A bis-exTTF macrocyclic receptor that associates C60 with micromolar affinity

Journal of the American Chemical Society

Volumn 132, Issue 6, 2010, Pages 1772-1773

  Isla, Helena ^a   Gallego, María ^a   Pérez, Emilio M ^a,b   Viruela, Rafael ^c   Ort, Enrique ^c   Martín, Nazario ^a,b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

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

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING CONSTANT; MACROCYCLIC RECEPTORS; ORDERS OF MAGNITUDE; ROOM TEMPERATURE;

OPTICAL DEVICES;

ANTHRACENE DERIVATIVE; BIS 2 [ 9 ( 1,3 DITHIOL 2 YLIDENE)ANTHRACENE 10 (9H)YLIDENE] 1,3 DITHIOLE; CHLOROBENZENE; FULLERENE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CYCLIZATION; MAGNITUDE ESTIMATION METHOD; MOLECULAR STABILITY; ROOM TEMPERATURE; STOICHIOMETRY; SYNTHESIS;

EID: 77249143416     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910107m     Document Type: Article

References (25)

1. Pérez, E. M.; Martín, N. Chem. Soc. Rev. 2008, 37, 1512.
2. Tashiro, K.; Aida, T. Chem. Soc. Rev. 2007, 36, 189.
3. Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250.
4. Steed, J. W.; Junk, P. C.; Atwood, J. L.; Barnes, M. J.; Raston, C. L.; Burkhalter, R. S. J. Am. Chem. Soc. 1994, 116, 10346.
5. Huerta, E.; Metselaar, G. A.; Fragoso, A.; Santos, E.; Bo, C.; de Mendoza, J. Angew. Chem., Int. Ed. 2007, 46, 202.
6. Sygula, A.; Fronczek, F. R.; Sygula, R.; Rabideau, P. W.; Olmstead, M. M. J. Am. Chem. Soc. 2007, 129, 3842.
7. Mizyed, S.; Georghiou, P.; Bancu, M.; Cuadra, B.; Rai, A. K.; Cheng, P.; Scott, L. T. J. Am. Chem. Soc. 2001, 123, 12770.
8. Kawase, T.; Tanaka, K.; Shiono, N.; Seirai, Y.; Oda, M. Angew. Chem., Int. Ed. 2004, 43, 1722.
9. Kawase, T.; Tanaka, K.; Seirai, Y.; Shiono, N.; Oda, M. Angew. Chem., Int. Ed. 2003, 42, 5597.
10. Kawase, T.; Tanaka, K.; Fujiwara, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. 2003, 42, 1624.
11. Gayathri, S. S.; Wielopolski, M.; Pérez, E. M.; Fernández, G.; Sánchez, L.; Viruela, R.; Ortí, E.; Guldi, D. M.; Martín, N. Angew. Chem., Int. Ed. 2009, 48, 815.
12. Pérez, E. M.; Capodilupo, A. L.; Fernández, G.; Sánchez, L.; Viruela, P. M.; Viruela, R.; Ortí, E.; Bietti, M.; Martín, N. Chem. Commun. 2008, 4567.
13. Pérez, E. M.; Sierra, M.; Sánchez, L.; Torres, M. R.; Viruela, R.; Viruela, P. M.; Ortí, E.; Martín, N. Angew. Chem., Int. Ed. 2007, 46, 1847.
14. Pérez, E. M.; Sánchez, L.; Fernández, G.; Martín, N. J. Am. Chem. Soc. 2006, 128, 7172.
15. Zheng, J.-Y.; Tashiro, K.; Hirabayashi, Y.; Kinbara, K.; Saigo, K.; Aida, T.; Sakamoto, S.; Yamaguchi, K. Angew. Chem., Int. Ed. 2001, 40, 1857.
16. Yanagisawa, M.; Tashiro, K.; Yamasaki, M.; Aida, T. J. Am. Chem. Soc. 2007, 129, 11912.
17. a ) 3.01 in PhCl at room temperature.
18. a ) 8.4 (2.5.
19. The BH&H functional has been shown to provide good performance for supramolecular systems dominated by dispersion interactions (see: Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2007, 3, 289). The Z and E isomers define cavities of similar size.
20. As might be expected, the magnitude of the shielding effect is significantly smaller than that observed for porphyrin-based receptors (see ref 2) since in our case (as opposed to the strong ring currents of porphyrins) the shielding capacity of 2 is comparable to that of the aromatic solvent.
21. Hosseini, A.; Taylor, S.; Accorsi, G.; Armaroli, N.; Reed, C. A.; Boyd, P. D. W. J. Am. Chem. Soc. 2006, 128, 15903.
22. Wu, Z.-Q.; Shao, X.-B.; Li, C.; Hou, J.-L.; Wang, K.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2005, 127, 17460.
23. Fernández, G.; Sánchez, L.; Pérez, E. M.; Martín, N. J. Am. Chem. Soc. 2008, 130, 10674.
24. Fernández, G.; Pérez, E. M.; Sánchez, L.; Martín, N. J. Am. Chem. Soc. 2008, 130, 2410.
25. Fernández, G.; Pérez, E. M.; Sánchez, L.; Martín, N. Angew. Chem., Int. Ed. 2008, 47, 1094.