2,3,7,8,12,13,17,18-Octafluoro-5,10,15,20-tetraarylporphyrins and Their Zinc Complexes: First Spectroscopic, Electrochemical, and Structural Characterization of a Perfluorinated Tetraarylmetalloporphyrin

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1588-1593

  Woller, Eric K ^a   DiMagno, Stephen G ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000972547     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962159t     Document Type: Article

References (53)

1. Chang, D. K.; Ebina, F. J. Chem. Soc., Chem. Commun. 1981, 778.
2. Hoffman, P.; Robert, A.; Meunier, B. Bull. Soc. Chim. Fr. 1992, 129, 85.
3. Traylor, P. S.; Dolphin, D.; Traylor, T. G. J. Chem. Soc., Chem. Commun. 1984, 279.
4. Traylor, T. G.; Tsuchiya, S. Inorg. Chem. 1987, 26, 1338.
5. Traylor, T. G.; Hill, K. W.; Fann, W.-P.; Tsuchiya, S.; Dunlap, B. E. J. Am. Chem. Soc. 1992, 114, 1308.
6. Gonsalves, A. M. d. A. R.; Johnstone, R. W. W.; Pereira, M. M.; Shaw, J.; Sobral, A. J. F. d. N. Tetrahedron Lett. 1991, 32, 1355.
7. Mansuy, D. Coord. Chem. Rev. 1993, 125, 129.
8. Meunier, B. Chem. Rev. 1992, 92, 1411.
9. Fujii, H. J. Am. Chem. Soc. 1993, 115, 4641.
10. Wijesekera, T. P.; Lyons, J. E.; Ellis, P. E., Jr. Catal. Lett. 1996, 36, 69.
11. Ellis, P. E., Jr.; Lyons, J. W. Coord. Chem. Rev. 1990, 105, 181.
12. Ellis, P. E., Jr.; Lyons, J. E. Catal. Lett. 1989, 3, 389.
13. Grinstaff, M. W.; Hill, M. G.; Labinger, J. A.; Gray, H. B. Science 1994, 264, 1311.
14. Ochsenbein, P.; Ayougou, K.; Mandon, D.; Fischer, J.; Weiss, R.; Austin, R. N.; Jayaraj, K.; Gold, A.; Terner, J.; Fajer, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 348.
15. Bhyrappa, P.; Krishnan, V. Inorg. Chem. 1991, 30, 239.
16. Wijeskera, T.; Matsumoto, A.; Dolphin, D.; Lexa, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 1028.
17. Birnbaum, E. R.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chem. 1995, 34, 1751.
18. Grinstaff, M. W.; Hill, M. F.; Birnbaum, E. R.; Schaefer, W. P.; Labinger, J. A.; Gray, H. B. Inorg. Chem. 1995, 34, 4896.
19. Gassman, P. G.; Ghosh, A.; Almlof, J. J. Am. Chem. Soc. 1992, 114, 9990.
20. Ghosh, A. J. Am. Chem. Soc. 1995, 117, 4691.
21. DiMagno, S. G.; Williams, R. A.; Therien, M. J. J. Org. Chem. 1994, 59, 6943.
22. Goll, J. G., Moore, K. T., Ghosh, A.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 8344.
23. DiMagno, S. G.; Wertsching, A. K.; Ross, C. R., II. J. Am. Chem. Soc. 1995, 117, 8279.
24. Results from the AM1 semiempirical calculations (Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902) are included in the Supporting Information. These calculations predict a planar macrocycle for 1(Zn), The free base is predicted to have a shallow potential energy surface on which the planar structure is a local minimum approximately 3 kcal/mol above the global minimum.
25. Tsuchiya, S.; Seno, M. Chem. Lett. 1989, 263.
26. Lyons, J. E., Ellis, P. E., Jr. U.S. Patent 5,120,886, 1992. Ellis, P. E., Jr.; Lyons, J. E. U.S. Patent 4,970,348, 1990.
27. Lyons, J. E., Ellis, P. E., Jr. U.S. Patent 5,120,886, 1992. Ellis, P. E., Jr.; Lyons, J. E. U.S. Patent 4,970,348, 1990.
28. Leroy, J.; Wakselman, C. Tetrahedron Lett. 1992, 35, 8605.
29. Lindsey, J. S.; Schrieman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827.
30. Typical isolated yields for TPP and TPFTPP are 36% and 15%, respectively, in our hands.
31. Birnbaum, E. R.; Hodge, J. A.; Grinstaff, M. W.; Schaefer, W. P.; Henling, L.; Labinger, J. A.; Gray, H. B. Inorg. Chem. 1995, 34, 3625.
32. Crossley, M. J.; Field, L. D.; Harding, M. M.; Sternhell, S. J. Am. Chem. Soc. 1987, 109, 2335.
33. Eaton, S. S.; Eaton, G. R. J. Am. Chem. Soc. 1977, 99, 1601. Values for proton tautomerism in tetraaryl porphyrins are in the range 11.9-12.5 kcal/mol.
34. Gouterman, M. J. Mol. Spectrosc. 1961, 6, 138.
35. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. III, p 1.
36. Binstead, R. A.; Crossley, M. J.; Hush, N. S. Inorg. Chem. 1991, 30, 1259.
37. Spellane, P. J.; Gouterman, M.; Antipas, A.; Kim, S.; Liu, Y. C. Inorg. Chem. 1980, 19, 386.
38. l〉, depends upon the interelectronic distances (g = 1/r). Mataga, N.; Kubota, T. Molecular Interactions and Electronic Spectra; Marcel Dekker: New York, 1970.
39. Merz, A.; Schropp, R.; Lex, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 291.
40. Merz, A.; Schropp, R.; Dötterl, E. Synthesis 1995, 795.
41. The atomic coordinates for this structure have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
42. Hoard, J. L. Ann. N. Y. Acad. Sci. 1973, 206, 18.
43. Schauer, C. K.; Anderson, O. P.; Eaton, S. R.; Eaton, G. R. Inorg. Chem. 1985, 24, 4082.
44. Collins, D. M.; Hoard, J. L. J. Am. Chem. Soc. 1970, 92, 3761.
45. Scheidt, W. R.; Kastner, M. E.; Hatano, K. Inorg. Chem. 1978, 17, 706.
46. Marsh, R. E.; Schaefer, W. P.; Hodge, J. A.; Hughes, M. E.; Gray, H. B. Acta Crystallogr. 1993, C49, 1339.
47. Scheldt, W. R.; Lee, Y. J. Struct. Bonding 1987, 64, 1.
48. Ravikanth, M.; Chandrashekar, T. K. Struct. Bonding 1995, 82, 105.
49. Mandon, D.; Ochsenbein, P.; Fischer, J.; Weiss, R.; Jayaraj, K.; Austin, R. N.; Gold, A.; White, P. S.; Brigaud, O.; Battioni, P.; Mansuy, D. Inorg. Chem. 1992, 31, 2044.
50. Henling, L. M.; Schaefer, W. P.; Hodge, J. A.; Hughes, M. E.; Gray, H. B. Acta Crystallogr. 1993, C49, 1743.
51. Schaefer, W. P.; Hodge, J. A.; Hughes, M. E.; Gray, H. B. Acta Crystallogr. 1993, C49, 1342.
52. Bondi, A. J. Phys. Chem. 1964, 68, 441.
53. Hodge, J. A.; Hill, M. G.; Gray, H. B. Inorg. Chem. 1995, 34, 809.