1,3-Indane-based chromogenic calixpyrroles with push-pull chromophores: Synthesis and anion sensing

Organic Letters

Volumn 8, Issue 3, 2006, Pages 359-362

  Nishiyabu, Ryuhei ^a   Anzenbacher Jr , Pavel ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 32644431886     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0521782     Document Type: Article

References (32)

1. (a) Schmidt, R. F.; Thews, G. Human Physiology, 2nd ed.; Springer-Verlag: Berlin, 1989.
2. (b) Marshall, W. J.; Bangert, S. K. Clinical Chemistry, 5th ed.; Elsevier: Edinburg, 2004.
3. (c) Ullmann's Encyclopedia of Industrial Chemistry, 6th ed.; Wiley VCH: New York, 1999.
4. (a) Martínez-Máñez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419.
5. (b) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
6. (a) Cho, E. J.; Ryu, B. J.; Lee, Y. J.; Nam, K. C. Org. Lett. 2005, 7, 2607.
7. (b) Boiocchi, M.; Boca, L. D.; Esteban-Gómez, D.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. J. Am. Chem. Soc. 2004, 726, 16507.
8. (c) Kwon, J. Y.; Jang, Y. J.; Kim, S. K.; Lee, K.-H.; Kim, J. S.; Yoon, J. J. Org. Chem. 2004, 69, 5155.
9. (d) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438.
10. (a) Das, A.; Ganguly, B.; Kumar, D. K.; Jose, D. A. Org. Lett. 2004, 6, 3445.
11. (b) Miyaji, H.; Sessler, J. L. Angew. Chem., Int. Ed. 2001, 40, 154.
12. (c) Jimenez D.; Martínez-Máñez, R.; Sancenón, F.; Soto, J. Tetrahedron Lett. 2002, 43, 2823.
13. (d) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777.
14. (a) Lee, D. H.; Im, J. H.; Son, S. U.; Chung, Y. K.; Hong, J.-I. J. Am. Chem. Soc. 2003, 725, 7752.
15. (b) Sancenón, F.; Martínez-Máñez, R.; Soto, J. Angew. Chem., Int. Ed. 2002, 41, 1416.
16. (c) Lee, D. H.; Lee, K. H.; Hong, J.-I. Org. Lett. 2001, 3, 5.
17. Recent examples of electron-acceptor chromophores for anion sensing: (a) Nishiyabu, R.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2005, 727, 8270.
18. (b) Esteban-Gómez, D.; Fabbrizzi, L.; Licchelli, M. J. Org. Chem. 2005, 70, 5717.
19. (a) Baeyer, A. Ber. Dtsch. Chem. Ges. 1886, 19, 2184.
20. (b) Gale, P. A.; Sessler, J. L.; Král, V. Chem. Commun. 1998, 1.
21. (c) Gale, P. A.; Anzenbacher, P., Jr.; Sessler, J. L. Coord. Chem. Rev. 2001, 222, 57.
22. Anzenbacher, P., Jr.; Jursíková, K.; Shriver, J. A.; Miyaji, H.; Lynch, V. M.; Sessler, J. L.; Gale, P. A. J. Org. Chem. 2000, 65, 7641.
23. (a) Sun, S.-S.; Zhang, C.; Dalton, L. R. Chem. Mater. 1996, 8, 2539.
24. (b) González, M.; Martín, N.; Segura, J. L.; Seoane, C.; Garín, J.; Orduna, J.; Alcalá, R.; Sánchez, C.; Villacampa, B. Tetrahedron Lett. 1999, 40, 8599.
25. (c) Raimundo, J.-M.; Blanchard, P.; Ledoux-Rak, I.; Hierle, R.; Michaux, L.; Roncali, J. Chem. Commun. 2000, 1597.
26. (d) Raimundo, J.-M.; Blanchard, P.; Gallego-Planas, N.; Mercier, N.; Ledoux-Rak, I.; Hierle, R.; Roncali, J. J. Org. Chem. 2002, 67, 205.
27. (e) Janowska, I.; Zakrzewski, J.; Nakatani, K.; Delaire, J. A.; Palusiak, M.; Walak, M.; Scholl, H. J. Organomet. Chem. 2003, 675, 35.
28. (a) Compounds 6, 7, and 8 were obtained from commercial sources.
29. (b) 9 was prepared according to Batsanov, A. S.; Bryce, M. R.; Davies, S. R.; Howard, J. A. K.; Whitehead, R.; Tanner, B. K. J. Chem. Soc., Perkin Trans. 2 1993, 313.
30. 2O). The degree of hydration was estimated from elemental analyses.
31. (a) Camiolo, S.; Gale, P. A.; Hursthouse, M. B.; Light, M. E.; Shi, A. J. Chem. Commun. 2002, 758.
32. (b) Gale, P. A.; Navakhun, K.; Camiolo, S.; Light, M. E.; Hursthouse, M. B. J. Am. Chem. Soc. 2002, 124, 11228.