Modular Synthesis of Benzene-Centered Porphyrin Trimers and a Dendritic Porphyrin Hexamer

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5568-5580

  Mongin, Olivier ^a   Papamicaël, Cyril ^a   Hoyler, Nicolas ^a   Gossauer, Albert ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000875859     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980846+     Document Type: Article

References (53)

1. . (1) Dolphin, D., Ed. The Porphyrins; Academic Press: New York, 1979; Vol. 1, Chapters 3-6.
2. Webb, L. E.; Fleischer, E. B. J. Am. Chem. Soc. 1965, 87, 667-669.
3. Milgrom, L. R. J. Chem. Soc., Perkin Trans. 1 1983, 2535-2539.
4. Davila, J.; Harriman, A.; Milgrom, L. R. Chem. Phys. Lett. 1987, 136, 427-430.
5. Bonnett, R.; Ioannou, S.; Pearson, C.; Petty, M. C.; Roger-Evans, M.; Wilkins, R. F. J. Mater. Chem. 1995, 5, 237-242.
6. O'Neil, M. P.; Niemczyk, M. P.; Svec, W. A.; Gosztola, D.; Gaines, G. L., III; Wasielewski, M. R. Science 1992, 257, 63-65.
7. Crossley, M. J.; Burn, P. L. J. Chem. Soc., Chem. Commun. 1991, 1569-1571.
8. Wagner, R. W.; Lindsey, J. S. J. Am. Chem. Soc. 1994, 116, 9759-9760.
9. Sessler, J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 4618-4628.
10. Ono, N.; Tomita, H.; Maruyama, K. J. Chem. Soc., Perkin Trans. 1 1992, 2453-2456.
11. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996-3997.
12. Wennerström, O.; Ericsson, H.; Raston, I.; Svensson, S.; Pimlott, W. Tetrahedron Lett. 1989, 30, 1129-1132.
13. Prathapan, S.; Johnson, T. E.; Lindsey, J. S. J. Am. Chem. Soc. 1993, 115, 7519-7520.
14. Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578-10592.
15. Wagner, R. W.; Johnson, T. E.; Li, F.; Lindsey, J. S. J. Org. Chem. 1995, 60, 5266-5273.
16. Wagner, R. W.; Johnson, T. E.; Lindsey, J. S. J. Am. Chem. Soc. 1996, 118, 11166-11180.
17. Hsiao, J.-S.; Krueger, B. P.; Wagner, R. W.; Johnson, T. E.; Delaney, J. K.; Mauzerall, D. C.; Fleming, G. R.; Lindsey, J. S.; Bocian, D. F.; Donohoe, R. J. J. Am. Chem. Soc. 1996, 118, 11181-11193.
18. Seth, J.; Palaniappan, V.; Wagner, R. W.; Johnson, T. E.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 11194-11207.
19. Gauler, R.; Risch, N. Tetrahedron Lett. 1997, 38, 223-224.
20. Young, J. K.; Moore, J. S. In Modern Acetylen Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; pp 415-442.
21. Morgenroth, F.; Reuther, E.; Müllen, K. Angew. Chem. 1997, 109, 647-649; Angew. Chem., Int. Ed. Engl. 1997, 36, 631-634 and references therein.
22. Morgenroth, F.; Reuther, E.; Müllen, K. Angew. Chem. 1997, 109, 647-649; Angew. Chem., Int. Ed. Engl. 1997, 36, 631-634 and references therein.
23. Iyer, V. S.; Wehmeier, M.; Brand, J. D.; Keegstra, M. A.; Müllen, K. Angew. Chem. 1997, 109, 1676-1679; Angew. Chem., Int. Ed. Engl. 1997, 36, 1604-1607.
24. Iyer, V. S.; Wehmeier, M.; Brand, J. D.; Keegstra, M. A.; Müllen, K. Angew. Chem. 1997, 109, 1676-1679; Angew. Chem., Int. Ed. Engl. 1997, 36, 1604-1607.
25. Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
26. Constable, E. C. J. Chem. Soc., Chem. Commun. 1997, 1073-1080.
27. Lindsey, J. S.; Prathapan, S.; Johnson, T. E.; Wagner, R. W. Tetrahedron 1994, 50, 8941-8968.
28. Mongin, O.; Gossauer, A. Tetrahedron Lett. 1996, 37, 3825-3828.
29. Mongin, O.; Gossauer, A. Tetrahedron 1997, 53, 6835-6846.
30. (a) Willgerodt, C.; Arnold, E. Chem. Ber. 1901, 34, 3343-3354.
31. (b) Ozasa, S.; Fujioka, Y.; Hashino, H.; Kimura, N.; Ibuki, E. Chem. Pharm. Bull. 1983, 31, 2313-2320.
32. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-630.
33. (a) Hübel, W.; Merényi, R. Angew. Chem. 1962, 74, 781. Angew. Chem., Int. Ed. Engl. 1963, 2, 42.
34. (a) Hübel, W.; Merényi, R. Angew. Chem. 1962, 74, 781. Angew. Chem., Int. Ed. Engl. 1963, 2, 42.
35. (b) Weber, E.; Hecker, M.; Koepp, E.; Orlia, W.; Czugler, M.; Csöregh, I. J. Chem. Soc., Perkin Trans. 1 1988, 1251-1257.
36. 2, as a catalyst, to avoid the formation of dimers of 1c, as byproducts (cf.: Villemin, D.; Schigeko, E. J. Organomet. Chem. 1985, 293, C10-C12.
37. Hsung, R. P.; Chidsey, C. E. D.; Sita, L. R. Organometallics 1995, 14, 4808-4815.
38. Moore, J. S.; Weinstein, E. J.; Wu, Z. Tetrahedron Lett. 1991, 32, 2465-2466.
39. (a) Ulman, A. An Introduction to Ultrathin Organic Films: From Langmuir-Blodgett Films to Self-Assembly; Academic Press: Boston, 1991.
40. (b) Dubois, L. H.; Nuzzo, R. G. Annu. Rev. Phys. Chem. 1992, 43, 437-463.
41. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
42. Tabushi, I.; Sasaki, T. Tetrahedron Lett. 1982, 23, 1913-1916.
43. Gust, D.; Moore, T. A.; Moore, A. L.; Gao, F.; Luttrull, D.; DeGraziano, J. M.; Ma, X. C.; Makings, L. R.; Lee, S.-J.; Trier, T. T.; Bittersmann, E.; Seely, G. R.; Woodward, S.; Bensasson, R. V.; Rougée, M.; De Schryver, F. C.; Van der Auweraer, M. J. Am. Chem. Soc. 1991, 113, 3638-3649.
44. Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Nishimura, Y. J. Org. Chem. 1995, 60, 7177-7185.
45. Brookfield, R. L.; Ellul, H.; Harriman, A.; Porter, G. J. Chem. Soc., Faraday Trans. 2, 1986, 82, 219-233.
46. Quimby, D. J.; Longo, F. R. J. Am. Chem. Soc. 1975, 97, 5111-5117.
47. Seybold, P. G.; Gouterman, M. J. Mol. Spectrosc. 1969, 31, 1-13.
48. Anderson, S.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1995, 2255-2267.
49. Xu, Z.; Kahr, M.; Walker, K. L.; Wilkins, C. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4537-4550.
50. Lavastre, O.; Ollivier, L.; Dixneuf, P. H. Tetrahedron 1996, 52, 5495-5504.
51. Lee, C.-H.; Lindsey, J. S. Tetrahedron 1994, 50, 11427-11440.
52. Novikov, A. N.; Grigor'ev, M. G. Zh. Org. Khim. 1978, 14, 1790.
53. Syrbu, S. A.; Semeikin, A. S.; Berezin, B. D. Khim. Geterotsikl. Soedin. 1990, 11, 1507-1509.