Synthesis and photophysical studies of new porphyrin-phthalocyanine dyads with hindered rotation

European Journal of Organic Chemistry

Volumn , Issue 1, 2006, Pages 257-267

  Tomé, João P C ^a,b   Pereira, Ana M V M ^a   Alonso, Cristina M A ^a   Neves, Maria G P M S ^a   Tomé, Augusto C ^a   Silva, Artur M S ^a   Cavaleiro, José A S ^a   Martínez Díaz, M Victoria ^b   Torres, Tomás ^b   Rahman, G M Aminur ^c   Ramey, Jeff ^d   Guldi, Dirk M ^c  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^c UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^d UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Covalent dyads; Harvesting systems; Photoinduced energy transfer; Phthalocyanines; Porphyrins

Indexed keywords

EID: 33748777687     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500558     Document Type: Article

References (42)

1. I. Rosenthal, in Phthalocyanines - Properties and Applications (Eds.: C. C. Leznoff, A. B. P. Lever), VCH, New York, 1996, vol. 4, chapter 13.
2. E. Ben-Hur, W.-S. Chan, in The Porphyrin Handbook (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2003, vol. 19, chapter 117.
3. D. Wohrle, O. Suvorova, R. Gerdes, O. Bartels, L. Lapok, N. Baziakina, S. Makarov, A. Slodek, J. Porphyrins Phthalocyanines 2004, 8, 1020.
4. M. Kimura, H. Shirai, in The Porphyrin Handbook (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2003, vol. 19, chapter 120.
5. N. B. McKeown, Phthalocyanine Materials: Synthesis, Structure and Function, Cambridge University Press, Cambridge, 1998.
6. a) G. de la Torre, P. Vázquez, F. Agulló-López, T. Torres, J. Mater. Chem. 1998, 8, 1671;
7. b) G. de la Torre, P. Vázquez, F. Agulló-López, T. Torres, Chem. Rev. 2004, 104, 3723.
8. a) D. Dini, M. Hanack, J. Porphyrins Phthalocyanines 2004, 8, 915;
9. b) D. Dini, M. Hanack, in The Porphyrin Handbook (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2003, vol. 16, chapter 107.
10. a) M. R. Wasielewski, Chem. Rev. 1992, 92, 435;
11. b) D. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res. 2001, 34, 40;
12. c) D. M. Guldi, Pure Appl. Chem. 2003, 75, 1069;
13. d) H. Imahori, Y. Mori, Y. L. Matano, Photochem. Photobiol. 2003, 4, 51;
14. e) D. Wöhrle, D. Meissner, Adv. Mater. 1991, 3, 129;
15. f) M. A. Loi, P. Denk, H. Hoppe, H. Neugebauer, C. Winder, D. Meissner, C.-J. Brabec, N. S. Sariciftci, A. Gouloumis, P. Vázquez, T. Torres, J. Mater. Chem. 2003, 13, 700.
16. a) A. Gouloumis, S.-G. Liu, A. Sastre, P. Vázquez, L. Echegoyen, T. Torres, Chem. Eur. J. 2000, 6, 3600;
17. b) A. Gouloumis, S.-G. Liu, P. Vázquez, L. Echegoyen, T. Torres, Chem. Commun. 2001, 399;
18. c) D. M. Guldi, J. Ramey, M. V. Martínez-Díaz, A. de la Escosura, T. Torres, T. Da Ros, M. Prato, Chem. Commun. 2002, 2774;
19. d) A. González-Cabello, P. Vázquez, T. Torres, D. M. Guldi, J. Org. Chem. 2003, 68, 8635;
20. e) H. Li, J. O. Jeppesen, E. Levillain, J. Becher, Chem. Commun. 2003, 846;
21. f) D. González-Rodríguez, T. Torres, M. A. Herranz, J. Rivera, L. Echegoyen, D. M. Guldi, J. Am. Chem. Soc. 2004, 126, 6301;
22. g) J. L. Sessler, J. Jayawickramarajah, A. Gouloumis, T. Torres, D. M. Guldi, S. Maldonado, K. J. Stevenson, Chem. Commun. 2005, 1892.
23. a) E. M. Maya, P. Vázquez, T. Torres, Chem. Eur. J. 1999, 5, 2004;
24. b) A. de la Escosura, M. V. Martínez-Díaz, P. Thordarson, A. E. Rowan, R. J. M. Nolte, T. Torres, J. Am. Chem. Soc. 2003, 125, 12300.
25. G. de la Torre, M. V. Martínez-Díaz, P. A. Ashton, T. Torres, J. Org. Chem. 1998, 63, 8888.
26. D. González-Rodríguez, C. G. Claessens, Chem. Eur. J., in press.
27. a) N. Kobayashi, Y. Nishiyama, T. Ohya, M. Sato, J. Chem. Soc., Chem. Commun. 1987, 390-392;
28. b) H.-J. Tian, Q.-F. Zhou, S.-Y. Shen, H.-J. Xu, J. Photochem. Photobiol. A 1993, 72, 163;
29. c) H.-J. Tian, Q.-F. Zhou, S.-Y. Shen, H.-J. Xu, Chin. J. Chem. 1996, 14, 412;
30. d) H.-J. Tian, Q.-F. Zhou, S.-Y. Shen, H.-J. Xu, Chin. J. Chem. 1998, 16, 97.
31. a) S. I. Yang, J. Li, H. S. Cho, D. Kim, D. F. Bocian, D. Holten, J. S. Lindsey, J. Mater. Chem. 2000, 10, 283;
32. b) A. Ambroise, R. W. Wagner, P. D. Rao, J. A. Riggs, P. Hascoat, J. R. Diers, J. Seth, R. K. Lammi, D. F. Bocian, D. Holten, J. S. Lindsey, Chem. Mater. 2001, 13, 1023;
33. c) M. A. Miller, R. K. Lammi, S. Prathapan, D. Holten, J. S. Lindsey, J. Org. Chem. 2000, 65, 6634;
34. d) J. M. Sutton, R. W. Boyle, Chem. Commun. 2001, 2014.
35. K. Kameyama, A. Satake, Y. Kobuke, Tetrahedron Lett. 2004, 45, 7617.
36. C. M. A. Alonso, M. G. P. M. S. Neves, A. C. Tomé, A. M. S. Silva, J. A. S. Cavaleiro, Tetrahedron Lett. 2000, 41, 5679.
37. H. K. Hombrecher, V. M. Gherdan, S. Ohm, J. A. S. Cavaleiro, M. G. P. M. S. Neves, M. F. Condesso, Tetrahedron 1993, 49, 8569.
38. Taking into account the large red-shifts observed in the Q-band of phthalocyanine- and subphthalocyanine-fused dimers wherein the chromophores are fully π-conjugated and forced to be planar with respect to each other (see: G. de la Torre, M. V. Martínez-Díaz, P. R. Ashton, T. Torres, J. Org. Chem. 1998, 63, 8888;
39. C. G. Claessens, T. Torres, Angew. Chem. Int. Ed. 2002, 41, 2561), the dyads reported herein may adopt an orthogonal or pseudo-orthogonal geometry, which additionally avoids steric hindrance between the meso-phenyl groups and the phthalocyanine moiety, rather than a planar arrangement of the porphyrin and phthalocyanine rings.
40. S. L. Murov, I. Carmichael, G. L. Hug, Handbook of Photochemistry, Marcel Dekker Inc., New York, 1993.
41. a) H. J. Callot, Tetrahedron Lett. 1973, 14, 4987;
42. b) M. J. Callot, Bull. Soc. Chim. Fr. 1974, 1492.