Electrochemically controlled formation/dissociation of phosphonate- cavitand/methylpyridinium complexes

Chemistry - A European Journal

Volumn 14, Issue 29, 2008, Pages 8964-8971

  Gadenne, Benoît ^a   Semeraro, Monica ^a   Yebeutchou, Roger M ^b   Tancini, Francesca ^b   Pirondini, Laura ^b   Dalcanale, Enrico ^b   Credi, Alberto ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

Cavitands; Electrochemistry; Host guest systems; Luminescence; Supramolecular chemistry

Indexed keywords

CHEMISTRY; ELECTROCHEMICAL PROPERTIES; FLUORESCENCE; LIGHT EMISSION; LUMINESCENCE; MATERIALS PROPERTIES; PHOSPHORUS; QUENCHING; REDUCTION; SUPRAMOLECULAR CHEMISTRY;

CAVITAND; CAVITANDS; ELECTROCHEMICAL STIMULUS; ELECTRON REDUCTIONS; HOST-GUEST SYSTEMS; NANOSCALE DEVICES; PHOSPHONATE; REDOX PROCESSES; REDUCTION POTENTIALS; SPECTROELECTROCHEMICAL MEASUREMENTS; STRUCTURE AND PROPERTIES; SUPRAMOLECULAR COMPLEXES; SUPRAMOLECULAR MATERIALS; SWITCHABLE; VOLTAMMETRIC;

RHENIUM COMPOUNDS;

EID: 55049124939     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800966     Document Type: Article

References (63)

1. S. Zampolli, P. Betti, I. Elmi, E. Dalcanale, Chem. Commun. 2007, 2790-2792.
2. a) V. A. Azov, A. Schlegel, F. Diederich, Bull. Chem. Soc. Jpn. 2006, 79, 1926-1940;
3. b) V. A. Azov, A. Beeby, M. Cacciarini, A. G. Cheetham, F. Diederich, M. Frei, J. K. Gimzewski, V. Gramlich, B. Hecht, B. Jaun, T. Latychevskaia, A. Lieb, Y. Lill, F. Marotti, A. Schlegel, R. R. Schlitler, P. J. Skinner, P. Sciler, Y. Yamakoshi, Adv. Funct. Mater. 2006, 16, 147-156;
4. c) V. A. Azov, A. Schlegel, F. Diederich, Angew. Chem. 2005, 117, 4711-4715;
5. Angew. Chem. Int. Ed. 2005, 44, 4635-4638;
6. d) M. Frei, F. Diederich, R. Tremont, T. Rodriguez, L. Echegoyen, Helv. Chim. Acta 2006, 89, 2040-2057.
7. a) J. Rebek, Jr., Chem. Commun. 2007, 2777-2789;
8. b) D. Ajami, J. Rebek, Jr., J. Am. Chem. Soc. 2006, 128, 15038-15039;
9. c) M. P. Schramm, J. Rebek, Jr., Chem. Eur. J. 2006, 12, 5924-5933.
10. L. Pirondini, A. G. Stendardo, S. Geremia, M. Campagnolo, P. Samorì, J. P. Rabe, R. Fokkens, E. Dalcanale, Angew. Chem. 2003, 115, 1422-1425;
11. Angew. Chem. Int. Ed. 2003, 42, 1384-1387.
12. J.-M. Lehn, Chem. Soc. Rev. 2007, 36, 151-170.
13. Molecular Switches, 2nd ed. (Ed.: B. L. Feringa), Wiley-VCH, Weinheim, 2008.
14. V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines-Concepts and Perspectives for the Nanoworld, Wiley-VCH, Weinheim, 2008.
15. Recent examples: a) Y. H. Ling, J.T. Mague, A.E. Kaifer, Chem. Eur. J. 2007, 13, 7908-7914;
16. b) B. J. Jordan, M. A. Pollier, L. A. Miller, C. Tiernan, G. Clavier, P. Audebert, V. M. Rotello, Org. Lett. 2007, 9, 2835-2838;
17. c) S. Silvi, A. Arduini, A. Pochini, A. Secchi, M. Tomasulo, F. M. Raymo, M. Baroncini, A. Credi, J. Am. Chem. Soc. 2007, 129, 13378-13379;
18. d) S. Angelos, Y.W. Yang, K. Palel, J.F. Stoddart, J. I. Zink, Angew. Chem. 2008, 120, 2254-2258;
19. Angew. Chem. Int. Ed. 2008, 47, 2222-2226;
20. e) H. Tian, L. Feng, J. Mater. Chem. 2008, 18, 1617-1622;
21. f) K. Yamauchi, Y. Takashima, A. Hashidzume, H. Yamaguchi, A. Harada, J, Am. Chem. Soc. 2008, 130, 5024-5025.
22. For a review on phosphonate cavitands and the nomenclature adopted see: R. Pinalli, M. Suman, E. Dalcanale, Eur. J. Org. Chem. 2004, 451-462.
23. D. J. Cram, J. M. Cram, Container Molecules and Their Guests, The Royal Society of Chemistry, Cambridge, 1994.
24. P. Delangle, J.-P. Dutasta, Tetrahedron Lett. 1995, 36, 9325-9328.
25. J.-P. Dutasta, Top. Curr. Chem. 2004, 232, 55-91.
26. M. Melegari, M. Suman, L. Pirondini, D. Moiani, C. Massera, F. Ugozzoli, E. Kalenius, P. Vainiotalo, J.-C. Mulatier, J.-P. Dutasta, E. Dalcanale, Chem. Eur. J. 2008, 14, 5772-5779.
27. E. Biavardi, G. Battistini, M. Montalti, R. M. Yebeutchou, L. Prodi, E. Dalcanale, Chem. Commun. 2008, 1638-1640.
28. R. M. Yebeutchou, F. Tancini, N. Demitri, S. Geremia, R. Mendichi, E. Dalcanale, Angew. Chem. 2008, 120, 4580-4584;
29. Angew. Chem. Int. Ed. 2008, 47, 4504-4508.
30. M. Montalti, L. Prodi, Chem. Commun. 1998, 1461-1462.
31. J. W. Jones, H. W. Gibson, J. Am. Chem. Soc. 2003, 125, 7001-7004.
32. F. Huang, J.W. Jones, C. Slebodnik, H. W. Oibson, J. Am. Chem. Soc. 2003, 125, 14458-14464.
33. M. Clemente-Léon, C. Pasquini, V. Hebbe-Viton, J. Lacour, A. Dalla Cort, A. Credi, Eur. J. Org. Chem. 2006, 105-112.
34. For reviews on ion-pair recognition, see: a) M. T. Reetz, in Comprehensive Supramolecular Chemistry, Vol. 2 (Eds. ; J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vogue, J.-M. Lehn), Pergamon Press, Oxford, 1996, p. 553;
35. b) P. A. Gale, Coord. Chem. Rev. 2003, 240, 191-221;
36. c) P. A. Gale, S. E. Garcia-Garrido, J. Garric, Chem. Soc. Rev. 2008, 37, 151-190.
37. A. Credi, S. Dumas, S. Silvi, M. Venturi, A. Arduini, A. Pochini, A. Secchi, J. Org. Chem. 2004, 69, 5881-5887.
38. R. Ballardini, A. Credi, M. T. Gandolfi, C. Giansante, G. Marconi, S. Silvi, M. Venturi, Inorg. Chim. Acta 2007, 360, 1072-1082.
39. A. E. Kaifer, M. Gomez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, Chapter 9.
40. As the reduced and oxidised forms of the species considered here should exhibit very similar diffusion coefficients, we can safely assume that the standard potentials are coincident with the halfwave potentials.
41. For examples of redox-controlled assembly-disassembly of host-guest complexes, see references [8a,b,g], [21] and: a) G. Cooke, Angew. Chem. 2003, 115, 5008-5018;
42. Angew. Chem. Int. Ed. 2003, 42, 4860-4870;
43. b) W. S. Jeon, E. Kim, Y. H. Ko, I. H. Hwang, J. W. Lee, S. Y. Kim, H. J. Kim, K. Kim, Angew. Chem. 2005, 117, 89-93;
44. Angew. Chem. Int. Ed. 2005, 44, 87-91;
45. c) W. Wang, A.E. Kaifer, Angew. Chem. 2006, 118, 7200-7204;
46. Angew. Chem. Int. Ed. 2006, 45, 7042-7046;
47. d) V. Balzani, H. Bandmann, P. Ceroni, C. Giansante, U. Hahn, F.-G. Klamer, U. Müller, W. M. Müller, C. Verhaelen, V. Vicinelli, F. Vögtle, J. Am. Chem. Soc. 2006, 128, 637-648;
48. e) M. D. Pluth, K. N. Raymond, Chem. Soc. Rev. 2007, 36, 161-171;
49. f) C. A. Nijhuis, B. J. Ravoo, J. Huskens, D. N. Reinhoudt, Coord. Chem. Rev. 2007, 251, 1761-1780.
50. P. M. S. Monk, The Viologens-Physicochemical Properties, Synthesis and Applications of the Salts of 4,4'-Bipyridine, Wiley, Chichester, 1998, p. 56 and 115.
51. H.-J. Kim, W. S. Jeon, Y. H. Ko, K. Kim, Proc. Natl. Acad. Sci. USA 2002, 99, 5007-5011.
52. V. Balzani, M. Clemente-León, A. Credi, B. Ferrer, M. Venturi, A. H. Flood, J. F. Stoddart, Proc. Natl. Acad. Sci. USA 2006, 103, 1178-1183.
53. a) J.-M. Lehn, Prog. Polym. Sci. 2005, 30, 814-831;
54. b) K. Ohga, Y. Takashima, H. Takahashi, Y. Kawaguchi, H. Yamaguchi, A. Harada, Macromolecules 2005, 38, 5897-5904;
55. c) C. A. Hunter, S. Tomas, J. Am. Chem. Soc. 2006, 128, 8975-8979;
56. d) T. Park, S. C. Zimmerman, J. Am. Chem. Soc. 2006, 128, 14236-14237;
57. e) K. A. Burke, S. Sivakova, B. M. McKenzie, P. T. Mather, S. J. Rowan, J. Polym. Sci. Part A 2006, 44, 5049-5059;
58. f) H. Ohkawa, G. B. W. L. Ligthart, R. P. Sijbesma, E. W. Meijer, Macromolecules 2007, 40, 1453-1459;
59. g) F. Huang, D. S. Nagvekar, H. W. Gibson, Macromolecules 2007, 40, 3561 -3567;
60. h) T. F. A. de Greef, E. W. Meijer, Nature 2008, 453, 171-173.
61. L. M. Tunstad, J. A. Tucker, E. Dalcanale, J. Weiser, J. A. Bryant, J. C. Sherman, R. C. Hegelson, C. B. Knobler, D. J. Cram, J. Org. Chem. 1989, 54, 1305-1312.
62. A. Credi, L. Prodi, Spectrochim. Acta A 1998, 54, 159-170.
63. R. A. Binstead, SPECFIT, Spectrum Software Associates, Chapel Hill, NC, 1996.