Structural and photophysical characterization of multichromophoric pyridylporphyrin-rhenium(I) conjugates

Inorganic Chemistry

Volumn 47, Issue 22, 2008, Pages 10407-10418

  Casanova, Massimo ^a   Zangrando, Ennio ^a   Iengo, Elisabetta ^a   Alessio, Enzo ^a   Indelli, Maria Teresa ^b   Scandola, Franco ^b   Orlandi, Michele ^b  

^a UNIVERSITY OF TRIESTE   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57149121681     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic800971e     Document Type: Article

References (59)

1. (a) Iengo, E.; Zangrando, E.; Alessio, E. Eur. J. Inorg. Chem. 2003, 2371-2384.
2. (b) Scandola, F.; Chiorboli, C.; Prodi, A.; Iengo, E.; Alessio, E. Coord. Chem. Rev. 2006, 250, 1471-1496.
3. (c) Iengo, E.; Scandola, F.; Alessio, E. Struct. Bonding (Berlin) 2006, 121, 105-144.
4. (d) Iengo, E.; Zangrando, E.; Alessio, E. Act: Chem. Res. 2006, 39, 841-851.
5. (a) Shi, C.; Anson, F. C. J. Am. Chem. Soc. 1991, 113, 9564-9570.
6. (b) Shi, C.; Anson, F. C. Inorg. Chem. 1992, 31, 5078-5083.
7. (c) Steiger, B.; Shi, C.; Anson, F. C. Inorg. Chem. 1993, 32, 2107-2113.
8. (a) Araki, K.; Toma, H. E. J. Coord. Chem. 1993, 30, 9-17.
9. (b) Araki, K.; Toma, H. E. J. Photochem. Photobiol. A 1994, 83, 245-250.
10. (c) Toma, H. E.; Araki, K. Coord. Chem. Rev. 2000, 196, 307-329.
11. (d) Araki, K.; Losco, P.; Engelmann, F. M.; Winnischofer, H.; Toma, H. E. J. Photochem. Photobiol. A 2001, 142, 25-30.
12. (e) Engelmann, F. M.; Losco, P.; Winnischofer, H.; Araki, K.; Toma, H. E. J. Porphyrins Phthalocyanines 2002, 6, 33-42.
13. (f) Nogueira, A. F.; Furtado, L. F. O.; Forminga, A. L. B.; Nakamura, M.; Araki, K.; Toma, H. E. Inorg. Chem. 2004, 43, 396-398.
14. Kon, H.; Tsuge, K.; Imamura, T.; Sasaki, Y.; Ishizaka, S.; Kitamura, N. Inorg. Chem. 2006, 45, 6875-6883.
15. Schmitt, F.; Govindaswamy, P.; Süss-Fink, G.; Ang, W. H.; Dyson, P. J.; Juillerat-Jeanneret, L.; Therrien, B. J. Med. Chem. 2008, 51, 1811-1816.
16. (a) Allwood, J. L.; Burrell, A. K.; Officer, D. L.; Scott, S. M.; Wild, K. Y.; Gordon, K. C. Chem. Commun. 2000, 747-748.
17. (b) Elliot, C. M.; Dunkle, J. R.; Paulson, S. C. Langmuir 2005, 21, 8605-8608.
18. (c) Cho, T. J.; Shreiner, C. D.; Hwang, S.-H.; Moorefield, C. N.; Courneya, B.; Godinez, L. A.; Manriquez, J.; Jeong, K.-U.; Cheng, S. Z. D.; Newkome, G. R. Chem. Commun. 2007, 4456-4458.
19. (a) Collin, J.-P.; Heitz, V.; Sauvage, J.-P. Tetrahedron Lett. 1991, 32, 5977-5980.
20. (b) Collin, J.-P.; Harriman, A.; Heitz, V.; Odobel, F.; Sauvage, J.-P. J. Am. Chem. Soc. 1994, 116, 5679-5690.
21. (c) Harriman, A.; Odobel, F.; Sauvage, J.-P. J. Am. Chem. Soc. 1995, 117, 9461-9472.
22. (d) Collin, J.-P.; Dalbavie, J.-O.; Heitz, V.; Sauvage, J.-P.; Flamigni, L.; Armaroli, N.; Balzani, V.; Barigelletti, F.; Montanari, I. Bull. Soc. Chim. Fr. 1996, 133, 749-754.
23. (e) Flamigni, L.; Armaroli, N.; Barigelletti, F.; Balzani, V.; Collin, J.-P.; Dalbavie, J.-O.; Heitz, V.; Sauvage, J.-P. J. Phys. Chem. B 1997, 101, 5936-5943.
24. (f) Flamigni, L.; Barigelletti, F.; Armaroli, N.; Collin, J.-P.; Sauvage, J.-P.; Williams, J. A. G. Chem.-Eur. J. 1998, 4, 1744-1754.
25. Casanova, M.; Zangrando, E.; Munini, F.; Iengo, E.; Alessio, E. Dalton Trans. 2006, 5033-5045.
26. (a) Slone, R. V.; Hupp, J. T. Inorg. Chem. 1997, 36, 5422-5423.
27. (b) Splan, K. E.; Keefe, M. H.; Massari, A. M.; Walters, K. A.; Hupp, J. T. Inorg. Chem. 2002, 41, 619-621.
28. (c) Benkstein, K. D.; Stern, C. L.; Splan, K. E.; Johnson, R. C.; Walters, K. A.; Vanhelmont, F. W. M.; Hupp, J. T. Eur. J. Inorg. Chem. 2002, 2818-2822.
29. (d) Splan, K. E.; Stern, C. L.; Hupp, J. T. Inorg. Chim. Acta 2004, 357, 4005-4014.
30. (e) Hupp, J. T. Struct. Bonding (Berlin) 2006, 121, 145-165.
31. (a) Striplin, D. R.; Crosby, G. A. Coord. Chem. Rev. 2001, 211, 163-175.
32. (b) Kirgan, R. A.; Sullivan, B. P.; Rillema, D. P. Top. Curr. Chem. 2007, 281, 45-100.
33. (a) Gholamkhass, B.; Mametsuka, H.; Koika, K.; Tanabe, T.; Furue, M.; Ishitani, O. Inorg. Chem. 2005, 44, 2326-2336.
34. (b) Sato, S.; Koike, K.; Inoue, H.; Ishitani, O. Photochem. Photobiol. Sci. 2007, 454-461.
35. Chartrand, D.; Hanan, G. S. Chem. Commun. 2008, 727-729.
36. (a) Aspley, C. J.; Lindsay Smith, J. R.; Perutz, R. N. J. Chem. Soc., Dalton Trans. 1999, 2269-2271.
37. (b) Gabrielsson, A.; Hartl, F.; Lindsay Smith, J. R.; Perutz, R. N. Chem. Commun. 2002, 950-951.
38. Gabrielsson, A.; Hartl, F.; Zhang, H.; Lindsay Smith, J. R.; Towrie, M.; Vlcek, A., Jr.; Perutz, R. N. J. Am. Chem. Soc. 2006, 128, 4253-4266.
39. Liu, X.; Liu, J.; Pan, J.; Chen, R.; Na, Y.; Gao, W.; Sun, L. Tetrahedron 2006, 62, 3674-3680.
40. Ghirotti, M.; Chiorboli, C.; Indelli, M. T.; Scandola, F.; Casanova, M.; Iengo, E.; Alessio, E. Inorg. Chim. Acta 2007, 360, 1121-1130.
41. Alessio, E.; Macchi, M.; Heath, S. L.; Marzilli, L. G. Inorg. Chem. 1997, 36, 5614-5623.
42. Sugata, S.; Yamanouchi, S.; Matsushima, Y. Chem. Pharm. Bull. 1977, 25, 884-889.
43. Chiorboli, C.; Rodgers, M. A. J.; Scandola, F. J. Am. Chem. Soc. 2003, 125, 483-491.
44. Otwinowski, Z.; Minor, W. In Processing of X-ray Diffraction Data Collected in Oscillation Mode; Carter, C. W., Jr., Sweet, R. M., Eds.; Methods in Enzymology, Macromolecular Crystallography Part A; Academic Press: New York, 1997; Vol. 276, pp 307-326.
45. Sheldrick, G. M. SHELX97. Programs for Crystal Structure Analysis (Release 97-2); University of Göttingen: Göttingen, Germany, 1998.
46. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
47. Presumably for the same reason, 6 turns green (from purple) in the solid state upon drying.
48. -5 M, where no further changes were observed upon dilution. In these conditions, Zn·4′MPyP and Zn·3′MPyP showed spectral patterns and photophysical behaviors almost identical to Zn·TPP that was therefore selected as reference compound.
49. 1H NMR spectrum was monitored in time. Only after one day, very weak signals corresponding to the resonances of free Zn·4′MPyP started to appear, indicating that the Re-PyP bond has an excellent kinetic stability.
50. Gust, D.; Moore, T. A.; Moore, A. L.; Kang, H. K.; DeCraziano, J. M.; Liddell, P. A.; Seely, G. R. J. Phys. Chem. 1993, 97, 13637-13642.
51. Similarly to what reported by Gust and co-workers for the Zn·TPP chromophore (ref 26), the addition of pyridine caused small but significant spectral shifts (ca. 15 nm) in the absorption (Q region) as well as in the emission spectra of the dyad 5, clearly indicating the coordination of pyridine to the zinc center.
52. Kadish, K. M.; Shiue, L. R.; Rhodes, R. K.; Bottomley, L. A. Inorg. Chem. 1981, 20, 1274-1277.
53. Alessio, E.; Geremia, S.; Mestroni, S.; Srnova, I.; Slouf, M.; Gianferrara, T.; Prodi, A. Inorg. Chem. 1999, 38, 2527-2529.
54. Fujita, N.; Birhadha, K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Angew. Chem., Int. Ed. 2001, 40, 1718-1721.
55. No correction for electrostatic work terms is required in this case because of the charge shift character of the process involved.
56. (a) Prodi, A.; Indelli, M. T.; Kleverlaan, C. J.; Scandola, F.; Alessio, E.; Gianferrara, T.; Marzilli, L. G. Chem. Eur. J. 1999, 5, 2668-2679.
57. (b) Alessio, E.; Geremia, S.; Mestroni, S.; Iengo, E.; Srnova, I.; Slouf, M. Inorg. Chem. 1999, 38, 869-875.
58. Remarkably, the increase of the extent of quenching (τ°/τ) with increasing the number of rhenium centers from one to four (see Table 6) is the same as that observed for the corresponding free base adducts (see ref16).
59. Abegg, P. W.; Ha, T.-K. Mol. Phys. 1974, 27, 763-767.