Molecular recognition of chiral diporphyrin receptor with a macrocyclic cavity for intercalation of aromatic compounds

Bulletin of the Chemical Society of Japan

Volumn 85, Issue 1, 2012, Pages 101-109

  Ema, Tadashi ^a   Ura, Norichika ^a   Eguchi, Katsuya ^a   Sakai, Takashi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC GUESTS; BINDING CONSTANT; CHIRAL COMPOUNDS; CHIRAL DISCRIMINATION; COLLOIDAL SUSPENSIONS; DINITROPHENYL; ELECTRON-DEFICIENT; FORCE FIELDS; INCLUSION COMPLEX; MACROCYCLIC CAVITIES; NAKED-EYE; NAKED-EYE DETECTION; NITROAROMATIC COMPOUND; SELECTIVE DETECTION;

AROMATIC COMPOUNDS; AROMATIZATION; ELECTRON AFFINITY; EXPLOSIVES DETECTION; EYE PROTECTION; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PORPHYRINS; STEREOCHEMISTRY; SUSPENSIONS (FLUIDS); SYNTHESIS (CHEMICAL);

INTERCALATION COMPOUNDS;

EID: 84856002678     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20110230     Document Type: Article

References (72)

1. Recent reports on chiral recognition (enantioselective binding): a) G. Fukuhara, S. Madenci, J. Polkowska, F. Bastkowski, F.-G. Klärner, Y. Origane, M. Kaneda, T. Mori, T. Wada, Y. Inoue, Chem. Eur. J. 2007, 13, 2473.
2. b)F. Gasparrini, M. Pierini, C. Villani, A. Filippi, M. Speranza, J. Am. Chem. Soc. 2008, 130, 522.
3. c)S. Bartoli, T. Mahmood, A. Malik, S. Dixon, J. D. Kilburn, Org. Biomol. Chem. 2008, 6, 2340.
4. d)T. Haino, H. Fukuoka, H. Iwamoto, Y. Fukazawa, Supramol. Chem. 2008, 20, 51.
5. e)S. Shirakawa, A. Moriyama, S. Shimizu, Eur. J. Org. Chem. 2008, 5957.
6. f)R. Carrillo, M. López-Rodríguez, V. S. Martín, T. Martín, Angew. Chem., Int. Ed. 2009, 48, 7803.
7. g)M. E. Amato, F. P. Ba llistreri, S. Gentile, A. Pappalardo, G. A. Tomaselli, R. M. Toscano, J. Org. Chem. 2010, 75, 1437.
8. T. J. Wenzel, Discrimination of Chiral Compounds Using NMR Spectroscopy, Wiley, New Jersey, 2007.
9. Recent reports on chiral discrimination in NMR: a) F. Ma, X. Shen, X. Ming, J. Wang, J. Ou-Yang, C. Zhang, Tetrahedron: Asymmetry 2008, 19, 1576.
10. b)K. Tanaka, N. Fukuda, Tetrahedron: Asymmetry 2009, 20, 111.
11. c)S. Sambasivan, D. Kim, K. H. Ahn, Chem. Commun. 2010, 46, 541.
12. d)L. S. Moon, M. Pal, Y. Kasetti, P. V. Bharatam, R. S. Jolly, J. Org. Chem. 2010, 75, 5487.
13. e)D. P. Iwaniuk, C. Wolf, J. Org. Chem. 2010, 75, 6724.
14. f)E. Busto, A. González-Álvarez, V. Gotor-Fernández, I. Alfonso, V. Gotor, Tetrahedron 2010, 66, 6070.
15. g)M. Durmaz, M. Yilmaz, A. Sirit, Org. Biomol. Chem. 2011, 9, 571.
16. h)K. Tanaka, Y. Nakai, H. Takahashi, Tetrahedron: Asymmetry 2011, 22, 178.
17. i)N. H. Pham, T. J. Wenzel, J. Org. Chem. 2011, 76, 986.
18. a)T. Ema, D. Tanida, T. Sakai, Org. Lett. 2006, 8, 3773.
19. b)T. Ema, D. Tanida, T. Sakai, J. Am. Chem. Soc. 2007, 129, 10591.
20. c)T. Ema, D. Tanida, K. Hamada, T. Sakai, J. Org. Chem. 2008, 73, 9129.
21. d)T. Ema, D. Tanida, K. Sugita, T. Sakai, K. Miyazawa, A. Ohnishi, Org. Lett. 2008, 10, 2365.
22. e)T. Ema, K. Hamada, K. Sugita, Y. Nagata, T. Sakai, A. Ohnishi, J. Org. Chem. 2010, 75, 4492.
23. Reviews and accounts: a) J. H. Williams, Acc. Chem. Res. 1993, 26, 593.
24. b)C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc., Perkin Trans. 2 2001, 651.
25. c)E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem., Int. Ed. 2003, 42, 1210.
26. d)M. Harmata, Acc. Chem. Res. 2004, 37, 862.
27. Theoretical studies: a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525.
28. b)A. P. West, Jr., S. Mecozzi, D. A. Dougherty, J. Phys. Org. Chem. 1997, 10, 347.
29. c)M. Kamieth, F.-G. Klärner, F. Diederich, Angew. Chem. Int. Ed., 1998. 37, 3303.
30. a)J. Landauer, H. McConnell, J. Am. Chem. Soc. 1952, 74, 1221.
31. b)D. M. G. Lawrey, H. McConnell, J. Am. Chem. Soc. 1952, 74, 6175.
32. c)S. C. Zimmerman, C. M. VanZyl, J. Am. Chem. Soc. 1987, 109, 7894.
33. d)S. C. Zimmerman, C. M. VanZyl, G. S. Hamilton, J. Am. Chem. Soc. 1989, 111 , 1373.
34. e)T. Korenaga, Y. Kawauchi, T. Kosaki, T. Ema, T. Sakai, Bull. Chem. Soc. Jpn. 78, 2175.
35. f)T. Haino, T. Fujii, Y. Fukazawa, J. Org. Chem. 71, 2572.
36. g)S. L. Cockroft, J. Perkins, C. Zonta, H. Adams, S. E. Spey, C. M. R. Low, J. G. Vinter, K. R. Lawson, C. J. Urch, C. A. Hunter, Org. Biomol. Chem. 2007, 5, 1062.
37. h)B. Branchi, V. Balzani, P. Ceroni, M. C. Kuchenbrandt, F.-G. Klärner, D. Bläser, R. Boese, J. Org. Chem. 2008, 73, 5839.
38. i)B. Legouin, P. Uriac, S. Tomasi, L. Toupet, A. Bondon, P. van de Weghe, Org. Lett. 2009, 11, 745.
39. a)B. Askew, P. Ballester, C. Buhr, K. S. Jeong, S. Jones, K. Parris, K. Williams, J. Rebek, Jr., J. Am. Chem. Soc. 1989, 111 , 1082.
40. b)B. J. Whitlock, H. W. Whitlock, J. Am. Chem. Soc. 1994, 116 , 2301.
41. c)T. Hayashi, T. Miyahara, N. Koide, Y. Kato, H. Masuda, H. Ogoshi, J. Am. Chem. Soc. 1997, 119, 7281.
42. d)A. I. Oliva, L. Simón, F. M. Muñiz, F. Sanz, C. Ruiz-Valero, J. R. Morán, J. Org. Chem. 2004, 69, 6883.
43. a)Y. Shoji, K. Tashiro, T. Aida, J. Am. Chem. Soc. 2006, 128, 10690.
44. b)Y. Shoji, K. Tashiro, T. Aida, J. Am. Chem. Soc. 2010, 132, 5928.
45. a)X. Peng, N. Komatsu, S. Bhattacharya, T. Shimawaki, S. Aonuma, T. Kimura, A. Osuka, Nat. Nanotechnol. 2007, 2, 361.
46. b)X. Peng, N. Komatsu, T. Kimura, A. Osuka, J. Am. Chem. Soc. 2007, 129, 15947.
47. c)X. Peng, N. Komatsu, T. Kimura, A. Osuka, ACS Nano 2008, 2, 2045.
48. T. Ema, N. Ura, K. Eguchi, Y. Ise, T. Sakai, Chem. Commun. 2011, 47, 6090.
49. a)T. Kurtán, N. Nesnas, Y.-Q. Li, X. Huang, K. Nakanishi, N. Berova, J. Am. Chem. Soc. 2001, 123, 5962.
50. b)T. Kurtán, N. Nesnas, F. E. Koehn, Y.-Q. Li, K. Nakanishi, N. Berova, J. Am. Chem. Soc. 2001, 123, 5974.
51. c)Y. Kubo, Y. Ishii, T. Yoshizawa, S. Tokita, Chem. Commun. 2004, 1394.
52. d)T. Ema, N. Ouchi, T. Doi, T. Korenaga, T. Sakai, Org. Lett. 2005, 7, 3985.
53. e)A. Ouchi, K. Tashiro, K. Yamaguchi, T. Tsuchiya, T. Akasaka, T. Aida, Angew. Chem., Int. Ed. 2006, 45, 3542.
54. f)J. Aimi, K. Oya, A. Tsuda, T. Aida, Angew. Chem., Int. Ed. 2007, 46, 2031.
55. h)H. Uno, K. Nakamoto, K. Kuroki, A. Fujimoto, N. Ono, Chem. Eur. J. 2007, 13, 5773.
56. i)Y. Ishii, T. Yoshizawa, Y. Kubo, Org. Biomol. Chem. 2007, 5, 1210.
57. j)L. Jiao, E. Hao, F. R. Fronczek, K. M. Smith, M. G. H. Vicente, Tetrahedron 2007, 63, 4011.
58. k)Y. Matano, K. Matsumoto, Y. Nakao, H. Uno, S. Sakaki, H. Imahori, J. Am. Chem. Soc. 2008, 130, 4588.
59. l)V. Borovkov, T. Yamamoto, H. Higuchi, Y. Inoue, Org. Lett. 2008, 10, 1283.
60. m)A. Takai, C. P. Gros, J.-M. Barbe, R. Guilard, S. Fukuzumi, Chem. Eur. J. 2009, 15, 3110.
61. n)C.-H. Lee, H. Yoon, W.-D. Jang, Chem. Eur. J. 2009, 15, 9972.
62. o)J. Song, N. Aratani, J. H. Heo, D. Kim, H. Shinokubo, A. Osuka, J. Am. Chem. Soc. 2010, 132, 11868.
63. p)C.-L. Mai, W.-K. Huang, H.-P. Lu, C.-W. Lee, C.-L. Chiu, Y.-R. Liang, E. W.-G. Diau, C.-Y. Yeh, Chem. Commun. 2010, 46, 809.
64. q)H. Nobukuni, Y. Shimazaki, H. Uno, Y. Naruta, K. Ohkubo, T. Kojima, S. Fukuzumi, S. Seki, H. Sakai, T. Hasobe, F. Ta ni, Chem. Eur. J. 2010, 16, 11611.
65. K. A. Connors, Binding Constants, Wiley, New York, 1987.
66. a)D. Zhao, T. M. Swager, Macromolecules 2005, 38, 9377.
67. b)Y. H. Lee, H. Liu, J. Y. Lee, S. H. Kim, S. K. Kim, J. L. Sessler, Y. K im, J. S. Kim, Chem. Eur. J. 2010, 16, 5895.
68. c)Y. Peng, A.-J. Zhang, M. Dong, Y.-W. Wang, Chem. Commun. 2011, 47, 4505.
69. For the toxicity of nitroaromatic compounds, see the Web site of the Agency for Toxic Substances and Disease Registry (ATSDR) of the, Department of Health and Human Services (Atlanta, Georgia, USA) (http://www.atsdr.cdc.gov/).
70. M. R. Edwards, P. G. Jones, A. J. Kirby, J. Am. Chem. Soc. 1986, 108, 7067.
71. B. Denegri, O. Kronja, J. Phys. Org. Chem. 2009, 22, 495.
72. G. Stork, P. Rosen, N. Goldman, R. V. Coombs, J. Tsuji, J. Am. Chem. Soc. 1965, 87, 275.