2,7,12,17-Tetra(p-butylphenyl)-3,6,13,16-tetraazaporphycene: The first example of a straightforward synthetic approach to a new class of photosensitizing macrocycles

European Journal of Organic Chemistry

Volumn , Issue 9, 2003, Pages 1635-1640

  Nonell, Santi ^a   Borrell, José I ^a   Borrós, Salvador ^a   Colominas, Carles ^a   Rey, Oscar ^a   Rubio, Noemí ^a   Sánchez García, David ^a   Teixidó, Jordi ^a  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

Author keywords

C C coupling; Density functional calculations; Macrocycles; Photochemistry; Synthesis design

Indexed keywords

2,7,12,17 TETRA(4 BUTYLPHENYL) 3,6,13,16 TETRAAZAPORPHYCENE; 4,4' BIS(4 BUTYLPHENYL) 2,2' BISIMIDAZOLE 5,5' DICARBALDEHYDE; ALDEHYDE DERIVATIVE; MACROCYCLIC COMPOUND; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; PHOTOCHEMISTRY; PHOTOCHEMOTHERAPY; PHOTODYNAMIC THERAPY; SUZUKI REACTION;

EID: 0038327709     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200200684     Document Type: Article

References (39)

1. C. C. Dierickx, R. Rox Anderson, Int. Photodyn. 1996, 1, 2-5.
2. Y. Nitzan, M. Gutterman, Z. Malik, B. Ehrenberg, Photochem. Photobiol. 1992, 55, 89-96.
3. M. J. Rivellese, C. R. Baumal, J. Ophthalmic Nurs. Technol. 2000, 19, 134-141.
4. M. Merchat, A. Villanueva, P. Giacomoni, G. Bertoloni, G. Jori, J. Braz. Chem. Soc. 1995, 6, 123-125.
5. A. Minnock, D. I. Vernon, J. Schofield, J. Griffiths, J. H. Parish, S. B. Brown, J. Photochem. Photobiol. B: Biol. 1996, 32, 159-164.
6. M. Grandadam, D. Ingrand, J. M. Huraux, B. Aveline, O. Delgado, C. Vever-Bizet, D. Brault, J. Photochem. Photobiol. B: Biol. 1995, 31, 171-177.
7. C. M. Allen, J. M. Weber, J. E. Van Lier, Photochem. Photobiol. 1995, 62, 184-189.
8. R. Bonnett, Chemical Aspects of Photodynamic Therapy, Gordon and Breach Science Publishers, Amsterdam, 2000.
9. H. Ali, J. E. Van Lier, Chem. Rev. 1999, 99, 2379-2450.
10. E. Vogel, M. Koecher, H. Schmickler, J. Lex, Angew. Chem. 1986, 98, 262-264.
11. S. Nonell, N. Bou, J. I. Borrell, J. Teixidó, A. Villanueva, A. Juarranz, M. Cañete, Tetrahedron Lett. 1995, 36, 3405-3408.
12. A. Gavaldá, J. I. Borrell, J. Teixidó, S. Nonell, O. Arad, R. Grau, M. Cañete, A. Juarranz, A. Villanueva, J. C. Stockert, J. Porphyrins Phthalocyanines 2001, 5, 846-852.
13. M. Cañete, A. Ortiz, A. Juarranz, A. Villanueva, S. Nonell, J. I. Borrell, J. Teixidó, J. C. Stockert, Anti-Cancer Drug Des. 2000, 15, 143-150.
14. A. Villanueva, M. Cañete, S. Nonell, J. I. Borrell, J. Teixidó, A. Juarranz, Anti-Cancer Drug Des. 1996, 11, 89-99.
15. M. Cañete, M. Lapeña, A. Juarranz, V. Vendrell, J. I. Borrell, J. Teixidó, S. Nonell, A. Villanueva, Anti-Cancer Drug Des. 1997, 12, 543-554.
16. T. Nußbaumer, C. Krieger, R. Neidlein, Eur. J. Org. Chem. 2000, 2449-2457.
17. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
18. A. D. Becke, J. Chem. Phys. 1996, 104, 1040-1046.
19. M. E. Casida, C. Jamorski, K. C. Casida, D. R. Salahub, J. Chem. Phys. 1998, 108, 4439-4449.
20. F. Fernandez-Lazaro, T. Torres, B. Hauschel, M. Hanack, Chem. Rev. 1998, 98, 563-575.
21. Ch. Kirchner, B. Krebs, Inorg. Chem. 1987, 26, 3569-3576.
22. H. Ikeda, J. L. Sessler, J. Org. Chem. 1993, 58, 2340-2341.
23. G. Shapiro, B. Gomez-Lor, J. Org. Chem. 1994, 59, 5524-5526.
24. J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524.
25. T. N. Mitchell, Synthesis 1992, 803-815.
26. D. Sánchez-Garcia, S. Borrós, S. Nonell, J. I. Borrell, C. Colominas, J. Teixidó, J. Heterocycl. Chem. 2002, 39, 733-735.
27. J. E. McMurry, Chem. Rev. 1989, 89, 1513-1524.
28. G. M. Robertson, Comp. Org. Syn. 1991, 3, 583-595.
29. T. Lectka, Act. Met. 1996, 85-131.
30. M. Ephritikhine, Chem. Commun. 1998, 23, 2549-2554.
31. A. L. Sargent, I. C. Hawkins, W. E. Allen, Abstracts of Papers, 222nd ACS National Meeting, Chicago, IL, United States, August 26-30, 2001.
32. T. Nussbaumer, R. Neidlein, Helvetica Chim. Acta 2000, 83, 1161-1167.
33. Ch. Kirchner, B. Krebs, Inorg. Chem. 1987, 26, 3569-3576.
34. M. Tadokoro, K. Isobe, H. Uekusa, Y. Oshashi, J. Toyoda, K. Tashiro, K. Nakasuji, Angew. Chem. Int. Ed. 1999, 38, 95-98.
35. M. E. Casida, C. Jamorski, K. C. Casida, D. R. Salahub, J. Chem. Phys. 1998, 108, 4439-4449.
36. R. Stratmann, G. E. Scuseria, M. J. Frisch, J. Chem. Phys. 1998, 109, 8218-8224.
37. R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 1996, 256, 454-464.
38. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, GAUSSIAN 98, A9 Revision, Gaussian, Inc., Pittsburgh PA, 1998.
39. D. S. Pedersen, C. Rosenbohm, Synthesis 2001, 2431-2434.