Two modes of self-coordinating edge-over-edge Zn(II) porphyrin dimerization: A structural and spectroscopic comparison

Journal of the American Chemical Society

Volumn 118, Issue 16, 1996, Pages 3980-3981

  Stibrany, Robert T ^a   Vasudevan, Jayasree ^a   Knapp, Spencer ^a   Potenza, Joseph A ^a   Emge, Tom ^a   Schugar, Harvey J ^a  

^a Rutgers University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE;

ARTICLE; DIMERIZATION; DRUG STRUCTURE; SPECTROPHOTOMETRY;

EID: 0029994865     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9536734     Document Type: Article

References (29)

1. (a) Thompson, M. A.; Zerner, M. C.; Fajer, J. J. Phys. Chem. 1991, 95, 5693-5700.
2. (b) Lathrop. E. J. P.; Freisner. R. A. J. Phys. Chem. 1994, 98, 3056-66.
3. (a) Deisenhofer. J.; Michel, H. Science 1989, 245, 1463-73.
4. (b) Allen, J. P.; Feher, G., Yeates, T. O.; Komiya. H.; Rees, D. C. Proc. Natl. Acad. Sci U.S.A. 1988, 85, 8487-91.
5. Boxer, S. G. Photosynth. Res. 1992, 33, 113-9.
6. (a) Scheldt, W. R.; Lee, Y. J. Struct. Banding (Berlin) 1987, 64, 1-70.
7. (b) Song, H.; Rath, N. P.: Reed. C. A., Scheidt, W. R. Inorg. Chem. 1989, 28, 1839-47.
8. (a) Morgan B.; Dolphin, D. Struct. Bonding (Berlin) 1987, 64, 115-203.
9. (b). Lin, V. S.-Y; DiMagno, S. G; Therien, M. J. Science 1994, 264, 1105-11.
10. (c) Osuka, A.; Liu. B.; Maruyama. K. J. Org. Chem. 1993, 58, 3582-85.
11. (d) Bookser, B. C; Bruice, T. C. J. Am. Chem. Soc. 1991, 113, 4208-18.
12. (e) Bied-Charreton, C.; Merienne, C , Gaudemer, A. New J. Chem. 1987, 11, 633-9.
13. (f) Kobuke. Y.; Miyaji, H. J. Am. Chem. Soc. 1994, 116, 4111-2.
14. (g) Nozawa, T.; Ohtomo, K.; Suzuki, M.; Morishita, Y.; Madigan, M. T. Bull. Chem. Soc. Jpn. 1993, 66, 231-37.
15. (h) Bucks, R. R.; Boxer, S. G. J. Am. Chem. Soc. 1982, 104, 340-3.
16. (a) Gonsalves, A. M. d'A. R.; Varejao, J. M. T. B.; Pereira, M. M. J. Heteracycl. Chem. 1991, 28, 635-640.
17. (b) Onaka, M.; Shinoda, T.; Izumi, Y.; Nolen. E. Chem. Lett. 1993, 117-120.
18. 3 solution: 2D, 1785 (calcd for dimer 1791); 3D, 1654 (calcd 1574); 5D, 1403 (calcd 1491).
19. The analogue of ID having a 5-(4-pyridjl) substituent crystallizes as a coordination polymer. Fleischer, E. B.; Schachter, A. M. Inorg. Chem. 1991, 30, 3763-9.
20. (a) Senge. M. O.; Vicente, M. G. H.: Gerzevske, K. R., Forsyth, T. P.; Smith, K. M. Inorg. Chem. 1994, 33, 5625-38.
21. (b) Smith, K. M , Bobe, F. W.: Goff, D. A.; Abraham, R. J. J. Am. Chem. Soc. 1986, 108, 1111-1120.
22. (a) Walker, F. A.; Benson, M. J. Am. Chem. Soc. 1980, 102, 5530-38.
23. b) Abraham, R. J.; Bedford, G. R.; Wright, B. Org. Magn. Reson. 1982, 18, 45-52.
24. Nappa, M.; Valentine, J. S. J. Am. Chem. Soc. 1978, 100, 5075-5080.
25. 3 molecules with the total occupancy of Cl = 4 5.
26. DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993. 58, 5983-5993.
27. Prepared by bromination of 5, 10.15,20-tetra-n-heptylporphyrin according to Callot, H. J Bull. Soc. Chim. Fr. 1974, 41, 1492-1496.
28. Zerner M. C.: Loew, G. H.; Kirchner, R. F.; Mueller-Westerhoff, U. T J. Am. Chem. Soc 1980, 102, 589-99. The stacked structure also was calculated to be preferred by AM-1 and MM2 methods.
29. McDermott, G. A.; Walker, F. A. Inorg. Chim. Acta 1984, 91, 95-102.