. Stoddart, N. Spencer. Eur. J. Org. Chem. 995 (1999);Search in Google Scholar

26. (r) doi:10.1002/1099-0690(200004)2000:7<1121::AID-EJOC1121>3.0.CO;2-3, P. R. Ashton, V. Baldoni, V. Balzani, C. G. Claessens, A. Credi, H. D. A. Hoffmann, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams. Eur. J. Org. Chem. 1121 (2000);Search in Google Scholar

26. (s) doi:10.1070/MC2003v013n03ABEH001809, E. Alcalde, L. Perez-Garcia, S. Ramos, J. F. Stoddart, S. A. Vignon, A. J. P. White, D. J. Williams. Mendeleev Commun. 13, 1 (2003);Search in Google Scholar

26. (t) doi:10.1070/MC2004v014n06ABEH002075, E. Alcalde, L. Perez-Garcia, S. Ramos, J. F. Stoddart, A. J. P. White, D. J. Williams. Mendeleev Commun. 14, 233 (2004).Search in Google Scholar

27. doi:10.1002/anie.198913961, P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams. Angew. Chem., Int. Ed. Engl. 28, 1396 (1989).Search in Google Scholar

28. doi:10.1021/jo980543f, F. M. Raymo, K. N. Houk, J. F. Stoddart. J. Org. Chem. 63, 6523 (1998).Search in Google Scholar

29. (a) doi:10.1002/anie.199523781, D. B. Amabilino, P. R. Ashton, L. Perez-Garcia, J. F. Stoddart. Angew. Chem., Int. Ed. Engl. 34, 2378 (1995);Search in Google Scholar

29. (b) doi:10.1021/ja00150a015, P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. Menzer, L. Perez-Garcia, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams. J. Am. Chem. Soc. 117, 11171 (1995).Search in Google Scholar

30. (a) doi:10.1002/anie.199505711, P. R. Ashton, L. Perez-Garcia, J. F. Stoddart, A. J. P. White, D. J. Williams. Angew. Chem., Int. Ed. Engl. 34, 571 (1995);Search in Google Scholar

30. (b) doi:10.1039/a809433k, P. R. Ashton, S. E. Boyd, A. Brindle, S. J. Langford, S. Menzer, L. Perez-Garcia, J. A. Preece, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams. New J. Chem. 23, 587 (1999);Search in Google Scholar

30. (c) doi:10.1021/ja994454b, V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi. J. Am. Chem. Soc. 122, 3542 (2000).Search in Google Scholar

31. (a) doi:10.1002/(SICI)1099-0690(199905)1999:5<985::AID-EJOC985>3.0.CO;2-O, 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. 985 (1999);Search in Google Scholar

31. (b) doi:10.1039/b007836k, R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Belcher, J. Lau, M. Brondsted Nielsen, J. F. Stoddart. New J. Chem. 25, 293 (2001).Search in Google Scholar

32. (a) doi:10.1002/(SICI)1521-3773(19980216)37:3<333::AID-ANIE333>3.0.CO;2-P, M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams. Angew. Chem., Int. Ed. 37, 333 (1998);Search in Google Scholar

32. (b) doi:10.1021/jo991781t, 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. 65, 1924 (2000).Search in Google Scholar

33. doi:10.1135/cccc19960001, M. Belohradsky, F. M. Raymo, J. F. Stoddart. Collect. Czech. Chem. Commun. 61, 1 (1996).Search in Google Scholar

34. (a) doi:10.1021/ja9806229, F. M. Raymo, K. N. Houk, J. F. Stoddart. J. Am. Chem. Soc. 120, 9318 (1998);Search in Google Scholar

34. (b) doi:10.1016/S0040-4039(98)01071-5, P. R. Ashton, M. C. T. Fyfe, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams. Tetrahedron Lett. 39, 5455 (1998);Search in Google Scholar

34. (c) doi:10.1351/pac199769091987, F. M. Raymo, J. F. Stoddart. Pure Appl. Chem. 69, 1987 (1997);Search in Google Scholar

34. (d) doi:10.1039/c39930001274, P. R. Ashton, M. Belohradsky, D. Philp, N. Spencer, J. F. Stoddart. J. Chem. Soc., Chem. Commun. 1274 (1993).Search in Google Scholar

35. doi:10.1021/ja00013a096, P.-L. Anelli, N. Spencer, J. F. Stoddart. J. Am. Chem. Soc. 113, 5131 (1991).Search in Google Scholar

36. (a) doi:10.1039/c39920001124, P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart. J. Chem. Soc., Chem. Commun. 1124 (1992);Search in Google Scholar

36. (b) doi:10.1002/ejoc.200500947, A. B. Braunschweig, C. M. Ronconi, J.-Y. Han, F. Arico, S. J. Cantrill, J. F. Stoddart, S. I. Khan, A. J. P. White, D. J. Williams. Eur. J. Org. Chem. 1857 (2006).Search in Google Scholar

37. (a) doi:10.1021/ja954334d, 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. 118, 4931 (1996);Search in Google Scholar

37. (b) doi:10.1039/c39930001269, P. R. Ashton, M. Belohradsky, D. Philp, J. F. Stoddart. J. Chem. Soc., Chem. Commun. 1269 (1993);Search in Google Scholar

37. (c) doi:10.1021/ja961817o, 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. 119, 302 (1997).Search in Google Scholar

38. (a) doi:10.1055/s-1992-21540, P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley. Synlett 914 (1992);Search in Google Scholar

38. (b) doi:10.1055/s-1992-21541, P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley. Synlett 919 (1992);Search in Google Scholar

38. (c) doi:10.1055/s-1992-21542, P. R. Ashton, R. A. Bissell, N. Spencer, J. F. Stoddart, M. S. Tolley. Synlett 923 (1992).Search in Google Scholar

39. (a) doi:10.1038/369133a0, R. A. Bissell, E. Cordova, A. E. Kaifer, J. F. Stoddart. Nature 369, 133 (1994);Search in Google Scholar

39. (b) doi:10.1021/jo00076a008, E. Cordova, R. A. Bissell, N. Spencer, P. R. Ashton, J. F. Stoddart, A. E. Kaifer. J. Org. Chem. 58, 6550 (1993).Search in Google Scholar

40. (a) doi:10.1021/ol006387s, J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart. Org. Lett. 2, 3547 (2000);Search in Google Scholar

40. (b) doi:10.1002/1521-3773(20010401)40:7<1216::AID-ANIE1216>3.0.CO;2-W, J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart. Angew. Chem., Int. Ed. 40, 1216 (2001);Search in Google Scholar

40. (c) doi:10.1002/chem.200204589, J. O. Jeppesen, K. A. Nielsen, J. Perkins, S. A. Vignon, A. Di Fabio, R. Ballardini, M. T. Gandolfi, M. Venturi, V. Balzani, J. Becher, J. F. Stoddart. Chem.Eur. J. 9, 2982 (2003).Search in Google Scholar

41. doi:10.1002/chem.200305204, H.-R. Tseng, S. A. Vignon, P. C. Celestre, J. Perkins, J. O. Jeppesen, A. Di Fabio, R. Ballardini, M. T. Gandolfi, M. Venturi, V. Balzani, J. F. Stoddart. Chem.Eur. J. 10, 155 (2004).Search in Google Scholar

42. doi:10.1002/anie.200701722, S. Nygaard, B. W. Laursen, T. S. Hansen, A. D. Bond, A. H. Flood, J. O. Jeppesen. Angew. Chem., Int. Ed. 46, 6093 (2007).Search in Google Scholar

43. doi:10.1002/chem.200305725, S. Kang, S. A. Vignon, H.-R. Tseng, J. F. Stoddart. Chem.Eur. J. 10, 2555 (2004).Search in Google Scholar

44. (a) doi:10.1073/pnas.0504109102, T. D. Nguyen, H.-R. Tseng, P. C. Celestre, A. H. Flood, Y. Liu, J. F. Stoddart, J. I. Zink. Proc. Acad. Natl. Sci. USA 102, 10029 (2005);Search in Google Scholar

44. (b) doi:10.1021/ja065485r, T. D. Nguyen, Y. Liu, S. Saha, K. C.-F. Leung, J. F. Stoddart, J. I. Zink. J. Am. Chem. Soc. 129, 626 (2007);Search in Google Scholar

44. (c) doi:10.1002/adfm.200600989, S. Saha, K. C.-F. Leung, T. D. Nguyen, J. F. Stoddart, J. I. Zink. Adv. Funct. Mater. 17, 685 (2007).Search in Google Scholar

45. doi:10.1002/cphc.200300992, H.-R. Tseng, D. Wu, N. X. Fang, X. Zhang, J. F. Stoddart. ChemPhysChem 5, 111 (2004).Search in Google Scholar

46. doi:10.1002/anie.200700305, I. Aprahamian, T. Yasuda, T. Ikeda, S. Saha, W. R. Dichtel, K. Isoda, T. Kato, J. F. Stoddart. Angew. Chem., Int. Ed. 46, 4675 (2007).Search in Google Scholar

47. (a) doi:10.1002/chem.200400651, T. Iijima, S. A. Vignon, H.-R. Tseng, T. Jarrosson, J. K. M. Sanders, F. Marchioni, M. Venturi, E. Apostoli, V. Balzani, J. F. Stoddart. Chem.Eur. J. 10, 6375 (2004);Search in Google Scholar

47. (b) doi:10.1021/ja048080k, S. A. Vignon, T. Jarrosson, T. Iijima, H.-R. Tseng, J. K. M. Sanders, J. F. Stoddart. J. Am. Chem. Soc. 126, 9884 (2004).Search in Google Scholar

48. (a) doi:10.1002/asia.200600355, T. Ikeda, S. Saha, I. Aprahamian, K. C.-F. Leung, A. Williams, W.-Q. Deng, A. H. Flood, W. A. Goddard III, J. F. Stoddart. Chem. Asian J. 2, 76 (2007);Search in Google Scholar

48. (b) doi:10.1021/ja0431298, W.-Q. Deng, A. H. Flood, J. F. Stoddard, W. A. Goddard III. J. Am. Chem. Soc. 127, 15994 (2005);Search in Google Scholar

48. (c) doi:10.1021/ol070170h, T. Ikeda, I. Aprahamian, J. F. Stoddart. Org. Lett. 9, 1481 (2007).Search in Google Scholar

49. (a) doi:10.1126/science.289.5482.1172, C. P. Collier, G. Mattersteig, E. W. Wong, Y. Luo, K. Beverly, J. Sampaio, F. M. Raymo, J. F. Stoddart, J. R. Heath. Science 289, 1172 (2000);Search in Google Scholar

49. (b) doi:10.1002/1521-4095(200008)12:15<1099::AID-ADMA1099>3.0.CO;2-2, M. Asakawa, M. Higuchi, G. Mattersteig, T. Nakamura, A. R. Pease, F. M. Raymo, T. Shimizu, J. F. Stoddart. Adv. Mater. 12, 1099 (2000);Search in Google Scholar

49. (c) doi:10.1021/ja0117884, C. P. Collier, J. O. Jeppesen, Y. Luo, J. Perkins, E. W. Wong, J. R. Heath, J. F. Stoddart. J. Am. Chem. Soc. 123, 12623 (2001);Search in Google Scholar

49. (d) doi:10.1002/1439-7641(20020617)3:6<519::AID-CPHC519>3.0.CO;2-2, Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. De Ionno, G. Ho, J. Perkins, H.-R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath. ChemPhysChem 3, 519 (2002);Search in Google Scholar

49. (e) doi:10.1002/cphc.200300871, M. R. Diehl, D. W. Steuerman, H.-R. Tseng, S. A. Vignon, A. Star, P. C. Celestre, J. F. Stoddart, J. R. Heath. ChemPhysChem 4, 1335 (2003);Search in Google Scholar

49. (f) doi:10.1038/nature05462, J. E. Green, J. W. Choi, A. Boukai, Y. Bunimovich, E. Johnston-Halperin, E. Delono, Y. Luo, B. A. Sheriff, K. Xe, Y. S. Shin, H.-R. Tseng, J. F. Stoddart, J. R. Heath. Nature 445, 414 (2007).Search in Google Scholar

50. (a) doi:10.1002/anie.200461723, D. W. Steuerman, H.-R. Tseng, A. J. Peters, A. H. Flood, J. O. Jeppesen, K. A. Nielsen, J. F. Stoddart, J. R. Heath. Angew. Chem., Int. Ed. 43, 6486 (2004);Search in Google Scholar

50. (b) doi:10.1002/chem.200401052, A. H. Flood, A. J. Peters, S. A. Vignon, D. W. Steuerman, H.-R. Tseng, S. Kang, J. R. Heath, J. F. Stoddart. Chem.Eur. J. 10, 6558 (2004).Search in Google Scholar

51. (a) doi:10.1021/la0361518, I. C. Lee, C. W. Frank, T. Yamamoto, H.-R. Tseng, A. H. Flood, J. F. Stoddart, J. O. Jeppesen. Langmuir 20, 5809 (2004);Search in Google Scholar

51. (b) doi:10.1021/nl035099x, T. J. Huang, H.-R. Tseng, J. Sha, W. Lu, B. Brough, A. H. Flood, B.-D. Yu, P. C. Celestre, J. P. Chang, J. F. Stoddart, C.-M. Ho. Nano Lett. 4, 2065 (2004).Search in Google Scholar

Published Online: 2009-01-01
Published in Print: 2008-01-01

© 2013 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 7.5.2024 from https://www.degruyter.com/document/doi/10.1351/pac200880030485/html
Scroll to top button