Spin transfer and solvato-/thermochromism induced by intramolecular electron transfer in a purely organic open-shell system

Angewandte Chemie - International Edition

Volumn 44, Issue 44, 2005, Pages 7277-7280

  Nishida, Shinsuke ^a   Morita, Yasushi ^a,c   Fukui, Kozo ^c   Sato, Kazunobu ^b   Shiomi, Daisuke ^b   Takui, Takeji ^b   Nakasuji, Kazuhiro ^a  

^a OSAKA UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Electron transfer; EPR spectroscopy; Radicals; Solvatochromism; Thermochromism

Indexed keywords

ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRON TRANSITIONS; FREE RADICALS; ORGANIC SOLVENTS;

ELECTRON TRANSFER; SOLVATOCHROMISM; THERMOCHROMISM;

ORGANIC COMPOUNDS;

EID: 27844519388     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502180     Document Type: Article

References (35)

1. a) K. Matsuda, Bull. Chem. Soc. Jpn. 2005, 78, 383-392;
2. b) S. Nakatsuji, Chem. Soc. Rev. 2004, 33, 348-353.
3. M. E. Itkis, X. Chi, A. E. Cordes, R. C. Haddon, Science 2002, 296, 1443-1445.
4. As for transition-metal complexes, such an interconversion is known as valence tautomerism, see: a) R. M. Buchanan, C. G. Pierpont, J. Am. Chem. Soc. 1980, 102, 4951-4957;
5. b) P. Gütlich, A. Dei, Angew. Chem. 1997, 109, 2852-2857;
6. Angew. Chem. Int. Ed. Engl. 1997, 36, 2734-2736;
7. c) D. A. Shultz in Magnetism: Molecule to Materials, Vol. II (Eds.: J. S. Miller, M. Drillon), Wiley-VCH, Weinheim, 2001, chap. 8, pp. 281-306;
8. d) I. Ratera, D. Ruiz-Molina, F. Renz, J. Ensling, K. Wurst, C. Rovira, P. Gütlich, J. Veciana, J. Am. Chem. Soc. 2003, 125, 1462-1463;
9. e) A. Dei, D. Gatteschi, C. Sangregorio, L. Sorace, Acc. Chem. Res. 2004, 37, 827-835.
10. a) Y. Morita, T. Ohba, N. Haneda, S. Maki, J. Kawai, K. Hatanaka, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, J. Am. Chem. Soc. 2000, 122, 4825-4826;
11. b) Y. Morita, S. Maki, K. Fukui, T. Ohba, J. Kawai, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, Org. Lett. 2001, 3, 3099-3102;
12. c) Y. Morita, S. Nishida, J. Kawai, K. Fukui, S. Nakazawa, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, Org. Lett. 2002, 4, 1985-1988;
13. d) Y. Morita, J. Kawai, S. Nishida, N. Haneda, K. Fukui, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, Synth. Met. 2003, 137, 1217-1218.
14. TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalene (Eds.: J. Yamada, T. Sugimoto), Kodansha & Springer, Heidelberg, 2004.
15. a) K. Yamaguchi, H. Namimoto, T. Fueno, T. Nogami, Y. Shirota, Chem. Phys. Lett. 1990, 166, 408-414;
16. b) K. Yamaguchi, M. Okumura, T. Fueno, K. Nakasuji, Synth. Met. 1991, 41-43, 3631-3634.
17. K. Maekawa, D. Shiomi, T. Ise, K. Sato, T. Takui, J. Phys. Chem. B 2005, 109, 9299-9304, and references therein.
18. a) Molecular Magnetism (Eds.: K. Itoh, M. Kinoshita), Kodansha & Gordon and Breach, Tokyo, 2000;
19. b) Magnetic Properties of Organic Materials (Ed.: P. M. Lahti), Dekker, New York, 1999.
20. For zwitterionic radicals as single-component conductors, see: a) Y. Tsubata, T. Suzuki, T. Miyashi, Y. Yamashita, J. Org. Chem. 1992, 57, 6749-6755;
21. b) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353-355;
22. c) T. Suzuki, S. Miyanari, H. Kawai, K. Fujiwara, T. Fukushima, T. Miyashi, Y. Yamashita, Tetrahedron 2004, 60, 1997-2003;
23. See also: d) D. F. Perepichka, M. R. Bryce, C. Pearson, M. C. Petty, E. J. L. McInnes, J. P. Zhao, Angew. Chem. 2003, 115, 4784-4787;
24. Angew. Chem. Int. Ed. 2003, 42, 4636-4639.
25. For nonlinear optical materials, see: a) S. R. Marder, B. Kippelen, A. K.-Y. Jen, N. Peyghambarian, Nature 1997, 388, 845-851;
26. b) S. Houbrechts, E. Hendrickx, T. Verbiest, K. Clays, A. Persoons in Electron Transfer in Chemistry, Vol. 5 (Ed.: V. Balzani), Wiley-VCH, Weinheim, 2001, chap. 8, pp. 241-281.
27. For a unimolecular rectifier, see: R. M. Metzger, Chem. Rev. 2003, 103, 3803-3834.
28. 4: C 63.49, H 5.13, N 0.00; found: C 63.34, H 5.23, N 0.00.
29. 3: C 63.84, H 5.45, N 0.00, S 22.35; found: C 63.67, H 5.22, N 0.00, S 22.25.
30. N. Gupta, H. Linschitz, J. Am. Chem. Soc. 1997, 119, 6384-6391.
31. a) Influence from solvent polarity on this effect seems to be negligible because the relative permittivity (å) in the mixed solvents was kept constant (ε ≈ 26), and the use of higher ε aprotic solvent does not cause this effect;
32. 2OH) = 26.67. Y. Marcus, Ion Salvation, Wiley, New York, 1985, chap. 7.
33. Structural changes accompanying IET have been discussed: Z. R. Grabowski, K. Rotkiewicz, W. Rettig, Chem. Rev. 2003, 103, 3899-4031.
34. S. V. Rosokha, D.-L. Sun, J. K. Kochi, J. Phys. Chem. A 2002, 106, 2283-2292.
35. A. Terahara, H. Ohya-Nishiguchi, N. Hirota, H. Awaji, T. Kawase, S. Yoneda, T. Sugimoto, Z. Yoshida, Bull. Chem. Soc. Jpn. 1984, 57, 1760-1765.