A novel stepwise degradation of porphyrins. Synthesis and structural characterization of meso-tetraphenylchlorophinato Nickel(II) and meso- tetraphenylsecochlorinato Nickel(II) [7]

Journal of the American Chemical Society

Volumn 121, Issue 11, 1999, Pages 2609-2610

  Brückner, Christian ^a,b   Sternberg, Ethan D ^a   MacAlpine, Jill K ^a   Rettig, Steven J ^a   Dolphin, David ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEGRADATION; LETTER; STRUCTURE ANALYSIS;

EID: 0033599519     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981417w     Document Type: Letter

References (40)

1. (a) Photodynamic Theory: Basic Principles and Clinical Applications; Henderson, B. W., Dougherty, T. J., Eds.; Marcel Dekker: New York, 1992.
2. For overview articles of PDT, see: (b) Bonnett, R. Chem. Soc. Rev. 1995, 19. (c) Sternberg, E. D.; Dolphin, D.; Brückner, C. Tetrahedron Reports Number 447 1998, 54, 4151.
3. For overview articles of PDT, see: (b) Bonnett, R. Chem. Soc. Rev. 1995, 19. (c) Sternberg, E. D.; Dolphin, D.; Brückner, C. Tetrahedron Reports Number 447 1998, 54, 4151.
4. (a) Expanded, Contracted and Isomeric Porphyrins, Sessler, J. L.; Weghorn, S. J. Pergamon: New York, 1997 and references therein.
5. (b) Jasat, A.; Dolphin, D. Chem. Rev. 1997, 97, 2267.
6. For brief overviews, see: (a) Vogel, E. Pure Appl. Chem. 1996, 68, 1355.
7. (a) Brückner, C.; Rettig, S. J.; Dolphin, D. J. Org. Chem. 1998, 63, 2095.
8. (b) Lash, T. D.; Hayes, M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 840.
9. (c) Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839.
10. (d) Lash, T. D.; Chaney, S. T. Chem. Eur. J. 1996, 2, 944.
11. (e) Berlin, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1820 and references therein.
12. The crystal structure of the octaethylporphyrin-derived analogue to 1 has been determined, although details have not yet been published: (a) Adams, K. R.; Bonnett, R.; Burke, P. J.; Salgado, A.; Asunción Vallés, M. J. Chem. Soc., Perkin 1 1997, 1769. (b) Adams, K. R.; Bonnett, R.; Burke, P. J.; Salgado, A.: Vallés, M. A. J. Chem. Soc., Chem. Commun. 1993, 1860.
13. The crystal structure of the octaethylporphyrin-derived analogue to 1 has been determined, although details have not yet been published: (a) Adams, K. R.; Bonnett, R.; Burke, P. J.; Salgado, A.; Asunción Vallés, M. J. Chem. Soc., Perkin 1 1997, 1769. (b) Adams, K. R.; Bonnett, R.; Burke, P. J.; Salgado, A.: Vallés, M. A. J. Chem. Soc., Chem. Commun. 1993, 1860.
14. (a) Shelnutt, J. A.; Song, X.-Z.; Ma, J.-G.; Jia, S.-L.; Jantzen, W.; Medforth, C. J. Chem. Soc. Rev. 1998, 27, 31.
15. (b) Ravikanth, M.; Chandrashekar, T. K. Struct. Bonding (Berlin) 1995, 82, 107.
16. Classification of porphyrin distortion modes: (c) Scheidt, W. R.; Lee, Y. J. Struct. Bonding (Berlin) 1987, 64, 1. For recent developments see: (d) Nurco, D. J.; Medforth, C. J.; Forsyth, T. P.; Olmstead, M. M.; Smith, K. M. J. Am. Chem. Soc. 1996, 118, 10918. (e) Cheng, B.; Munro, O. Q.; Marques. H. M.; Scheidt, W. R. J. Am. Chem. Soc. 1997, 119, 10732. (f) Senge, M. O.; Kalisch, W. W.; Runge, S. Liebigs Ann./Recueil 1997, 1345.
17. Classification of porphyrin distortion modes: (c) Scheidt, W. R.; Lee, Y. J. Struct. Bonding (Berlin) 1987, 64, 1. For recent developments see: (d) Nurco, D. J.; Medforth, C. J.; Forsyth, T. P.; Olmstead, M. M.; Smith, K. M. J. Am. Chem. Soc. 1996, 118, 10918. (e) Cheng, B.; Munro, O. Q.; Marques. H. M.; Scheidt, W. R. J. Am. Chem. Soc. 1997, 119, 10732. (f) Senge, M. O.; Kalisch, W. W.; Runge, S. Liebigs Ann./Recueil 1997, 1345.
18. Classification of porphyrin distortion modes: (c) Scheidt, W. R.; Lee, Y. J. Struct. Bonding (Berlin) 1987, 64, 1. For recent developments see: (d) Nurco, D. J.; Medforth, C. J.; Forsyth, T. P.; Olmstead, M. M.; Smith, K. M. J. Am. Chem. Soc. 1996, 118, 10918. (e) Cheng, B.; Munro, O. Q.; Marques. H. M.; Scheidt, W. R. J. Am. Chem. Soc. 1997, 119, 10732. (f) Senge, M. O.; Kalisch, W. W.; Runge, S. Liebigs Ann./Recueil 1997, 1345.
19. Classification of porphyrin distortion modes: (c) Scheidt, W. R.; Lee, Y. J. Struct. Bonding (Berlin) 1987, 64, 1. For recent developments see: (d) Nurco, D. J.; Medforth, C. J.; Forsyth, T. P.; Olmstead, M. M.; Smith, K. M. J. Am. Chem. Soc. 1996, 118, 10918. (e) Cheng, B.; Munro, O. Q.; Marques. H. M.; Scheidt, W. R. J. Am. Chem. Soc. 1997, 119, 10732. (f) Senge, M. O.; Kalisch, W. W.; Runge, S. Liebigs Ann./Recueil 1997, 1345.
20. We follow the trivial nomenclature suggested by Flitsch (ref 22) and propagated by Chang et al. (ref 21a) . Systematic nomenclature: 4, [1,4-didecarbo-1H,4H-1,5,10,15-tetraphenylporphyrinato]Ni(II) ; 3, [1-decarbo-1H-3-oxo-3H-1,5,10,15-tetraphenylporphyrinato]Ni(II) .
21. w = 0.051. Additional details are available in the Supporting Information.
22. James, B. R.; Young, C. G. J. Organomet. Chem. 1985, 285, 321.
23. 2/wet MeOH) C 75.81 (75.89) , H 4.54 (4.55) , N 8.42 (8.30) .
24. Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341..
25. w = 0.038. Additional details are available in the Supporting Information.
26. Dolphin, D.; Rettig, S. J.; Tang, H.; Wijesekera, T.; Xie, L. Y. J. Am. Chem. Soc. 1993, 115, 9301.
27. Hoard, J. L. Ann. N.Y. Acad. Sci. 1973, 206, 18.
28. Jentzen, W.; Turowska-Tyrk, I.; Scheidt, W. R.; Shelnutt, J. A. Inorg. Chem. 1996, 35, 3559.
29. Barkigia, K. M.; Renner, M. W.; Furenlid, L. R.; Medforth, C. J.; Smith, K. M.; Fajer, J. J. Am. Chem. Soc. 1993, 115, 3627.
30. (a) Henrick, K.; Tasker, P. A.; Lindoy, L. F. Prog. Inorg. Chem. 1985, 33, 1.
31. (b) Ni-N bond distance in bis(meso-phenyl) dipyrrinato Ni(II) 1.879(2) Å: Brückner, C.; Karunaratne, V.; Rettig, S. J.; Dolphin, D. Can. J. Chem. 1996, 27, 2182.
32. Gallucci, J. C.; Swepston, P. N.; Ibers, J. A. Acta Crystallogr., Sect. B 1982, 38, 2134.
33. Stolzenberg, A. M.; Stershic, M. T. J. Am. Chem. Soc. 1988, 110, 6391.
34. MM2 force field, CAChe System, Oxford Molecular Systems, V.3.9, 1996.
35. Bohusch, M.; Flitsch, W.; Kneip, H.-G. Liebigs Ann. Chem. 1991, 67.
36. (a) Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun. 1984, 920.
37. (b) Crossley, M. J.; Hambley, T. W.; King, L. G. Bull. Soc. Chim. Fr. 1996, 133, 735.
38. (a) Flitsch, W. Pure Appl. Chem. 1986, 58, 153.
39. (b) Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73.
40. Isaak, M.; Senge, M. O.; Smith, K. M. J. Chem. Soc., Perkin Trans 1 1995, 705, and references therein.