Complex formation between a nucleobase and tetraeyanoquinodimethane derivatives: Crystal structures and transport properties of charge-transfer solids of cytosine

Bulletin of the Chemical Society of Japan

Volumn 81, Issue 3, 2008, Pages 331-344

  Murata, Tsuyoshi ^a   Saito, Gunzi ^a,b   Nishimura, Kazukuni ^a   Enomoto, Yuichiro ^a   Honda, Genki ^a   Shimizu, Yasuhito ^a   Matsui, Shogo ^a   Sakata, Masafumi ^a   Drozdova, Olga O ^c   Yakushi, Kyuya ^c  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANION SALTS; BIOLOGICAL MOLECULES; CHEMICAL STRUCTURES; COMPLEX FORMATIONS; ELEMENTAL ANALYSES; HIGH POTENTIALS; IONIC SALTS; IONIC SOLIDS; LAYERED STRUCTURES; LOW TEMPERATURES; MAGNETIC MEASUREMENTS; METALLIC BEHAVIORS; METHOXY; MOLECULAR ARRANGEMENTS; NUCLEOBASE; OPTICAL-; PROTONATED; TCNQ RADICAL ANIONS; TETRACYANOQUINODIMETHANE;

ACETONITRILE; BINDING SITES; CHEMICAL ANALYSIS; COMPLEXATION; GROUP TECHNOLOGY; HYDROGEN; IONS; METHANOL; NEGATIVE IONS; SALTS; TRANSPORT PROPERTIES;

HYDROGEN BONDS;

EID: 58149305408     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.81.331     Document Type: Review

References (123)

1. 4TCNQ (1 and 2), see: T. Murata, G. Saito, Chem. Lett. 2006, 35, 1342.
2. b) The radical anion salt of TCNQ (9), see: T. Murata, K. Nishimura, G. Saito, Mol. Cryst. Liq. Cryst. 2007, 466, 101.
3. a) J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
4. b) N. C. Seeman, Nature 2003, 421, 427.
5. c) E. Katz, I. Willner, Angew. Chem., Int. Ed. 2004, 43, 6042.
6. a) R. Foster, Organic Charge-Transfer Complexes, Academic Press, New York, 1969, Chap. 12.
7. b) J. B. Birks, M. A. Slifkin, Nature 1963,197, 42.
8. c) E. M. Kosower, Molecular Biochemistry, McGraw-Hill, New York, 1962.
9. d) Y. Matsunaga, Nature 1966, 211, 182.
10. e) U. Thewalt, C. E. Bugg, Acta Crystallogr., Sect. B 1972, 28, 82.
11. f) M. Tanaka, Bull. Chem, Soc. Jpn. 1977, 50, 3194.
12. g) G. Saito, A. K. Colter, Tetrahedron Lett. 1977, 18, 3325.
13. h) M. Suzuki, T. Fujii, T. Nogami, T. Hirano, T. Ishida, Chem. Lett. 2006, 35, 250.
14. a) G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997.
15. b) G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1991.
16. c) G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond, Oxford University Press, New York, 1999.
17. a) J. D. Watson, F. H. C. Crick, Nature 1953, 171, 737.
18. b) W. Saenger, Principles of Nucleic Acid Structure, 1st ed., Springer-Verlag, New York, 1984.
19. a) Chem. Mater. 1994, 6, No. 8.
20. b) Organic Molecular Solids, Properties and Applications, ed. by W. Jones, CRC Press, New York, 1997, Chap. 6.
21. c) J. L. Sessler, C. M. Lawrence, J. Jayawickramarajah, Chem. Soc. Rev. 2007, 36, 314.
22. a) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Org. Lett. 2002, 4, 2185.
23. b) M. Ohmoto, S. Maki, Y. Morita, T. Kubo, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Synth. Met. 2003, 133-134, 337.
24. c) E. Miyazaki, Y. Morita, Y. Umemoto, K. Fukui, K. Nakasuji, Chem. Lett. 2005, 34, 1326.
25. d) Y. Morita, E. Miyazaki, Y. Umemoto, K. Fukui, K. Nakasuji, J. Org. Chem. 2006, 71, 5631.
26. TTF derivative having adenine moiety, see: e) Y. Morita, S. Maki, M. Ohmoto, H. Kitagawa, T. Okubo, T. Mitani, K. Nakasuji, Synth. Met. 2003, 135-136, 541.
27. TTF derivative having cytosine moiety, see: f) E. Miyazaki, Y. Morita, Y. Yakiyama, S. Maki, Y. Umemoto, M. Ohmoto, K. Nakasuji, Chem. Lett. 2007, 36, 1102.
28. a) O. Neilands, V. Tilika, I. Sudmale, I. Grigorjeva, A. Edzina, E. Fonavs, I. Muzikante, Adv. Mater. Opt. Electron. 1997, 7, 39.
29. b) O. Neilands, Mol. Cryst. Liq. Cryst. 2001, 355, 331.
30. c) K. Balodis, S. Khasanov, C. Chong, M. Maesato, H. Yamochi, G. Saito, O. Neilands, Synth. Met. 2003, 133-134, 353.
31. M. A. Slifkin, A. P. Kushelevsky, Spectrochim. Acta, Part A 1971, 27, 1999.
32. I. N. Bazhina, V. S. Verzilov, V. S. Grechishkin, R. V. Grechishkina, V. M. Gusarov, Zh. Strukt. Khim. 1973, 14, 930.
33. G. G. Sheina, E. D. Radchenko, Y. P. Blagoi, B. I. Verkin, Dokl. Akad. Nauk SSSR 1978, 240, 463.
34. a) V. M. Orlov, A. N. Smimov, Y. M. Varshavsky, Tetrahedron Lett. 1976, 17, 4377.
35. b) D. Dougherty, E. S. Younathan, R. Voll, S. Abdulnur, S. P. McGlynn, J. Electron Spectrosc. Relat. Phenom. 1978, 13, 379.
36. c) S. G. Lias, J. E. Bartmess, J. F. Liebman, J. L. Holmes, R. D. Levin, W. G. Mallard, J. Phys. Chem. Ref. Data 1988, 17, 861.
37. d) S. D. Wetmore, R. J. Boyd, L. A. Eriksson, Chem. Phys. Lett. 2000, 322, 129, and references are therein.
38. a) A. J. Berlinsky, J. F. Carolan, L. Weiler, Can. J. Chem. 1974, 52, 3373.
39. b) N. Sato, G. Saito, H. Inokuchi, Chem. Phys. 1983, 76, 79.
40. C. A. M. Seidel, A. Schulz, M. H. M. Sauer, J. Phys. Chem. 1996, 100, 5541.
41. a) W. Flossmann, E. Westhof, A. Müller, Int. J. Radiat. Biol. 1976, 30, 301.
42. b) J. Geimer, K. Hildenbrand, S. Naumov, D. Beckert, Phys. Chem. Chem. Phys. 2000, 2, 4199.
43. a) G. Saito, J. P. Ferraris, Bull. Chem. Soc. Jpn. 1980, 53, 2141.
44. b) S. Horiuchi, H. Yamochi, G. Saito, K. Sakaguchi, M. Kusunoki, J. Am. Chem. Soc. 1996, 118, 8604.
45. c) T. Senga, K. Kamoshida, L. A. Kushch, G. Saito, T. Inayoshi, I. Ono, Mol. Cryst. Liq. Cryst. 1997, 296, 97.
46. d) S.-S. Pac, G. Saito, J. Solid State Chem. 2002, 168, 486.
47. Data for Biochemical Research, 3rd ed., ed. by R. M. C. Dawson, W. H. Elliot, K. M. Jones, Clarendon Press, Oxford, 1986.
48. a) R. E. Marsh, R. Bierstedt, E. L. Eichhorn, Acta Crystallogr. 1962, 15, 310.
49. b) T. J. Kistemacher, M. Rossi, L. G. Marzilli, Biopolymers 1978, 17, 2581.
50. c) F. Fujinami, K. Ogawa, Y. Arakawa, S. Shirotake, S. Fujii, K. Tomita, Acta Crystallogr., Sect. B 1979, 35, 968.
51. d) E. Westhof, M. Sundaralingam, Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 1852.
52. e) M. Gdaniec, B. Brycki, M. Szafran, J. Chem. Soc., Perkin Trans. 2 1988, 1775.
53. f) K. Gehring, J.-L. Leroy, M. Guéron, Nature 1993, 363, 561.
54. g) L. Chen, L. Cai, X. Zhang, A. Rich, Biochemistry 1994, 33, 13540.
55. h) S. Metzger, B. Lippert, Angew. Chem., Int. Ed. Engl. 1996, 35, 1228.
56. i) Md. A. Salam, K. Aoki, Inorg. Chim. Acta 2000, 311, 15.
57. j) J. Müller, E. Freisinger, Acta Crystallogr., Sect. E 2005, 61, o320.
58. k) D. Armentano, G. De Munno, R. Rossi, New J. Chem. 2006, 30, 13.
59. K. Tanemura, Y. Nishida, T. Suzuki, K. Satsumabayashi, T. Horaguchi, J. Chem. Res., Synop. 1999, 40.
60. ·- in MeOH has been reported, see: H. Miyasaka, K. Sugimoto, K. Sugiura, T. Ishii, M. Yamashita, Mol. Cryst. Liq. Cryst. 2002, 379, 197.
61. B. Borah, J. L. Wood, J. Mol. Struct. 1976, 30, 13.
62. A. Bondi, J. Phys. Chem. 1964, 68, 441.
63. N. S. Mandel, Acta Crystallogr., Sect. B 1977, 33, 1079.
64. a) H. Okamoto, Y. Tokura, T. Koda, Phys. Rev. B 1987, 36, 3858.
65. b) S. Etemad, Phys. Rev. B 1981, 24, 4959.
66. C≡N and the degree of CT (δ) is held only below δ= 0.5.
67. a) M. Meneghetti, C. Pecile, J. Chem. Phys. 1986, 84, 4149.
68. b) C. J. Fritchie, P. Arthur, Acta Crystallogr. 1966, 21, 139.
69. c) K. D. Cummings, D. B. Tanner, J. S. Miller, Phys. Rev. B 1981, 24, 4142.
70. S. Matsuzaki, R. Kuwata, K. Toyoda, Solid State Commun. 1980, 33, 403.
71. a) J. B. Torrance, B. A. Scott, B. Welber, F. B. Kaufman, P. E. Seiden, Phys. Rev. B 1979, 19, 730.
72. b) J. B. Torrance, Acc. Chem. Res. 1979, 12, 79.
73. c) S. Yamaguchi, Y. Moritomo, Y. Tokura, Phys. Rev. B 1993, 48, 6654.
74. d) M. Meneghetti, Phys. Rev. B 1994, 50, 16899.
75. a) M. Konno, Y. Saito, Acta Crystallogr., Sect. B 1974, 30, 1294.
76. b) M. Konno, Y. Saito, Acta Crystallogr., Sect. B 1975, 31, 2007.
77. c) M. Konno, T. Ishii, Y. Saito, Acta Crystallogr., Sect. B 1977, 33, 763.
78. d) H. Kobayashi, Bull. Chem. Soc. Jpn. 1981, 54, 3669.
79. e) H. Kobayashi, Acta Crystallogr., Sect. B 1978, 34, 2818.
80. a) P. S. Flandrois, D. Chasseau, Acta Crystallogr., Sect. B 1977, 33, 2744.
81. b) T. J. Kistenmacher, T. J. Emge, A. N. Bloch, D. O. Cowan, Acta Crystallogr., Sect. B 1982, 38, 1193.
82. a) Semiconductors and Semimetals: Highly Conducting Quasi-One-Dimensional Organic Crystals, ed. by E. M. Conwell, Academic Press, New York, 1988, Vol. 27.
83. b) L. R. Melby, R. J. Harder, W. R. Hertler, W. Mahler, R. E. Benson, W. E. Mochel, J. Am. Chem. Soc. 1962, 84, 3374.
84. c) N. Sakai, I. Shirotani, S. Minomura, Bull. Chem. Soc. Jpn. 1972, 45, 3314.
85. d) R. Bozio, C. Pecile, J. Chem. Phys. 1977, 67, 3864.
86. a) T. Ishiguro, K. Yamaji, G. Saito, Organic Superconductors, 2nd ed., Springer-Verlag, Berlin, 1998.
87. b) D. Jérome, H. J. Schulz, Adv. Phys. 1982, 31, 299.
88. J. Šponer, J. Leszczynski, V. Vetterl, P. Hobza, J. Biomol. Struct. Dyn. 1996, 13, 695.
89. R. H. Boyd, W. D. Phillips, J. Chem. Phys. 1965, 43, 2927.
90. C. Coulon, R. Clérac, Chem. Rev. 2004, 104, 5655.
91. T. Hibma, J. Kommandeur, Phys. Rev. B 1975, 12, 2608.
92. stat values (T > 240 K) were fitted by the singlet-triplet model, see: B. Bleaney, K. D. Bowers, Proc. R. Soc. London, Ser. A 1952, 214, 451.
93. J. Kommandeur, in The Physics and Chemistry of Low Dimensional Solids, ed. by L. Alcácer, D. Reidel Pub., Dordrecht, 1980, pp. 197-212.
94. J. G. Vegter, J. Kommandeur, Mol. Cryst. Liq. Cryst. 1975, 30, 11.
95. L. C. Tippie, W. G. Clark, Phys. Rev. B 1981, 23, 5854.
96. a) T. Inabe, K. Okaniwa, H. Ogata, H. Okamoto, T. Mitani, Y. Maruyama, Acta Chim. Hung. 1993, 130, 537.
97. b) T. Sekikawa, H. Okamoto, T. Mitani, T. Inabe, Y. Maruyama, T. Kobayashi, Phys. Rev. B 1997, 55, 4182.
98. K. Holczer, A. Jánossy, Solid State Commun. 1978, 26, 689.
99. C. Nakano, K. Yakushi, M. Kohama, K. Ueda, T. Sugimoto, Solid State Comnuin. 2000, 113, 677.
100. M. Fourmiguè, P. Batail, Chem. Rev. 2004, 104, 5379, and references therein.
101. a) T. Murata, Y. Morita, K. Fukui, K. Sato, D. Shiomi, T. Takui, M. Maesato, H. Yamochi, G. Saito, K. Nakasuji, Angew. Chem., Int. Ed. 2004, 43, 6343.
102. b) T. Murata, Y. Morita, Y. Yakiyama, K. Fukui, H. Yamochi, G. Saito, K. Nakasuji, J. Am. Chem. Soc. 2007, 129, 10837.
103. a) L. M. Goldenberg, O. Neilands, J. Electroanal. Chem. 1999, 463, 212.
104. b) A. S. F. Boyd, G. Cooke, F. M. A. Duclairoir, V. M. Rotello, Tetrahedron Lett. 2003, 44, 303.
105. c) Y. Morita, E. Miyazaki, K. Fukui, S. Maki, K. Nakasuji, Bull. Chem. Soc. Jpn. 2005, 78, 2014.
106. a) Y. Matsunaga, G. Saito, Bull. Chem. Soc. Jpn. 1971, 44, 958.
107. b) T. Inoue, H. Yamochi, G. Saito, K. Matsumoto, Synth. Met. 1995, 70, 1139.
108. For reviews, see: a) B. Giese, Acc. Chem. Res. 2000, 33, 631.
109. b) M. Taniguchi, T. Kawai, Physica E 2006, 33, 1,
110. and references therein. For examples of individual works, see: c) J. Ladik, Acta Phys. Acad. Sci. Hung. 1960, 11, 239.
111. d) M. E. Burnel, D. O. Eley, V. Subramanyan, Ann, N.Y. Acad. Sci. 1969, 158, 191.
112. e) H.-W. Fink, C. Schönenberger, Nature 1999, 398, 407.
113. f) D. Porath, A. Bezryadin, S. Vries, C. Dekker, Nature 2000, 403, 635.
114. g) P. J. De Pablo, F. Moreno-Herrero, J. Colchero, J. Gómez-Herrero, P. Herrero, A. M. Baró, P. Ordejón, J. M. Soler, E. Artacho, Phys. Rev. Lett. 2000, 85, 4992.
115. h) P. Tran, B. Alavi, G. Gruner, Phys. Rev. Lett. 2000, 85, 1564.
116. i) A. Y. Kasumov, M. Kociak, S. Guéron, B. Reulet, V. T. Volkov, D. V. Klinov, H. Bouchiat, Science 2001, 291, 280.
117. j) A. Rakitin, P. Aich, C. Papadopoulos, Y. Kobzar, A. S. Vedeneev, J. S. Lee, J. M. Xu, Phys. Rev. Lett. 2001, 86, 3670.
118. k) K.-H. Yoo, D. H. Ha, J.-O. Lee, J. W. Park, J. Kim, J. J. Kim, H.-Y. Lee, T. Kawai, H. Y. Choi, Phys. Rev. Lett. 2001, 87, 198102.
119. l) Y. Zhang, R. H. Austin, J. Kraeft, E. C. Cox, N. P. Ong, Phys. Rev. Lett. 2002, 89, 198102.
120. m) B. Hartzell, B. McCord, D. Asare, H. Chen, J. J. Heremans, V. Soghomonian, Appl. Phys. Lett. 2003, 82, 4800.
121. n) M. Taniguchi, H.-Y. Lee, H. Tanaka, T. Kawai, Jpn. J. Appl. Phys. 2003, 42, L215.
122. G. M. Sheldrick, Program for the Solution of Crystal Structures, University of Göttingen, Göttingen, Germany, 1997.
123. G. M. Sheldrick, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen, Germany, 1997.