The Organic Chemistry of 1,3-Dithiole-2-thione-4,5-dithiolate (DMIT)

Svenstrup, Niels; Becher, Jan

doi:10.1055/s-1995-3910

Cited by 221 publications

(146 citation statements)

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“…21 All Table 1. TDDFT energies, oscillator strengths (f) and assignments of the electronic transitions of 2 (geometry of X-ray structure) and 2 D (adopting the X-ray geometry of 2 without change), B3LYP functional, Ahlrichs SVP basis set, 13 , which are not present for 2 because of the doubly filled orbital (95) are denoted by an asterisk (*).…”

Section: General Considerationsmentioning

confidence: 99%

Preparation and characterization of 3-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)naphthopyranone: a luminescent redox-active donor–acceptor compound

Dolder¹,

Liu²,

Guégano³

et al. 2006

Tetrahedron

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Abstract-A new 1,3-dithiol-2-ylidene substituted naphthopyranone 2 has been synthesized and characterized. UV-vis spectroscopic and cyclic voltammetry results, interpreted on the basis of density functional theory, show that 2 displays an intramolecular charge-transfer transition and acts like a donor-acceptor (D-A) system. Furthermore, a weak fluorescence originating from the excited charge-transfer state is observed.

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Section: General Considerationsmentioning

confidence: 99%

Preparation and characterization of 3-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)naphthopyranone: a luminescent redox-active donor–acceptor compound

Dolder¹,

Liu²,

Guégano³

et al. 2006

Tetrahedron

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“…2-salts have received much attention for their use as stable dmit precursors in the syntheses of other metal-dmit salts [6,7]. The crystal structure of the title compound and related Zn-dmit complexes was previously reported [8,9].…”

Section: Discussionmentioning

confidence: 99%

Refinement of the crystal structure of tetrabutylammonium bis(2- thioxo-1,3-dithiole-4,5-dithiolato)zincate(II), [C16H36N]2[Zn(C3S5)2], at room temperature

Zhao¹,

Wang²,

Zhang³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe synthesis of the title compound involved amodification of literature methods [ 1]. CS 2 (24 ml) was added to degassed dimethyl formamide (DMF, 48 ml), and the mixturewas cooled to 273 K. Sodium (1.45 g) was added to the solution and the mixture was vigorously stirred under cooling until the reaction was completed. Several ml of MeOH were slowly added. To this solution, separate solutions of (i) ZnCl 2 · 2H 2 O(2.13 g) dissolved in 25-28% NH 3 (40 ml) and (ii) Bu 4 NBr (10.12 g) in water (30 ml) were added consecutively with stirring at room temperature. The mixture was stirred overnight. The product was isolated by filtration, washed with water and MeOH, and then solved in acetone. Single crystals of the title compound used for X-ray structure analysis were obtained by evaporation of acetone from the solution held at room temperature. Experimental detailsAll Ha toms were placed in geometrically calculated positions and refined using ariding model with U iso(H) =1.2 Ueq(C). 2-anion has C 2 symmetry with the Zn(II) ion located on the twofold axis. The dmit ligand shows its typical behaviour as abidentate ligand and coordinates the Zn 2+ ion through vicinal exocyclic sulfur atoms of two dmit molecules in adistorted tetrahedral manner. The bond lengths of dmit ligand show typical conjugation character. The C=S double bond (1.666(3) Å)ismuch longer than that of typical C=S (1.599 Å) [10]. The other C-S bonds span the range of 1.709(3) to 1.74 Å (1.819 Å)a nd are essentially single bonds with some double-bond character. The C=C bond lengths of the dmit ion are 1.359(3) Å and very close to the corresponding double-bond value of 1.34 Å.T he S-Zn-S bond angles range from 95.12(2)°to 123.93(4)°.The Zn-Sbond lengths are 2.3391(7) Å and 2.3435(7) Å,respectively. In the crystal packing of the compound, the intermolecular contacts are consistent with avan der Waals type of packing and the structure displays no sizable intermolecular voids. The packing is formed by channels of cations and anions viewing along [010]. Discussion

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“…17 The second procedure, introduced by Neilands, 18 uses a hetero Diels Alder reaction of the trithione 7 with a mono-substituted alkene to provide the racemic thione. The disodium salt of dithiolate 5 19 and the trithione 7 18,19 can be readily prepared from 4, a zinc(II) complex of the dithiolate, which is readily prepared from carbon disulfide and sodium, 20 all reactions being feasible on a large scale. The less reactive zinc complex 4 will also undergo reaction with some vic-dibromides to give the bicyclic thiones e.g.…”

Section: Introductionmentioning

confidence: 99%

Substituted BEDT‐TTF Derivatives: Synthesis, Chirality, Properties and Potential Applications

Wallis

Griffiths

2005

ChemInform

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Abstract.The increasing availability of functionalized BEDT-TTF derivatives in both racemic and enantiopure forms opens up great opportunities for preparing multifunctional materials and chiral conducting systems in the form of crystals, thin films and polymers. Functionalities such as amino and carboxyl will allow attachment to other molecular systems, while intermolecular interactions between substituents, e.g. hydrogen bonding and halegon---halegon interactions, provides additional tools for designing solid state radical cation structures. In this review the syntheses of substituted derivatives of BEDT-TTF and closely related donors are surveyed, along with the structures and properties of the radical cation salts so far prepared, as a stimulus for future application of these versatile and attractive molecules. Particular attention is paid to the preparation of single enantiomers, and to the stereochemical consequences of the synthetic procedures. IntroductionOrganosulfur donor molecules have been a major focus for research in the preparation of molecular conducting systems, with tetrathiafulvalene 1 and its derivatives playing a leading role initially.1 However, breakthroughs in the last decade for preparing superconducting and hybrid materials have featured bis(ethylenedithio)tetrathiafulvalene 2, also known as BEDT-TTF or ET.2 This molecule shows two reversible oxidations at 0.50 and 0.91 V relative to the Ag/AgCl electrode, ca. 0.15 V more positive than those for TTF, and has been converted into a very large number of radical cation salts. These have been studied by a wide range of techniques stimulated in part by formation of superconducting radical cation salts with anions Cu(NCS) 2

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The Organic Chemistry of 1,3-Dithiole-2-thione-4,5-dithiolate (DMIT)

Cited by 221 publications

References 0 publications

Preparation and characterization of 3-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)naphthopyranone: a luminescent redox-active donor–acceptor compound

Preparation and characterization of 3-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)naphthopyranone: a luminescent redox-active donor–acceptor compound

Refinement of the crystal structure of tetrabutylammonium bis(2- thioxo-1,3-dithiole-4,5-dithiolato)zincate(II), [C16H36N]2[Zn(C3S5)2], at room temperature

Substituted BEDT‐TTF Derivatives: Synthesis, Chirality, Properties and Potential Applications

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