Selective formation of a single atropisomer of meso-meso-linked Zn II diporphyrin through supramolecular self-assembly

Chemistry - A European Journal

Volumn 15, Issue 38, 2009, Pages 9681-9684

  Maeda, Chihiro ^a   Kamada, Taisuke ^a   Aratani, Naoki ^a   Sasamori, Takahiro ^b   Tokitoh, Norihiro ^b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Atropisomerism; Entropy; Porphyrinoids; Self assembly; Self sorting

Indexed keywords

ATROPISOMERISM; ATROPISOMERS; CYCLIC HEXAMERS; DIPORPHYRINS; PORPHYRINOIDS; SELECTIVE FORMATION; SELF-ASSEMBLE; SELF-SORTING; SUPRAMOLECULAR AGGREGATES; SUPRAMOLECULAR SELF-ASSEMBLIES;

PORPHYRINS; SUPRAMOLECULAR CHEMISTRY; ZINC;

SELF ASSEMBLY;

EID: 70450159428     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901475     Document Type: Article

References (29)

1. a) L. K. Gottwald, E. F. Ullman, Tetrahedron Lett. 1969, 10, 3071-3074;
2. b) S. S. Eaton, G. R. Eaton, J. Am. Chem. Soc. 1975, 97, 3660-3666;
3. c) P. Fournari, R. Guilard, M. Fontesse, J.-M. Latour, J.-C. Marchon, J. Organomet. Chem. 1976, 110, 205-217;
4. d) S. S. Eaton, G. R. Eaton, J. Am. Chem. Soc. 1977, 99, 6594-6599.
5. a) J. P. Collman, R. R. Gagne, C. A. Reed, T. R. Halbert, G. Lange, W. T. Robinson, J. Am. Chem. Soc. 1975, 97, 1427-1439;
6. b) J. S. Lindsey, D. C. Mauzerall, J. Am. Chem. Soc. 1982, 104, 4498-4500;
7. c) J. P. Coliman, N. K. Devaraj, R. A. Decréau, Y. Yang, Y.-L. Yan, W. Ebina, T. A. Eberspacher, and C. E. D. Chidsey, Science 2007, 315, 1565-1568.
8. a) J. S. Lindsey, J. Org. Chem. 1980, 45, 5215;
9. b) T. Hayashi, T. Asai, H. Hokazono, H. Ogoshi, J. Am. Chem. Soc. 1993, 115, 12210-12211.
10. a) T. Imamura, K. Fukushima, Coord. Chem. Rev. 2000, 198, 133-156;
11. b) J. Wojaczyński, L. Latos-Grażyński, Coord. Chem. Rev. 2000, 204, 113-171;
12. c) E. Iengo, E. Zangrando, E. Alessio, Eur. J. Inorg. Chem. 2003, 2371-2384;
13. d) A. Satake, Y. Kobuke, Tetrahedron 2005, 61, 13-41.
14. a) A. Tsuda, T. Nakamura, S. Sakamoto, K. Yamaguchi, A. Osuka, Angew. Chem. 2002, 114, 2941-2945;
15. Angew. Chem. Int. Ed. 2002, 41, 2817-2821;
16. b) I.-W. Hwang, T. Kamada, T. K. Ahn, D. M. Ko, T. Nakamura, A. Tsuda, A. Osuka, D. Kim, J. Am. Chem. Soc. 2004, 126, 16187-16198;
17. c) T. Kamada, N. Aratani, T. Ikeda, N. Shibata, Y. Higuchi, A. Wakamiya, S. Yamaguchi, K. S. Kim, Z. S. Yoon, D. Kim, A. Osuka, J. Am. Chem. Soc. 2006, 128, 7670-7678.
18. 2 = 0.1040 (all data).
19. a) A. Tsuda, S. Sakamoto, K. Yamaguchi, T. Aida, J. Am. Chem. Soc. 2003, 125, 15722-15723;
20. b) M. Vinodu, Z. Stein, I. Goldberg, Inorg. Chem. 2004, 43, 7582-7584.
21. A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93-95;
22. Angew. Chem. Int. Ed. Engl. 1997, 36, 135-137.
23. 3 and ethanol.
24. in-out shows two sets of signals (see the Supporting Information).
25. Assembly sizes were estimated by comparison to the similar reference compounds (see Figure S13 in the Supporting Information).
26. -3M.
27. The rotation about the central meso-meso link does not occur even at harder conditions (e.g., heating at reflux in pyridine for 12 h or in tetrachloroethane for 3 h; N. Yoshida, A. Osuka, Tetrahedron Lett. 2000, 41, 9287-9291).
28. a) A. L. Spek, PLATON, A Multipurpose Crystallographic Tool; Utrecht, The Netherlands, 2005;
29. b) P. van der Sluis, A. L. Spek, Acta Crystallogr. Sect. A 1990, 46, 194-201.