Water-soluble 1,3-diphenylisobenzofuran derivatives. Synthesis and evaluation as singlet molecular oxygen acceptors for biological systems

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 93, Issue 1, 1996, Pages 49-56

  Amat Guerri, F ^a   Lempe, E ^b   Lissi, E A ^b   Rodriguez, F J ^c   Trull, F R ^c  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^c UNIVERSITY OF BARCELONA   (Spain)

Author keywords

1,3 Diphenylisobenzofuran derivatives; Singlet molecular oxygen acceptors

Indexed keywords

EID: 0030568187     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/1010-6030(95)04149-4     Document Type: Article

References (43)

1. [1] A.A. Frimer (ed.), Singlet Oxygen, CRC Press, Boca Ratón, 1985,and references cited therein.
2. [2] H. Schuchart and W. Nultsch, J. Photochem., 25 (1984) 317.
3. [3] K.R. Weisthaupt, C.J. Gomer and T.J. Dougherty, Cancer Res., 36 (1976) 2326.
4. [4] N. Duran, in W. Adam and G. Cilento (eds.), Chemical and Biological Generation of Excited States, Academic Press, New York, 1982, p. 345.
5. [5] C.S. Foote, in H.H. Wasserman and R.W. Murray (eds.), Singlet Oxygen, Academic Press, New York, 1979, p. 139.
6. [6] M.A.J. Rodgers and P.T. Snowden, J. Am. Chem. Soc., 104 (1982) 5541.
7. [7] A.U. Khan, Int. J. Quantum Chem., 39 (1991) 251.
8. [8] A.U. Khan, P. Gebauer and L.P. Hager, Proc. Natl. Acad. Sci. USA, 80 (1983) 5195.
9. [9] J.M. Aubry, J. Rigaudy and N.K. Cuong, Photochem. Photobiol., 33 (1981) 149; 33 (1981) 155.
10. [9] J.M. Aubry, J. Rigaudy and N.K. Cuong, Photochem. Photobiol., 33 (1981) 149; 33 (1981) 155.
11. [10] L.L. Smith and M.J. Kuling, J. Am. Chem. Soc., 98 (1976) 1027.
12. [11] J. Cadet and R. Teoule, FEBS Lett., 123 (1978) 225.
13. [12] D.F. Evans and M.W. Upton, J. Photochem., 25 (1984) 545.
14. [13] E. Lissi and M.A. Rubio, Pure Appl. Chem., 62 (1990) 1503.
15. [14] S. Ecary, Ann. Chim., 12 (1948) 445.
16. [15] C. Dufraisse and S. Ecary, C.R. Acad. Sci., Ser. C, 233 (1946) 735.
17. [16] N.I. Krinsky, in H.H. Wasserman and R.W. Murray (eds.), Singlet Oxygen, Academic Press, New York, 1979, p. 597.
18. [17] B. Stevens, S.R. Perez and J.A. Ors, J. Am. Chem. Soc., 90 (1974) 6846.
19. [18] P.B. Merkel and D.R. Kearns, J. Am. Chem. Soc., 94 (1972) 7244.
20. [19] P.B. Merkel and D.R. Kearns, J. Am. Chem. Soc., 97 (1975) 462.
21. [20] A. Guyot and J. Catel, Bull. Soc. Chim. Fr., 35 (1906) 1124.
22. [21] G.D. Mendenhall and J.A. Howard, Can. J. Chem., 53 (1975) 2199.
23. [22] D.D. Perrin, D.R. Perrin and W.L.F. Armarego, in Purification of Laboratory Chemicals, Pergamon, Oxford, 1980.
24. [23] (a) E.A. Lissi, M.V. Encinas, E. Lemp and M.A. Rubio, Chem. Rev., 93 (1993) 699;
25. (b) F. Wilkinson, W.P. Helman and A.B. Ross, J. Phys. Chem. Ref. Data, 22 (1993) 113.
26. [24] F. Amat-Guerri, J.M. Botija and R. Sastre, J. Polym. Sci., Part A: Polym. Chem., 31 (1993) 2609.
27. [25] R.V. Bensasson, E.J. Land and T.G. Truscott, in Excited States and Free Radicals in Biology and Medicine, Oxford University Press, Oxford, 1993, p. 119.
28. [26] C.S. Foote and T.Y. Ching, J. Am. Chem. Soc., 97 (1975) 6209.
29. [27] F. Wilkinson and J.G. Brummer, J. Phys. Chem. Ref. Data, 10 (1981) 893.
30. [28] M.P. Cava, M.J. Mitchell and A.A. Deana, J. Org. Chem., 25 (1960) 1481.
31. [29] R. Adams and M.H. Gold, J. Am. Chem. Soc., 62 (1940) 56.
32. [30] W. Zajac and D.E. Pichler, Can. J. Chem., 44 (1966) 833.
33. [31] H.Z. Sommer and L.L. Jackson, J. Org. Chem., 35 (1970) 1558.
34. [32] H.Z. Sommer, H.J. Lipp and L.L. Jackson, J. Org. Chem., 36 (1971) 824.
35. [33] (a) P. Bilski, R. Dabestani and C.F. Chignell, J. Phys. Chem., 95 (1991) 5784;
36. (b) P. Bilski, R. Dabestani and C.F. Chignell, J. Photochem. Photobiol. A: Chem., 79 (1994) 121.
37. [34] D.P. Hessler, F.H. Frimmel, E. Oliveros and A.M. Braun, Helv. Chim. Acta, 77 (1994) 859.
38. [35] M. Krieg, J. Biochem. Biophys. Methods, 27 (1993) 143.
39. [36] A.F. McDonagh, in D. Dolphin (ed.), The Porphyrins, Vol. 6, Academic Press, New York, 1979, p. 293.
40. [37] (a) A.A. Gorman and M.A.J. Rodgers, Chem. Phys. Lett., 55 (1977) 52;
41. (b) B.A. Linding and M.A.J. Rodgers, Photochem. Photobiol., 33 (1981) 627;
42. (c) M.A.J. Rodgers and A.L. Bates, Photochem. Photobiol., 35 (1982) 473;
43. (d) P.C. Lee and M.A.J. Rodgers, J. Phys. Chem., 87 (1983) 4894.