The electrochemical polymerisation of a [2]rotaxane

Tetrahedron Letters

Volumn 47, Issue 5, 2006, Pages 783-786

  Cooke, Graeme ^a   Garety, James F ^a   Mabruk, Suhil ^b   Rabani, Gouher ^a   Rotello, Vincent M ^c   Surpateanu, Gheorghe ^d   Woisel, Patrice ^d  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF MASSACHUSETTS   (United States)

^d UNIVERSITÉ DU LITTORAL CÔTE D OPALE   (France)

Author keywords

Electrochemistry; Electropolymerisation; Rotaxane; Supramolecular chemistry

Indexed keywords

CATION; CYCLOPHANE DERIVATIVE; PLATINUM; POLYMER; ROTAXANE;

ARTICLE; CHEMICAL REACTION; ELECTROCHEMISTRY; ELECTRODE; POLYMERIZATION; SYNTHESIS;

EID: 29544446443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.106     Document Type: Article

References (24)

1. B. Odell, M.V. Reddington, A.M.Z. Slawin, N. Spencer, J.F. Stoddart, and D.J. Williams Angew. Chem., Int. Ed. Engl. 27 1988 1547 1550
2. A.H. Flood, Y. Liu, and J.F. Stoddart H. Hopf H. Gleiter Modern Cyclophane Chemistry 2004 Wiley-VCH Weinheim 485
3. For recent examples of surface immobilised machines and devices incorporating the cyclophane cyclobis(paraquat-p-phenylene) see: M. Asakawa, M. Higuchi, G. Mattersteig, T. Nakamura, A.R. Pease, F.M. Raymo, T. Shimizu, and J.F. Stoddart Adv. Mater. 12 2000 1099 1102
4. C.P. Collier, G. Mattersteig, E.W. Wong, Y. Luo, K. Beverly, J. Sampaio, F.M. Raymo, J.F. Stoddart, and J.R. Heath Science 289 2000 1172 1175
5. C.P. Collier, J.O. Jeppersen, Y. Luo, J. Perkins, E.W. Wong, J.R. Heath, and J.F. Stoddart J. Am. Chem. Soc. 123 2001 12632 12641
6. Y. Luo, C.P. Collier, J.O. Jeppesen, K.A. Nielsen, E. Delonno, G. Ho, J. Perkins, H.-R. Tseng, T. Yamamoto, J.F. Stoddart, and J.R. Heath Chem. Phys. Chem. 3 2002 519 525
7. S. Chia, J. Cao, J.F. Stoddart, and J.I. Zink Angew. Chem., Int. Ed. 40 2001 2447 2450
8. J.O. Jeppesen, S. Nygaard, S.A. Vignon, and J.F. Stoddart Eur. J. Org. Chem. 2004 196 220
9. D.W. Steuerman, H.-R. Tseng, A.J. Peters, A.H. Flood, J.O. Jeppesen, K.A. Nielsen, J.F. Stoddart, and J.R. Heath Angew. Chem., Int. Ed. 43 2004 6486 6491
10. I.C. Lee, C.W. Frank, T. Yamamoto, H.-R. Tseng, A.H. Flood, J.F. Stoddart, and J.O. Jeppesen Langmuir 20 2004 5809 5828
11. R. Hernandez, H.-R. Tseng, J.W. Wong, J.F. Stoddart, and J.I. Zink J. Am. Chem. Soc. 126 2004 3370 3371
12. 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, and J.F. Stoddart Chem. Eur. J. 10 2004 155 172
13. H.-R. Tseng, D. Wu, N.X. Fang, X. Zhang, and J.F. Stoddart Chem. Phys. Chem. 5 2004 111 115
14. For recent examples of electropolymerised interlocked structures see: S.S. Zhou, P.C. Carroll, and T.M. Swager J. Am. Chem. Soc. 118 1996 8713 8714
15. S.S. Zhou, and T.M. Swager J. Am. Chem. Soc. 119 1997 12568 12577
16. P.L. Vidal, M. Billon, B. Divisia-Blohorn, G. Bidan, J.M. Kern, and J.P. Sauvage Chem. Commun. 1998 629 630
17. M. Billon, B. Divisia-Blohorn, J.-M. Kern, and J.-P. Sauvage J. Mater. Chem. 7 1997 1169 1173
18. J.A. Bravo, F.M. Raymo, J.F. Stoddart, A.J.P. White, and D.J. Williams Eur. J. Org. Chem. 1998 2565 2571
19. Y. Lui, A.H. Flood, and J.F. Stoddart J. Am. Chem. Soc. 126 2004 9150 9151
20. 6 and dry toluene, acetonitrile or DMSO. A three-electrode configuration was used with a platinum disc (2 mm diameter) working electrode, a Ag/AgCl reference electrode and a platinum wire as the counter electrode. The solution was purged with nitrogen prior to recording the electrochemical data, and all measurements were recorded under a nitrogen atmosphere.
21. For examples see: P. Bäuerle, and A. Emge Adv. Mater. 3 1998 324 330
22. A. Emge, and P. Bäuerle Synth. Met. 102 1999 1370 1373
23. 3CN/toluene 1:1. Γ was calculated from the average charge recorded under the first reduction wave of the cyclophane. In these calculations, we assumed that this wave corresponds to a two electron reduction per molecule of the cyclophane moiety of the rotaxane.
24. K. Ono, S. Yamada, M. Ohkita, K. Saito, S. Tanaka, and T. Hanaichi Chem. Lett. 32 2003 516 517