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Volumn 296, Issue , 1997, Pages 165-180

Tetracyanoquinodimethanes fused with a [1,2,5]chalcogenadiazole ring

Author keywords

Electron acceptor; Intermolecular interaction; Multi redox system; Organic conductor; TCNQ

Indexed keywords

CHARGE TRANSFER; DERIVATIVES; ELECTRIC CONDUCTIVITY OF SOLIDS; ELECTRON SOURCES; FUSED SALTS; MOLECULAR CRYSTALS; MOLECULAR ORIENTATION; ORGANIC CONDUCTORS; REDOX REACTIONS; X RAY ANALYSIS;

EID: 0031349403     PISSN: 1058725X     EISSN: None     Source Type: Journal    
DOI: 10.1080/10587259708032319     Document Type: Article
Times cited : (21)

References (36)
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    • Y. Yamashita, T. Suzuki, T. Mukai and G. Saito, J. Chem. Soc., Chem. Commun., 1985, 1044; K. Kobayashi, C. L. Gajurel and K. Umemoto, Bull., Chem. Soc. Jpn., 65, 2168 (1992); F. Iwasaki, N. Toyoda, M. Hirota, N. Yamazaki, M. Yasui and K. Kobayashi, Bull. Chem. Soc. Jpn., 65, 2173 (1992); Y. Tsubata, T. Suzuki, Y. Yamashita, T. Mukai and T. Miyashi, Heterocycles, 33, 337 (1992). Acceptor molecules containing heteroquinoid structures are also interesting from the same point of view. S. Yoshida, M. Fujii, Y. Aso, T. Otsubo and F. Ogura, J. Org. Chem., 59, 3077 (1994); K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Commun., 1994, 519.
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    • Y. Yamashita, T. Suzuki, T. Mukai and G. Saito, J. Chem. Soc., Chem. Commun., 1985, 1044; K. Kobayashi, C. L. Gajurel and K. Umemoto, Bull., Chem. Soc. Jpn., 65, 2168 (1992); F. Iwasaki, N. Toyoda, M. Hirota, N. Yamazaki, M. Yasui and K. Kobayashi, Bull. Chem. Soc. Jpn., 65, 2173 (1992); Y. Tsubata, T. Suzuki, Y. Yamashita, T. Mukai and T. Miyashi, Heterocycles, 33, 337 (1992). Acceptor molecules containing heteroquinoid structures are also interesting from the same point of view. S. Yoshida, M. Fujii, Y. Aso, T. Otsubo and F. Ogura, J. Org. Chem., 59, 3077 (1994); K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Commun., 1994, 519.
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    • Y. Yamashita, T. Suzuki, T. Mukai and G. Saito, J. Chem. Soc., Chem. Commun., 1985, 1044; K. Kobayashi, C. L. Gajurel and K. Umemoto, Bull., Chem. Soc. Jpn., 65, 2168 (1992); F. Iwasaki, N. Toyoda, M. Hirota, N. Yamazaki, M. Yasui and K. Kobayashi, Bull. Chem. Soc. Jpn., 65, 2173 (1992); Y. Tsubata, T. Suzuki, Y. Yamashita, T. Mukai and T. Miyashi, Heterocycles, 33, 337 (1992). Acceptor molecules containing heteroquinoid structures are also interesting from the same point of view. S. Yoshida, M. Fujii, Y. Aso, T. Otsubo and F. Ogura, J. Org. Chem., 59, 3077 (1994); K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Commun., 1994, 519.
    • (1992) Bull. Chem. Soc. Jpn. , vol.65 , pp. 2173
    • Iwasaki, F.1    Toyoda, N.2    Hirota, M.3    Yamazaki, N.4    Yasui, M.5    Kobayashi, K.6
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    • Y. Yamashita, T. Suzuki, T. Mukai and G. Saito, J. Chem. Soc., Chem. Commun., 1985, 1044; K. Kobayashi, C. L. Gajurel and K. Umemoto, Bull., Chem. Soc. Jpn., 65, 2168 (1992); F. Iwasaki, N. Toyoda, M. Hirota, N. Yamazaki, M. Yasui and K. Kobayashi, Bull. Chem. Soc. Jpn., 65, 2173 (1992); Y. Tsubata, T. Suzuki, Y. Yamashita, T. Mukai and T. Miyashi, Heterocycles, 33, 337 (1992). Acceptor molecules containing heteroquinoid structures are also interesting from the same point of view. S. Yoshida, M. Fujii, Y. Aso, T. Otsubo and F. Ogura, J. Org. Chem., 59, 3077 (1994); K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Commun., 1994, 519.
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    • Tsubata, Y.1    Suzuki, T.2    Yamashita, Y.3    Mukai, T.4    Miyashi, T.5
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    • Y. Yamashita, T. Suzuki, T. Mukai and G. Saito, J. Chem. Soc., Chem. Commun., 1985, 1044; K. Kobayashi, C. L. Gajurel and K. Umemoto, Bull., Chem. Soc. Jpn., 65, 2168 (1992); F. Iwasaki, N. Toyoda, M. Hirota, N. Yamazaki, M. Yasui and K. Kobayashi, Bull. Chem. Soc. Jpn., 65, 2173 (1992); Y. Tsubata, T. Suzuki, Y. Yamashita, T. Mukai and T. Miyashi, Heterocycles, 33, 337 (1992). Acceptor molecules containing heteroquinoid structures are also interesting from the same point of view. S. Yoshida, M. Fujii, Y. Aso, T. Otsubo and F. Ogura, J. Org. Chem., 59, 3077 (1994); K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Commun., 1994, 519.
    • (1994) J. Org. Chem. , vol.59 , pp. 3077
    • Yoshida, S.1    Fujii, M.2    Aso, Y.3    Otsubo, T.4    Ogura, F.5
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    • Y. Yamashita, T. Suzuki, T. Mukai and G. Saito, J. Chem. Soc., Chem. Commun., 1985, 1044; K. Kobayashi, C. L. Gajurel and K. Umemoto, Bull., Chem. Soc. Jpn., 65, 2168 (1992); F. Iwasaki, N. Toyoda, M. Hirota, N. Yamazaki, M. Yasui and K. Kobayashi, Bull. Chem. Soc. Jpn., 65, 2173 (1992); Y. Tsubata, T. Suzuki, Y. Yamashita, T. Mukai and T. Miyashi, Heterocycles, 33, 337 (1992). Acceptor molecules containing heteroquinoid structures are also interesting from the same point of view. S. Yoshida, M. Fujii, Y. Aso, T. Otsubo and F. Ogura, J. Org. Chem., 59, 3077 (1994); K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Commun., 1994, 519.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 519
    • Takahashi, K.1    Tarutani, S.2
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  • 27
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    • Recently, an attractive interaction between a cyano group and a pyridine lone pair was reported. The very similar atomic arrangement in 1 - 3 suggests that such an interaction is also at work in 1 - 3. P. N. W. Baxter, J. A. Connor, D. C. Povey and J. D. Wallis, J. Chem. Soc., Chem. Commun., 1991, 1135.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 1135
    • Baxter, P.N.W.1    Connor, J.A.2    Povey, D.C.3    Wallis, J.D.4
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    • Cornell University Press: New York
    • The sums of van der Waals radii are 2.70, 3.35, and 3.50 Å for H⋯N, S⋯N, and Se⋯N contacts, respectively. L. Pauling, The Nature of the Chemical Bond, 3rd ed; Cornell University Press: New York, pp 260 (1960).
    • (1960) The Nature of the Chemical Bond, 3rd Ed , pp. 260
    • Pauling, L.1
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    • note
    • Although neutral 2 no longer exhibits the S⋯N=C interaction, such an electrostatic force would appear in the CT state or anion radical state. In fact the X-ray analysis on the CT complex of 2 with TMTTTF indicated the presence of short intermolecular S⋯N≡C contacts (3.15Å); K. Iwasaki, Ph. D Thesis of the Graduate University for Advanced Studies (1992).
  • 35
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    • Y. Jia-xing, Acta Crystallogr. Sect. A. 37, 642 (1981); 39, 35 (1983).
    • (1983) Acta Crystallogr. Sect. A. , vol.39 , pp. 35


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