- Improved Synthesis of Bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF): ?-Donor for Synthetic Metals
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2,5,7,9-Tetrathiabicyclonon-1(6)-en-8-thione (3) is prepared in increased yield by isolating the intermediate 4,5-dimercapto-1,3-dithiole-2-thione disodium salt (2) which undergoes efficient ringclosure with 1,2-dibromoethane.Quantitative oxidation of (3) with mercuric acetate to 2,5,7,9-tetrathiabicyclonon-1(6)-en-8-one (4) followed by coupling with triethyl phosphite yields bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) in high overall yield.
- Varma, K. Sukumar,Bury, Adrian,Harris, Nigel J.,Underhill, Allan E.
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- Structure and physical properties of a hydrogen-bonded self-assembled material composed of a carbamoylmethyl substituted TTF derivative
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Crystal structures of the carbamoylmethyl substituted TTF derivative AMET are characterized by polymeric hydrogen bonding between amide groups. As a result, the TTF moieties stack in parallel even in the neutral crystal. The νNH absorbtions of
- Ono, Go,Izuoka, Akira,Sugawara, Tadashi,Sugawara, Yoko
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- New tetrathiafulvalenes containing carbazole and 1,3,5-triazine fragments: Synthesis, electro-chemical and optical properties
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New tetrathiafulvalenes, containing carbazole and 1,3,5-triazine fragments added to the tetrathia-fulvalene ring by means of a S-CH2-CH 2-O bridge, were synthesized. The electrochemical properties of the initial compounds and of the final products were investigated by cyclic voltammetry. The optical characteristics of their solutions were studied by UV absorption spectroscopy and fluorescence spectroscopy.
- Ignatenko,Gorbunov,Shklyaeva,Abashev
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p. 691 - 698
(2014/08/18)
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- Synthesis of unsymmetrical tetrathiafulvalene derivatives via Me3Al-promoted reactions of organotin compounds with esters
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Efficient synthetic methods for the construction of a wide variety of unsymmetrical tetrathiafulvalenes (TTFs) via the Me3Al-promoted reactions of organotin thiolates or selenolates with esters are described. Reaction of tin thiolates (3a-c and 10) and selenolates (3d, 5, and 7) with esters (11a,b) in the presence Of Me3Al as a Lewis acid gave dihydrotetrathiafulvalene derivatives (12, 14, 15, and 17-20) and 1,3-dithiane derivatives (13 and 16). In addition, the synthesis of diselenadithiafulvalene derivatives (25-28) could be accomplished by Me3Al-mediated reaction of tin thiolate (2a) or selenolates (3d and 5) with esters (22a, 22d, and 24). Furthermore, the application of the Me3Al-promoted reaction of tin thiolate (34) with esters (11a-b, 22a-d, and 35a-b) for the synthesis of unsymmetrical TTFs-fused donors enabled us to obtain various TTFs-fused systems (29-33) in short steps.
- Yamada, Jun-Ichi,Satoki, Shyuji,Mishima, Sachinori,Akashi, Nobutaka,Takahashi, Kouhei,Masuda, Nobuyuki,Nishimoto, Yasushi,Takasaki, Satoshi,Anzai, Hiroyuki
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p. 3987 - 3995
(2007/10/03)
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- Bis(methylthio)ethylenedithiotetrathia-fulvalene
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The title compound {alternative nomenclature: 2-[4,5-bis(methylthio)-1,3-dithiol-2-ylidene]-5,6-dihydro-1,3-dithiolo[4,5-b][1, 4]dithiine}, C10H10S8, is a molecular crystal with typical values for bond distances and angles. The molecules form columns along the c axis. The intermolecular S...S distances indicate the presence of van der Waals interactions between the columns.
- Zhang, Bin,Li, Yu-Liang,Han, Hong-Xian,Yang, Jing-Kui,Zhu, Dao-Ben,Maruyama, Yu-Sei
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p. 400 - 403
(2007/10/03)
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- STUDY ON THE SYNTHESIS OF THE ELECTRON DONOR MOLECULE OF (BEDT-TTF)
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Two kinds of synthetic methods for the organic donor molecule BEDT-TTF or ET are reviewed and compared.Through detailed and systematic studies of the synthesis of BEDT-TTF, a convenient, reliable, ready and high-yield synthetic procedure is presented, which is superior to the methods reported to date in terms of the yield and reproducibility.Key words: Electron donor, BEDT-TTF, ET, synthesis, synthetic metal.
- Liu, Sheng-Gao,Wu, Pei-Ji,Liu, Yun-Qi,Zhu, Dao-Ben
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p. 145 - 154
(2007/10/03)
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- A facile synthesis of bis(ethylenedithio)tetrathiafulvalene
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5,6-Dihydro-1,3-dithiolo[4,5-b][1,4]dithiin-2-one (3) was prepared in one step starting from thiapendione (1; [1,3]dithiolo[4,5-d][1,3]dithiole-2,5-dione) in 55% yield via 4,5-dimercapto-1,3-dithiol-2-one (2). Coupling of 3 in triethyl phosphite gave bis(
- Muller,Ueba
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p. 853 - 854
(2007/10/02)
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- An Unusual Synthesis of Tetrakis(trifluoromethyl)tetrathiafulvalene
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Tetrakis(trifluoromethyl)tetrathiafulvalene (5) was formed in a phase-tranfer-catalyzed unusual one-step reaction by basic cleavage and subsequent alkylation of 1,3,4,6-tetrathiapentalene-2,5-dione (thiapendione) (1) with 2,3-dichlorohexafluoro-2-butene.As an example of the normal course of this reaction the synthesis of 4,5-(ethylenedithio)-1,3-dithiol-2-one (3) is described.
- Mueller, Harald,Lerf, Anton,Fritz, Heinz P.
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p. 395 - 396
(2007/10/02)
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- TRANSITION-METAL 1,2-DIHETEROLENES AND POLYHETEROTETRAHETERAFULVALENES: PRECURSORS OF CONDUCTING SOLIDS
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Methods for synthesis and properties of oxygen-, sulfur-, selenium-, and nitrogen-containing transition-metal 1,2-diheterolenes and polyheterotetraheterafulvalenes are described.Also, the preparation and properties of some conducting salts based on these compounds are briefly discussed.
- Papavassiliou, G. C.,Kakoussis, V. C.,Lagouvardos, D. J.,Mousdis, G. A.
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p. 171 - 184
(2007/10/02)
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- Synthesis of Bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF)
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2-Oxo-5,6-dihydro-1,3-dithiolodithiin (4) was prepared in four steps from cheap starting materials in high overall yield.Coupling of 4 with trimethyl phosphite in toluene gave bis(ethylenedithio)tetrathiafulvalene (5; BEDT-TTF); 2,2'-bi-5,6-dihydro-1,3-dithiolodithiinylidene) in 96percent yield.
- Larsen, Jan,Lenoir, Christine
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- THE STUDY OF CHARGE TRANSFER COMPLEXES OF BEDT-TTF DERIVATIVES
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We have synthesized BEDT-TTF derivatives, which include eight sulfur atoms per molecule, and prepared several charge transfer (CT) complexes with TCNQs, p-quinones, and TCNEs in order to clarify the steric effect of substituents, R.Some of the CT complexes revealed high conductivities.
- Saito, Gunzi,Hayashi, Hitoshi,Enoki, Toshiaki,Inokuchi, Hiroo
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p. 341 - 344
(2007/10/02)
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- Comparison of the Thermal, Photochemical, and Mass Spectrometric Fragmentation of Sulphur Heterocycles with cis-Dithioethene-Structure
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The mass spectrometric primary fragmentation of 3-methylthio-1,4,2-dithiazines 1, 1,4-dithiins 2, 2,3-dihydro-1,4-dithiin-2-ones 4, 1,3-dithiole-2-ones 5, 2-imino-1,3-dithioles 6 and 1,3-dithiole-2-thiones 7 is compared with their thermolytical and photochemical reaction.In the mass spectra an intense peak of the dithiete radical ion is observed, if in the compounds an energetically favourable neutral molecule is preformed: in 1 methyl rhodanide, in 3 ethene, in 4 ketene, in 5 carbon monoxide and in 6 hydrogen cyanide.The substances 1, 3-6 - with the restriction by 3 - yield photochemically the dithiete, too.The photolysis of dithiazines 1 is wave length dewpendent.Mass spectrometrically, thermally and photochemically the dithiins 2 form thiophenes.The dithiolethiones 7 decompose mass spectrometrically and thermally into carbon disulfide, sulfur and ethynes, but photochemically they form tetrathiafulvalenes.The fragmentation of the compounds 1-6 is analogous in mass spectrometry and photolysis; 2, 3, 5 and with reservation 1 show similar mass spectrometric, thermal and photochemical reactivity.Posible reasons for these analogies are discussed.The dithietes, generated by photolysis of the compounds 1, 4, 5 or 6 react with iron penta-, nickel tetra-, molybdenum hexa- and tungsten hexacarbonyl in the preparative scale to the corresponding dithiolene complexes.
- Fanghaenel, E.,Poleschner, H.
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- Thion- und Dithioester, XXIV Synthese von Tetrathiooxalestern
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Reduction of carbon disulfide with potassium in dimethylformamide and subsequent alkylation yields the isotrithiones 2, which have been desulfurised with mercury acetate to give the 1,3-dithiol-2-ones 3. 2a is also available by a stepwise synthesis starting with methyl (methylthio)dithioacetate (6).The photochemical decarbonylation of 4,5-bis(methylthio)-1,3-dithiol-2-one (3a) leads to the formation of dimethyl tetrathiooxalate (11a).In solution 11a is in equilibrium with its dimer 13.Cyclic tetrathiooxalates are probably unstable at room temperature.
- Hartke, Klaus,Kissel, Thomas,Quante, Josef,Matusch, Rudolf
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p. 1898 - 1906
(2007/10/02)
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