Charge Transfer Complexes for Organic Metals

The discovery in 1973 of the metal-like electronic behavior of charge transfer complexes, consisting of an electron donor, Tetrathiafulvalene (TTF) and an electron acceptor, 7,7,8,8-Tetracyanoquinodimethane (TCNQ)1)‚ has led to intensive studies of the organic metals.
In 1980 Jérome2), Bechgaad3) and their co-workers have found that each complex of (TMTSF)2PF6 or (TMTSF)2ClO4 using TMTSF analogue of TTF, becomes a superconductor at very low temperatures. Afterwards, organic superconductors utilizing BEDT-TTF4), M(dmit)25) (M=Ni, Pd), etc. have successively been designed one after another. Moreover, the complexes κ-(BEDT-TTF)2Cu[N(CN)2]Br (Tc=11.6K)6), and κ-(BEDT-TTF)2Cu[N(CN)2]Cl (0.3kbar; Tc=12.8K)7) having higher Tc have been found and vigorous studies have been conducted toward the development of still higher Tc organic superconductor8).

Donors

Acceptors

Other Donors & Acceptors

Synthetic Intermediates

Donors

TTF Derivatives

B1200 B1200 B1218 B1218 B1244 B1244
D2067 D2067 T1119 T1119 T1143 T1143
T1205 T1205 T0980 T0980 T2468 T2468
T1282 T1282
B1200 Bis(ethylenedithio)tetrathiafulvalene [Organic Electronic Material]
B1218 Bis(methylenedithio)tetrathiafulvalene [Organic Electronic Material]
B1244 Bis(trimethylenedithio)tetrathiafulvalene [Organic Electronic Material]
D2067 Dimethyltetrathiafulvalene
T1119 Tetrakis(methylthio)tetrathiafulvalene [Organic Electronic Material]
T1143 Tetrakis(octadecylthio)tetrathiafulvalene [Organic Electronic Material]
T1205 Tetrakis(pentylthio)tetrathiafulvalene [Organic Electronic Material]
T0980 Tetrathiafulvalene
T2468 Tetrathiafulvalene - 7,7,8,8-Tetracyanoquinodimethane Complex
T1282 Tris(tetrathiafulvalene) Bis(tetrafluoroborate) Complex
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Acceptors

TCNQ Derivatives

T1246 T1246 B2309 B2309 D3200 D3200
D2021 D2021 F0509 F0509 T0078 T0078
B1466 B1466 T0077 T0077 T1131 T1131
T2468 T2468
T1246 11,11,12,12-Tetracyanonaphtho-2,6-quinodimethane
B2309 2,5-Bis(2-hydroxyethoxy)-7,7,8,8-tetracyanoquinodimethane
D3200 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane
D2021 2,5-Dimethyl-7,7,8,8-tetracyanoquinodimethane
F0509 2-Fluoro-7,7,8,8-tetracyanoquinodimethane
T0078 7,7,8,8-Tetracyanoquinodimethane
B1466 Bis(tetra-n-butylammonium) Tetracyanodiphenoquinodimethanide
T0077 Tetracyanoethylene
T1131 Tetrafluorotetracyanoquinodimethane sublimed [Organic Electronic Material]
T2468 Tetrathiafulvalene - 7,7,8,8-Tetracyanoquinodimethane Complex
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Metal Dithiolenes

T0279 T0279 B1350 B1350 B1437 B1437
B1438 B1438 B1371 B1371 B1221 B1221
D2134 D2134 T1272 T1272 T1415 T1415
T1416 T1416
T0279 (Toluene-3,4-dithiolato)zinc(II)
B1350 Bis(dithiobenzil)nickel(II)
B1437 Bis(tetra-n-butylammonium) Bis(1,3-dithiole-2-thione-4,5-dithiolato)palladium(II)
B1438 Bis(tetra-n-butylammonium) Bis(1,3-dithiole-2-thione-4,5-dithiolato)platinum(II)
B1371 Bis(tetra-n-butylammonium) Bis(maleonitriledithiolato) Nickel Complex
B1221 Bis(tetrabutylammonium) Bis(1,3-dithiole-2-thione-4,5-dithiolato)zinc Complex [Organic Electronic Material]
D2134 Dioctadecyldimethylammonium Bis(1,3-dithiole-2-thione-4,5-dithiolato)aurate(III)
T1272 Tetra-n-butylammonium Bis(1,3-dithiole-2-thione-4,5-dithiolato) Nickel (III) Complex
T1415 Tetra-n-butylammonium Bis(maleonitriledithiolato)nickel(III) Complex
T1416 Tetra-n-butylphosphonium Bis(1,3-dithiole-2-thione-4,5-dithiolato)nickel(III) Complex
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Other Donors & Acceptors

B1416 B1416 B0089 B0089 D0101 D0101
D1070 D1070 D1956 D1956 D2152 D2152
D2249 D2249 D2250 D2250 D2234 D2234
B1601 B1601 B1595 B1595 C1336 C1336
T1503 T1503 T1023 T1023 T0617 T0617
T0061 T0061 M1045 M1045 T0151 T0151
P0106 P0106 T1221 T1221
B1416 1,3-Bis(dicyanomethylidene)indan
B0089 1,4-Benzoquinone
D0101 1,5-Diaminonaphthalene
D1070 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
D1956 2,3-Dimethoxy-5-methyl-1,4-benzoquinone
D2152 2,5-Di-tert-amylbenzoquinone
D2249 2,5-Dibromo-1,4-benzoquinone
D2250 2,5-Dimethoxy-1,4-benzoquinone
D2234 2,6-Dimethyl-1,4-benzoquinone
B1601 2-Bromo-1,4-benzoquinone
B1595 2-Bromo-5-methyl-1,4-benzoquinone
C1336 2-Chloro-5-methyl-1,4-benzoquinone
T1503 3,3',5,5'-Tetra-tert-butyl-4,4'-diphenoquinone
T1023 3,3',5,5'-Tetramethylbenzidine
T0617 Bromanil
T0061 Chloranil
M1045 Methoxybenzoquinone
T0151 N,N,N',N'-Tetramethyl-1,4-phenylenediamine Dihydrochloride
P0106 Phenothiazine
T1221 Tetrakis(dimethylamino)ethylene
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Synthetic Intermediates

B1322 B1322 T1132 T1132 D2133 D2133
B2233 B2233 B2228 B2228 B1199 B1199
B1777 B1777 B1778 B1778 D3252 D3252
E0460 E0460 E0429 E0429 M1154 M1154
M1112 M1112 P1635 P1635 B1272 B1272
D2127 D2127 D1930 D1930 T0266 T0266
B1322 1,2-Benzenedithiol
T1132 1,3,4,6-Tetrathiapentalene-2,5-dione
D2133 1,3-Dithiole-2-thione
B2233 4,5-Bis(2-cyanoethylthio)-1,3-dithiol-2-one
B2228 4,5-Bis(2-cyanoethylthio)-1,3-dithiol-2-thione
B1199 4,5-Bis(benzoylthio)-1,3-dithiole-2-thione
B1777 4,5-Bis(methylthio)-1,3-dithiol-2-one
B1778 4,5-Bis(methylthio)-1,3-dithiole-2-thione
D3252 4,5-Dicyano-1,3-dithiol-2-one
E0460 4,5-Ethylenedithio-1,3-dithiol-2-one
E0429 4,5-Ethylenedithio-1,3-dithiole-2-thione
M1154 4,5-Methylenedithio-1,3-dithiol-2-one
M1112 4,5-Methylenedithio-1,3-dithiole-2-thione
P1635 5-Propyl-1,3-dithiolo[4,5-d][1,3]dithiole-2-thione
B1272 Bis(carbonyldithio)tetrathiafulvalene
D2127 Dimethyl 1,3-Dithiole-2-thione-4,5-dicarboxylate
D1930 Disodium Dimercaptomaleonitrile
T0266 Toluene-3,4-dithiol
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Literature

1)(a) J. Ferraris, D. O. Cowan, V. Walatka, Jr., J. H. Perlstein, J. Am. Chem. Soc., 1973, 95, 948.
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8)H. Kobayashi, T. Udagawa, H. Tomita, K. Bun, T. Naito, A. Kobayashi, Chem. Lett., 1993, 1559.
H. Kobayashi, H. Tomita, T. Naito, H. Tanaka, A. Kobayashi, T. Saito, J. Chem. Soc., Chem. Commun., 1995, 1225.
K. Takimiya, Y. Kataoka, Y. Aso, T. Otsubo, H. Fukuoka, S. Yamanaka, Angew. Chem. Int. Ed., 2001, 40, 1122.
J. Yamada, M. Watanabe, H. Akutsu, S. Nakatsuji, H. Nishikawa, I. Ikemoto, K. Kikuchi, J. Am. Chem. Soc., 2001, 123, 4174.

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