Newly modified TTF and DSDTF donors for developing molecular-based organic metals

Journal of Materials Chemistry

Volumn 9, Issue 3, 1999, Pages 617-628

  Yamada, Jun Ichi ^a   Nishikawa, Hiroyuki ^b   Kikuchi, Koichi ^b  

^a UNIVERSITY OF HYOGO   (Japan)

^b TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC HYDROCARBON; CHALCOGEN; METAL; ORGANOTIN COMPOUND; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CRYSTALLIZATION; ELECTRIC CONDUCTIVITY; ELECTRON; ISOMERISM; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032903315     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807698g     Document Type: Article

References (102)

1. 1 J. Ferraris, D. O. Cowan, V. Walatka, Jr. and J. H. Perlstein, J. Am. Chem. Soc., 1973, 95, 948.
2. 2 (a) J. M. Williams, A. J. Schultz, U. Geiser, K. D. Carlson, A. M. Kini, H. H. Wang, W.-K. Kwok, M.-H. Whangbo and J. E. Schirber, Science, 1991, 252, 1501;
3. (b) J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geiser, H. H. Wang, A. M. Kini and M.-H. Whangbo, Organic Superconductors (Including Fullerenes) Synthesis, Structure, Properties, and Theory, Prentice Hall, Englewood Cliffs, NJ, 1992;
4. (c) A. E. Underhill, J. Mater. Chem., 1992, 2, 1;
5. (d) T. Ishiguro, K. Yamaji and G. Saito, Organic Superconductors, 2nd edn., Springer Ser. Solid-State Sci., vol. 88, ed. P. Fulde, Springer, Berlin, Heidelberg, 1998. For the ET-based superconductor with an organic anion, see: U. Geiser, J. A. Schlueter, H. H. Wang, A. M. Kini, J. M. Williams, P. P. Sche, H. I. Zakowicz, M. L. VanZiele and J. D. Dudek, J. Am. Chem. Soc., 1996, 118, 9996. For the ET-based superconductor containing a magnetic anion, see:
6. (d) T. Ishiguro, K. Yamaji and G. Saito, Organic Superconductors, 2nd edn., Springer Ser. Solid-State Sci., vol. 88, ed. P. Fulde, Springer, Berlin, Heidelberg, 1998. For the ET-based superconductor with an organic anion, see: U. Geiser, J. A. Schlueter, H. H. Wang, A. M. Kini, J. M. Williams, P. P. Sche, H. I. Zakowicz, M. L. VanZiele and J. D. Dudek, J. Am. Chem. Soc., 1996, 118, 9996. For the ET-based superconductor containing a magnetic anion, see:
7. (e) M. Kurmoo, A. W. Graham, P. Day, S. J. Coles, M. B. Hursthouse, J. L. Caulfield, J. Singleton, F. J. Pratt, W. Hayes, L. Ducasse and P. Guionneau, J. Am. Chem. Soc., 1995, 117, 12209;
8. (f) P. Cassoux, Science, 1996, 272, 1277;
9. (g) P. Day and M. Kurmoo, J. Mater. Chem., 1997, 7, 1291.
10. 3 (a) K. Kikuchi, M. Kikuchi, T. Namiki, K. Saito, I. Ikemoto, K. Murata, T. Ishiguro and K. Kobayashi, Chem. Lett., 1987, 931;
11. (b) K. Kikuchi, K. Murata, Y. Honda, T. Namiki, K. Saito, K. Kobayashi, T. Ishiguro and I. Ikemoto, J. Phys. Soc. Jpn., 1987, 56, 2627;
12. (c) K. Kikuchi, K. Murata, Y. Honda, T. Namiki, K. Saito, T. Ishiguro, K. Kobayashi and I. Ikemoto, J. Phys. Soc. Jpn., 1987, 56, 3436;
13. (d) K. Kikuchi, K. Murata, Y. Honda, T. Namiki, K. Saito, H. Anzai, K. Kobayashi, T. Ishiguro and I. Ikemoto, J. Phys. Soc. Jpn., 1987, 56, 4241.
14. 4 (a) G. C. Papavassiliou, G. A. Mousdis, J. S. Zameounis, A. Terzis, A. Hountas, B. Hilti, C. W. Mayer and J. Pfeiffer, Synth. Met., 1988, 27, B379;
15. (b) A. M. Kini, M. A. Beno, D. Son, H. H. Wang, K. D. Carlson, L. C. Porter, U. Welp, B. A. Vogt, J. M. Williams, D. Jung, M. Evain, M.-H. Whangbo, D. L. Overmyer and J. E. Schirber, Solid State Commun., 1989, 69, 503.
16. 5 H. Tajima, M. Inokuchi, A. Kobayashi, T. Ohta, R. Kato, H. Kobayashi and H. Kuroda, Chem. Lett., 1993, 1235.
17. 6 (a) M. Narita and C. U. Pittman, Jr., Synthesis, 1976, 489;
18. (b) M. R. Bryce, Aldrichimica Acta, 1985, 18, 73;
19. (c) A. Krief, Tetrahedron, 1986, 42, 1209;
20. (d) G. Schukat, A. M. Richter and E. Fanghänel, Sulfur Rep., 1987, 7, 155;
21. (e) M. R. Bryce, Chem. Soc. Rev., 1991, 20, 355;
22. (f) J. Garin, Adv. Heterocycl. Chem., 1995, 62, 249.
23. 7 (a) T. K Hansen and J. Becher, Adv. Mater., 1993, 5, 288;
24. (b) M. Adam and K Müllen, Adv. Mater., 1994, 6, 439;
25. (c) M. R. Bryce, J. Mater. Chem., 1995, 5, 1481;
26. (d) G. Schukat and E. Fanghänel, Sulfur Rep., 1996, 18, 1;
27. (e) T. Otsubo, Y. Aso and K. Takimiya, Adv. Mater., 1996, 8, 203;
28. (f) G. C. Papavassiliou, A. Terzis and P. Delhaes, in Handbook of Organic Conductive Molecules and Polymers, ed. H. S. Nalwa, J. Wiley & Sons, Chichester, 1997, vol. 1, ch. 3;
29. (g) J. Becher, P. Mork and J. Lau, in Electronic Materials: The Oligomer Approach, eds. K. Müllen and G. Gerhard, Wiley-VCH, Weinheim, 1998, ch. 2.
30. 8 (a) Proceedings of ICSM'94, Seoul, Synth. Met., 1995, 69-71;
31. (b) Proceedings of ICSM'96, Snowbird, Synth. Met., 1997, 84-86;
32. (c) Proceedings of ICSM'98, Montpellier, Synth. Met., 1999, in the press.
33. 9 (a) D. O. Cowan, R. McCullough, A. Bailey, K. Lerstrup, D. Talham, D. Herr and M. Mays, Phosphorus, Sulfur, Silicon, 1992, 67, 277;
34. (b) D. E. Herr, M. D. Mays, R. D. McCullough, A. B. Bailey and D. O. Cowan, J. Org. Chem., 1996, 61, 7006.
35. 10 (a) M. A. Beno, H. H. Wang, A. M. Kini, K. D. Carlson, U. Geiser, W. K. Kwok, J. E. Thompson, J. M. Williams, J. Ren and M.-H. Whangbo, Inorg. Chem., 1990, 29, 1601;
36. (b) S. Kahlich, D. Schweitzer, I. Heinen, S. E. Lan, B. Nuber, H. J. Keller, K. Winzer and H. W. Heiberg, Solid State Commun., 1991, 80, 191.
37. 11 (a) H. Kobayashi, T. Udagawa, H. Tomita, K. Bun, T. Naito and A. Kobayashi, Chem. Lett., 1993, 1559;
38. (b) L. K. Montgomery, T. Burgin, J. C. Huffman, J. Ren, M.-H. Whangbo, Physica C, 1994,219, 490;
39. (c) H. Kobayashi, H. Tomita, T. Naito, H. Tanaka, A. Kobayashi and T. Saito, J. Chem. Soc., Chem. Commun., 1995, 1225;
40. (d) H. Tanaka, A. Kobayashi, T. Saito, K. Kawano, T. Naito and H. Kobayashi, Adv. Mater., 1996, 8, 812;
41. (e) H. Kobayashi, H. Akutsu, E. Arai, H. Tanaka and A. Kobayashi, Phys. Rev. B, 1997, 56, R8526. For the BETS-based superconductor containing mixed magnetic anions, see: H. Kobayashi, A. Sato, E. Arai, H. Akutsu, A. Kobayashi and P. Cassoux, J. Am. Chem. Soc., 1997,119, 12392.
42. (e) H. Kobayashi, H. Akutsu, E. Arai, H. Tanaka and A. Kobayashi, Phys. Rev. B, 1997, 56, R8526. For the BETS-based superconductor containing mixed magnetic anions, see: H. Kobayashi, A. Sato, E. Arai, H. Akutsu, A. Kobayashi and P. Cassoux, J. Am. Chem. Soc., 1997,119, 12392.
43. 12 (a) N. Svenstrup and J. Becher, Synthesis, 1995, 215;
44. (b) K. B. Simonsen, N. Svenstrup, J. Lau, O. Simonsen, P. Mørk, G. J. Kristensen and J. Becher, Synthesis, 1996, 407.
45. (a) J. M. Fabre, L. Giral, E. Dupart, C. Coulon, J. P. Manceau and P. Delhaes, J. Chem. Soc., Chem. Commun., 1983, 1477;
46. (b) K. Kikuchi, K. Yakushi, H. Kuroda, I. Ikemoto and K. Kobayashi, Mol. Cryst. Liq. Cryst., 1985, 125, 345. For DSDTFs, see:
47. (c) K. Kikuchi, T. Namiki, I. Ikemoto and K. Kobayashi, J. Chem. Soc., Chem. Commun., 1986, 1472;
48. (d) K. Kobayashi, K. Kikuchi, T. Namiki and I. Ikemoto, Synth. Met., 1987, 19, 555;
49. (e) S. Aonuma, Y. Okano, H. Sawa, R. Kato and H. Kobayashi, J. Chem. Soc., Chem. Commun., 1992, 1193.
50. 14 J. Yamada and Y. Yamamoto, Rev. Heteroatom Chem., 1991, 5, 250.
51. 15 J. Yamada, in Recent Research Developments in Organic Chemistry, ed. S. G. Pandalai, Transworld Research Network, Trivandrum, 1999, in the press.
52. 16 (a) J. Yamada, Y. Amano, S. Takasaki, R. Nakanishi, K. Matsumoto, S. Satoki and H. Anzai, J. Am. Chem. Soc., 1995, 117, 1149;
53. (b) J. Yamada, S. Takaski, M. Kobayashi, H. Anzai, N. Tajima, M. Tamura, Y. Nishio and K. Kajita, Chem. Lett., 1995, 1069;
54. (c) J. Yamada, S. Satoki, S. Mishima, N. Akashi, K. Takahashi, N. Masuda, Y. Nishimoto, S. Takasaki and H. Anzai, J. Org. Chem., 1996, 61, 3986:
55. (d) J. Yamada, S. Satoki, H. Anzai, K. Hagiya, M. Tamura, Y. Nishio, K. Kajita, E. Watanabe, M. Konno, T. Sato, H. Nishikawa and K. Kikuchi, J. Chem. Soc., Chem. Commun., 1996, 1955;
56. (e) J. Yamada, S. Mishima, N. Akashi, S. Satoki and H. Anzai, Synth. Met., 1997, 86, 1823;
57. (f) J. Yamada, N. Akashi, H. Anzai, M. Tamura, Y. Nishio and K. Kajita, Mol. Cryst. Liq. Cryst., 1997, 296, 53;
58. (g) J. Yamada, M. Hamasaki, O. Jinih, S. Tanaka, K. Hagiya and H. Anzai, Tetrahedron Lett., 1997, 38, 3439.
59. 17 (a) J. Yamada, Y. Nishimoto, S. Tanaka, R. Nakanishi, K. Hagiya and H. Anzai, Tetrahedron Lett., 1995, 36, 9509;
60. (b) J. Yamada, S. Tanaka, J. Segawa, M. Hamasaki, K. Hagiya, H. Anzai, H. Nishikawa, I. Ikemoto and K. Kikuchi, J. Org. Chem., 1998, 63, 3952.
61. 18 D. L. Coffen, J. Q. Chambers, D. R. Williams, P. E. Garrett and N. D. Canfield, J. Am. Chem. Soc., 1971, 93, 2258.
62. 19 For examples, see: (a) M. Sallé, A. Gorgues, M. Jubault and Y. Gouriou, Synth. Met., 1991, 41-43, 2575;
63. (b) D. Lorcy, M.-P. L. Paillard and A. Robert, Tetrahedron Lett., 1993, 34, 5289. For the conducting complex and salt based on the bis(1,4-dithiafulven-6-yl)-substituted DHTTF, see:
64. M. Sallé, M. Jubault, A. Gorgues, K. Boubekeur, M. Fourmigué, P. Batail and E. Canadell, Chem. Mater., 1993, 5, 1196.
65. 20 H. Anzai, J. M. Delrieu, S. Takasaki, S. Nakatsuji and J. Yamada, J. Cryst. Growth, 1995, 154, 145.
66. 21 K. Kikuchi, H. Nishikawa, T. Sato, I. Sugano, T. Kodama, I. Ikemoto, H. Anzai and J. Yamada, presented at ICSM'98, Montpellier, Synth. Met., 1999, in the press.
67. 22 R. R. Schumaker and E. M. Engler, J. Am. Chem. Soc., 1977, 99, 5519.
68. 23 (a) Y. Misaki, K. Kawakami, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, Chem. Lett., 1995, 1125;
69. (b) Y. Misaki, H. Fujiwara and T. Yamabe, J. Org. Chem., 1996, 61, 3650, and references cited therein;
70. (c) Y. Misaki, T. Sasaki, T. Ohta, H. Fujiwara and T. Yamabe, Adv. Mater., 1996, 8, 804.
71. 24 Y. Misaki, N. Higuchi, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, Angew. Chem., Int. Ed. Engl., 1995, 34, 1222. For the revised stoichiometry of this salt, see: Y. Misaki, N. Higuchi, T. Ohta, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, Mol. Cryst. Liq. Cryst., 1996, 284, 27.
72. 24 Y. Misaki, N. Higuchi, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, Angew. Chem., Int. Ed. Engl., 1995, 34, 1222. For the revised stoichiometry of this salt, see: Y. Misaki, N. Higuchi, T. Ohta, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, Mol. Cryst. Liq. Cryst., 1996, 284, 27.
73. 25 J. Yamada, S. Mishima, H. Anzai, M. Tamura, Y. Nishio, K. Kajita, T. Sato, H. Nishikawa, I. Ikemoto and K. Kikuchi, J. Chem. Soc., Chem. Commun., 1996, 2517.
74. 26 J. Yamada, M. Watanabe, H. Anzai, H. Nishikawa, I. Ikemoto and K. Kikuchi, Angew. Chem., Int. Ed., 1999, 38, in the press.
75. 27 H. Müller and Y. Ueba, Synthesis, 1993, 853.
76. 28 K. Kikuchi, H. Nishikawa, I. Ikemoto, S. Maki, H. Anzai and J. Yamada, unpublished results.
77. 29 H. Urayama, H. Yamachi, G. Saito, S. Sato, A. Kawamoto, J. Tanaka, T. Mori, Y. Maruyama and H. Inokuchi, Chem. Lett., 1988, 463.
78. 30 For κ-type salts containing other TTF-fused donors with different stoichiometry, see: (a) Y. Misaki, H. Nishikawa, T. Yamabe, T. Mori, H. Inokuchi, H. Mori and S. Tanaka, Chem. Lett., 1993, 1341;
79. (b) Y. Misaki, H. Nishikawa, K. Kawakami, T. Yamabe, T. Mori, H. Inokuchi, H. Mori and S. Tanaka, Chem. Lett., 1993, 2073;
80. (c) Y. Misaki, T. Miura, M. Taniguchi, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, Adv. Mater., 1997, 9, 714;
81. (d) H. Fujiwara, Y. Misaki, M. Taniguchi, T. Yamabe, T. Kawamoto, T. Mori, H. Mori and S. Tanaka, J. Mater. Chem., 1998, 8, 1711.
82. 31 J. Yamada, R. Oka, H. Anzai, H. Nishikawa, I. Ikemoto and K. Kikuchi, Tetrahedron Lett., 1998, 39, 7709.
83. 32 For non-TTF donors which are designed to form 2D stacks, see: K. Takimiya, Y. Shibata, A. Ohnishi, Y. Aso, T. Otsubo and F. Ogura, J. Mater. Chem., 1995, 5, 1539, and references cited therein.
84. 33 H. Yamochi, T. Komatsu, N. Matsukawa, G. Saito, T. Mori, M. Kusunoki and K. Sakaguchi, J. Am. Chem. Soc., 1993, 115, 11319.
85. 34 H. Kobayashi, A. Kobayashi, T. Nakamura, T. Nogami and Y. Shirota, Chem. Lett., 1987, 559.
86. 35 H. Nakano, K Miyawaki, T. Nogami, Y. Shirota, S. Harada and N. Kasai, Bull Chem. Soc. Jpn., 1989, 62, 2604.
87. 4, see: R. Kato, K. Yamamoto, Y. Okano, H. Tajima and H. Sawa, Chem. Commun., 1997, 947.
88. 37 (a) A. Kobayashi, R. Kato, T. Naito and H. Kobayashi, Synth. Met., 1993, 55-57, 2078;
89. (b) M. Inokuchi, H. Tajima, A. Kobayashi, T. Ohta, H. Kuroda, R. Kato, T. Naito and H. Kobayashi, Bull. Chem. Soc. Jpn., 1995, 68, 547;
90. (c) T. Naito, H. Kobayashi and A. Kobayashi, Bull. Chem. Soc. Jpn., 1997, 70, 107.
91. 38 H. Nishikawa, T. Sato, T. Kodama, I. Ikemoto, K. Kikuchi, H. Anzai and J. Yamada, J. Mater. Chem., 1999, 9, 693.
92. 3 salt, see:
93. (b) A. M. Kini, U. Geiser, H.-H. Wang, K. R. Lykke, J. M. Williams and C. F. Campara, J. Mater. Chem., 1995, 5, 1647.
94. 40 J. Hellberg, K. Balodis, M. Moge, P. Korall and J.-U. von Schütz, J. Mater. Chem., 1997, 7, 31.
95. 41 J. Yamada, S. Tanaka, H. Anzai, T. Sato, H. Nishikawa, I. Ikemoto and K. Kikuchi, J. Mater. Chem., 1997, 7, 1311.
96. 42 H. Nishikawa, H. Ishikawa, T. Sato, T. Kodama, I. Ikemoto, K. Kikuchi, S. Tanaka, H. Anzai and J. Yamada, J. Mater. Chem., 1998, 8, 1321.
97. 43 H. Nishikawa, H. Ishikawa, T. Sato, T. Kodama, I. Ikemoto, K. Kikuchi, S. Tanaka, H. Anzai and J. Yamada, unpublished results.
98. 44 For the molecular structure of ET, see: H. Kobayashi, A. Kobayashi, Y. Sasaki, G. Saito and H. Inokuchi, Bull. Chem. Soc. Jpn., 1986, 59, 301.
99. 3 salts have been quite recently presented at ICSM'98, Montpellier, by A. I. Kotov, L. I. Buravov, S. V. Konovalikhin, O. A. Dyachenko, E. B. Yagubskii, P. Cassoux, J. Akimoto, K. Honda and M. Mizuno, Synth. Met., 1999, in the press.
100. 46 For the molecular structure of MET, see: A. M. Kini, M. A. Beno and J. M. Williams, J. Chem. Soc., Chem. Commun., 1987, 335.
101. 47 A detailed study will be reported in the near future.
102. 48 For an another example, see: M. Ashizawa, M. Aragaki, T. Mori, Y. Misaki and T. Yamabe, Chem. Lett., 1997, 649.