Synthesis and excited-state photodynamics of phenylethyne-linked porphyrin-phthalocyanine dyads

Journal of Materials Chemistry

Volumn 10, Issue 2, 2000, Pages 283-296

  Yang, Sung Ik ^a   Li, Junzhong ^b   Cho, Hyun Sun ^c   Kim, Dongho ^c   Bocian, David F ^d   Holten, Dewey ^a   Lindsey, Jonathan S ^b  

^a WASHINGTON UNIVERSITY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c Natl C R I C for U O C C   (South Korea)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; MAGNESIUM; METALLOPORPHYRIN; PALLADIUM; PHTHALOCYANINE DERIVATIVE; PORPHYRIN DERIVATIVE; ZINC;

ABSORPTION SPECTROSCOPY; ARTICLE; CHROMATOPHORE; COVALENT BOND; ENERGY TRANSFER; FLUORESCENCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; PHOTODYNAMICS; SYNTHESIS;

EID: 0033982611     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906273d     Document Type: Article

References (63)

1. 1 (a) S. Prathapan, T. E. Johnson and J. S. Lindsey, J. Am. Chem. Soc., 1993, 115, 7519;
2. (b) F. Li, S. Gentemann, W. A. Kalsbeck, J. Seth, J. S. Lindsey, D. Holten and D. F. Bocian, J. Mater. Chem., 1997, 7, 1245.
3. 2 R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759.
4. 3 R. W. Wagner, J. S. Lindsey, J. Seth, V. Palaniappan and D. F. Bocian, J. Am. Chem. Soc., 1996, 118, 3996.
5. 4 (a) P. G. Seybold and M. Gouterman, J. Mol. Spectrosc., 1969, 31, 1;
6. (b) M. Gouterman, in The Porphyrins, ed. D. Dolphin, Academic Press, New York, 1978, vol. 3, pp. 1-165.
7. 5 M. J. Stillman and T. Nyokong, in Phthalocyanines: Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH Publishers, New York, 1989, vol. 1, p. 133.
8. 6 (a) M. Hanack and M. Lang, Adv. Mater., 1994, 6, 819;
9. (b) H. Schultz, H. Lehmann, M. Rein and M. Hanack, Struct. Bonding (Berlin), 1991, 74, 41.
10. 7 G. Ferraudi, in Phthalocyanines: Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH Publishers, New York, 1989, vol. 1, p. 291.
11. 8 K. Teuchner, A. Pfarrherr, H. Stiel, W. Freyer and D. Leupold, Photochem. Photobiol., 1993, 57, 465.
12. 9 M. J. Stillman, in Phthalocyanines: Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH Publishers, New York, 1993, vol. 3, p. 227.
13. 10 (a) J. Li, J. R. Diers, J. Seth, S. I. Yang, D. F. Bocian, D. Holten and J. S. Lindsey, J. Org. Chem., in the press;
14. (b) J. Li and J. S. Lindsey J. Org. Chem., in the press.
15. 11 T.-H. Tran-Thi, Coord. Chem. Rev., 1997, 160, 53.
16. 12 (a) S. Gaspard, C. Giannotti, P. Maillard, C. Schaeffer and T.-H. Tran-Thi, J. Chem. Soc., Chem. Commun., 1986, 1239;
17. (b) T.-H. Tran-Thi, C. Desforge, C. Thiec and S. Gaspard, J. Phys. Chem., 1989, 93, 1226;
18. (c) T.-H. Tran-Thi, H. Ali, J. F. Lipskier, S. Gaspard and J. E. van Lier, J. Chim. Phys., 1991, 88, 1151;
19. (d) L. Li, S. Shen, Q. Yu, Q. Zhou and H. Xu, J. Chem. Soc., Chem. Commun., 1991, 619;
20. (e) H. Tian, Q. Zhou, S. Shen and H. Xu, J. Photochem. Photobiol. A: Chem., 1993, 72, 163;
21. (f) K. Dou, J. Zhang, W. Xu, S. Huang, J. Yu and X. Xu, J. Lumin., 1994, 465;
22. (g) H. Tian, Q. Zhou, S. Shen and H. Xu, Chin. J. Chem., 1996, 14, 412;
23. (h) X. Li, Q. Zhou, H. Tian and H. Xu, Chin. J. Chem., 1998, 16, 97.
24. 13 (a) C. C. Leznoff and T. W. Hall, Tetrahedron Lett., 1982, 23, 3023;
25. (b) C. C. Leznoff, P. I. Svirskaya, B. Khouw, R. L. Cerny, P. Seymour and A. B. P. Lever, J. Org. Chem., 1991, 56, 82;
26. (c) D. Wöhrle and G. Krawczyk, Polym. Bull., 1986, 15, 193.
27. 14 B. Cabezon, S. Rodriguez-Morgade and T. Torres, J. Org. Chem., 1995, 60, 1872.
28. 15 (a) N. Kobayashi, R. Kondo, S. Nakajima and T. Osa, J. Am. Chem. Soc., 1990, 112, 9640;
29. (b) M. Geyer, F. Plenzig, J. Rauschnabel, M. Hanack, B. del Rey, A. Sastre and T. Torres, Synthesis, 1996, 1139;
30. (c) S. V. Kudrevich, S. Gilbert and J. E. van Lier, J. Org. Chem., 1996, 61, 5706;
31. (d) A. Sastre, B. del Rey and T. Torres, J. Org. Chem., 1996, 61, 8591;
32. (e) A. Weitemeyer, H. Kliesch and D. Wöhrle, J. Org. Chem., 1995, 60, 4900.
33. 16 (a) T. G. Linssen and M. Hanack, Chem. Ber., 1994, 127, 2051;
34. (b) C. C. Leznoff, C. R. McArthur and Y. Qin, Can. J. Chem., 1993, 71, 1319.
35. 17 (a) S. V. Kudrevich, H. Ali and J. E. van Lier, J. Chem. Soc., Perkin Trans. 1, 1994, 2767;
36. (b) H. Ali and J. E. van Lier, Tetrahedron Lett., 1997, 38, 1157.
37. 18 R. W. Wagner, T. E. Johnson and J. S. Lindsey, J. Am. Chem. Soc., 1996, 118, 11166.
38. 19 N. Kobayashi, N. Sasaki, Y. Higashi and T. Osa, Inorg. Chem., 1995, 34, 1636.
39. 20 H. Nishi, N. Azuma and K. Kitahara, J. Heterocycl. Chem., 1992, 29, 475.
40. 21 M. Hanack, P. Haisch, H. Lehmann and L. R. Subramanian, Synthesis, 1993, 387.
41. 22 E. M. Maya, P. Haisch, P. V́zquez and T. Torres, Tetrahedron, 1998, 54, 4397.
42. 23 (a) H. Tomoda, S. Saito, S. Ogawa and S. Shiraishi, Chem. Lett., 1980, 1277;
43. (b) H. Tomoda, S. Saito and S. Shiraishi, Chem. Lett., 1983, 313.
44. 24 M. Hanack, S. Deger and A. Lange, Coord. Chem. Rev., 1988, 83, 115.
45. 25 R. W. Wagner, T. E. Johnson, F. Li and J. S. Lindsey, J. Org. Chem., 1995, 60, 5266.
46. 26 E. M. Maya, P. Vázquez and T. Torres, Chem. Commun., 1997, 1175.
47. 27 N. Srinivasan, C. A. Haney, J. S. Lindsey, W. Zhang and B. T. Chait, J. Porphyrins Phthalocyanines, 1999, 3, 283.
48. 28 R. W. Wagner, Y. Ciringh, C. Clausen and J. S. Lindsey, Chem. Mater., 1999, 11, 2974.
49. 29 J. S. Lindsey and J. N. Woodford, Inorg. Chem., 1995, 34, 1063.
50. 30 D. F. O'Shea, M. A. Miller, H. Matsueda and J. S. Lindsey, Inorg. Chem., 1996, 35, 7325.
51. 31 (a) M. Yoon, Y. Cheon and D. Kim, Photochem. Photobiol., 1993, 58, 31;
52. (b) S. Dhami, A. J. deMello, G. Rumbles, S. M. Bishop, D. Phillips and A. Beeby, Photochem. Photobiol., 1995, 61, 341.
53. * emission dramatically quenches when the polarity of the solvent is increased by addition of 20% dimethyl sulfoxide or acetonitrile to toluene. It is noteworthy that the addition of significantly more of the polar solvent caused a broadening and decrease in intensity of the porphyrin Soret band (a reversible effect). This complicating factor, involving likely changes in axial ligation of metal-containing chromophores and/or changes in aggregation equilibria with solvent polarity, precludes carrying out meaningful studies of the solvent dependence of charge-transfer phenomena in these systems.
54. 33 (a) J. S. Lindsey, P. A. Brown and D. A. Siesel, Tetrahedron, 1989, 45, 4845;
55. (b) J. B. Birks, Photophysics of Aromatic Molecules, Wiley-Interscience, New York, 1970.
56. 31 The lifetimes given in Table 1 are for low concentrations ( < 1 μΜ) and are in good agreement for the fluorescence modulation and TCSCP technique on samples (mainly the monomers) in which both techniques are employed.
57. 35 S. I. Yang, J. Seth, J.-P. Strachan, S. Gentemann, D. Kim, D. Holten, J. S. Lindsey and D. F. Bocian, J. Porphyrins Phthalocyanines, 1999, 3, 117.
58. 37
59. 37 However, we have seen such behavior in covalently-linked porphyrin boron-dipyrrin complexes involving photoinduced conformational changes in the latter component. See: F. Li, S. I. Yang, Y. Ciringh, J. Seth, C. H. Martin III, D. L. Singh, D. Kim, R. R. Birge, D. F. Bocian, D. Holten and J. S. Lindsey, J. Am. Chem. Soc., 1998, 120, 10001.
60. 38 (a) J.-P. Strachan, S. Gentemann, J. Seth, W. A. Kalsbeck, J. S. Lindsey, D. Holten and D. F. Bocian, J. Am. Chem. Soc., 1997, 119, 11191;
61. (b) S. I. Yang, R. K. Lammi, J. Seth, J. Riggs, T. Arai, D. Kim, D. F. Bocian, D. Holten and J. S. Lindsey, J. Phys. Chem. B, 1998, 102, 9426.
62. 39 H. Du, R.-C. A. Fuh, J. Li, L. A. Corkan and J. S. Lindsey, Photochem. Photobiol., 1998, 68, 141.
63. 40 D. Fenyo, B. T. Chait, T. E. Johnson and J. S. Lindsey, J. Porphyrins Phthalocyanines, 1997, 1, 93.