Complexed nitrogen heterosuperbenzene: The coordinating properties of a remarkable ligand

Journal of the American Chemical Society

Volumn 126, Issue 28, 2004, Pages 8694-8701

  Draper, Sylvia M ^a   Gregg, Daniel J ^a   Schofield, Emma R ^a   Browne, Wesley R ^b   Duati, Marco ^b   Vos, Johannes G ^b   Passaniti, Paolo ^c  

^a TRINITY COLLEGE DUBLIN   (Ireland)

^b DUBLIN CITY UNIVERSITY   (Ireland)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ENERGY ABSORPTION; HETEROJUNCTIONS; INFRARED SPECTROSCOPY; NITROGEN; NUCLEAR MAGNETIC RESONANCE;

MONOTOPIC LIGAND; NITROGEN HETEROSUPERBENZENE;

BENZENE;

2,2' BIPYRIDINE; BENZENE DERIVATIVE; LIGAND; NITROGEN; RUTHENIUM; TETRAPERI(TERT BUTYL BENZO)DIPERI(PYRIMIDINO)CORONENE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; ENERGY; INFRARED SPECTROSCOPY; LIGAND BINDING; MASS SPECTROMETRY; METAL BINDING; PHOTOCHEMICAL EFFICIENCY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; TEMPERATURE DEPENDENCE;

EID: 3242671761     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0491634     Document Type: Article

References (67)

1. Draper, S. M.; Gregg, D. J.; Madathil, R. J. Am. Chem. Soc. 2002, 124, 3486-3487.
2. (a) Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267-1300.
3. (b) Herwig, P. T.; Kayser, C. W.; Müllen, K.; Spiess, H. W. Adv. Mater. 1996, 8, 510-513.
4. (c) Stabel, A.; Herwig, P. T.; Müllen, K.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611.
5. (d) van de Craats, A. M.; Warman, J. M.; Fechtenkötter, A.; Brand, J. D.; Harbison, M.; Müllen, K. Adv. Mater. 1999, 11, 1469-1472.
6. Scheibel, T.; Parthasarathy, R.; Sawicki, G.; Lin, X.-M.; Jaeger, H.; Lindquist, S. L. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 4527-4532.
7. Dijkstra, H. P.; Steenwinkel, P.; Grove, D. M.; Lutz, M.; Spek, A. L.; van Koten, G. Angew. Chem., Int. Ed. 1999, 38, 2185-2188.
8. (a) Balzani, V.; Juris, A.; Venturi, M.; Campagna, S.; Serroni, S. Chem. Rev. 1996, 96, 759-833.
9. (b) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: Chichester, UK, 1991.
10. (c) Meyer, T. J. Pure Appl. Chem. 1986, 58, 1193-1206.
11. (d) Meyer, T. J. Pure Appl. Chem. 1990, 62, 1003-1009.
12. (e) Juris, A.; Balzani, V.; Barigelletti, F.; Campagna, S.; Belser, P.; von Zelewsky, A. Coord. Chem. Rev. 1988, 84, 85-277.
13. (f) De Cola, L.; Belser, P. Coord. Chem. Rev. 1998, 177, 301-346.
14. (g) Treadway, J. A.; Strouse, G. F.; Ruminski, R. R.; Meyer, T. J. Inorg. Chem. 2001, 40, 4508-4509.
15. (h) Aiello, I.; Ghedini, M.; La Deda, M. J. Lumin. 2002, 96, 249-259.
16. Albano, G.; Belser, P.; De Cola, L.; Gandolfi, M. T. Chem. Commun. 1999, 1171-1172.
17. (a) Chiorboli, C.; Bignozzi, C. A.; Scandola, F.; Ishow, E.; Gourdon, A.; Launay, J.-P. Inorg. Chem. 1999, 38, 2402-2410.
18. (b) Nazeeruddin, M. K.; Péchy, P.; Grätzel, M. Chem. Commun. 1997, 1705-1706.
19. Anderson, P. A.; Strouse, G. F.; Treadway, J. A.; Keene, F. R.; Meyer, T. J. Inorg. Chem. 1994, 33, 3863-3864 and references within.
20. Glazer, E. C.; Tor, Y. Angew. Chem., Int. Ed. 2002, 41, 4022-4026.
21. (a) Gourdon, A.; Launay, J.-P. Inorg. Chem. 1998, 37, 5336-5341.
22. (b) Ishow, E.; Gourdon, A.; Launay, J.-P.; Chiorboli, C.; Scandola, F. Inorg. Chem. 1999, 38, 1504-1510.
23. (c) Gut, D.; Goldberg, I.; Kol, M. Inorg. Chem. 2003, 42, 3483-3491.
24. (a) Tsuji, J. Palladium Reagents and Catalysts, Innovation in Organic Synthesis; Wiley: Chichester, 1995.
25. (b) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 49, 4387-4388.
26. (c) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1976, 98, 630-632.
27. (d) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
28. (e) Canal, J. M.; Gómez, M.; Jiménez, F.; Cano, F. H. Organometallics 2000, 19, 966-978.
29. (f) Canovese, L.; Visentin, F.; Chessa, G.; Niero, A.; Uguagliati, P. Inorg. Chim. Acta 1999, 293, 44-52.
30. (g) Jikei, M.; Ishida, Y.; Kakimoto, M.; Imai, Y. React. Funct. Polym. 1996, 30, 117-124.
31. (h) Satake, A.; Koshino, H.; Nakata, T. Organometallics 1999, 18, 5108-5111.
32. (i) Tsukada, N.; Sato, T.; Mori, H.; Sugawara, S.; Kabuto, C.; Miyano, S.; Inoue, Y. J. Organomet. Chem. 2001, 627, 121-126.
33. Browne, W. R.; Coates, C. G.; Brady, C.; Matousek, P.; Towrie, M.; Botchway, S. W.; Parker, A. W.; Vos, J. G.; McGarvey, J. J. J. Am. Chem. Soc. 2003, 125, 1706-1707.
34. Sakakibara, M.; Takahashi, Y.; Sakai, S.; Ishii, Y. J. Chem. Soc., Chem. Commun. 1969, 396-397.
35. Simpson, C. D.; Brand, J. D.; Berresheim, A. J.; Przybilla, L.; Räder, H. J.; Müllen, K. Chem.-Eur. J. 2002, 8, 1424-1429.
36. See Supporting Information.
37. (a) Lytle, F. E.; Hercules, D. M. J. Am. Chem. Soc. 1969, 91, 253.
38. (b) Wayne, R. P. Principles and Applications of Photochemistry; Oxford University Press: New York, 1980.
39. Baranoff, E.; Collin, J.-P.; Furusho, Y.; Laemmel, A. C.; Sauvage, J.-P. Chem. Commun. 2000, 1935-1936.
40. (a) Laemmel, A. C.; Collin, J.-P.; Sauvage, J.-P. Eur. J. Inorg. Chem. 1999, 383-386.
41. (b) Fanni, S.; Keyes, T. E.; O'Connor, C. M.; Hughes, H.; Wang, R.; Vos, J. G. Coord. Chem. Rev. 2000, 208, 77-86.
42. (a) Ye, B. H.; Chen, X. M.; Zeng, T. X.; Ji, L. N. Inorg. Chim. Acta 1995, 240, 5-11.
43. (b) Hua, X.; von Zelewsky, A. Inorg. Chem. 1995, 34, 5791-5797.
44. (c) Wu, F.; Riesgo, E.; Pavalova, A.; Kipp, R. A.; Schmehl, R. H.; Thummel, R. P. Inorg. Chem. 1999, 38, 5620-5628.
45. (a) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027.
46. (b) Bilakhiya, A. K.; Tyagi, B.; Paul, P.; Natarajan, P. Inorg. Chem. 2002, 41, 3830-3842.
47. (c) Gut, D.; Rudi, A.; Kopilov, J.; Goldberg, I.; Kol, M. J. Am. Chem. Soc. 2002, 124, 5449-5456.
48. (d) Ishow, E.; Gourdon, A.; Launay, J.-P. Chem. Commun. 1998, 1909-1910.
49. (e) Rudi, A.; Kashman, Y.; Gut, D.; Lellouche, F.; Kol, M. Chem. Commun. 1997, 17-18.
50. (f) Bolger, J.; Gourdon, A.; Ishow, F.; Launay, J.-P. Inorg. Chem. 1996, 35, 2937-2944.
51. (g) Bolger, J.; Gourdon, A.; Ishow, E.; Launay, J.-P. J. Chem. Soc., Chem. Commun. 1995, 1799-1800.
52. (h) Fechtenkötter, A.; Tchebotareva, N.; Watson, M. D.; Müllen, K. Tetrahedron 2001, 57, 3769-3783.
53. Caspar, J. V.; Meyer, T. J. Inorg. Chem. 1983, 22, 2444-2453.
54. Amouyal, E.; Homsi, A.; Chambron, J.-C.; Sauvage, J.-P. J. Chem. Soc., Dalton Trans. 1990, 6, 1841-1845.
55. (a) Seddon, E. A.; Seddon, K. R. The Chemistry of Ruthenium; Elsevier: New York, 1984; Chapter 15.
56. (b) Thummel, R.; Lefoulon, F.; Korp, J. D. Inorg. Chem. 1987, 26, 2370-2376.
57. (a) Nazeeruddin, M. K.; Zakeeruddin, S. M.; Kalyanasundaram, K. J. Phys. Chem. 1993, 97, 9607.
58. (b) Kalyanasundaram, K.; Zakeeruddin, S. M.; Nazeeruddin, Md. K. Coord. Chem. Rev. 1994, 132, 259-264
59. Danzer, G. D.; Golus, J. A.; Kincaid, J. R. J. Am. Chem. Soc. 1993, 115, 8643-8648.
60. Caspar, J. V.; Meyer, T. J. J. Am. Chem. Soc. 1983, 105, 5583-5590.
61. Di Donato, E.; Tommasini, M.; Fustella, G.; Brambilla, L.; Castiglioni, C.; Zerbi, G.; Simpson, C. D.; Müllen, K.; Negri, F. Chem. Phys. 2004, 301, 81-93.
62. Barigelletti, F.; De Cola, L.; Balzani, V.; Belser, P.; von Zelewsky, A.; Vögtle, F.; Ebmeyer, F.; Grammenudi, S. J. Am. Chem. Soc. 1989, 111, 4662-4668.
63. Browne, W. R.; Vos, J. G. Coord. Chem. Rev. 2001, 219-221, 761-787.
64. Slinker, J.; Bernards, D.; Houston, P. L.; Abruña, H. D.; Bernhard, S.; Malliaras, G. G. Chem. Commun. 2003, 2392-2399.
65. Welter, S.; Brunner, K.; Hofstraat, J. W.; De Cola, L. Nature 2003, 421, 54-57.
66. Sullivan, B. P., Salmon, D. J.; Meyer, T. J. Inorg. Chem. 1978, 17, 3334-3341.
67. Nakamaru, K. Bull. Chem. Soc. Jpn. 1982, 55, 2697.