Synthesis of new cholesterol- and sugar-anchored squaraine dyes: Further evidence of how electronic factors influence dye formation

Organic Letters

Volumn 8, Issue 1, 2006, Pages 111-114

  Jyothish, Kuthanapillil ^a   Avirah, Rekha R ^a   Ramaiah, Danaboyina ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30944469014     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052639j     Document Type: Article

References (40)

1. (a) Kukrer, B.; Akkaya, E. U. Tetrahedron Lett. 1999, 40, 9125.
2. (b) Xie, J.; Comeau, A. B.; Seto, C. T. Org. Lett. 2004, 6, 83.
3. (c) Ros-Lis, J. V.; Garcia, B.; Jimenez, D.; Martinez-Manez, R.; Sancenon, F.; Soto, J.; Gonzalvo, F.; Valldecabres, M. C. J. Am. Chem. Soc. 2004, 126, 4064.
4. (d) Arunkumar, E.; Forbes, C. C.; Noll, B. C.; Smith, B. D. J. Am. Chem. Soc. 2005, 127, 3288.
5. (e) Bablo Block, M. A.; Hecht, S. Macromolecules 2004, 37, 4761.
6. (f) Arunkumar, E.; Ajayaghosh, A.; Daub, J. J. Am. Chem. Soc. 2005, 127, 3156.
7. (g) Wallace, K. J.; Gray, M.; Zhong, Z.; Lynch, V. M.; Anslyn, E. V. Dalton Trans. 2005, 2436.
8. (h) Arun, K. T.; Ramaiah, D. J. Phys. Chem. A 2005, 109, 5571.
9. (a) Liang, K.; Farahat, M. S.; Perlstein, J.; Law, K. Y.; Whitten, D. G. J. Am. Chem. Soc. 1997, 119, 830.
10. (b) Chen, H.; Farahat, M. S.; Law, K. Y.; Whitten, D. G. J. Am. Chem. Soc. 1996, 118, 2584.
11. (c) Das, S.; Thomas, K. G.; Kamat, P. V.; George, M. V. J. Phys. Chem. 1994, 98, 9291.
12. (d) Law, K. Y. Chem. Rev. 1993, 93, 449.
13. (e) Kamat, P. V.; Das, S.; Thomas, K. G.; George, M. V. J. Phys. Chem. 1992, 96, 195.
14. (a) Law, K. Y.; Bailey, F. C. J. Imaging Sci. 1987, 31, 172.
15. (b) Tam, A. C.; Balanson, R. D. IBM J. Res. Develop. 1982, 26, 186.
16. (a) Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197.
17. (b) Emmelius, M.; Pawlowski, G.; Vollmann, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1445.
18. (a) Liang, K. N.; Law, K. Y.; Whitten, D. G. J. Phys. Chem. 1995, 99, 16704.
19. (b) Piechowski, A. P.; Bird, G. R.; Morel, D. L.; Stogryn, E. L. J. Phys. Chem. 1984, 88, 934.
20. (c) Loufty, R. O.; Hsiao, C. K.; Kazmaier, P. M. Photogr. Sci. Eng. 1983, 27, 5.
21. (a) Ramaiah, D.; Joy, A.; Chandrasekhar, N.; Eldho, N. V.; Das, S.; George, M. V. Photochem. Photobiol. 1997, 65, 783.
22. (b) Ramaiah, D.; Eckert, I.; Arun, K. T.; Weidenfeller, L.; Epe, B. Photochem. Photobiol. 2002, 76, 672.
23. (c) Arun, K. T.; Epe, B.; Ramaiah, D. J. Phys. Chem. B 2002, 106, 11622.
24. (d) Ramaiah, D.; Eckert, I.; Arun, K. T.; Weidenfeller, L.; Epe, B. Photochem. Photobiol. 2004, 79, 99.
25. (e) Beverina, L.; Abbotto, A.; Landenna, M.; Cerminara, M.; Tubino, R.; Meinardi, F.; Bradamante, S.; Pagani, G. A. Org. Lett. 2005, 7, 4257.
26. (a) Treibs, A.; Jacob, K. Angew. Chem., Int. Ed. Engl. 1965, 4, 694.
27. (b) Schmidt, A. H. Synthesis 1980, 961.
28. (a) Law, K. Y.; Bailey, F. C. Can. J. Chem. 1986, 64, 2267.
29. (b) Law, K. Y.; Bailey, F. C. J. Org. Chem. 1992, 57, 3278.
30. (c) Block, M. A. B.; Khan, A.; Hecht, S. J. Org. Chem. 2004, 69, 184.
31. Jyothish, K.; Arun, K. T.; Ramaiah, D. Org. Lett. 2004, 23, 3965.
32. (a) Hussey, S. L.; He, E.; Peterson, B. R. J. Am. Chem. Soc. 2001, 123, 12712 and references therein.
33. (b) Carreon, J. R.; Roberts, M. A.; Wittenhagen, L. M.; Kelley, S. O. Org. Lett. 2005, 7, 99.
34. (a) Bell, G. I.; Burant, C. F.; Takaka, J.; Gould, G. W. J. Biol. Chem. 1993, 268, 19161.
35. (b) Mellanen, P.; Minn, H.; Greman, R.; Harkonen, P. Int. J. Cancer 1994, 56, 622.
36. (c) Chen, Y.; Janczuk, A.; Chen, X.; Wang, J.; Ksebati, M.; Wang, P. G. Carbohydr. Res. 2002, 337, 1043.
37. (d) Hussey, S. L.; He, E.; Peterson, B. R. Org. Lett. 2002, 4, 415.
38. (e) Chen, X.; Hui, L.; Foster, D. A.; Drain, C. M. Biochemistry 2004, 43, 10918.
39. All geometries were optimized using semiemperical AM1 calculations. DFT B3LYP/6-31G* single-point energy calculations were used to obtain the electrostatic potential surfaces using Titan (Wavefunction, Inc.).
40. The color at each point on these surfaces reflects the interaction energy between a positive test charge at that point. Red indicates an attractive potential while blue represents a repulsive potential. The areas of red therefore indicate a "negative" region; yellow/green indicates a more neutral or "positive" region, depending on how bluish is the color.