Solid-state supramolecular chirogenesis: High optical activity and gradual development of zinc octaethylporphyrin aggregates

Angewandte Chemie - International Edition

Volumn 42, Issue 15, 2003, Pages 1746-1749

  Borovkov, Victor V ^a   Harada, Takunori ^b   Hembury, Guy A ^a   Inoue, Yoshihisa ^a   Kuroda, Reiko ^b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Chirality; Circular dichroism; Porphyrinoids; Solidstate structure; Supramolecular chemistry

Indexed keywords

ALCOHOLS; ZINC COMPOUNDS;

CIRCULAR DICHROISM SPECTRA;

SUPRAMOLECULAR CHEMISTRY;

ETHYLAMINE; MONOMER; PORPHYRIN DERIVATIVE;

ARTICLE; BIOMIMETICS; CHIRALITY; CHROMATOPHORE; CIRCULAR DICHROISM; COMPLEX FORMATION; ENANTIOMER; OPTICAL ROTATION; SOLID STATE; SUPRAMOLECULAR CHEMISTRY;

EID: 0037879264     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250524     Document Type: Article

References (33)

1. a) J. M. Ribó, J. Crusats, F. Sagués, J. Claret, R. Rubires, Science 2001, 292, 2063-2066;
2. b) H. Nakashima, J. R. Koe, K. Torimitsu, M. Fujiki, J. Am. Chem. Soc. 2001, 123, 4847-4849;
3. c) J. M. Fox, T. J. Katz, S. Van Elshocht, T. Verbiest, M. Kauranen, A. Persoons, T. Thongpanchang, T. Kraus, L. Brus, J. Am. Chem. Soc. 1999, 121, 3453-3459;
4. d) R. Purrello, A. Raudino, L. M. Scolaro, A. Loisi, E. Bellacchio, R. Lauceri, J. Phys. Chem. B 2000, 104, 10900-10908;
5. e) D. B. Steensgaard, H. Wackerbarth, P. Hildebrandt, A. R. Holzwarth, J. Phys. Chem. B 2000, 104, 10379-10386;
6. f) D. Iarossi, A. Mucci, F. Parenti, L. Schenetti, R. Seeber, C. Zanardi, A. Forni, M. Tonelli, Chem. Eur. J. 2001, 7, 676-685;
7. g) M. de Loos, J. van Esch, R. M. Kellogg, B. L. Feringa, Angew. Chem. 2001, 113, 633-636; Angew. Chem. Int. Ed. 2001, 40, 613-616;
8. g) M. de Loos, J. van Esch, R. M. Kellogg, B. L. Feringa, Angew. Chem. 2001, 113, 633-636; Angew. Chem. Int. Ed. 2001, 40, 613-616;
9. h) W. Steffen, B. Kohler, M. Altmann, U. Scherf, K. Stitzer, H.-C. zur Loye, U. H. F. Bunz, Chem. Eur. J. 2001, 7, 117-126;
10. i) J. H. Jung, H. Kobayashi, M. Masuda, T. Shimizu, S. Shinkai, J. Am. Chem. Soc. 2001, 123, 8785-8789;
11. j) L. Brunsveld, E. W. Meijer, R. B. Prince, J. S. Moore, J. Am. Chem. Soc. 2001, 123, 7978-7984;
12. k) M. Wang, G. L. Silva, B. A. Armitage, J. Am. Chem. Soc. 2000,122, 9977-9986;
13. l) P. Wittung, P. Nielsen, O. Buchart, M. Egholm, B. Norden, Nature 1994, 368, 561-563.
14. a) V. V. Borovkov, T. Harada, Y. Inoue, R. Kuroda, Angew. Chem. 2002, 114, 1436-1439; Angew. Chem. Int. Ed. 2002, 41, 1378-1381;
15. a) V. V. Borovkov, T. Harada, Y. Inoue, R. Kuroda, Angew. Chem. 2002, 114, 1436-1439; Angew. Chem. Int. Ed. 2002, 41, 1378-1381;
16. b) V. V. Borovkov, J. M. Lintuluoto, M. Sugiura, Y. Inoue, R. Kuroda, J. Am. Chem. Soc. 2002, 124, 11282-11283;
17. c) V. V. Borovkov, J. M. Lintuluoto, H. Sugeta, M. Fujiki, R. Arakawa, Y. Inoue, J. Am. Chem. Soc. 2002, 124, 2993-3006;
18. d) V. V. Borovkov, J. M. Lintuluoto, Y. Inoue, J. Am. Chem. Soc. 2001, 123, 2979-2989;
19. e) V. V. Borovkov, J. M. Lintuluoto, Y. Inoue, Org. Lett. 2002, 4, 169-171;
20. f) V. V. Borovkov, J. M. Lintuluoto, Y. Inoue, Org. Lett. 2000, 2, 1565-1568;
21. g) V. V. Borovkov, J. M. Lintuluoto, M. Fujiki, Y. Inoue, J. Am. Chem. Soc. 2000, 122, 4403-4407;
22. h) V. V. Borovkov, J. M. Lintuluoto, Y. Inoue, J. Phys. Chem. A 2000, 104, 9213-9219.
23. The interaction of ZnOEP with other chiral amines in the solid state will be reported elsewhere.
24. R. Kuroda, Y. Saito, Bull. Chem. Soc. Jpn. 1976, 49, 433-436.
25. All solid-state samples have been kept in a desiccator under dark conditions.
26. M. Kasha, H. R. Rawls, M. A. El-Bayoumi, Pure Appl. Chem. 1965, 11, 371-392.
27. a) R. Rubires, J.-A. Farrera, J. M. Ribó, Chem. Eur. J. 2001, 7, 436-446;
28. b) Z. Bikádi, F. Zsila, J. Deli, G. Mády, M. Simonyi, Enantiomer 2002, 7, 67-76;
29. c) H. von Berlepsch, C. Böttcher, A. Ouart, C. Burger, S. Dähne, S. Kirstein, J. Phys. Chem. B 2000, 104, 5255-5262;
30. d) W. Xu, H. Guo, D. L. Akins, J. Phys. Chem. B 2001, 105, 1543-1546;
31. e) I. Struganova, J. Phys. Chem. A 2000, 104, 9670-9674.
32. Using a solid-state specialized universal chiroptical spectrophotometer UCS: J-800KCM (R. Kuroda, T. Harada, Y. Shindo, Rev. Sci. Instrum. 2001, 72, 3802-3810) it was shown that optical anisotropies of the solid-state samples are negligibly small (see the Supporting Information). For example, linear dichroism, which is the major source of the artifacts observed in the CD signal of solid-state samples, contributes less than 1% to the total observed amplitude.
33. N. Harada, K. Nakanishi, Circular Dichroic Spectroscopy. Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, CA, 1983.