- Efficient synthesis of EDO-S,S-DMEDT-TTF, a potent organic-donor for synthetic metals
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Optically active ethylenedioxy-S,S-dimethylethylene-dithiotetrathiafulvalene (EDO-S,S-DMEDT-TTF: 1) has been synthesized in satisfactory yield using a triethyl phosphite-mediated cross-coupling of (5S,6S)-5,6-dimethyl-1,3-dithiolane-2-one 4 with unsubstituted 1,3-dithiolane-2-thione 6.
- Konoike,Namba,Shinada,Sakaguchi,Papavassiliou,Murata,Ohfune
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- 4,5-Ethylenedioxy-4',5'-ethylenedithiotetrathiafulvalene (EOET): a New Unsymmetrical Electron Donor
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The synthesis, characterization, electrochemical properties, and preliminary X-ray structural data of the title electron donor, a hybrid of bis(ethylenedithio)tetrathiafulvalene and bis(ethylenedioxy)tetrathiafulvalene, are presented.
- Kini, Aravinda M.,Mori, Takehiko,Geiser, Urs,Budz, Sandra M.,Williams, Jack M.
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- Synthesis of some new electron π-donors containing methoxy groups
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The synthesis of some new electron π-donors carrying four or two methoxy groups is described. The precursor 5,6-dimethoxy-5,6-dihydro[1,3]dithiolo[4,5- b] [1,4]dithiin-2-thione was synthesized and by coupling reactions the symmetrical 5,6,5′,6′-tetramethoxy-5,6,5′,6′-tetrahydro- [2,2′]bi[[1,3]dithiolo[4,5-b][1,4]dithiinylidene] and unsymmetrical 5,6-dimethoxy-5,6,5′,6′-tetrahydro-[2,2′]bi[[1,3]-dithiolo[4, 5-[1,4]dithiinylidene], 2-(5,6-dimethoxy-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4] dithiin-2-ylidene)-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]-dioxine and (5,6-dimethoxy-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-6, 7-dihydro-5H-[1,3]dithiolo[4,5-6][1,4]dithiepine donors were prepared. They have been characterized spectroscopically and their redox potentials determined using cyclic voltammetry.
- Mousdis,Papavassiliou,Psaroudakis,Anyfantis
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- Anomalous ring cleavage of 1,3-dithiole- and 1,3-diselenole-2-thiones under the cross-coupling conditions using triethyl phosphite
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The ring cleavage of 4,5-ethylenedioxy-1,3-dithiole- and -1,3-diselenole-2-thiones, followed by the reaction with 4,5- bis(methoxycarbonyl)-1,3-diselenole-2-one took place under the phosphite-mediated cross-coupling conditions to afford 2-thioxo- and 2-(s
- Iyoda, Masahiko,Watanabe, Ryoji,Miyake, Yosihiro
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p. 570 - 571
(2007/10/03)
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- Syntheses, structure and conducting properties of halogenated ethylenedioxytetrathiafulvalenes
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4,5-Diiodo-, 4,5-dibromo-, and 4,5-dichloro-4′,5′-ethylenedioxytetrathiafulvalenes (EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2) were synthesized in moderate to good yields by the two routes. The first route contains the reaction of EDO-TTF with LDA, followed by quenching with halogenated reagents, and the second route consists of the P(OR)3-mediated cross-coupling of 4,5-dihalogenated 1,3-dithiole-2-ones with 4,5-ethylenedioxy-1,3-dithiole-2-thione. The structures of EDO-TTFI2 and EDO-TTFCl2 were determined by X-Ray analysis. The radical-cation salts derived from EDO-TTFI2, EDO-TTFBr2, and EDO-TTFCl2 show high conductivities, although these compounds contain electron-withdrawing halogens as the substituent.
- Iyoda, Masahiko,Kuwatani, Yoshiyuki,Ogura, Eiji,Hara, Kenji,Suzuki, Hironori,Takano, Takahiro,Takeda, Koji,Takano, Jun-ichi,Ugawa, Kohei,Yoshida, Masato,Matsuyama, Haruo,Nishikawa, Hiroyuki,Ikemoto, Isao,Kato, Takehiro,Yoneyama, Naoki,Nishijo, Jun-ichi,Miyazaki, Akira,Enoki, Toshiaki
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p. 833 - 848
(2007/10/03)
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- Ethylenedithio(ethylenedioxo)diselenadithiafulvalene (TOST) and Ethylenediseleno(ethylenedioxo)tetrathiafulvalene (SO): New Unsymmetrical ?-Donors containing Three Elements in Group 16 (O, S, and Se)
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The synthesis and characterization of new unsymmetrical bis(ethylenedithio)tetrathiafulvalene (ET) analogues ethylenedithio(ethylenedioxo)diselenadithiafulvalene (TOST) and ethylenediseleno(ethylenedioxo)tetrathiafulvalene (SO) that contain three elements in group 16 (O, S and Se) and their cation radical salts are reported.
- Imakubo, Tatsuro,Okano, Yoshinori,Sawa, Hiroshi,Kato, Reizo
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p. 2493 - 2494
(2007/10/03)
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- 4,5-Ethylenedithio-1-selenole-3-thiole-2-one as Starting Material for the Preparation of New Tetrachalcogenafulvalenes
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Starting from 3-chloro-2-oxo-1,4-dithiane the title compound was prepared and characterized analytically and spectroscopically.It was used then for the preparation of some new tetrachalcogenafulvalenes (?-donor molecules). Key words: Tetrachalcogenafulvalenes, ?-Donors, Organic Conductors
- Lagouvardos, D. J.,Papavassiliou, G. C.
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p. 898 - 900
(2007/10/02)
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- 5,6-Ethylenediseleno-1,3-dithiolo-dithiin-2-thione as Starting Material for the Preparation of New Tetrathiafulvalenes
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Tetrathiafulvalenes, ?-Donors, Organic ConductorsStarting from 1,3-dithiolodithiin-2-thione, the title thione was prepared by a fourstep sequence (lithiation with lithium diisopropylamide, addition of Se, treatment with ZnCl2 in the presence of n-Bu4NBr, and alkylation with 1,2-dibromoethane).Self-coupling as well as cross-coupling with similar compounds via triethyl phosphite afforded new tetrathiafulvalenes, precursors of conducting salts.
- Papavassiliou, G. C.,Lagouvardos, D. J.,Kakoussis, V. C.
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p. 1730 - 1732
(2007/10/02)
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- Unsymmetrically Substituted Ethylenedioxytetrathiafulvalenes
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Seven new electron donors, 4,5-ethylenedioxytetrathiafulvalenes where 4',5'-substituents are trimethylenedithio, ethylenedithio, methylenedithio, 2-oxatrimethylenedithio, methylthio, hydrogen and methyl carboxylate, are prepared, and their electrochemical properties are investigated.
- Mori, Takehiko,Inokuchi, Hiroo,Kini, Aravinda M.,Williams, Jack M.
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p. 1279 - 1282
(2007/10/02)
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- Ethylenedioxytetrathiafulvenes: New Unsymmetrical ?-Donors
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Ethylenedioxybenzotetrathiafulvalene (EDOBTTF), ethylenedioxypyridinotetrathiafulvalene (EDOPTTF), ethylenedioxymethylenedithiotetrathiafulvalene (EDOMDTTTF), ethylenedioxyvinylenedithiotetrathiafulvalene (EDOVDTTTF), and ethylenedioxymethylenediselenotetrathiafulvalene (EDOMDSTTF) have been prepared and characterized analytically and spectroscopically.
- Papavassiliou, G. C.,Lagouvardos, D. J.,Kakoussis, V. C.,Mousdis, G. A.
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p. 1216 - 1218
(2007/10/02)
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