Macrocyclic hosts for fullerenes: Extreme changes in binding abilities with small structural variations.

Journal of the American Chemical Society

Volumn 133, Issue 9, 2011, Pages 3184-3190

  Canevet, David ^a   Gallego, María ^b   Isla, Helena ^b   De Juan, Alberto ^b   Pérez, Emilio M ^a,b   Martín, Nazario ^a,b  

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

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ABILITIES; BINDING CONSTANT; DIFFERENT SIZES; DIMETHYLNAPHTHALENE; M-XYLENE; MACROCYCLES; MACROCYCLIC RECEPTORS; MACROCYCLICS; ORGANIC RECEPTORS; P-XYLENE; RING CLOSING METATHESIS; SMALL VARIATIONS; STRUCTURAL VARIATIONS; TETRATHIAFULVALENES;

AROMATIC HYDROCARBONS; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; NAPHTHALENE; OLEFINS; STOICHIOMETRY; XYLENE;

FULLERENES;

FULLERENE DERIVATIVE; NAPHTHALENE DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE; XYLENE;

ARTICLE; BINDING AFFINITY; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; NONHUMAN; RING CLOSING METATHESIS; STRUCTURE ANALYSIS;

EID: 79952269541     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja111072j     Document Type: Article

References (81)

1. Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162
2. Effing, J.; Jonas, U.; Jullien, L.; Plesnivy, T.; Ringsdorf, H.; Diederich, F.; Thilgen, C.; Weinstein, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1599
3. Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström, O. Chem. Commun. 1992, 604
4. For reviews, see: Pérez, E. M.; Martín, N. Pure Appl. Chem. 2010, 82, 523-533
5. Pérez, E. M.; Martín, N. Chem. Soc. Rev. 2008, 37, 1512-1519
6. Tashiro, K.; Aida, T. Chem. Soc. Rev. 2007, 36, 189-197
7. Kawase, T.; Oda, M. Pure Appl. Chem. 2006, 78, 831-839
8. Boyd, P. D. W.; Reed, C. A. Acc. Chem. Res. 2005, 38, 235-242
9. For recent examples, see: Franco, J. U.; Hammons, J. C.; Rios, D.; Olmstead, M. M. Inorg. Chem. 2010, 49, 5120-5125
10. Shoji, Y.; Tashiro, K.; Aida, T. J. Am. Chem. Soc. 2010, 132, 5928-5929
11. Huerta, E.; Isla, H.; Pérez, E. M.; Bo, C.; Martín, N.; de Mendoza, J. J. Am. Chem. Soc. 2010, 132, 5351-5353
12. Balandier, J.-Y.; Chas, M.; Dron, P. I.; Goeb, S.; Canevet, D.; Belyasmine, A.; Allain, M.; Sallé, M. J. Org. Chem. 2010, 75, 1589-1599
13. Zhang, E.-X.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. Org. Lett. 2008, 10, 2565-2568
14. Xiao, W.; Passerone, D.; Ruffieux, P.; Aiet-Mansour, K.; Gröning, O.; Tosatti, E.; Siegel, J. S.; Fasel, R. J. Am. Chem. Soc. 2008, 130, 4767-4771
15. Pérez, E. M.; Capodilupo, A. L.; Fernández, G.; Sánchez, L.; Viruela, P. M.; Viruela, R.; Ortí, E.; Bietti, M.; Martín, N. Chem. Commun. 2008, 4567-4569
16. Marois, J.-S.; Cantin, K.; Desmarais, A.; Morin, J.-F. Org. Lett. 2008, 10, 33-36
17. Liu, S.-Q.; Wang, D.-X.; Zheng, Q.-Y.; Wang, M.-X. Chem. Commun. 2007, 3856-3858
18. 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, 1847-1851
19. Sygula, A.; Fronczek, F. R.; Sygula, R.; Rabideau, P. W.; Olmstead, M. M. J. Am. Chem. Soc. 2007, 129, 3842-3843
20. Huerta, E.; Metselaar, G. A.; Fragoso, A.; Santos, E.; Bo, C.; de Mendoza, J. Angew. Chem., Int. Ed. 2007, 46, 202-205
21. Huerta, E.; Cequier, E.; de Mendoza, J. Chem. Commun. 2007, 5016-5018
22. Yanagisawa, M.; Tashiro, K.; Yamasaki, M.; Aida, T. J. Am. Chem. Soc. 2007, 129, 11912-11913
23. Pérez, E. M.; Sánchez, L.; Fernández, G.; Martín, N. J. Am. Chem. Soc. 2006, 128, 7172-7173
24. Hosseini, A.; Taylor, S.; Accorsi, G.; Armaroli, N.; Reed, C. A.; Boyd, P. D. W. J. Am. Chem. Soc. 2006, 128, 15903-15913
25. Shoji, Y.; Tashiro, K.; Aida, T. J. Am. Chem. Soc. 2006, 128, 10690-10691
26. For a review on fullerene materials constructed by self-assembly, see: Nakanishi, T. Chem. Commun. 2010, 46, 3425-3436 For selected recent examples, see: Xue, P.; Lu, R.; Zhao, L.; Xu, D.; Zhang, X.; Li, K.; Song, Z.; Yang, X.; Takafuji, M.; Ihara, H. Langmuir 2010, 26, 6669-6675
27. Haino, T.; Hirai, E.; Fujiwara, Y.; Kashihara, K. Angew. Chem., Int. Ed. 2010, 49, 7899-7903
28. Zhang, X.; Takeuchi, M. Angew. Chem., Int. Ed. 2009, 48, 9646-9651
29. D'Souza, F.; Maligaspe, E.; Ohkubo, K.; Zandler, M. E.; Subbaiyan, N. K.; Fukuzumi, S. J. Am. Chem. Soc. 2009, 131, 8787-8797
30. Wang, J.; Shen, Y.; Kessel, S.; Fernandes, P.; Yoshida, K.; Yagai, S.; Kurth, D. G.; Mohwald, H.; Nakanishi, T. Angew. Chem., Int. Ed. 2009, 48, 2166-2170
31. Tsunashima, R.; Noro, S.-i.; Akutagawa, T.; Nakamura, T.; Kawakami, H.; Toma, K. Chem.-Eur. J. 2008, 14, 8169-8176
32. Nakanishi, T.; Michinobu, T.; Yoshida, K.; Shirahata, N.; Ariga, K.; Mohwald, H.; Kurth, D. G. Adv. Mater. 2008, 20, 443-446
33. Fernández, G.; Sánchez, L.; Pérez, E. M.; Martín, N. J. Am. Chem. Soc. 2008, 130, 10674-10683
34. Fernández, G.; Pérez, E. M.; Sánchez, L.; Martín, N. J. Am. Chem. Soc. 2008, 130, 2410-2411
35. Fernández, G.; Pérez, E. M.; Sánchez, L.; Martín, N. Angew. Chem., Int. Ed. 2008, 47, 1094-1097
36. Araki, Y.; Chitta, R.; Sandanayaka, A. S. D.; Langenwalter, K.; Gadde, S.; Zandler, M. E.; Ito, O.; D'Souza, F. J. Phys. Chem. C 2008, 112, 2222-2229
37. Barrau, S.; Heiser, T.; Richard, F.; Brochon, C.; Ngov, C.; van de Wetering, K.; Hadziioannou, G.; Anokhin, D. V.; Ivanov, D. A. Macromolecules 2008, 41, 2701-2710
38. Schmittel, M.; He, B.; Mal, P. Org. Lett. 2008, 10, 2513-2516
39. Yoshimoto, S.; Tsutsumi, E.; Narita, R.; Murata, Y.; Murata, M.; Fujiwara, K.; Komatsu, K.; Ito, O.; Itaya, K. J. Am. Chem. Soc. 2007, 129, 4366-4376
40. Wessendorf, F.; Gnichwitz, J.-F.; Sarova, G. H.; Hager, K.; Hartnagel, U.; Guldi, D. M.; Hirsch, A. J. Am. Chem. Soc. 2007, 129, 16057-16071
41. Zhong, Y.-W.; Matsuo, Y.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 3052-3053
42. Hahn, U.; Gegout, A.; Duhayon, C.; Coppel, Y.; Saquet, A.; Nierengarten, J.-F. Chem. Commun. 2007, 516-518
43. Bonifazi, D.; Kiebele, A.; Stohr, M.; Cheng, F.; Jung, T.; Diederich, F.; Spillmann, H. Adv. Funct. Mater. 2007, 17, 1051-1062
44. Pan, G.-B.; Cheng, X.-H.; Hoeger, S.; Freyland, W. J. Am. Chem. Soc. 2006, 128, 4218-4219
45. Nielsen, K. A.; Sarova, G. H.; Martín-Gomis, L.; Fernández-Lazaro, F.; Stein, P. C.; Sanguinet, L.; Levillain, E.; Sessler, J. L.; Guldi, D. M.; Sastre-Santos, A.; Jeppesen, J. O. J. Am. Chem. Soc. 2008, 130, 460-462
46. Haino, T.; Matsumoto, Y.; Fukazawa, Y. J. Am. Chem. Soc. 2005, 127, 8936-8937
47. Haino, T.; Yanase, M.; Fukunaga, C.; Fukazawa, Y. Tetrahedron 2006, 62, 2025-2035
48. Haino, T.; Fukunaga, C.; Fukazawa, Y. Org. Lett. 2006, 8, 3545-3548
49. Haino, T.; Araki, H.; Fujiwara, Y.; Tanimoto, Y.; Fukazawa, Y. Chem. Commun. 2002, 2148-2149
50. Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. 1998, 37, 997-998
51. Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. 1997, 36, 259-260
52. Wu, J.-C.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. Tetrahedron Lett. 2009, 50, 7209-7212
53. Raston, C. L.; Atwood, J. L.; Nichols, P. J.; Sudria, I. B. N. Chem. Commun. 1996, 2615-2616
54. Araki, K.; Akao, K.; Ikeda, A.; Suzuki, T.; Shinkai, S. Tetrahedron Lett. 1996, 37, 73-76
55. Rio, Y.; Nierengarten, J.-F. Tetrahedron Lett. 2002, 43, 4321-4324
56. Felder, D.; Heinrich, B.; Guillon, D.; Nicoud, J.-F.; Nierengarten, J.-F. Chem.-Eur. J. 2000, 6, 3501-3507
57. Nierengarten, J.-F.; Oswald, L.; Eckert, J.-F.; Nicoud, J.-F.; Armaroli, N. Tetrahedron Lett. 1999, 40, 5681-5684
58. Matsubara, H.; Shimura, T.; Hasegawa, A.; Semba, M.; Asano, K.; Yamamoto, K. Chem. Lett. 1998, 1099-1100
59. Atwood, J. L.; Barnes, M. J.; Gardiner, M. G.; Raston, C. L. Chem. Commun. 1996, 1449-1450
60. Steed, J. W.; Junk, P. C.; Atwood, J. L.; Barnes, M. J.; Raston, C. L.; Burkhalter, R. S. J. Am. Chem. Soc. 1994, 116, 10346-10347
61. Mueck-Lichtenfeld, C.; Grimme, S.; Kobryn, L.; Sygula, A. Phys. Chem. Chem. Phys. 2010, 12, 7091-7097
62. Georghiou, P. E.; Tran, A. H.; Mizyed, S.; Bancu, M.; Scott, L. T. J. Org. Chem. 2005, 70, 6158-6163
63. Mizyed, S.; Georghiou, P.; Bancu, M.; Cuadra, B.; Rai, A. K.; Cheng, P.; Scott, L. T. J. Am. Chem. Soc. 2001, 123, 12770-12774
64. Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250-5273
65. Kawase, T.; Tanaka, K.; Shiono, N.; Seirai, Y.; Oda, M. Angew. Chem., Int. Ed. 2004, 43, 1722-1724
66. Kawase, T.; Fujiwara, N.; Tsutumi, M.; Oda, M.; Maeda, Y.; Wakahara, T.; Akasaka, T. Angew. Chem., Int. Ed. 2004, 43, 5060-5062
67. Kawase, T.; Tanaka, K.; Seirai, Y.; Shiono, N.; Oda, M. Angew. Chem., Int. Ed. 2003, 42, 5597-5600
68. Sato, H.; Tashiro, K.; Shinmori, H.; Osuka, A.; Murata, Y.; Komatsu, K.; Aida, T. J. Am. Chem. Soc. 2005, 127, 13086-13087
69. Shoji, Y.; Tashiro, K.; Aida, T. J. Am. Chem. Soc. 2004, 126, 6570-6571
70. Ayabe, M.; Ikeda, A.; Kubo, Y.; Takeuchi, M.; Shinkai, S. Angew. Chem., Int. Ed. 2002, 41, 2790-2792
71. Sun, D.; Tham, F. S.; Reed, C. A.; Chaker, L.; Boyd, P. D. W. J. Am. Chem. Soc. 2002, 124, 6604-6612
72. Kubo, Y.; Sugasaki, A.; Ikeda, M.; Sugiyasu, K.; Sonoda, K.; Ikeda, A.; Takeuchi, M.; Shinkai, S. Org. Lett. 2002, 4, 925-928
73. Zheng, J.-Y.; Tashiro, K.; Hirabayashi, Y.; Kinbara, K.; Saigo, K.; Aida, T.; Sakamoto, S.; Yamaguchi, K. Angew. Chem., Int. Ed. 2001, 40, 1857-1861
74. Gil-Ramírez, G.; Karlen, S. D.; Shundo, A.; Porfyrakis, K.; Ito, Y.; Briggs, G. A. D.; Morton, J. J. L.; Anderson, H. L. Org. Lett. 2010, 12, 3544-3547
75. Song, J.; Aratani, N.; Shinokubo, H.; Osuka, A. J. Am. Chem. Soc. 2010, 132, 16356-16357
76. Isla, H.; Gallego, M.; Pérez, E. M.; Viruela, R.; Ortí, E.; Martín, N. J. Am. Chem. Soc. 2010, 132, 1772-1773
77. 60 can bee seen in ref 12.
78. Minimizations were carried out utilizing the AMBER force field included in the HyperChem molecular modelling system. The AMBER force field was selected because it includes a term for van der Waals and electrostatic interactions. See: Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179 In the case of p -xylmac12, we have previously reported calculations at the DFT (BH&H/6-31G) level (see ref 12). Because of the size of the collection of macrocycles, in this case we have resorted to less demanding molecular mechanics. The geometry optimization yields nearly identical results with both approaches. All optimizations were carried out with the E isomer of the corresponding macrocycle. We have previously shown that there is hardly any difference between the cavities of the E and Z macrocycles (see ref 12).
79. Mizyed, S.; Georghiou, P. E.; Ashram, M. J. Chem. Soc., Perkin Trans. 2 2000, 277-280
80. Semenov, K. N.; Charykov, N. A.; Keskinov, V. A.; Piartman, A. K.; Blokhin, A. A.; Kopyrin, A. A. J. Chem. Eng. Data 2010, 55, 13-36
81. 3 and o -DCB, respectively: Pal, D.; Goswami, D.; Nayak, S. K.; Chattopadhyay, S.; Bhattacharya, S. J. Phys. Chem. A 2010, 114, 6776-6786