A multistate switchable [3]rotacatenane

Chemistry - A European Journal

Volumn 17, Issue 1, 2011, Pages 213-222

  Barin, Gokhan ^a   Coskun, Ali ^a   Friedman, Douglas C ^a   Olson, Mark A ^a   Colvin, Michael T ^a   Carmielli, Raanan ^a   Dey, Sanjeev K ^a   Bozdemir, O Altan ^a   Wasielewski, Michael R ^a   Stoddart, J Fraser ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

molecular switches; radical dimerization; rotacatenanes; template directed synthesis; tetrathiafulvalenes

Indexed keywords

MOLECULAR SWITCHES; RADICAL DIMERIZATION; ROTACATENANES; TEMPLATE-DIRECTED SYNTHESIS; TETRATHIAFULVALENES;

AROMATIC COMPOUNDS; CYCLIC VOLTAMMETRY; DIMERIZATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; MOLECULAR ELECTRONICS; POSITIVE IONS; X RAY CRYSTALLOGRAPHY;

DIMERS;

EID: 78651085711     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002152     Document Type: Article

References (49)

1. H. Spanggaard, J. Prehn, M. B. Nielsen, E. Levillain, M. Allain, J. Becher, J. Am. Chem. Soc. 2000, 122, 9486-9494
2. J. Lyskawa, M. Sallé, J. Y. Balandier, F. Le Derf, E. Levillain, M. Allain, P. Viel, S. Palacin, Chem. Commun. 2006, 2233-2235
3. I. Aprahamian, J.-C. Olsen, A. Trabolsi, J. F. Stoddart, Chem. Eur. J. 2008, 14, 3889-3895.
4. R. Bozio, I. Zanon, A. Girlando, C. Pecile, J. Chem. Phys. 1979, 71, 2282-2293
5. J. B. Torrance, B. A. Scott, B. Welber, F. B. Kaufman, P. E. Seiden, Phys. Rev. B 1979, 19, 730-741
6. T. JØrgensen, T. K. Hansen, J. Becher, Chem. Soc. Rev. 1994, 23, 41-51
7. M. B. Nielsen, C. Lomholt, J. Becher, Chem. Soc. Rev. 2000, 29, 153-164
8. V. Khodorkovsky, L. Shapiro, P. Krief, A. Shames, G. Mabon, A. Gorgues, M. Giffard, Chem. Commun. 2001, 2736-2737
9. S. V. Rosokha, J. K. Kochi, J. Am. Chem. Soc. 2007, 129, 828-838
10. I. Garcia-Yoldi, J. S. Miller, J. J. Novoa, J. Phys. Chem. A 2009, 113, 484-492
11. K. Tanaka, T. Kunita, F. Ishiguro, K. Naka, Y. Chujo, Langmuir 2009, 25, 6929-6933.
12. A. Y. Ziganshina, Y. H. Ko, W. S. Jeon, K. Kim, Chem. Commun. 2004, 806-807
13. M. Yoshizawa, K. Kumazawa, M. Fujita, J. Am. Chem. Soc. 2005, 127, 13456-13457
14. P.-T. Chiang, N.-C. Chen, C.-C. Lai, S.-H. Chiu, Chem. Eur. J. 2008, 14, 6546-6552.
15. J. M. Spruell, A. Coskun, D. C. Friedman, R. S. Forgan, A. A. Sarjeant, A. Trabolsi, A. C. Fahrenbach, G. Barin, W. F. Paxton, S. K. Dey, M. A. Olson, D. Benítez, E. Tkatchouk, M. T. Colvin, R. Carmielli, S. T. Caldwell, G. M. Rosair, S. G. Hewage, F. Duclairoir, J. L. Seymour, A. M. Z. Slawin, W. A. Goddard III, M. R. Wasielewski, G. Cooke, J. F. Stoddart, Nat. Chem. 2010, 2, 870-879.
16. M. Asakawa, P. R. Ashton, S. Menzer, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 877-893.
17. D. B. Amabilino, P. R. Ashton, J. A. Bravo, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Eur. J. Org. Chem. 1999, 1295-1302.
18. W. R. Dichtel, O. Å. MiljaniÄ, J. M. Spruell, J. R. Heath, J. F. Stoddart, J. Am. Chem. Soc. 2006, 128, 10388-10390
19. A. B. Braunschweig, W. R. Dichtel, O. Å. MiljaniÄ, M. A. Olson, J. M. Spruell, S. I. Khan, J. R. Heath, J. F. Stoddart, Chem. Asian J. 2007, 2, 634-647
20. W. R. Dichtel, O. Å. MiljaniÄ, W. Zhang, J. M. Spruell, K. Patel, I. Aprahamian, J. R. Heath, J. F. Stoddart, Acc. Chem. Res. 2008, 41, 1750-1761
21. J. M. Spruell, W. R. Dichtel, J. R. Heath, J. F. Stoddart, Chem. Eur. J. 2008, 14, 4168-4177.
22. D. H. Busch, N. A. Stephenson, Coord. Chem. Rev. 1990, 100, 119-154
23. S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475
24. T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200, 5-52
25. M.-J. Blanco, J.-C. Chambron, M.-C. Jimenez, J.-P. Sauvage, Top. Stereochem. 2002, 23, 125-173
26. C. A. Schalley, T. Weilandt, J. Bruggemann, F. Vögtle, Top. Curr. Chem. 2004, 232-242, 141-200
27. F. Aricõ, J. D. BadjiÄ, S. J. Cantrill, A. H. Flood, K. C.-F. Leung, Y. Liu, J. F. Stoddart, Top. Curr. Chem. 2005, 249, 203-259
28. M. S. Vickers, P. D. Beer, Chem. Soc. Rev. 2007, 36, 211-225.
29. M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, M. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992-1996.
30. 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.
31. D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Cõrdova, L. A. Godínez, T. T. Goodnow, A. E. Kaifer, S. P. Newton, M. Pietraszkiewicz, D. Philp, F. M. Raymo, A. S. Reder, M. T. Rutland, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 1271-1293.
32. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
33. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
34. 2 by using the program SHELXTL. CCDC-785976 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
35. 2 by using the program SHELXTL. CCDC-785977 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
36. 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
37. F. M. Raymo, M. D. Bartberger, K. N. Houk, J. F. Stoddart, J. Am. Chem. Soc. 2001, 123, 9264-9267.
38. N. G. Connelly, W. E. Geiger, Chem. Rev. 1996, 96, 877-910
39. H.-R. Tseng, S. A. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533
40. Angew. Chem. Int. Ed. 2003, 42, 1491-1495.
41. 4+ ring.
42. 2+ unit to its radical-cationic state, the crown ether component is no longer engaged in significant donor-acceptor interactions.
43. The dilution resulting from the addition of oxidant is negligible, since the total volume of solution added during the entire titration is much smaller than the volume of the original [3]rotacatenane solution.
44. 6+ allows us to calculate the percentage populations of the state under equilibrium conditions.
45. 6+.
46. 4+; see Figure S7 in the Supporting Information.
47. C. J. Bruns, S. Basu, J. F. Stoddart, Tetrahedron Lett. 2010, 51, 983-986.
48. M. J. Plater, T. Jackson, Tetrahedron 2003, 59, 4673-4685.
49. M. J. Bayer, A. Herzog, M. Diaz, G. A. Harakas, H. Lee, C. B. Knobler, M. F. Hawthorne, Chem. Eur. J. 2003, 9, 2732-2744.