Preparation of a copper ion complex of sterically congested diphenyldiazomethanes having a pyridine ligand and characterization of their photoproducts

Journal of Physical Chemistry B

Volumn 109, Issue 44, 2005, Pages 20763-20772

  Itoh, Tetsuji ^a   Matsuno, Masayoshi ^a   Ozaki, Shuhei ^a   Hirai, Katsuyuki ^a   Tomioka, Hideo ^a,b  

^a MIE UNIVERSITY   (Japan)

^b AICHI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; IONS; MAGNETIC PROPERTIES; MAGNETIZATION; PARAMAGNETIC RESONANCE; QUANTUM INTERFERENCE DEVICES;

COMPLEXED CARBENES; COPPER ION COMPLEX; DIPHENYLDIAZOMETHANES; HETERO SPIN SYSTEMS;

POLYCARBONATES;

CARBENE; COPPER; DIAZOMETHANE; DRUG DERIVATIVE; HYDROCARBON; LIGAND; METHANE; PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; PHOTOLYSIS;

COPPER; DIAZOMETHANE; HYDROCARBONS; LIGANDS; METHANE; PHOTOLYSIS; PYRIDINES;

EID: 28144438920     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp053622l     Document Type: Article

References (78)

1. (a) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179.
2. (b) Dougherty, D. A. Acc. Chem. Res. 1991, 24, 88.
3. (c) Rajca, A. Chem. Rev. 1994, 94, 871.
4. (d) Lahti, P. M., Ed. Molecular Magnetism in Organic-Based Materials; Marcel Dekker: New York, 1999.
5. (e) Itoh, K.; Kinoshita, M., Eds. Molecular Magnetism; Kodansha-Gordon and Breach: Tokyo, Japan, 2000.
6. (a) Kahn, O. Molecular Magnetism; VCH Publishers: Weinheim, Germany, 1993.
7. (b) Gatteschi, D. Adv. Mater. 1994, 6, 635.
8. (c) Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. 1994, 33, 385.
9. (d) Miller, J. S.; Epstein, A. J. Chem. Eng. News 1995, October 2, 30.
10. (e) Kahn, O., Ed. Magnetism: A Supramolecular Function; NATO ASI Series C; Kluwer: Dordrecht, The Netherlands, 1996.
11. (f) Turnbull, M. M.; Sugimoto, T.; Thompson, L. K., Eds. Molecule-Based Magnetic Materials; ACS Symp. Ser. No. 644; American Chemical Society: Washington, DC, 1996.
12. (g) Gatteschi, D. Curr. Opin. Solid State & Mater. Sci. 1996, 1, 192.
13. (h) Miller, J. S.; Epstein, A. J., Eds. MRS Bull. 2000, 25, 21.
14. (i) Miller, J. S.; Drillon, M., Eds. Magnetism: Molecules to Materials; Wiley-VCH: New York, 2001; Vol. II.
15. (a) Kinoshita, M. In Handbook of Organic Conductive Molecules and Polymers; Nalva, H. S., Ed.; Wiley: New York, 1997; Vol. 1, pp 781-800.
16. (b) Allemand, P.-M.; Khemani, K. C.; Koch, A.; Wudl, F.; Holczer, K.; Donovan, S.; Gruner, G.; Thompson, J. D. Science 1991, 253, 301.
17. (c) Narymbetov, B.; Omerzu, A.; Kabanov, V. V.; Tokumoto, M.; Kobayashi, H.; Mihailovic, D. Nature 2000, 407, 883.
18. (d) Hosokoshi, Y.; Katoh, K.; Nakazawa, Y.; Nakano, H.; Inoue, K. J Am. Chem. Soc. 2001, 123, 7921.
19. (e) Shiomi, D.; Kanaya, T.; Sato, K.; Mito, M.; Takeda, T.; Takui, T. J. Am. Chem. Soc. 2001, 123, 11823.
20. (f) Crayston, J. A.; Devine, J. N.; Walton, J. C. Tetrahedron 2000, 56, 7829.
21. Malaga, N. Theor. Chim. Acta 1968, 10, 1509.
22. (a) Rajca, A.; Rajca, S.; Wongsriatanakul, J. J. Am. Chem. Soc. 1999, 121, 6308.
23. (b) Rajca, A.; Wongsriatanakul, J.; Rajca, S. Science 2001, 294, 1503.
24. (c) Anderson, K. K.; Dougherty, D. A. Adv. Mater. 1998, 10, 688.
25. (d) Bushby, R. J.; McGill, D. R.; Ng, K. M.; Taylor, N. J. Mater. Chem. 1997, 7, 2343.
26. (e) Nishide, H.; Ozawa, T.; Miyasaka, M.; Tsuchida, E. J. Am. Chem. Soc. 2001, 123, 5942.
27. See for instance: Rajca, A.; Wongsriatanakul, J.; Rajca, S.; Cerny, R. L. Chem. Eur. J. 2004, 10, 3144.
28. See for instance: Matsuda, K.; Nakamura, N.; Inoue, K.; Koga, N.; Iwamura, H. Chem. Eur. J. 1996, 2, 259.
29. (a) Koga, N.; Iwamura, H. In Carbene Chemistry; Bertrand, G., Ed,: Fontis Media: Lausanne, 2002; pp 271-296.
30. (b) Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. Molecule-based Magnetic Materials; ACS Symp. Ser. No. 644; American Chemical Society: Washington, DC, 1996; p 142.
31. (a) Koga, N.; Iwamura, H. In Molecular Magnetism in Organic-Based Materials; Lahti, P. M., Ed.; Marcel Dekker: New York, 1999; pp 629-659.
32. (b) Koga. N.; Iwamura, H. Mol. Crsyt. Liq. Cryst. 1997, 305, 415.
33. (c) Iwamura, H.; Koga, N. Mol. Crsvt. Liq. Cryst. 1999, 334, 437.
34. (d) Iwamura, H.; Koga, N. Pure Appl. Chem. 1999, 71, 231.
35. (a) Lehn, J.-M. Supramolecular Chemistry; VCH Publisher: New York, 1995.
36. (b) Nierengarten, J.-F.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. J. Am. Chem. Soc. 1994, 116, 375.
37. (c) Leininger, J.-F.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853.
38. Matsuno, M.; Itoh, T.; Hirai, K.; Tomioka, H. J. Org. Chem. 2005, 70, 7054.
39. Itoh, T.; Matsuno, M.; Kamiya, E.; Hirai, K.; Tomioka, H. J. Am. Chem. Soc. 2005, 127, 7078.
40. (a) Tomioka, H.; Nakajima, J.; Mizuno, H.; Iiba, E.; Hirai, K. Can. J. Chem. 1999, 77, 1066.
41. (b) Itakura, H.; Tomioka, H. Org. Lett. 2000, 2, 2995.
42. (c) Takahashi, Y.; Tomura, M.; Yoshida, K.; Murata, S.; Tomioka, H. Angew. Chem., Int. Ed. 2000, 39, 3478.
43. (d) Tomioka, H.; Iwamoto, E.; Itakura, H.; Hirai, K. Nature 2001, 412, 626.
44. (e) Iwamoto, E.; Hirai, K.; Tomioka, H. J. Am. Chem. Soc. 2003, 125, 14664.
45. (f) Yoshida, K.; Iiba, E.; Nozaki, Y.; Hirai, K.; Takahashi, Y.; Tomioka, H.; Lin, C.-T.; Gaspar, P. Bull. Chem. Soc. Jpn. 2004, 77, 1509.
46. Rajca, A. Chem. Eur. J. 2002, 8, 4835.
47. See reviews for persistent triplet carbenes: (a) Tomioka, H. Acc. Chem. Res. 1997, 30, 315.
48. (b) Tomioka, H. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 2, pp 175-214.
49. (c) Tomioka, H. In Carbene Chemistry; Bertrand, G., Ed.; Fontis Media S. A.; Lansanne, 2002; pp 103-152.
50. (a) Tomioka, H.; Watanabe, T.; Hirai, K.; Furukawa, K.; Takui, T.; Itoh, K. J. Am. Chem. Soc. 1995, 117, 6376.
51. (b) Tomioka, H.; Hattori, M.; Hirai, K.; Murata, S. J. Am. Chem. Soc. 1996, 118, 8723.
52. (c) Tomioka, H.; Watanabe, T.; Hattori, M.; Nomura, N.; Hirai, K. J. Am. Chem. Soc. 2002, 124, 474.
53. (d) Hirai, K.; Iikubo, T.; Tomioka, H. Chem. Lett. 2002, 1226.
54. See for reviews of the EPR spectra of triplet carbenes: (a) Sander, W.; Bucher, G.; Wierlacher. S. Chem. Rev. 1993, 93, 1583.
55. (b) Trozzolo, A. M.; Wasserman, E. In Carbenes; Jones. M., Jr., Moss, R. A., Eds.; Wiley: New York, 1975; Vol. 2, pp 185-206.
56. (a) Hu, Y.-M.; Hirai, K.; Tomioka, H. J. Chem. Phys. A 1999, 103, 9280.
57. (b) Hu, Y.-M.; Hirai, K.; Tomioka, H. Chem. Lett. 2000, 94.
58. (c) Hu, Y.-M.; Ishikawa, Y.; Hirai, K.; Tomioka, H. Bull. Chem. Soc. Jpn. 2001, 74, 2207.
59. (a) Platz, M. S. In Diradicals; Borden, W. T., Ed.; Wiley: New York, 1982; pp 195-258.
60. (b) Wasserman, E.; Hutton, R. S. Acc. Chem. Res. 1977, 10, 27.
61. (c) Breslow, R.; Chang, H. W.; Wasserman, E. J. Am. Chem. Soc. 1967, 89, 1112.
62. (a) See for review: Sander, W. Angew. Chem., Int. Ed. Engt. 1990, 29, 344.
63. (b) Bunnelle, W. Chem. Rev. 1991, 91, 336.
64. Scaiano, J. C.; McGimpsey, W. G.; Casal, H. L. J. Org. Chem. 1989, 54, 1612.
65. Monguchi, K.; Itoh, T.; Hirai, K.; Tomoka, H. J. Am. Chem. Soc. 2004, 126, 11900.
66. (a) See also: Dorra, M.; Gomann, K.; Guth, M.; Kirmse, W. J. Phys. Org. Chem. 1996, 9, 598.
67. (b) It is likely that the triplet state of 3 is detected simply because the initially formed 3 is excited, by laser instantaneously after its formation.
68. Sugiura, Y. Inorg. Chem. 1978, 17, 2178.
69. (a) Sano, Y.; Tanaka, M.; Koga, N.; Matsuda, K.; Iwamura, H.; Rabu, P.; Drillon, M. J. Am. Chem. Soc. 1997, 119, 8246.
70. (b) Karasawa, S.; Koga, N. Polyhedron 2001, 20, 1387.
71. (c) Karasawa, S.; Sano, Y.; Akita, T.; Koga, N.; Itoh, T.; Iwamura, H.; Rabu, P.; Drillon, M. J. Am. Chem. Soc. 1998, 120, 10080.
72. (d) Karasawa, S.; Kumada, H.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 2001, 123, 9685.
73. (e) Morikawa, H.; Imamura, F.; Tsurukami, Y.; Itoh, T.; Kumada, H.; Karasawa, S.; Koga, N.; Iwamura, H. J. Mater. Chem. 2001, 11, 493.
74. (f) Karasawa, S.; Koga, N. Polyhedron 2003, 22, 1877.
75. The measurements were carried out at this low concentration not only to avoid intermolecular magnetic interaction of sample but also to increase photolysis efficiency. The latter is important especially because we generate magnetic species (carbene-Cu complexes) in situ by photolysis of precursory diazo-Cu complexes: carbene-Cu complexes show broad absorption bands at 450-550 nm and hence, at higher concentration, the bands due to carbene-Cu complexes grow and overlap with the bands due to the starting complex (see Figures 8 and 9).
76. Carlin, R. L. Magnetochemistry; Springer-Verlag: Berlin, Germany, 1986.
77. In the present study, magnetic measurements were made in a frozen solution where the chain may be more flexible than in a solid state. Hence, it is still unsettled whether the complexes are formed by a one-dimensional chain having alternating S = 1/2 and 1 spins and hence we cannot estimate unequivocally the magnitude of the exchange coupling between Cu 3d spin and carbene 2p spin. However, our results apparently indicate that the pyridyl group ligates with Cu ion to form 1:1 complexes and the spin quantum numbers of the complexes increase to some extent in this system.
78. 2 can be presumed to be very much smaller than that between Cu ion and the carbenic center for photoproducts. Hence, we did not take into consideration this interaction to magnetic analysis for the photoproducts.