Ruthenium(II) dendrimers containing carbazole-based chromophores as branches

Journal of the American Chemical Society

Volumn 125, Issue 18, 2003, Pages 5356-5365

  McClenaghan, Nathan D ^a   Passalacqua, Rosalba ^a   Loiseau, Fredérique ^a   Campagna, Sebastiano ^a   Verheyde, Bert ^b   Hameurlaine, Ahmed ^b   Dehaen, Wim ^b  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CHARGE TRANSFER; CHROMOPHORES; LUMINESCENCE OF LIQUIDS AND SOLUTIONS; REDOX REACTIONS; RUTHENIUM COMPOUNDS;

COORDINATION COMPOUNDS; EXCITATION SPECTROSCOPY;

DENDRIMERS;

1,10 PHENANTHROLINE; ACID; CARBAZOLE DERIVATIVE; DENDRIMER; LIGAND; PYRIDINE DERIVATIVE; RUTHENIUM COMPLEX; ZINC ACETATE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHROMATOPHORE; COMPLEX FORMATION; LUMINESCENCE; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE;

EID: 0037690723     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021373y     Document Type: Article

References (62)

1. (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood: Chichester, U.K., 1991.
2. (b) Sauvage, J.-P.; Collin, J.-P.; Chambron, J.-C.; Guillerez, S.; Coudret, C.; Balzani, V.; Barigelletti, F.; De Cola, L.; Flamigni, L. Chem. Rev. 1994, 94, 993.
3. (c) Balzani, V.; Juris, A.; Venturi, M.; Campagna, S.; Serroni, S. Chem. Rev. 1996, 96, 759.
4. (d) Bignozzi, C. A.; Schoonover, J. R.; Scandola, F. Progr. Inorg. Chem. 1997, 44, 1.
5. (e) De Cola, L.; Belser, P. Coord. Chem. Rev. 1998, 177, 301.
6. (f) Blanco, M.-J.; Jiménez, M. C.; Chambron, J.-C.; Heitz, V.; Linke, M.; Sauvage, J.-P. Chem. Soc. Rev. 1999, 28, 293.
7. (g) Barigelletti, F.; Flamigni, L. Chem. Soc. Rev. 2000, 29, 1.
8. Newkome, G. R.; Moorefield, C.; Vögtle, F. Dendrimers and Dendrons; Wiley-VCH: Weinheim, Germany, 2001 and references therein.
9. (a) Balzani, V.; Campagna, S.; Denti, G.; Juris, A.; Serroni, S.; Venturi, M. Acc. Chem. Res. 1998, 31, 26.
10. (b) Constable, E. C. Chem. Commun. 1997, 1073.
11. (c) Issberner, J.; Vögtle, F.; De Cola, L.; Balzani, V. Chem. Eur. J. 1997, 3, 706.
12. (d) Vögtle, F.; Pleovets, M.; Nieger, M.; Azzellini, G. C.; Credi, A.; De Cola, L.; Marchis, V.; Venturi, M.; Balzani, V. J. Am. Chem. Soc. 1999, 121, 6290.
13. (e) Balzani, V.; Ceroni, P.; Juris, A.; Venturi, M.; Campagna, S.; Puntoriero, F.; Serroni, S. Coord. Chem. Rev. 2001, 219-221, 545 and references therein.
14. (f) Lo, S.-C.; Male, N. A. H.; Markham, J. P. J.; Magennis, S. W.; Burn, P. L.; Salata, O. V.; Samuel, I. D. W. Adv. Mater. 2002, 14, 975.
15. Complementary information on purely organic photoactive and redox-active dendrimers can be found in many reviews and papers: a list of recent ones is as follows: (g) Yang, S. I.; Seth, J.; Balasubramanian, T.; Kim, D.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Am. Chem. Soc. 1999, 121, 4008. (h) Nielsen, M. B.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153. (i) Adronov, A.; Fréchet, J. M. J. Chem. Commun. 2000, 1701. (j) Lor, M.; Thielemans, J.; Viaene, L.; Cotlet, M.; Hofkens, J.; Weil, T.; Hampel, C.; Müllen, K.; Verhoeven, J. W.; Van der Auweraer, M.; De Schryver, F. C. J. Am. Chem. Soc. 2002, 124, 9918.
16. Complementary information on purely organic photoactive and redox-active dendrimers can be found in many reviews and papers: a list of recent ones is as follows: (g) Yang, S. I.; Seth, J.; Balasubramanian, T.; Kim, D.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Am. Chem. Soc. 1999, 121, 4008. (h) Nielsen, M. B.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153. (i) Adronov, A.; Fréchet, J. M. J. Chem. Commun. 2000, 1701. (j) Lor, M.; Thielemans, J.; Viaene, L.; Cotlet, M.; Hofkens, J.; Weil, T.; Hampel, C.; Müllen, K.; Verhoeven, J. W.; Van der Auweraer, M.; De Schryver, F. C. J. Am. Chem. Soc. 2002, 124, 9918.
17. Complementary information on purely organic photoactive and redox-active dendrimers can be found in many reviews and papers: a list of recent ones is as follows: (g) Yang, S. I.; Seth, J.; Balasubramanian, T.; Kim, D.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Am. Chem. Soc. 1999, 121, 4008. (h) Nielsen, M. B.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153. (i) Adronov, A.; Fréchet, J. M. J. Chem. Commun. 2000, 1701. (j) Lor, M.; Thielemans, J.; Viaene, L.; Cotlet, M.; Hofkens, J.; Weil, T.; Hampel, C.; Müllen, K.; Verhoeven, J. W.; Van der Auweraer, M.; De Schryver, F. C. J. Am. Chem. Soc. 2002, 124, 9918.
18. Complementary information on purely organic photoactive and redox-active dendrimers can be found in many reviews and papers: a list of recent ones is as follows: (g) Yang, S. I.; Seth, J.; Balasubramanian, T.; Kim, D.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Am. Chem. Soc. 1999, 121, 4008. (h) Nielsen, M. B.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153. (i) Adronov, A.; Fréchet, J. M. J. Chem. Commun. 2000, 1701. (j) Lor, M.; Thielemans, J.; Viaene, L.; Cotlet, M.; Hofkens, J.; Weil, T.; Hampel, C.; Müllen, K.; Verhoeven, J. W.; Van der Auweraer, M.; De Schryver, F. C. J. Am. Chem. Soc. 2002, 124, 9918.
19. (a) Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. - Eur. J. 1995, 1, 211.
20. (b) Serroni, S.; Juris, A.; Venturi, M.; Campagna, S.; Resino Resino, I.; Denti, G.; Credi, A.; Balzani, V. J. Mater. Chem. 1997, 7, 1227.
21. (a) Zhou, X.; Tyson, D. S.; Castellano, F. N. Angew. Chem., Int. Ed. 2000, 39, 4301.
22. (b) Tyson, D. S.; Henbest, K. B.; Bialecki, J.; Castellano, F. N. J. Phys. Chem. A 2001, 105, 8154.
23. (c) McClenaghan, N. D.; Loiseau, F.; Puntoriero, F.; Serroni, S.; Campagna, S. Chem. Commun. 2001, 2634.
24. (d) Tyson, D. S.; Luman, C. R.; Castellano, F. N. Inorg. Chem. 2002, 41, 3578.
25. (a) Hoegl, H. J. Phys. Chem. 1965, 69, 755.
26. (b) Johnston, G. E. J. Phys. Chem. 1974, 78, 1512.
27. (c) Nitzche, L. E.; Chabalowski, C.; Christofferson, R. E. J. Am. Chem. Soc. 1978, 100, 1371.
28. (d) Zhang, Y.; Wada, T.; Wang, L.; Aoyama, T.; Sasabe, H. J. Chem. Soc., Chem. Commun. 1996, 2325.
29. (e) Grigalevicius, S.; Grazulevicius, J. V.; Gaidelis, V.; Jankauskas, V. Polymer 2002, 43, 2603.
30. (f) Schaerlaekens, M.; Hendrickx, E.; Hameurlaine, A.; Dehaen, W.; Persoons, A. Chem. Phys. 2002, 277, 43.
31. Ribou, A.-C.; Wada, T.; Sasabe, H. Inorg. Chim. Acta 1999, 288, 134.
32. (a) de Silva, A. P.; Gunaratne, H. Q. N.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
33. (b) Chemosensors of Ion and Molecule Recognition; Desvergne, J.-P., Czarnik, A. W., Eds.; Kluwer: Dordrecht, The Netherlands, 1997.
34. (c) Armaroli, N.; Eckert, J.-F.; Nierengarten, J.-F. Chem. Commun. 2000, 2105.
35. (d) Credi, A.; Balzani, V.; Langford, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 1997, 119, 2679.
36. (e) de Silva, A. P.; McClenaghan, N. D. J. Am. Chem. Soc. 2000, 122, 3965.
37. (f) de Silva, A. P.; McClenaghan, N. D.; McCoy, C. P. in Handbook of Electron Transfer in Chemistry; Balzani, V. (Editor-in-Chief), de Silva, A. P. (Section Editor); Wiley-VCH: Weinheim, Germany, 2001; Vol. 5, p 156 and references therein.
38. Neugebauer, F. A.; Fisher, H.; Bamberger, S.; Smith, H. O. Chem. Ber 1972, 105, 2686.
39. Tucker, S. H. J. Chem. Soc. 1926, 546.
40. Sullivan, B. P.; Salomon, D. J.; Meyer, T. J. Inorg. Chem. 1978, 17, 3337.
41. Damrauer, N. H.; Boussie, T. R.; Devenney, M.; McCusker, J. K. J. Am. Chem. Soc. 1997. 119, 8253.
42. Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; von Zelewsky, A. Coord. Chem. Rev. 1988, 84, 85.
43. The interaction between the carbazole moieties of L1 can occur via the phenanthroline HOMO, according to a superexchange hole-transfer mechanism, and depends on the energy gap between carbazole-centered and phenanthroline-centered HOMOs (a larger interaction is obtained for a smaller energy gap). This energy gap increases upon phenanthroline metal coordination, leading to a reduced carbazole-carbazole interaction.
44. (a) Crosby, G. R. Acc. Chem. Res. 1975, 8, 221.
45. (b) Meyer, T. J. Acc. Chem. Res. 1989, 22, 163.
46. Dodsworth, E. S.; Vlcek, A. A.; Lever, A. B. P. Inorg. Chem. 1994, 33, 1045.
47. (a) Howell, A. G.; Taylor, A. G.; Phillips, D. Chem. Phys. Lett. 1992, 188, 119.
48. (b) Yu, H.; Mohd Zain, S.; Eigenbrot, I. V.; Phillips, D. Chem. Phys. Lett. 1993, 202, 141.
49. (c) Mohd Zain, S.; Hashim, R.; Taylor, A. G.; Phillips, D. THEOCHEM 1997, 401, 287.
50. (d) Kido, J.; Hongawa, K.; Okuyama, K.; Nagai, K. Appl. Phys. Lett. 1993, 63, 2627.
51. Phillips, D. J. Photochem. Photobiol., A. 1997, 105, 307.
52. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358 and references therein.
53. 22 In both cases, emission has been assigned to phenanthroline-centered π-π* triplet levels. Although the phenanthroline subunits in both the above-mentioned systems are expected to be differently perturbed than those in L1 and L2, the similitude in emission energies, shapes, and lifetimes (where available, i.e., in the rhodium species) strongly supports a similar assignment also for the 77 K emission of L1 and L2.
54. Hillis, J.; De Armond, M. K. J. Lumin. 1971, 4, 273.
55. (a) Ohsawa, Y.; Sprouse, S.; King, K. A.; De Armond, M. K.; Hanck, K. W.; Watts, R. J. J. Phys. Chem. 1987, 91, 1041.
56. (b) Maestri, M.; Balzani, V.; Deuschel-Cornioley, C.; von Zelewsky, A. Adv. Photochem. 1992, 17, 1.
57. (a) Freed, K. F.; Jortner, J. J. Chem. Phys. 1970, 52, 6275.
58. (b) Caspar, J. V.; Meyer, T. J. J. Phys. Chem. 1983, 87, 952.
59. (a) Bradley, P. C.; Kress, N.; Hornberger, B. A.; Dallinger, R. F.; Woodruff, W. H. J. Am. Chem. Soc. 1989, 103, 7441.
60. (b) Cooley, L. F.; Bergquist, P.; Kelley, D. F. J. Am. Chem. Soc. 1990, 104, 2612.
61. (c) Damrauer, N. H.; Cerullo, G.; Yeh, A.; McClusker, J. K. Science 1997, 275, 54.
62. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991.