Redox-responsive porphyrin-based molecular tweezers

Chemistry - A European Journal

Volumn 18, Issue 25, 2012, Pages 7648-7653

  Iordache, Adriana ^a   Retegan, Marius ^a   Thomas, Fabrice ^a   Royal, Guy ^a   Saint Aman, Eric ^a   Bucher, Christophe ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Bisporphyrins; Electron transfer; Molecular motion; Molecular tweezers; P dimer

Indexed keywords

BISPORPHYRINS; ELECTRON TRANSFER; MOLECULAR MOTIONS; MOLECULAR TWEEZERS; P-DIMER;

PORPHYRINS;

DIMERS;

EID: 84862604745     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200842     Document Type: Article

References (45)

1. C. A. Nijhuis, B. J. Ravoo, J. Huskens, D. N. Reinhoudt, Coord. Chem. Rev. 2007, 251, 1761-1780.
2. G. Pognon, J. A. Wytko, J. Weiss, J. Targets Heterocycl. Syst. 2007, 11, 21-43.
3. (a) J. P. Collman, J. E. Hutchison, M. S. Ennis, M. A. Lopez, R. Guilard, J. Am. Chem. Soc. 1992, 114, 8074-8080
4. (b) C. K. Chang, H. Y. Liu, I. Abdalmuhdi, J. Am. Chem. Soc. 1984, 106, 2725-2726.
5. a) P. D. Harvey, C. Stern, C. P. Gros, R. Guilard, Coord. Chem. Rev. 2007, 251, 401-428
6. (b) J. P. Collman, R. Boulatov, C. J. Sunderland, L. Fu, Chem. Rev. 2004, 104, 561-588.
7. B. Habermeyer, A. Takai, C. P. Gros, M. El Ojaimi, J.-M. Barbe, S. Fukuzumi, Chem. Eur. J. 2011, 17, 10670-10681.
8. a) G. Pognon, C. Boudon, K. J. Schenk, M. Bonin, B. Bach, J. Weiss, J. Am. Chem. Soc. 2006, 128, 3488-3489
9. (b) D. Jokic, C. Boudon, G. Pognon, M. Bonin, K. J. Schenk, M. Gross, J. Weiss, Chem. Eur. J. 2005, 11, 4199-4209.
10. Porphyrin radical cations have also been shown to form p-dimers. See for instance a) K. E. Brancato-Buentello, S.-J. Kang, W. R. Scheidt, J. Am. Chem. Soc. 1997, 119, 2839-2846
11. (b) A. Takai, C. P. Gros, J.-M. Barbe, R. Guilard, S. Fukuzumi, Chem. Eur. J. 2009, 15, 3110-3122
12. (c) J. Fajer, D. C. Borg, A. Forman, D. Dolphin, R. H. Felton, J. Am. Chem. Soc. 1992, 114, 3451-3459
13. (d) H. Song, C. A. Reed, W. R. Scheidt, J. Am. Chem. Soc. 1989, 111, 6867-6868
14. (e) J. H. Fuhrhop, P. Wasser, D. Riesner, D. Mauzerall, J. Am. Chem. Soc. 1972, 94, 7796-7801
15. (f) R. Guilard, J. M. Barbe, P. Richard, P. Petit, J. J. Andre, C. Lecomte, K. M. Kadish, J. Am. Chem. Soc. 1989, 111, 4684-4687.
16. a) J. W. Park, N. H. Choi, J. H. Kim, J. Phys. Chem. 1996, 100, 769-774
17. (b) W. S. Jeon, H.-J. Kim, C. Lee, K. Kim, Chem. Commun. 2002, 1828-1829
18. (c) M. Itoh, E. M. Kosower, J. Am. Chem. Soc. 1968, 90, 1843-1849.
19. (a) A. Trabolsi, N. Khashab, A. C. Fahrenbach, D. C. Friedman, M. T. Colvin, K. K. Cotí, E. Tkatchouk, J.-C. Olsen, M. E. Belowich, R. Carmielli, H. A. Khatib, W. A. Goddard, M. R. Wasielewski, J. F. Stoddart, Nat. Chem. 2010, 2, 42-49
20. (b) H. Li, A. C. Fahrenbach, A. Coskun, Z. Zhu, G. Barin, Y.-L. Zhao, Y. Y. Botros, J.-P. Sauvage, J. F. Stoddart, Angew. Chem. 2011, 123, 6914-6920
21. (c) A. Iordache, M. Oltean, A. Milet, F. Thomas, E. Saint-Aman, C. Bucher, J. Am. Chem. Soc. 2012, 134, 2653-2671
22. (d) A. Coskun, J. M. Spruell, G. Barin, A. C. Fahrenbach, R. S. Forgan, M. T. Colvin, R. Carmieli, E. Tkatchouk, D. C. Friedman, A. A. Sarjeant, M. R. Wasielewski, W. A. Goddard III, J. F. Stoddart, J. Am. Chem. Soc. 2011, 133, 4538-4547.
23. (a) P. Neta, M.-C. Richoux, A. Harriman, J. Chem. Soc. Faraday Trans. 2 1985, 81, 1427-1443
24. (b) R. Kannappan, C. Bucher, E. Saint-Aman, J.-C. Moutet, A. Milet, M. Oltean,S. Pellet- Rostaing, M. Lemaire, C. Chaix, New J. Chem. 2010, 34, 1373-1386
25. (c) W. Geuder, S. Huenig, A. Suchy, Tetrahedron 1986, 42, 1665-1677
26. (d) M. Furue, S.-I. Nozakura, Chem. Lett. 1980, 821-824
27. (e) A. Deronzier, B. Galland, E. Viera, Nouv. J. Chim. 1982, 6, 97-100
28. (f) S. J. Atherton, K. Tsukahara, R. G. Wilkins, J. Am. Chem. Soc. 1986, 108, 3380-3385.
29. (a) B. Emmert, N. Roh, Ber. Dtsch. Chem. Ges. 1925, 58, 503-508
30. (b) T. Zinke, Liebigs Ann. Chem. 1904, 330, 361-374
31. (c) J. G. Allen, Ger. Offen., DE2527638, 1976.
32. P. M. S. Monk, The Viologens: Physicochemical Properties, Synthesis and Applications of the Salts of 4,4' Bipyridine, J. Wiley and Sons, 1998, pp. 33-40.
33. It has been theoretically demonstrated that electron-transfers to or from molecules containing n identical, noninteracting, electroactive centres should yield a single current-potential CV curve similar to that observed with a single electroactive centre (DEp=58 mV at 2581) but with a magnitude determined by the total number [n] of redox centres. See, J. B. Flanagan, S. Margel, A. J. Bard, F. C. Anson, J. Am. Chem. Soc. 1978, 100, 4248-4253.
34. D. E. Richardson, H. Taube, Inorg. Chem. 1981, 20, 1278-1285.
35. With simple N-alkylated bipyridiniums, such supramolecular associations are observed at very low temperatures or at high concentrations of radicals in aqueous media. See, A. G. Evans, J. C. Evans, M. W. Baker, J. Am. Chem. Soc. 1977, 99, 5882-5884.
36. E. M. Kosower, J. L. Cotter, J. Am. Chem. Soc. 1964, 86, 5524-5527.
37. (a) G. Pognon, J. A. Wytko, P. D. Harvey, J. Weiss, Chem. Eur. J. 2009, 15, 524-535
38. (b) C. J. Chang, Y. Deng, A. F. Heyduk, C. K. Chang, D. G. Nocera, Inorg. Chem. 2000, 39, 959-966.
39. -5m.
40. This value is indeed smaller than those observed with bisporphyrins held in close proximity through rigid spacers. See ref. [17a].
41. (a) X. Chi, A. J. Guerin, R. A. Haycock, C. A. Hunter, L. D. Sarson, J. Chem. Soc. Chem. Commun. 1995, 2563-2565
42. (b) X. Chi, A. J. Guerin, R. A. Haycock, C. A. Hunter, L. D. Sarson, J. Chem. Soc. Chem. Commun. 1995, 2567-2569.
43. (a) At this point, each metal center is bound to one DABCO ligand to form a 1:2/6Zn2 4+:DABCO complex. See a) C. A. Hunter, R. Tregonning, Tetrahedron 2002, 58, 691-697
44. (b) P. Ballester, A. I. Oliva, A. Costa, P. M. Deya, A. Frontera, R. M. Gomila, C. A. Hunter, J. Am. Chem. Soc. 2006, 128, 5560-5569.
45. The distance between both metal centers in [6Zn2ACHTUNGTRENUNG(DABCO)2+ ]dim (in,in) has been estimated at 6.86 Å by theoretical calculations. This value is similar to that of 6.9 Å measured at the solid state for 2:1 TPPZn:DABCO sandwich complexes. See for instance B. Cheng, W. Scheidt, Inorg. Chim. Acta 1995, 237, 5-11