- Broadband near-IR absorbing Au-dithiolene complexes bearing redox-active oligothiophene ligands
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A series of three homoleptic, monoanionic gold dithiolene complexes of oligothiophene ligands which coordinate via a central thiophene-3,4-dithiolate chelate are presented. The oligomer chains are three, five and seven thiophenes long and the complexes display hybrid optoelectronic properties featuring characteristics of both the oligothiophene chains and the delocalised metal dithiolene centre. The properties of the complexes have been characterised using a variety of spectroscopic and electrochemical methods complemented by computational studies. Solid state spectroelectrochemistry has revealed that upon oxidation these complexes display intense and broad absorption across the visible spectrum. In attempting to produce nickel analogues of these materials a single crystal of a photo-oxidised nickel dithiolene complex has also been isolated.
- Wright, Iain A.,Wilson, Claire,Coles, Simon J.,Skabara, Peter J.
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- A Convenient Preparation of 1,3-Dithiole-2-thione and 1,3-Diselenole-2-selone Derivatives
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A convenient one-pot preparation of 1,3-dithiole-2-thiones and 1,3-diselenole-2-selones substituted with phenyl, alkyl, alkylthio, hydroxymethyl, and formyl groups was accomplished from readily available acetylenes in good to excellent yields.
- Takimiya,Morikami,Otsubo
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p. 319 - 321
(2007/10/03)
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- 1,3-Dithiol-4,5-dithiolate and 5,6-Dihydro-1,4-diselenin-2,3-dithiolate Nickel Complexes
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With the goal of obtaining new ethylenedithiolate transition metals complexes, unstable tetrabutylammonium bis(1,3-dithiol-4,5-dithiolato)niccolate(III) and stable tetrabutylammonium bis(5,6-dihydro-1,4-diselenin-2,3-dithiolato)niccolate(III) were synthesized. The two complexes were characterized by elemental analysis and IR and electron absorption spectroscopy, and the second, also by voltammetry. A new convenient procedure was proposed for preparation of 1,3-dithiol-2-thione which is a key initial compound in the synthesis of the title complexes.
- Abramov,Petrov
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p. 1635 - 1640
(2007/10/03)
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- Key Intermediates for the Synthesis of Organic Semiconductors: a Direct Dithiocarbamate Route to Unsubstituted 1,3-Dithiol-2-one Derivatives
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Acid-catalyzed cyclization of formylmethyl piperidine-1-carbodithioate dimethyl or diethyl acetals (2a,b) at elevated temperatures is a key step in a convenient route to 1,3-dithiole-2-thione (1b) and 1,3-dithiole-2-selone (1c) via the unsaturated dithiolium salt (4); attempted cyclizations of (2a) and (2b) at lower temperatures led to alkoxy-substituted dithiolium salts (3a) and (3b).
- Guziec, Frank S.,Russo, Joseph M.,Torres, Felix F.,Long, G. Cornell,Tellez, Mario R.
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p. 1068 - 1070
(2007/10/02)
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- Quelques aspects de la chimie des dioxa- et dithia-germoles
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Dithia- and dioxa-germoles: (X=S, O), have been prepared from diorganodihalogermanes and R'(NaS)C=C(SNa)R', 1,2-benzenedithiol, α-hydroxy ketones, R''(KO)C=C(OK)R'' or dioxastannole and by cleavage of Ge-N bonds of diorganobis(diethylamino)germanes by benzoin.The synthesis of spirobidithiagermoles is also reported.The thermal stability of dithiagermoles has been studied.Decomposition occurs mostly by a ring opening with formation of germathiones.In the presence of tertiary amines, dioxagermoles lead to germylenes and α-diketones through a ring opening.The chemical reactivity of dithia- and dioxa-germoles has been studied.Exchange reactions with dihalogenated covalent compounds occur readily leading to carbon, phosphorus and sulfur dithiole and dioxole analogs.From dichlorogermylene new stable functional cyclic germylenes are obtained and characterized.
- Lavayssiere, H.,Satge, G. Dousse et J.
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p. 440 - 448
(2007/10/02)
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- Thiocarbonyl Ylide Intermediates Generated by Deprotonation of 2-Phenacylthio- and 2-(p-Bromophenacylthio)-1,3-dithiolylium and 2-(p-Bromophenacylthio)-1,3-dithiolanylium Bromides
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2-(p-Bromophenacylthio)-1,3-dithiolynium bromide, when treated with triethylamine, gave 2-(p-bromophenacylidene)-1,3-dithiole (17percent) and bis-disulfide (72percent).Treatment of 2-phenacylthio-1,3-dithiolylium bromide with triethylamine also gave similar results.On the other hand, 2-(p-bromophenacylthio)-1,3-dithiolanylium bromide yielded 1-(p-bromophenyl)-2-(1,3-dithiolan-2-yl)-2-thioxoethanone (12percent) in addition to 2-(p-bromophenacylidene)-1,3-dithiolane (49percent) contrary to the reported results.These results can best be rationalized by 1,3-cyclization of thiocarbonyl ylide intermediates to the valence tautomeric episulfides.
- Nakayama, Juzo,Takemasa, Toshiro,Hoshino, Masamatsu
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p. 2281 - 2284
(2007/10/02)
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