Bis(dimethylamino)porphyrazines: Synthetic, structural, and spectroscopic investigations

Journal of Organic Chemistry

Volumn 65, Issue 8, 2000, Pages 2472-2478

  Garrido Montalban, Antonio ^a   Jarrell, Wade ^b   Riguet, Eric ^a   McCubbin, Quentin J ^a   Anderson, Mairin E ^b   White, Andrew J P ^a   Williams, David J ^a   Barrett, Anthony G M ^a   Huffman, Brian M ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(DIMETHYLAMINO)PORPHYRAZINE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; OXIDATION REDUCTION REACTION; POLYMERIZATION; SYNTHESIS;

CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; METALLOPORPHYRINS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0034696985     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991646g     Document Type: Article

References (39)

1. Dailey, K. K.; Yap, G. P. A.; Rheingold, A. L.; Rauchfuss, T. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1833.
2. Bonnet, R. Chem. Soc. Rev. 1995, 19.
3. (b) Rosenthal, I. In Phthalocyanines: Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH: New York, 1996; Vol. 4; pp 485-507.
4. (a) Ferraro, J. R.; Williams, J. M. In Introduction to Synthetic Electrical Conductors, 1st ed.; Academic Press: Orlando, FL, 1987; p 353.
5. (b) Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, K. D.; Geiser, U.; Wang, H. H.; Whangbo, M. H. In Organic Superconductors (Including Fullerenes): Synthesis, Structure, Properties and Theory; Prentice Hall: Englewood Cliffs, NJ, 1992.
6. (c) Crossley, M. J.; Burn, P. L.; Langford, S. J.; Prashar, J. K. J. Chem. Soc., Chem. Commun. 1995, 1921.
7. (a) Kahn, O. In Molecular Magnetism; VCH: New York, 1993; Vol. xvi; p 380.
8. (b) Miller, J. S.; Vazquez, C.; Calabrese, J. C.; McLean, R. S.; Epstein, A. J. Adv. Mater. 1994, 6, 217.
9. Leznoff, C.; Lever, A. In Phthalocyanines: Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH: New York, 1989; Vol. 1.
10. Gürek, A.; Bekaroglu, Ö. J. Chem. Soc., Dalton Trans. 1994, 1419.
11. Chabach, D.; Decian, A.; Fischer, J.; Weiss, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 898.
12. Lin, V. S.-Y.; Dimagno, S. G.; Therien, M. J. Science 1994, 264, 1105.
13. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996.
14. Wagner, R.; Johnson, T.; Li, F.; Lindsey, J. J. Org. Chem. 1995, 60, 5266.
15. Officer, D. L.; Burrell, A. K.; Reid, D. C. W. J. Chem. Soc., Chem. Commun. 1996, 1657.
16. Hamilton, A.; Lehn, J.-M.; Sessler, J. L. J. Am. Chem. Soc. 1986, 108, 5158.
17. Anderson, H. L. Inorg. Chem. 1994, 33, 972.
18. Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578.
19. Kobayashi, N.; Togashi, M.; Osa, T.; Ishii, K.; Yamauchi, S.; Hino, H. J. Am. Chem. Soc. 1996, 118, 1073.
20. Kocak, M.; Okur, A. I.; Bekaroglu, Ö. J. Chem. Soc., Dalton Trans. 1994, 323.
21. Terekhov, D.; Nolan, K.; McArthur, C.; Leznoff, C. J. Org. Chem. 1996, 61, 3034.
22. Garrido Montalban, A.; Lange, S. J.; Beall, L. S.; Mani, N. S.; Williams, D. J.; White, A. J. P.; Barrett, A. G. M.; Hoffman, B. M. J. Org. Chem. 1997, 62, 9284.
23. Eichhorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, A. G. M.; Hoffman, B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
24. Hochmuth, D. H.; Jarrell, W.; Michel, S. L. J.; White, A. J. P.; Williams, D. J.; Barrett, A. G. M.; Hoffman, B. M. Manuscript in preparation.
25. Chappell, J. S.; Bloch, A. N.; Bryden, W. A.; Maxfield, M.; Poehler, T. O.; Cowan, D. O. J. Am. Chem. Soc. 1981, 103, 2442.
26. (a) Kobayashi, N.; Numao, M.; Kondo, R.; Nakajima, S.-i.; Osa, T. Inorg. Chem. 1991, 30, 2241.
27. (b) Crossley, M. J.; Prashar, J. K. Tetrahedron Lett. 1997, 38, 6751 and references therein.
28. (a) Yang, J.; Mark, R. V. D. Tetrahedron Lett. 1993, 34, 5223.
29. (b) Lelievre, D.; Damette, O.; Simon, J. J. Chem. Soc., Chem. Commun. 1993, 939 and references therein.
30. (c) Ishii, K.; Kobayashi, N.; Higashi, Y.; Osa, T.; Lelievre, D.; Simon, J.; Yamauchi, S. Chem. Commun. 1999, 969 and references therein.
31. Sibert, J. W.; Baumann, T. F.; Williams, D. J.; White, A. J. P.; Barrett, A. G. M.; Hoffman, B. M. J. Am. Chem. Soc. 1996, 118, 10487.
32. (a) Forsyth, T. P.; Williams, D. B. G.; Garrido Montalban, A.; Stern, C. L.; Barrett, A. G. M.; Hoffman, B. M. J. Org. Chem. 1998, 63, 331.
33. (b) Lange, S. J.; Nie, H.; Stern, C. L.; Barrett, A. G. M.; Hoffman, B. M. Inorg. Chem. 1998, 37, 6435.
34. Baumann, T. F.; Sibert, J. W.; Olmstead, M. M.; Barrett, A. G. M.; Hoffman, B. M. J. Am. Chem. Soc. 1994, 116, 2639.
35. Baumann, T. F.; Nasir, M. S.; Sibert, J. W.; Olmstead, M. M.; White, A. J. P.; Williams, D. J.; Barrett, A. G. M.; Hoffman, B. M. J. Am. Chem. Soc. 1996, 118, 10479.
36. Begland, R. W.; Hartter, D. R.; Jones, F. N.; Sam, D. J.; Sheppard, W. A.; Webster, O. W.; Weigert, F. J. J. Org. Chem. 1974, 39, 2341.
37. Linstead, R. P.; Whalley, M. J. Chem. Soc. 1952, 4839.
38. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 3; pp 1-165.
39. Lever, A. B. P.; Milaeva, E. R.; Speier, G. In Phthalocyanines: Properties and Applications; Lezuoff, C. C., Lever, A. B. P., Eds.; VCH: New York, 1993; Vol. 3; pp 1-70.