First stable tetracyanodiphenoquinodimethane with a completely planar geometry: Preparation, X-ray structure, and highly conductive complexes of bis[1,2,5]thiadiazolo-TCNDQ
作者： Takanori Fukushima , Nobuharu Okazeri , Tsutomu Miyashi , Kazuharu Suzuki , Yoshiro Yamashita
DOI: 10.1016/S0040-4039(98)02557-X
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摘要: The titled tetracyanodiphenoquinodimethane (TCNDQ) derivative was newly designed and prepared as a novel component for highly conductive organic materials. Introduction of 1,2,5-thiadiazole rings into the TCNDQ skeleton leads to large stabilization in neutral state. X-ray analysis has revealed their structural details which suggest that interatomic interactions (CH…N, S…N) play an important role determining molecular crystal structure. electron acceptor shows strong affinity comparable with TCNQ, gave charge-transfer (CT) complexes anion radical salt.
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sci-hub.se 参考文章(16)
M. Pierrot, Structure and properties of molecular crystals Elsevier. ,(1990)
Robin Taylor, Olga Kennard, Crystallographic evidence for the existence of CH.cntdot..cntdot..cntdot.O, CH.cntdot..cntdot..cntdot.N and CH.cntdot..cntdot..cntdot.Cl hydrogen bonds Journal of the American Chemical Society. ,vol. 104, pp. 5063- 5070 ,(1982) , 10.1021/JA00383A012
Masahiko Iyoda, Hiroki Otsuka, Koichi Sato, Nobue Nisato, Masaji Oda, Homocoupling of Aryl Halides Using Nickel(II) Complex and Zinc in the Presence of Et4NI. An Efficient Method for the Synthesis of Biaryls and Bipyridines Bulletin of the Chemical Society of Japan. ,vol. 63, pp. 80- 87 ,(1990) , 10.1246/BCSJ.63.80
A. Ugawa, K. Iwasaki, A. Kawamoto, K. Yakushi, Y. Yamashita, T. Suzuki, Metallic behavior stable against Peierls instability in the one-dimensional organic conductor tetraselenotetracene-bis(1,2,5-thiadiazolo)tetracyanoquinodimethane [(TSeT)-(BTDA-TCNQ)] Physical Review B. ,vol. 43, pp. 14718- 14721 ,(1991) , 10.1103/PHYSREVB.43.14718
R. C. Wheland, E. L. Martin, Synthesis of substituted 7,7,8,8-tetracyanoquinodimethanes Journal of Organic Chemistry. ,vol. 40, pp. 3101- 3109 ,(1975) , 10.1021/JO00909A019
M. Uno, K. Seto, M. Masuda, W. Ueda, S. Takahashi, A new route to phenylenedimalononitrile and the analogues using palladium-catalyzed carbon-carbon bond formation Tetrahedron Letters. ,vol. 26, pp. 1553- 1556 ,(1985) , 10.1016/S0040-4039(00)98550-2
Gautam R. Desiraju, Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis Angewandte Chemie. ,vol. 34, pp. 2311- 2327 ,(1995) , 10.1002/ANIE.199523111
MacRae Maxfield, Aaron N. Bloch, Dwaine O. Cowan, Large electron acceptors for molecular metals: 13,13,14,14-tetracyano-4,5,9,10-tetrahydro-2,7-pyrenoquinodimethane (TCNTP) anions of 13,13,14,14-tetracyano-2,7-pyrenoquinodimethane (TCNP) Journal of Organic Chemistry. ,vol. 50, pp. 1789- 1796 ,(1985) , 10.1021/JO00211A001
Gunzi Saito, John P. Ferraris, Requirements for an “Organic Metal” Bulletin of the Chemical Society of Japan. ,vol. 53, pp. 2141- 2145 ,(1980) , 10.1246/BCSJ.53.2141
Takanori Suzuki, Yoshiro Yamashita, Takanori Fukushima, Tustomu Miyashi, Tetracyanoquinodimethanes Fused With A [1,2,5]Chalcogenadiazole Ring Molecular Crystals and Liquid Crystals. ,vol. 296, pp. 165- 180 ,(1997) , 10.1080/10587259708032319