Tripodal exTTF-CTV hosts for fullerenes

Journal of the American Chemical Society

Volumn 132, Issue 15, 2010, Pages 5351-5353

  Huerta, Elisa ^a   Isla, Helena ^b   Pérez, Emilio M ^b,c   Bo, Carles ^a   Martín, Nazario ^b,c   Mendoza, Javier De ^a  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ESR SPECTRA; PET PROCESS; STABLE COMPLEXES;

FULLERENES;

2 [9 (1,3 DITHIOL 2 YLIDENE)ANTHRACEN 10(9H) YLIDENE] 1,3 DITHIOLE; FULLERENE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 77951040001     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1006993     Document Type: Article

References (51)

1. Steed, J. W., Junk, P. C., Atwood, J. L., Barnes, M. J., Raston, C. L., and Burkhalter, R. S. J. Am. Chem. Soc. 1994, 116, 10346
2. Huerta, E., Metselaar, G. A., Fragoso, A., Santos, E., Bo, C., and de Mendoza, J. Angew. Chem., Int. Ed. 2007, 46, 202
3. Huerta, E., Cequier, E., and de Mendoza, J. Chem. Commun. 2007, 5016
4. Mendoza, J. D., Huerta Martinez, E., and Metselaar, G.; Institut Catala DInvestigacio Quimica, Spain; Application: US, 2008; 20 pp.
5. Hosseini, A., Taylor, S., Accorsi, G., Armaroli, N., Reed, C. A., and Boyd, P. D. W. J. Am. Chem. Soc. 2006, 128, 15903
6. Atwood, J. L., Barbour, L. J., Nichols, P. J., Raston, C. L., and Sandoval, C. A. Chem.-Eur. J. 1999, 5, 990
7. Nielsen, K. A., Martin-Gomis, L., Sarova, G. H., Sanguinet, L., Gross, D. E., Fernández-Lazaro, F., Stein, P. C., Levillain, E., Sessler, J. L., Guldi, D. M., Sastre-Santos, A., and Jeppesen, J. O. Tetrahedron 2008, 64, 8449
8. Nielsen, K. A., Sarova, G. H., Martin-Gomis, L., Fernández-Lazaro, F., Stein, P. C., Sanguinet, L., Levillain, E., Sessler, J. L., Guldi, D. M., Sastre-Santos, A., and Jeppesen, J. O. J. Am. Chem. Soc. 2008, 130, 460
9. Mizyed, S., Georghiou, P., Bancu, M., Cuadra, B., Rai, A. K., Cheng, P., and Scott, L. T. J. Am. Chem. Soc. 2001, 123, 12770
10. Georghiou, P. E., Tran, A. H., Mizyed, S., Bancu, M., and Scott, L. T. J. Org. Chem. 2005, 70, 6158
11. Georghiou, P. E., Dawe, L. N., Tran, H.-A., Strube, J., Neumann, B., Stammler, H.-G., and Kuck, D. J. Org. Chem. 2008, 73, 9040
12. Matsubara, H., Shimura, T., Hasegawa, A., Semba, M., Asano, K., and Yamamoto, K. Chem. Lett. 1998, 1099
13. Nierengarten, J.-F. Fullerenes, Nanotubes, Carbon Nanostruct. 2005, 13, 229
14. Hardie, M. J., Godfrey, P. D., and Raston, C. L. Chem.-Eur. J. 1999, 5, 1828
15. Pérez, E. M., Sánchez, L., Fernández, G., and Martin, N. J. Am. Chem. Soc. 2006, 128, 7172
16. Pérez, E. M., Capodilupo, A. L., Fernández, G., Sánchez, L., Viruela, P. M., Viruela, R., Orti, E., Bietti, M., and Martin, N. Chem. Commun. 2008, 4567
17. Gayathri, S. S., Wielopolski, M., Pérez, E. M., Fernández, G., Sánchez, L., Viruela, R., Orti, E., Guldi, D. M., and Martin, N. Angew. Chem., Int. Ed. 2009, 48, 815
18. Pérez, E. M. and Martín, N. Chem. Soc. Rev. 2008, 37, 1512
19. Isla, H., Gallego, M., Pérez, E. M., Viruela, R., Ortí, E., and Martín, N. J. Am. Chem. Soc. 2010, 132, 1772
20. In fact, these changes correspond to the (partial) formation of the exTTF radical cation; see
21. Jones, A. E., Christensen, C. A., Perepichka, D. F., Batsanov, A. S., Beeby, A., Low, P. J., Bryce, M. R., and Parker, A. W. Chem.-Eur. J. 2001, 7, 973
22. Guldi, D. M., Sánchez, L., and Martín, N. J. Phys. Chem. B 2001, 105, 7139
23. Schalley, C. Editor Analytical Methods in Supramolecular Chemistry, 2007.
24. Tashiro, K. and Aida, T. Chem. Soc. Rev. 2007, 36, 189-197
25. Zheng, J.-Y., Tashiro, K., Hirabayashi, Y., Kinbara, K., Saigo, K., Aida, T., Sakamoto, S., and Yamaguchi, K. Angew. Chem., Int. Ed. 2001, 40, 1857
26. Yanagisawa, M., Tashiro, K., Yamasaki, M., and Aida, T. J. Am. Chem. Soc. 2007, 129, 11912
27. Baerends, E. J., Ellis, D. E., and Ros, P. Chem. Phys. 1973, 2, 41
28. Baerends, E. J. and Ros, P. Chem. Phys. 1973, 2, 52
29. Guerra, C. F., Snijders, J. G., Te Velde, G., and Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391
30. Te Velde, G. and Baerends, E. J. J. Comput. Phys. 1992, 99, 84
31. Boerrigter, P. M., Te Velde, G., and Baerends, E. J. Int. J. Quantum Chem. 1988, 33, 87
32. Vosko, S. H., Wilk, L., and Nusair, M. Can. J. Phys. 1980, 58, 1200
33. Becke, A. D. Phys. Rev. A 1986, 33, 2786
34. Becke, A. D. Phys. Rev. A 1988, 38, 3098
35. Levy, M. and Perdew, J. P. J. Chem. Phys. 1986, 84, 4519
36. For a comprehensive comparative study of the performance of different DFT functionals for the evaluation of supramolecular systems, see
37. Zhao, Y. and Truhlar, D. G. J. Chem. Theory Comput. 2007, 3, 289. The authors demonstrate that BH&H is reliable for systems dominated by dispersion interactions, such as ours
38. •-@ exTTF-CTV (see
39. Fukuzumi, S., Mori, H., Suenobu, T., Gao, X., and Kadish, K. M. J. Phys. Chem. A 2000, 104, 10688)
40. + since similar compounds show ESR signals with g = 2.0028-2.0034
41. Perepichka, D. M., Bryce, M. R., Perepichka, I. F., Lyubchik, S. B., Christensen, C. A., Godbert, N., Batsanov, A. S., Levillain, E., McInnes, E. J. L., and Zhao, J. P. J. Am. Chem. Soc. 2002, 124, 14227)
42. Most probably, it is due to the overlap of both signals.
43. For recent reviews on the supramolecular chemistry of TTF derivatives, see
44. Canevet, D., Salle, M., Zhang, G., Zhang, D., and Zhu, D. Chem. Commun. 2009, 2245
45. Pérez, E. M., Illescas, B. M., Herranz, M. A., and Martín, N. New J. Chem. 2009, 33, 228
46. 60 derivatives, see
47. Fernández, G., Sánchez, L., Pérez, E. M., and Martin, N. J. Am. Chem. Soc. 2008, 130, 10674
48. Fernández, G., Pérez, E. M., Sánchez, L., and Martin, N. J. Am. Chem. Soc. 2008, 130, 2410
49. Fernández, G., Pérez, E. M., Sánchez, L., and Martin, N. Angew. Chem., Int. Ed. 2008, 47, 1094
50. For an example of enantioselective sensing of chiral fullerenes, see
51. Shoji, Y., Tashiro, K., and Aida, T. J. Am. Chem. Soc. 2006, 128, 10690