Highly fluorescent self-coordinated phthalocyanine dimers

Angewandte Chemie - International Edition

Volumn 44, Issue 30, 2005, Pages 4763-4766

  Kameyama, Kazuya ^a   Morisue, Mitsuhiko ^a   Satake, Akiharu ^a   Kobuke, Yoshiaki ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Aggregation; Fluorescence; Phthalocyanines; Self assembly; Supramolecular chemistry

Indexed keywords

AMINES; ASSOCIATION REACTIONS; FLUORESCENCE; ORGANOMETALLICS; QUANTUM THEORY; TOLUENE;

ASSOCIATION CONSTANTS; PHTHALOCYANINE DIMERS; QUANTUM YIELD;

DIMERS;

EID: 23044499110     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501199     Document Type: Article

References (37)

1. N. B. McKeown, Phthalocyanine Materials: Synthesis, Structure and Function, Cambridge University Press, Cambridge, 1998.
2. G. Torre, P. Vázquez, F. Agullü-Lüpez, T. Torres, Chem. Rev. 2004, 104, 3723-3750.
3. T. J. Marks, Science 1985, 227, 881-889.
4. a) Y. Kobuke, H. Miyaji, J. Am. Chem. Soc. 1994, 116, 4111-4112;
5. b) H. Ozeki, A. Nomoto, K. Ogawa, Y. Kobuke, M. Murakami, K. Hosoda, M. Ohtani, S. Nakashima, H. Miyasaka, T. Okada, Chem. Eur. J. 2004, 10, 6393-6401;
6. c) K. Ogawa, Y. Kobuke, Angew. Chem. 2000, 112, 4236-4239;
7. Angew. Chem. Int. Ed. 2000, 39, 4070-4073;
8. d) R. Takahashi, Y. Kobuke, J. Am. Chem. Soc. 2003, 125, 2372-2373.
9. A. W. Snow in The Porphyrin Handbook, Vol. 17 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Elsevier Science, USA, 2003, pp. 129-176.
10. M. J. Cook, I. Chambrier in The Porphyrin Handbook, Vol. 17, Elsevier Science, USA, 2003, pp. 37-127.
11. a) D. Dini, M. Hanack in The Porphyrin Handbook, Vol. 17, Elsevier Science, USA, 2003, pp. 1-36;
12. b) M. K. Engel in The Porphyrin Handbook, Vol. 20, Elsevier Science, USA, 2003, pp. 1-242;
13. c) P. Thordarson, R. J. M. Nolte, A. E. Rowan in The Porphyrin Handbook, Vol. 18, Elsevier Science, USA, 2003, pp. 281-301.
14. a) M. Hanack, D. Dini in The Porphyrin Handbook, Vol. 18, Elsevier Science, USA, 2003, pp. 251-280;
15. b) M. J. Cook, A. Jafari-Fini, J. Mater. Chem. 1997, 7, 2327-2329;
16. c) X. Li, D. K. P. Ng, Eur. J. Inorg. Chem. 2000, 1845-1848;
17. d) N. Kobayashi, A. Muranaka, V. N. Nemykin, Tetrahedron Lett. 2001, 42, 913-915;
18. e) K. Ishii, Y. Watanabe, S. Abiko, N. Kobayashi, Chem. Lett. 2002, 450-451.
19. M. V. Martinez-Diaz, M. S. Rodriguez-Morgade, M. C. Feiters, P. J. M. van Kan, R. J. M. Nolte, J. F. Stoddart, T. Torres, Org. Lett. 2000, 2, 1057-1060.
20. A. Escosura, M. V. Martínez-Díaz, P. Thordarson, A. E. Rowan, R. J. M. Nolte, T. Torres, J. Am. Chem. Soc. 2003, 125, 12 300-12 308.
21. a) E. E. Jelley, Nature 1936, 138, 1009-1010;
22. b) E. E. Jelley, Nature 1937, 139, 631-632.
23. N. Kobayashi, A. B. P. Lever, J. Am. Chem. Soc. 1987, 109, 7433-7441.
24. For fluorescent phthalocyanines, see: a) Y. Kaneko, T. Arai, K. Tokumaru, D. Matsunaga, H. Sakuragi, Chem. Lett. 1996, 345-346;
25. b) K. Ishii, S. Abiko, M. Fujitsuka, O. Ito, N. Kobayashi, J. Chem. Soc. Dalton Trans. 2002, 1735-1739;
26. c) X.-Y. Li, D. K. P. Ng, Tetrahedron Lett. 2001, 42, 305-309;
27. d) M. Kimura, T. Kuroda, K. Ohta, K. Hanabusa, H. Shirai, N. Kobayashi, Langmuir 2003, 19, 4825-4830.
28. For reports on noncovalent head-to-tail dimers and J-aggregates of porphyrin derivatives, see: a) R. F. Pasternack, P. R. Huber, P. Boyd, G. Engasser, L. Francesconi, E. Gibbs, P. Fasella, G. C. Venturo, L. deC. Hinds, J. Am. Chem. Soc. 1972, 94, 4511-4517;
29. b) J. Chiefari, K. Griebenow, N. Griebenow, T. S. Balaban, A. R. Holzwarth, K. Schaffner, J. Phys. Chem. 1995, 99, 1357-1365;
30. c) J. Vasudevan, R. T. Stibrany, J. Bumby, S. Knapp, J. A. Potenza, T. J. Emge, H. J. Schugar, J. Am. Chem. Soc. 1996, 118, 11 676-11 677;
31. d) J.-C. Chambron, V. Heitz, J.-P. Sauvage in The Porphyrin Handbook, Vol. 6, Academic Press, USA, 2000, pp. 1-42.
32. Two kinds of configurational isomers, oblique and parallel, are possible. The energy-minimized structures and their excited states were calculated using MOPAC (AM1) and INDO/S (see Supporting Information).
33. M. Kasha, M. Radiat. Res. 1963, 20, 55-70.
34. 2 by UV/ Vis absorption spectroscopy in a cell of 1-mm path length.
35. D. A. Fernandez, J. Awruch, L. E. Dicelio, Photochem. Photobiol. 1996, 63, 784-792.
36. 2, at 298 K (see Supporting Information).
37. D. E. Richardson, H. Taube, Inorg. Chem. 1981, 20, 1278-1285.