Malonate crown ethers as building blocks for novel D-π-A chromophores

Organic Letters

Volumn 4, Issue 1, 2002, Pages 23-26

  Pasini, Dario ^a   Righetti, Pier Paolo ^a   Rossi, Valerio ^a  

^a UNIVERSITY OF PAVIA   (Italy)

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ARTICLE;

EID: 0002025549     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016798o     Document Type: Article

References (32)

1. (a) Burland, D. M.; Miller, R. D.; Walsh, C. A. Chem. Rev. 1994, 94, 31-75.
2. (b) Kanis, D. R.; Marks, T. J.; Ratner, M. A. Chem. Rev. 1994, 94, 195-242.
3. (c) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21-28.
4. (d) Marks, T. J.; Ratner, M. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 155-173.
5. For a list of recent reports in the field, see: (a) Kenis, P. J. A.; Noordman, O. F. J.; Schönherr, H.; Kerver, E. G.; Snellink-Ruël, B. H. M.; van Hummel, G. J.; Harkema, S.; van der Vorst, C. P. J. M.; Hare, J.; Picken, S. J.; Engbersen, J. F. J.; van Hulst, N. F.; Vancso, G. J.; Reinhoudt, D. N. Chem. Eur. J. 1998, 7, 1225-1234.
6. (b) Alain, V.; Blanchard-Desce, M.; Ledoux-Rak, I.; Zyss, J. Chem. Commun. 2000, 353-354.
7. (c) Lin, W.; Ma, L.; Evans, O. R. Chem. Commun. 2000, 2263-2264.
8. (d) Moore, A. J.; Chesney, A.; Bryce, M. R.; Batsanov, A. S.; Kelly, J. F.; Howard, J. A. K.; Perepichka, I. F.; Perepichka, D. F.; Meshulam, G.; Berkovic, G.; Kotler, Z.; Mazor, R.; Khodorkovsky, V. Eur. J. Org. Chem. 2001, 2671-2687.
9. (e) Gangopadhyay, P.; Radhakrishnan, T. P. Angew. Chem., Int. Ed. 2001, 40, 2451-2455.
10. (f) Aqad, E.; Leriche, P.; Mabon, G.; Gorgues, A.; Khodorovsky, V. Org. Lett. 2001, 3, 2329-2332.
11. For selected recent examples, see: (a) Barlow, S.; Marder, S. R. Chem. Commun. 2000, 1555-1562.
12. (b) Jayaprakash, K. N.; Ray, P. C.; Matsuoka, I.; Bhadbhade, M. M.; Puranik, V. G.; Das, P. K.; Nishihara, H.; Sarkar, A. Organometallics 1999, 18, 3851-3858.
13. (c) Müller, T. J. J.; Netz, A.; Ansorge, M.; Schmälzlin, E.; Bräuchle, C.; Meerholz, K. Organometallics 1999, 18, 5066-5074.
14. (d) Di Bella, S.; Fragalà, I.; Ledoux, I.; Zyss, J. Chem. Eur. J. 2001, 7, 3738-3743.
15. (a) Bradshaw, J. S.; Bishop, C. T.; Nielsen, S. F.; Asay, R. E.; Masihdas, D. R. K.; Flanders, E. D.; Izatt, R. M.; Chrisensen, J. J. J. Chem. Soc., Perkin Trans. 1 1975, 2505-2508.
16. (b) Izatt, R. M.; Lamb, J. D.; Mass, G. E.; Asay, R. E.; Bradshaw, J. S. Christensen, J. J. J. Am. Chem. Soc. 1977, 99, 2365-6.
17. (c) Lamb, J. D.; Izatt, R. M.; Swain, C. S.; Bradshaw, J. S.; Christensen, J. J. J. Am. Chem. Soc. 1980, 102, 479-482.
18. (d) Izatt, R. M.; Bradshaw, J. S.; Nielsen, S. A.; Lamb, J. D.; Christensen, J. J. Chem. Rev. 1985, 85, 271-339.
19. Anchisi, C.; Corda, L.; Fadda, A. M.; Maccioni, A. M.; Podda, G. J. Heterocyle. Chem. 1988, 25, 735-737. See also: Ninagawa, A.; Maeda, T.; Matsuda, H. Chem. Lett. 1984, 1985-1988.
20. Anchisi, C.; Corda, L.; Fadda, A. M.; Maccioni, A. M.; Podda, G. J. Heterocyle. Chem. 1988, 25, 735-737. See also: Ninagawa, A.; Maeda, T.; Matsuda, H. Chem. Lett. 1984, 1985-1988.
21. Desimoni, G.; Faita, G.; Ricci, M.; Righetti, P. P. Tetrahedron 1998, 54, 9581-9602.
22. Bradshaw, J. S.; Jolley, S. T.; Jones, B. A. J. Heterocycle. Chem. 1980, 17, 1317-8.
23. 3-MeCN, similarly to what reported in ref 6.
24. For determination of stability constants between 18-crown-6 and lanthanide salts, see: (a) Bünzli, J.-C.; Wessner, D. Helv. Chim. Acta 1981, 64, 582-596.
25. (b) Bünzli, J.-C.; Pilloud, F. Inorg. Chem. 1989, 28, 2638-2642.
26. (c) Piguet, C.; Bünzli, J.-C. Chem. Soc. Rev. 1999, 28, 347-358. See also: Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Brueniong, R. L. Chem. Rev. 1991, 91, 1721-2085.
27. (c) Piguet, C.; Bünzli, J.-C. Chem. Soc. Rev. 1999, 28, 347-358. See also: Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Brueniong, R. L. Chem. Rev. 1991, 91, 1721-2085.
28. Connors, K. A. Binding Constants; Wiley: New York, 1987.
29. The possibility of using magnesium triflate was prevented by its almost total insolubility in MeCN.
30. Titration experiments were usually conducted adding increasing , amounts of metal salt to a solution at costant concentration of crown ether. In the case of ligand 1, a titration was also conducted adding increasing 1 amounts of ligand 1 to a solution at costant concentration of ET, obtaining essentially identical results in the calculation of the association constant.
31. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry; Wiley: New York, 1988.
32. Albeit compound 7 is crystalline, all attempts to grow good quality single crystals of the complex with ET failed.