Stoichiometry-controlled supramolecular chirality induction and inversion in bisporphyrin systems

Organic Letters

Volumn 4, Issue 2, 2002, Pages 169-171

  Borovkov, Victor V ^a   Lintuluoto, Juha M ^a   Inoue, Yoshihisa ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

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ARTICLE;

EID: 0001192328     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016870i     Document Type: Article

References (18)

1. (a) Hirschberg, J. H. K. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170.
2. (b) Nakashima, H.; Fujiki, M.; Koe, J. R.; Motonaga, M. J. Am. Chem. Soc. 2001, 123, 1963-1969.
3. (c) Zahn, S.; Canary, J. W. Science 2000, 288, 1404-1407.
4. (d) Koumura, N.; Zijlstra, R. W. J.; van Delden, R. A.; Harada, N.; Feringa, B. L. Nature 1999, 401, 152-155.
5. (e) Li, J.; Schuster, G. B.; Cheon, K.-S.; Green, M. M.; Selinger, J. V. J. Am. Chem. Soc. 2000, 122, 2603-2612.
6. (f) Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Shinkai, S. Angew. Chem., Int. Ed. 2000, 39, 3839-3842.
7. There is another example of the stoichiometry effect reported for a certain tetrapyrrole host; see: Edinger, J.; Falk, H.; Jungwirth, W.; Müller N.; Zrunek, U. Monatsh. Chem. 1984, 115, 1081-1099.
8. Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. Helv. Chim. Acta 1999, 82, 919-934.
9. (a) Borovkov, V. V.; Lintuluoto, J. M.; Fujiki, M.; Inoue, Y. J. Am. Chem. Soc. 2000, 122, 4403-4407.
10. (b) Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. J. Am. Chem. Soc. 2001, 123, 2979-2989.
11. (c) Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. J. Phys. Chem. A 2000, 104, 9213-9219.
12. Enantiopure 1,2-diphenylethylenediamine, 1,2-diaminocyclohexane, leucinol, and 1-amino-2-propanol have been investigated. Although all of these ligands showed formation of the same 1:1 tweezer complex, only 1,2-diphenylethylenediamine exhibited besides chirality induction the chirality inversion phenomenon.
13. There are also few examples of the 1:1 chiral tweezer complex formation upon interaction of achiral bisporphyrin hosts with various chiral guests; see: (a) Kurtan, T.; Nesnas, N.; Li, Y.-Q.; Huang, X.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2001, 123, 5962-5973. (b) Takeuchi, M.; Imada, T.; Shinkai, S. Bull. Chem. Soc. Jpn. 1998, 71, 1117-1123.
14. There are also few examples of the 1:1 chiral tweezer complex formation upon interaction of achiral bisporphyrin hosts with various chiral guests; see: (a) Kurtan, T.; Nesnas, N.; Li, Y.-Q.; Huang, X.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2001, 123, 5962-5973. (b) Takeuchi, M.; Imada, T.; Shinkai, S. Bull. Chem. Soc. Jpn. 1998, 71, 1117-1123.
15. 1H NMR spectral pattern in comparison to that of 1,2-diphenylethylenediamine and essentially the same UV - vis spectra of these two systems in the low ligand molar excess region (see Supporting Information). This study will be reported elsewhere.
16. A plot of the Soret band intensity at 411 nm against [ZnD]/([ZnD] + [L]), where L is 1,2-diphenylethylenediamine, has a minimum at 0.5 that corresponds to formation of the 1:1 complex at the low ligand molar excess region (see Supporting Information).
17. Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem. 1965, 11, 371-392.
18. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy. Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.