Water soluble sapphyrins: Potential fluorescent phosphate anion sensors

Organic and Biomolecular Chemistry

Volumn 1, Issue 22, 2003, Pages 4113-4123

  Sessler, Jonathan L ^a   Davis, Julian M ^a   Král, Vladimir ^b   Kimbrough, Thomas ^a   Lynch, Vincent ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; DIMERIZATION; FLUORESCENCE; METHANOL; NEGATIVE IONS; PH EFFECTS; PHASE EQUILIBRIA; PHOSPHATES; SENSORS; SOLUBILITY; SOLUTIONS;

MESO ARYL SUBSTITUENTS; SAPPHYRINS; SELF AGGREGATION;

ORGANIC COMPOUNDS;

ANION; PHOSPHATE; PORPHYRIN; PROTON; SAPPHYRIN; WATER;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; HYDROGEN BOND; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PROTEIN BINDING; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; X RAY; X RAY CRYSTALLOGRAPHY;

ANIONS; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; PHOSPHATES; PORPHYRINS; PROTEIN BINDING; PROTONS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY; WATER; X-RAYS;

EID: 0345566253     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b306964h     Document Type: Article

References (44)

1. D. Dolphin, in The Porphyrins, Academic Press, New York, 1978, vol. 1-8.
2. K. M. Smith, in Porphyrins and Metalloporphyrins, Elsevier, Amsterdam, 1976.
3. K. M. Kadish, K. M. Smith, and R. Guilard, in The Porphyrin Handbook, Academic Press, San Diego, 2000.
4. A. Jasat and D. Dolphin, Chem. Rev., 1997, 97, 2267-2340.
5. J. L. Sessler and S. J. Weghorn, in Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford, 1997.
6. C. A. Hunter and J. K. M. Sanders, J. Am. Chem. Soc., 1990, 112, 5525-5534.
7. D. L. Akins, H.-R. Zhu and C. Guo, J. Phys. Chem., 1996, 100, 5420-5425.
8. N. C. Maiti, S. Mazumdar and N. Periasamy, J. Phys. Chem. B, 1998, 102, 1528-1538.
9. K. Kano, K. Fukuda, H. Wakami, R. Nishiyabu and R. F. Pasternack, J. Am. Chem. Soc., 2000, 122, 7494-7502.
10. R.-H. Jin, S. Aoki and K. Shima, J. Chem. Soc., Faraday Trans., 1997, 93(22), 3945-3953.
11. K. Lang, P. Anzenbacher, P. Kapusta, V. Krá'l, P. Kubát and D. M. Wagnerová, J. Photochem. Photobiol., B, 2000, 57, 51-59.
12. B. G. Maiya, M. Cyr, A. Harriman and J. L. Sessler, J. Phys. Chem., 1990, 94, 3597-3601.
13. V. Král, H. Furuta, K. Shreder, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607.
14. B. L. Iverson, K. Shreder, V. Král, P. Sansom, V. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1608-1616.
15. V. J. Bauer, D. L. J. Clive, D. Dolphin, J. B. Paine III, F. L. Harris, M. M. King, J. Loder, S. W. C. Wang and R. B. Woodward, J. Am. Chem. Soc., 1983, 105, 6429-6436.
16. J. L. Sessler and J. M. Davis, Acc. Chem. Res., 2001, 34(12), 989-997.
17. J. L. Sessler, M. Cyr, H. Furuta, V. Král, T. Mody, T. Morishima, M. Shionoya and S. Weghorn, Pure Appl. Chem., 1993, 65, 393-398.
18. V. Král and J. L. Sessler, Tetrahedron, 1994, 51, 539-554.
19. B. L. Iverspn, R. E. Thomas, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1994, 116, 2663-2664.
20. V. Král, J. Davis, A. Andrievsky, J. Kralová, A. Synytsya, P. Poucková and J. L. Sessler, J. Med. Chem., 2002, 45(5), 1073-1078.
21. J. L. Sessler, A. Andrievsky, P. I. Sansom, V. Král and B. L. Iverson, Bioorg. Med. Chem. Lett., 1997, 7 (11), 1433-1436.
22. C. Brückner, E. D. Sternberg, R. W. Boyle and D. Dolphin, Chem. Commun., 1997, 1689-1690.
23. J. L. Sessler, J. Lisowski, K. A. Boudreaux, V. Lynch, J. Barry and T. J. Kodadek, J. Org. Chem., 1995, 60, 5975-5978.
24. J. W. Bohn, Annu. Rev. Phys. Chem., 1993, 44, 37-60.
25. S. S. Zumdahl, in Chemistry, D. C. Heath and Company, Lexinton, MA, 2nd edn., 1995, p. A25.
26. K. A. Connors, in Binding Constants. The Measurement of Molecular Complex Stability, Wiley, New York, 1987, pp. 339-343.
27. M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722.
28. D. Voet and J. G. Voet, in Biochemistry, John Wiley & Sons, Inc., New York, 2nd edn., 1995.
29. R. F. Pasternack, Ann. N. Y. Acad. Sci., 1973, 206, 614-630.
30. R. C. Weast and M. J. Astle, in CRC Handbook of Chemistry and Physics, CRC Press, Inc., Boca Raton, FL, 63rd edn., 1982, p. F-179.
31. P. J. Chmielewski, L. Latos-Grazyński and K. Rachlewicz, Chem. Eur. J., 1995, 1, 68-73.
32. K. Rachlewicz, N. Sprutta, L. Latos-Grazyński, P. J. Chmielewski and L. Szterenberg, J. Chem. Soc., Perkin Trans. 2, 1998, 959-967.
33. A. Srinivasan, S. K. Pushpan, M. R. Kumar, S. Mahajan, T. K. Chandrashekar, R. Roy and P. Ramamurthy, J. Chem. Soc., Perkin Trans. 2, 1999, 961-968.
34. L. Szterenberg and L. Latos-Grazyński, J. Phys. Chem. A, 1999, 103, 3302-3309.
35. K. Rachlewicz, L. Latos-Grazyński, A. Gebauer, A. Vivian and J. L. Sessler, J. Chem. Soc., Perkin Trans. 2, 1998, 2189-2195.
36. N. Sprutta and L. Latos-Grazyński, Org. Lett., 2001, 3(12), 1933-1936.
37. M. E. Huston, E. U. Akkaya and A. W. Czarnik, J. Am. Chem. Soc., 1989, 111, 8735-8737.
38. A. W. Czarnik, Acc. Chem. Res., 1994, 27, 302-308.
39. S. Watanabe, O. Snogawa, Y. Komatsu and K. Yoshida, J. Am. Chem. Soc., 1998, 120, 229-230.
40. S. Nishizawa, Y. Kato and N. Teramae, J. Am. Chem. Soc., 1999, 121, 9463-9464.
41. S. L. Wiskur, H. Ait-Hssou, J. J. Levine and E. Anslyn, Acc. Chem. Res., 2001, 34, 963-972.
42. M. S. Han and D. H. Kim, Angew. Chem. Int. Ed., 2002, 41(20), 3809-3811.
43. S. Shao, Y. Gou, L. He, S. Jiang and X. Yu, Tetrahedron Lett., 2003, 44, 2175-2178.
44. L.-J. Kuo, J.-H. Liao, C.-T. Chen, C-H. Huang, C.-S. Chen and J.-M. Fang, Org. Lett., 2003, 5(11), 1821-1824.