Halide anion mediated dimerization of a meso-unsubstituted N-confused porphyrin

Chemistry - An Asian Journal

Volumn 3, Issue 3, 2008, Pages 592-599

  Furuta, Hiroyuki ^a,b   Nanami, Hideki ^c   Morimoto, Tatsuki ^a   Ogawa, Takuji ^c,d   Král, Vladimir ^e   Sessler, Jonathan L ^e   Lynch, Vincent ^e  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c EHIME UNIVERSITY   (Japan)

^d INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^e UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Anion binding; Anion recognition; Dimerization; N confused porphyrins; Porphyrins

Indexed keywords

HALOGEN; PORPHYRIN;

ARTICLE; CHEMISTRY; CRYSTALLOGRAPHY; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CRYSTALLOGRAPHY; DIMERIZATION; HALOGENS; MAGNETIC RESONANCE SPECTROSCOPY; PORPHYRINS;

EID: 49249090956     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700130     Document Type: Article

References (58)

1. a) B. Dietrich, M. A. Hosseini in Supramolecular Chemistry of Anions (Eds: A. Bianchi, K. Bowman-James, E. Gracía-España), Wiley-VCH, New York, 1997, pp. 45-62;
2. b) Fundamentals and Applications of Anion Separations (Eds.: R. P. Singh, B. A. Moyer), Kluwer Academic/Plenum Publishers, New York, 2004;
3. c) J. L. Sessler, P. A. Gale, W.-S. Cho, Anion Receptor Chemistry, RSC, Cambridge, 2006.
4. a) M. W. Hosseini, A. J. Blacker, J.-M. Lehn, J. Am. Chem. Soc. 1990, 112, 3896-3904;
5. b) F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646;
6. c) P. D. Beer, Acc. Chem. Res. 1998, 31, 71-80;
7. d) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502-532;
8. Angew. Chem. Int. Ed. 2001, 40, 486-516;
9. e) R. Martínez-Máñez, F. Sancenón, Chem. Rev. 2003, 103, 4419-4476;
10. f) V. Amendola, M. Bonizzoni, D. Esteban-Gomez, L. Fabbrizzi, M. Licchelli, F. Sancenon, A. Taglietti, Coord. Chem. Rev. 2006, 250, 1451-1470;
11. g) P. A. Gale, Acc. Chem. Res. 2006, 39, 465-475;
12. h) V. Amendola, D. Esteban-Gomez, L. Fabbrizzi, M. Licchelli, Acc. Chem. Res. 2006, 39, 34 3-353.
13. a) P. A. Gale, J. L. Sessler, V. Král, V. Lynch, J. Am. Chem. Soc. 1996, 118, 5140-5141;
14. b) P. A. Gale, J. L. Sessler, V. Král, Chem. Commun. 1998, 1-8.
15. a) J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee, J. A. Ibers, J. Am. Chem. Soc. 1990, 112, 2810-2813;
16. b) M. Shionoya, H. Furuta, V. Lynch, A. Harriman, J. L. Sessler, J. Am. Chem. Soc. 1992, 114, 5714-5722;
17. c) J. L. Sessler, J. Davis, Acc. Chem. Res. 2001, 34, 989-997.
18. a) H. Furuta, T. Asano, T. Ogawa, J. Am. Chem. Soc. 1994, 116, 767-768;
19. b) P. J. Chmielewski, L. Latos-Grażyński, K. Rachlewicz, T. Głowiak, Angew. Chem. 1994, 106, 805-808;
20. Angew. Chem. Int. Ed. Engl. 1994, 33, 779-781;
21. c) T. Morimoto, S. Taniguchi, A. Osuka, H. Furuta, Eur. J. Org. Chem. 2005, 3887-3890.
22. a) J.-C. Liu, T. Ishizuka, A. Osuka, H. Furuta, Chem. Commun. 2003, 1908-1909;
23. b) H. Maeda, Y. Ishikawa, T. Matsuda, A. Osuka, H. Furuta, J. Am. Chem. Soc. 2003, 125, 11 822-11 823;
24. c) H. Maeda, A. Osuka, H. Furuta, J. Inclusion Phenom. 2004, 49, 33-36;
25. d) H. Maeda, T. Morimoto, A. Osuka, H. Furuta, Chem. Asian J. 2006, 1, 832-844.
26. a) N. A. Chaniotakis, A. M. Chasser, M. E. Meyerhoff, J. T. Groves, Anal. Chem. 1988, 60, 185-188;
27. b) L. Groski, E. Malinowska, P. Parzuchowski, W. Zhang, M. E. Meyerhoff, Electroanalysis 2003, 15, 1229-1235.
28. Y. Xie, T. Morimoto, H. Furuta, Angew. Chem. 2006, 118, 7061-7064;
29. Angew. Chem. Int. Ed. 2006, 45, 6907-6910.
30. a) H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 1999, 121, 2945-2946;
31. b) H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 2000, 122, 5748-5757;
32. c) H. Furuta, T. Ishizuka, A. Osuka, H. Dejima, H. Nakagawa, Y. Ishikawa, J. Am. Chem. Soc. 2001, 123, 6207-6208.
33. B. Y. Liu, C. Bruckner, D. Dolphin, Chem. Commun. 1996, 2141-2142.
34. a) T. D. Lash, D. T. Richter, C. M. Shiner, J. Org. Chem. 1999, 64, 7973-7982;
35. b) T. D. Lash, Synlett 1999, 279-295.
36. J. L. Sessler, M. R. Johnson, V. Lynch, J. Org. Chem. 1987, 52, 4394-4397.
37. J. H. Anderson, C. E. Loader, A. Foster, Can. J. Chem. 1980, 58, 2527-2530.
38. 4) is consistent with the proposed exocyclic C=O group.
39. I. Schmidt, P. J. Chmielewski, Tetrahedron Lett. 2001, 42, 6389-6392.
40. M. Smith, J. March, Advanced Organic Chemistry: Reactions, Mechanism, and Structures, 5th ed., Wiley, New York, 2001, p. 20.
41. See Supporting Information, Figure S1.
42. H. Furuta, T. Ishizuka, A. Osuka, Y. Uwatoko, Y. Ishikawa, Angew. Chem. 2001, 113, 2385 -2387; Angew. Chem. Int. Ed. 2001, 40, 2323-2325.
43. a) C.-H. Hung, W.-C. Chen, G.-H. Lee, S.-M. Peng, Chem. Commun. 2002, 1516-1517;
44. b) J. D. Harvey, C. J. Ziegler, Chem. Commun. 2002, 1942-1943;
45. c) H. Furuta, T. Ishizuka, A. Osuka, J. Am. Chem. Soc. 2002, 124, 5622-5623;
46. d) J. D. Harvey, C. J. Ziegler, Chem. Commun. 2003, 2890-2891;
47. e) H. Furuta, T. Morimoto, A. Osuka, Inorg. Chem. 2004, 43, 1618-1624;
48. f) M. Toganoh, N. Harada, T. Morimoto, H. Furuta, Chem. Eur. J. 2007, 13, 2257-2265;
49. g) T. Morimoto, H. Uno, H. Furuta, Angew. Chem. 2007, 119, 3746-3749;
50. Angew. Chem. Int. Ed. 2007, 46, 3672-3675.
51. a) V. Král, H. Furuta, K. Shreder, V. Lynch, J. L. Sessler, J. Am. Chem. Soc. 1996, 118, 1595-1607;
52. b) J. L. Sessler, A. Andrievsky, P. A. Gale, V. Lynch, Angew. Chem. 1996, 108, 2954-2957;
53. Angew. Chem. Int. Ed. Engl. 1996, 35, 2782-2785.
54. 1H splitting, made an assignment of the outer NH proton difficult for 6·HF; it is tentatively assigned to the signal at δ=9.59 ppm.
55. E. A. Katayev, Y. A. Ustynyuk, J. L. Sessler, Coord. Chem. Rev. 2006, 250, 3004-3037.
56. G. M. Sheldrick, SHELXTL/PC (Version 5.03), Siemens Analytical X-ray Instruments, Inc., Madison, WI (USA), 1994.
57. International Tables for X-ray Crystallography, Vol. C (Ed.: A. J. C. Wilson), Tables 4.2.6.8 and 6.1.1.4, Kluwer Academic Press, Boston, 1992.
58. S. M. Gadol, R. E. Davis, Organometallics 1982, 1, 1607-1613.