Molecule-based valence tautomeric bistability synchronized with a macroscopic crystal-melt phase transition

Journal of the American Chemical Society

Volumn 130, Issue 16, 2008, Pages 5515-5522

  Kiriya, Daisuke ^a   Chang, Ho Chol ^a   Kitagawa, Susumu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CRYSTAL STRUCTURE; LIGANDS; PHASE TRANSITIONS; SYNCHRONIZATION;

CATECHOLATE LIGANDS; COBALT-DIOXOLENE COMPLEXES; MOLECULAR INTERCONVERSION;

MOLECULAR STRUCTURE;

1,3 DIOXOLANE DERIVATIVE; COBALT; CRYSTALLIN; PYRIDINE DERIVATIVE; QUINOLINIC ACID DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; ENTHALPY; ENTROPY; HYSTERESIS; PHASE TRANSITION; THERMODYNAMICS;

EID: 42949177218     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja711268u     Document Type: Article

References (67)

1. Aviram, A.; Ratner, M. A. Chem. Phys. Lett. 1974, 29, 277-283.
2. Feringa, B. L. Molecular Switches; Wiley-VCH: Weinheim, Germany, 2001.
3. Kahn, O.; Launary, J. P. Chemtronics 1988, 3, 140-151.
4. Joachim, C.; Gimzewski, J. K.; Aviram, A. Nature 2000, 408, 541-548.
5. Irie, M. Chem. Rev. 2000, 100, 1685-1716.
6. Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
7. (a) Beauvais, L. G.; Shores, M. P.; Long, J. R. J. Am. Chem. Soc. 2000, 122, 2763-2772.
8. (b) Halder, G. J.; Kepert, C. J.; Mouvaraki, B.; Murray, K. S.; Cashion, J. D. Science 2002, 298, 1762-1765.
9. (c) Maspoch, D.; Ruiz-Molina, D; Wurst, K; Domingo, N; Cavallini, M; Biscarini, F.; Tejada, J.; Rovira, C.; Veciana, J. Nat. Mater. 2003, 2, 190-195.
10. (d) Ohkoshi, S.; Arai, K.; Sato, Y.; Hashimoto, K. Nat. Mater. 2004, 3, 857-861.
11. (a) Dürr, H.; Bouas-Laurent, H. Photochromism Molecules and Systems; Elsevier: Amsterdam, The Netherlands, 1990.
12. (b) Kahn, O.; Martinez, C. J. Science 1998, 279, 44-48.
13. (c) Gütlich, P.; Goodwin, H. A. Top. Curr. Chem. 2004, 233-235.
14. (d) Champin, B.; Mobian, P.; Sauvage, J.-P. Chem. Soc. Rev. 2007, 36, 358-366.
15. (e) Balzani, V.; Clemente-León, M.; Credi, A.; Ferrer, B.; Venturi, M.; Flood, A. H.; Stoddart, J. F. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 1178-1183.
16. Real, J. A.; Gasper, A. B.; Niel, V.; Muñoz, M. C. Coord. Chem. Rev. 2003, 236, 121-141.
17. Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172-1175.
18. Kobatake, S.; Yamada, T.; Uchida, K.; Kato, N.; Irie, M. J. Am. Chem. Soc. 1999, 121, 2380-2386.
19. Murray, K. S.; Kepert, C. J. Top. Curr. Chem. 2004, 233, 195-228.
20. Itkis, M., E.; Chi, X.; Cordes, A. W.; Haddon, R. C. Science 2002, 296, 1443-1445.
21. Braga, D.; Grepioni, F. Chem. Soc. Rev. 2000, 29, 229-238.
22. Bernstein, J.; Davery, R. J.; Henck, J. O. Angew. Chem., Int. Ed. 1999, 38, 3440-3461.
23. Fujita, W.; Awaga, K. Science 1999, 286, 261-262.
24. Brownridge, S.; Du, H.; Fairhurst, S. A.; Haddon, R. C.; Oberhammer, H.; Parsons, S.; Passmore, J.; Schriver, M. J.; Sutcliffe, L. H.; Westwood, N. P. C. J. Chem. Soc., Dalton Trans. 2000, 3365-3382.
25. McMillan, P. F. J. Mater. Chem. 2004, 14, 1506-1512.
26. Demus, D.; Goodby, J.; Gray, G. W.; Spiess, H. W. Handbook of Liquid Crystals: Fundamentals; Wiley-VCH: Weinheim, Germany, 1998; Vol. 1.
27. Aprahamian, I.; Yasuda, T.; Ikeda, T.; Saha, S.; Dichtel, W. R.; Isoda, K.; Kato, T.; Stoddart, J. F. Angew. Chem., Int. Ed. 2007, 46, 4675-4679.
28. Baranoff, E. D.; Voignier, J.; Yasuda, T.; Heitz, V.; Sauvage, J.-P.; Kato, T. Angew. Chem., Int. Ed. 2007, 46, 4680-4683.
29. Galyametdinov, Y.; Ksenofontov, V.; Prosvirin, A.; Ovchinnikov, I.; Ivanova, G.; Gütlich, P.; Haase, W. Angew. Chem., Int. Ed. 2001, 40, 4269-4271.
30. Seredyuk, M.; Gaspar, A. B.; Ksenofontov, V.; Reiman, S.; Galyametdinov, Y.; Haase, W.; Rentschler, E.; Gütlich, P. Chem. Mater. 2006, 18, 2513-2519.
31. Hayami, S.; Danjobara, K.; Inoue, K.; Ogawa, Y.; Matsumoto, N.; Maeda, Y. Adv. Mater. 2004, 16, 869-872.
32. Adams, D. M.; Dei, A.; Rheingold, A. L.; Hendrickson, D. N. J. Am. Chem. Soc. 1993, 115, 8221-8229.
33. Kiriya, D.; Chang, H.-C.; Kitagawa, S. Dalton Trans. 2006, 1377-1382.
34. Kobatake, S.; Takami, S.; Muto, H.; Ishikawa, T.; Irie, M. Nature 2007, 446, 778-781.
35. Hayami, S.; Moriyama, R.; Shuto, A.; Maeda, Y.; Ohta, K.; Inoue, K. Inorg. Chem. 2007, 46, 7692-7694.
36. Ikeda, T.; Mamiya, J.; Yanlei, Y. Angew. Chem., Int. Ed. 2007, 46, 506-528.
37. Fujigaya, T.; Jiang, D.-L.; Aida, T. J. Am. Chem. Soc. 2003, 125, 14690-14691.
38. Buchanan, R. M.; Pierpont, C. G. J. Am. Chem. Soc. 1980, 102, 4951-4957.
39. Pierpont, C. G. Coord. Chem. Rev. 2001, 216-217, 99-125.
40. Gütlich, P.; Dei, A. Angew. Chem., Int. Ed. 1997, 36, 2734-2736.
41. Pierpont C. G.; Kitagawa, S. Inorganic Chromotropism; Kodansha/Springer: Tokyo, 2007; pp 116-142.
42. Attia, A. S.; Jung, O.-S.; Pierpont, C. G. Inorg. Chim. Acta 1994, 226, 91-98.
43. (a) Pierpont, C. G.; Buchanan, R. M. Coord. Chem. Rev. 1981, 38, 45-87.
44. (b) Hendrickson, D. N.; Pierpont, C. G. Top. Curr. Chem. 2004, 234, 63-95.
45. (a) Roux, C.; Adams, D. M.; Itié, J. P.; Polian, A.; Hendrickson, D. N.; Verdaguer, M. Inorg. Chem. 1996, 35, 2846-2852.
46. (b) Adams, D. M.; Li, B. L.; Hendrickson, D. N. Angew. Chem., Int. Ed. 1995, 34, 1481-1483.
47. (a) Abakumov, G. A.; Cherkasov, V. K.; Bubnov, M. P.; Éllert, O. G.; Dobrokhotova, Zh. B.; Zakharov, L. N.; Struchkov, Yu. T. Dokl. Akad. Nauk 1993, 328, 332-335.
48. (b) Shultz, D. A. Magnetism: Molecules to Materials II; Wiley-VCH: Weinheim, Germany, 2001; pp 281-306.
49. (c) Dei, A.; Gatteschi, D.; Sangregorio, C.; Sorace, L. Acc. Chem. Res. 2004, 37, 827-835.
50. (d) Evangelio, E.; Ruiz-Molina, D. Eur. J. Inorg. Chem. 2005, 2957-2971.
51. (e) Sato, O.; Cui, J. A.; Matsuda, R.; Tao, J.; Hayami, S. Acc. Chem. Res. 2007, 40, 361-369.
52. Pierpont, C. G.; Jung, O.-S. Inorg. Chem. 1995, 34, 4281-4282.
53. Lange, C. W.; Conklin, B. J.; Pierpont, C. G. Inorg. Chem. 1994, 33, 1276-1283.
54. Testaferri, L.; Tingoli, M.; Bartoli, D.; Massoli, A. Tetrahedron 1985, 41, 1373-1384.
55. Kahn, O. Molecular Magnetism; Wiley-VCH: Weinheim, Germany. 1993.
56. Jacobson, R. A. REQABA Empirical Absorption Correction, version 1.1-0310; Molecular Structure Corp.: The Woodlands, TX, 1998.
57. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119.
58. Sheldrick, G. M. SHELXL97; University of Göttingen: Göttingen, Germany, 1997.
59. Adams, D. M.; Noodleman, L.; Hendrickson, D. N. Inorg. Chem. 1997, 36, 3966-3984.
60. g*).
61. The crystallinity becomes lower when the alkyl chain length is shortened. Compounds with shorter alkyl chains tend to require a slower cooling rate or longer aging time to return to the original state. This might be due to kinetically hindered crystal growing processes, which are significantly affected by the cooling rate.
62. Adams, D. M.; Hendrickson, D. N. J. Am. Chem. Soc. 1996, 118, 11515-11528.
63. Evans, D. F. J. Chem. Soc. 1959, 2003-2005.
64. Taga, T.; Miyasaka, T. Acta Crystallogr. 1987, C43, 748-751.
65. Fukunaga, H.; Takimoto, J.; Doi, M. J. Chem. Phys. 2004, 120, 7792-7800.
66. VT(crystal) could not be determined experimentally; however, this does not affect the discussion and the conclusion made in this manuscript.
67. Sorai, M.; Saito, K. The Chemical Record 2003, 3, 29-39.