Vicinal diamides as lanthanide complexers with two conformational states of different dipole moments - Elements for new molecular switches

Supramolecular Chemistry

Volumn 8, Issue 3, 1997, Pages 225-229

  Schneider, Hans Jörg ^a   Kasper, Christoph ^a   Palyulin, Vladimir ^b   Samoshin, Vyacheslav V ^c  

^a SAARLAND UNIVERSITY   (Germany)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c MIREA RUSSIAN TECHNOLOGICAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3342877299     PISSN: 10610278     EISSN: None     Source Type: Journal    
DOI: 10.1080/10610279708034939     Document Type: Article

References (30)

1. Most of the early synthetic allosteric systems comprised cooperativity between two metal binding centers: (a) Vögtle, (1992). Supramolekulare Chemie 2. Aufl, Thieme Stuttgart; Supramolecular Chemistry, Wiley 1991; (b) Rebek, Jr. J. (1984). Acc. Chem. Res., 17, 258; (c) Shinkai, S. (1992). Crown Ethers and Analogous Compounds, 45, 335.
2. Most of the early synthetic allosteric systems comprised cooperativity between two metal binding centers: (a) Vögtle, (1992). Supramolekulare Chemie 2. Aufl, Thieme Stuttgart; Supramolecular Chemistry, Wiley 1991; (b) Rebek, Jr. J. (1984). Acc. Chem. Res., 17, 258; (c) Shinkai, S. (1992). Crown Ethers and Analogous Compounds, 45, 335.
3. Most of the early synthetic allosteric systems comprised cooperativity between two metal binding centers: (a) Vögtle, (1992). Supramolekulare Chemie 2. Aufl, Thieme Stuttgart; Supramolecular Chemistry, Wiley 1991; (b) Rebek, Jr. J. (1984). Acc. Chem. Res., 17, 258; (c) Shinkai, S. (1992). Crown Ethers and Analogous Compounds, 45, 335.
4. Most of the early synthetic allosteric systems comprised cooperativity between two metal binding centers: (a) Vögtle, (1992). Supramolekulare Chemie 2. Aufl, Thieme Stuttgart; Supramolecular Chemistry, Wiley 1991; (b) Rebek, Jr. J. (1984). Acc. Chem. Res., 17, 258; (c) Shinkai, S. (1992). Crown Ethers and Analogous Compounds, 45, 335.
5. Recent references for allosteric systems with binding centers also for organic substrates: Inouye, M., Konishi, T. and Isagawa, K. (1993). J. Am. Chem. Soc., 115, 8091; Bauer, H., Matz, V., Lang, M., Krieger, C. and Staab, H. A. (1994). Chem. Ber., 127, 1993; Baldes, R. R. and Schneider, H.-J. (1995). Angew. Chem., 107, 380; Angew. Chem. Int. Ed. Engl., (1995). 34, 321; Ikeda, T., Yoshida, K. and Schneider, H.-J. (1995). J. Am. Chem. Soc., 117, 1453.
6. Recent references for allosteric systems with binding centers also for organic substrates: Inouye, M., Konishi, T. and Isagawa, K. (1993). J. Am. Chem. Soc., 115, 8091; Bauer, H., Matz, V., Lang, M., Krieger, C. and Staab, H. A. (1994). Chem. Ber., 127, 1993; Baldes, R. R. and Schneider, H.-J. (1995). Angew. Chem., 107, 380; Angew. Chem. Int. Ed. Engl., (1995). 34, 321; Ikeda, T., Yoshida, K. and Schneider, H.-J. (1995). J. Am. Chem. Soc., 117, 1453.
7. Recent references for allosteric systems with binding centers also for organic substrates: Inouye, M., Konishi, T. and Isagawa, K. (1993). J. Am. Chem. Soc., 115, 8091; Bauer, H., Matz, V., Lang, M., Krieger, C. and Staab, H. A. (1994). Chem. Ber., 127, 1993; Baldes, R. R. and Schneider, H.-J. (1995). Angew. Chem., 107, 380; Angew. Chem. Int. Ed. Engl., (1995). 34, 321; Ikeda, T., Yoshida, K. and Schneider, H.-J. (1995). J. Am. Chem. Soc., 117, 1453.
8. Recent references for allosteric systems with binding centers also for organic substrates: Inouye, M., Konishi, T. and Isagawa, K. (1993). J. Am. Chem. Soc., 115, 8091; Bauer, H., Matz, V., Lang, M., Krieger, C. and Staab, H. A. (1994). Chem. Ber., 127, 1993; Baldes, R. R. and Schneider, H.-J. (1995). Angew. Chem., 107, 380; Angew. Chem. Int. Ed. Engl., (1995). 34, 321; Ikeda, T., Yoshida, K. and Schneider, H.-J. (1995). J. Am. Chem. Soc., 117, 1453.
9. Recent references for allosteric systems with binding centers also for organic substrates: Inouye, M., Konishi, T. and Isagawa, K. (1993). J. Am. Chem. Soc., 115, 8091; Bauer, H., Matz, V., Lang, M., Krieger, C. and Staab, H. A. (1994). Chem. Ber., 127, 1993; Baldes, R. R. and Schneider, H.-J. (1995). Angew. Chem., 107, 380; Angew. Chem. Int. Ed. Engl., (1995). 34, 321; Ikeda, T., Yoshida, K. and Schneider, H.-J. (1995). J. Am. Chem. Soc., 117, 1453.
10. Selected reviews on photosensitive switches see ref 1 and: (a) Feringa, B. L., Jager, W. F. and de Lange, B. (1993). Tetrahedron, 49, 8267; (b) Photochromism. Molecules and Systems in Organic Chemistry, H. Dürr, H. Bouas-Laurent, Eds.; Elsevier Amsterdam 1990; (c) Shinkai, S. and Manabe, O. (1984). Top. Curr. Chem., 121, 67; (d) Balzani, V. and Scandola, F. (1991). Supramolecular Photochemistry, Ellis Horwood, Chichester.
11. Selected reviews on photosensitive switches see ref 1 and: (a) Feringa, B. L., Jager, W. F. and de Lange, B. (1993). Tetrahedron, 49, 8267; (b) Photochromism. Molecules and Systems in Organic Chemistry, H. Dürr, H. Bouas-Laurent, Eds.; Elsevier Amsterdam 1990; (c) Shinkai, S. and Manabe, O. (1984). Top. Curr. Chem., 121, 67; (d) Balzani, V. and Scandola, F. (1991). Supramolecular Photochemistry, Ellis Horwood, Chichester.
12. Selected reviews on photosensitive switches see ref 1 and: (a) Feringa, B. L., Jager, W. F. and de Lange, B. (1993). Tetrahedron, 49, 8267; (b) Photochromism. Molecules and Systems in Organic Chemistry, H. Dürr, H. Bouas-Laurent, Eds.; Elsevier Amsterdam 1990; (c) Shinkai, S. and Manabe, O. (1984). Top. Curr. Chem., 121, 67; (d) Balzani, V. and Scandola, F. (1991). Supramolecular Photochemistry, Ellis Horwood, Chichester.
13. Selected reviews on photosensitive switches see ref 1 and: (a) Feringa, B. L., Jager, W. F. and de Lange, B. (1993). Tetrahedron, 49, 8267; (b) Photochromism. Molecules and Systems in Organic Chemistry, H. Dürr, H. Bouas-Laurent, Eds.; Elsevier Amsterdam 1990; (c) Shinkai, S. and Manabe, O. (1984). Top. Curr. Chem., 121, 67; (d) Balzani, V. and Scandola, F. (1991). Supramolecular Photochemistry, Ellis Horwood, Chichester.
14. Cf. electrostatic interpretations of the anomeric effect: a) Kirby, A. J. (1983). The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer: New York etc; (b) Perrin, C. L., Armstrong, K. B. and Fabian, M. A. (1994). J. Am. Chem. Soc., 116, 715; (c) Wiberg, K. B. and Marquez, M. (1994). ibid., 116, 2197; (d) Jorgensen, W. L., Morales de Tirado, P. I. and Severance, D. L. (1994). ibid., 116, 2199; (e) Perrin, C. L. and Young, D. B. (1995). Tetrahedron Lett., 36, 7185; and references cited therein.
15. Cf. electrostatic interpretations of the anomeric effect: a) Kirby, A. J. (1983). The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer: New York etc; (b) Perrin, C. L., Armstrong, K. B. and Fabian, M. A. (1994). J. Am. Chem. Soc., 116, 715; (c) Wiberg, K. B. and Marquez, M. (1994). ibid., 116, 2197; (d) Jorgensen, W. L., Morales de Tirado, P. I. and Severance, D. L. (1994). ibid., 116, 2199; (e) Perrin, C. L. and Young, D. B. (1995). Tetrahedron Lett., 36, 7185; and references cited therein.
16. Cf. electrostatic interpretations of the anomeric effect: a) Kirby, A. J. (1983). The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer: New York etc; (b) Perrin, C. L., Armstrong, K. B. and Fabian, M. A. (1994). J. Am. Chem. Soc., 116, 715; (c) Wiberg, K. B. and Marquez, M. (1994). ibid., 116, 2197; (d) Jorgensen, W. L., Morales de Tirado, P. I. and Severance, D. L. (1994). ibid., 116, 2199; (e) Perrin, C. L. and Young, D. B. (1995). Tetrahedron Lett., 36, 7185; and references cited therein.
17. Cf. electrostatic interpretations of the anomeric effect: a) Kirby, A. J. (1983). The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer: New York etc; (b) Perrin, C. L., Armstrong, K. B. and Fabian, M. A. (1994). J. Am. Chem. Soc., 116, 715; (c) Wiberg, K. B. and Marquez, M. (1994). ibid., 116, 2197; (d) Jorgensen, W. L., Morales de Tirado, P. I. and Severance, D. L. (1994). ibid., 116, 2199; (e) Perrin, C. L. and Young, D. B. (1995). Tetrahedron Lett., 36, 7185; and references cited therein.
18. Cf. electrostatic interpretations of the anomeric effect: a) Kirby, A. J. (1983). The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer: New York etc; (b) Perrin, C. L., Armstrong, K. B. and Fabian, M. A. (1994). J. Am. Chem. Soc., 116, 715; (c) Wiberg, K. B. and Marquez, M. (1994). ibid., 116, 2197; (d) Jorgensen, W. L., Morales de Tirado, P. I. and Severance, D. L. (1994). ibid., 116, 2199; (e) Perrin, C. L. and Young, D. B. (1995). Tetrahedron Lett., 36, 7185; and references cited therein.
19. The use of external electric fields for orientation of chromophores in thin films has been reported: Kurihara, S., Iwamoto, K. and Nonaka, T. (1995). J. Chem. Soc., Chem. Commun., 2195.
20. (a) Bamann, E. and Trapmann, H. (1959). Adv. Enzym., 21, 169;
21. (b) Breslow, R. and Huang, D. L. (1991). Proc. Nat. Acad. Sci. USA, 88, 4080;
22. (c) Komiyama, M., Matsamura, K., Matsumoto, Y., Ushida, H., Shiiba, T., Kodamam, T. and Yashiro, M. (1995). J. Chem. Soc., Perkin Trans., 2, 269;
23. (d) Morrow, J. L., Buttrey, L. A., Shelton, V. M. and Berback, K. A. (1992). J. Am. Chem. Soc., 114, 1903;
24. (e) Rammo, J., Hettich, R., Roigk, A. and Schneider, H.-J. (1996). J. Chem. Soc., Chem. Commun., 105; and references cited therein.
25. Amin, S., Morrow, J. R., Lake, C.-H. and Churchill, M. R. (1995). Angew. Chem., 824; Angew. Chem. Int. Ed. Engl., (1995). 33, 773.
26. Amin, S., Morrow, J. R., Lake, C.-H. and Churchill, M. R. (1995). Angew. Chem., 824; Angew. Chem. Int. Ed. Engl., (1995). 33, 773.
27. Cf. O. I. Levina, Pothekin, K. A., Kurkotova, E. N., Struchkov, Y. T., Baskin, I. I., Palyulin, V. A. and Zefirov, N. S. (1985). Dokl. Akad. Nauk, 281, 1367; McCabe, P. H., Milne, N. J. and Sim, G. A. (1985). J. Chem. Soc., Chem. Commun., 625.
28. Cf. O. I. Levina, Pothekin, K. A., Kurkotova, E. N., Struchkov, Y. T., Baskin, I. I., Palyulin, V. A. and Zefirov, N. S. (1985). Dokl. Akad. Nauk, 281, 1367; McCabe, P. H., Milne, N. J. and Sim, G. A. (1985). J. Chem. Soc., Chem. Commun., 625.
29. Samoshin, V. V., Vereshchagina, Y. A., Lutsenko, A. I. and Zefirov, N. S. (1993). Zh. Org. Khim., 29, 1095, and references cited therein.
30. Cf. Samoshin, V. V., Chertkov, V. A., Vatlina, L. P., Dobretsova, E. K., Simonov, N. A., Kastorsky, L. P., Gremyachinsky, D. V. and Schneider, H.-J. (1996). Tetrahedron Lett., 37, 3981.