Crystal and molecular structure of the aromatic sulphur compound 2,2′-bi-1,3-dithiole. Evidence for d-orbital participation in bonding

Cooper, William F.; Kenny, N. C.; Edmonds, James W.; Nagel, A.; Wudl, Fred; Coppens, Philip

doi:10.1039/c29710000889

Cited by 130 publications

(68 citation statements)

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“…In both cases the structures of complexes were confirmed by single-crystal XRD (Figures 1 and 2). In complexes 1·2 and 1·3 2 , the molecular geometries of the components (Supporting Information, Tables S1-S3) are essentially unchanged from those observed by XRD for individual 1-3 [7,8,14], i.e. they do not indicate directly the CT which, therefore, should be moderate enough (see below).…”

Section: Methodsmentioning

confidence: 99%

First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties

et al. 2012

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The first charge-transfer complexes of tetrathiafulvalene (1) with 1,2,5-chalcogenadiazole derivatives, i.e. with [1,2,5]thiadiazolo [3,4-c][1,2,5]thiadiazole (2) and 3,4-dicyano-1,2,5-telluradiazole (3), were prepared in the form of single crystals and structurally defined by X-ray diffraction as 1·2 and 1·3 2 , respectively. Starting compound 2 was synthesized by a new efficient method from 3,4-diamino-1,2,5-oxadiazole and disulfur dichloride. The electronic structure and UV-vis spectral properties of complexes 1·2 and 1·3 2 were studied by means of DFT 2 calculations. The electrical properties of single crystals of the complexes were investigated revealing semiconductor properties with an activation energy of 0.34 eV for 1·2 and 0.40 eV for 1·3 2 . Both complexes displayed photoconductive effects with increased conductivity under white-light illumination.3

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Section: Methodsmentioning

confidence: 99%

First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties

et al. 2012

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“…In liquid crystals TTF was also found to adopt a non-planar conformation (16). Bond lengths and angles compare favorably with neutral TTF (17) and are generally not significantly different from those in TTF-chloranil and TTF-bromanil (13).…”

mentioning

confidence: 89%

Preparation, properties, and X-ray crystal structure of a 1:1 complex of tetrathiafulvalene and p-dinitrobenzene

Secco¹,

Trotter²,

Weiler³

1982

Can. J. Chem.

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A crystalline complex of tetrathiafulvalene and p-dinitrobenzene has been prepared and characterised by esr and ir spectroscopy, bulk magnetic susceptibility, dc conductivity, and an X-ray diffraction analysis. It is a neutral 1: 1 complex which is an insulator at room temperature, o,, = 2.5 x ohm-' cm-I. The complex crystallizes in the triclinic system, space group P 1 with cell constants a Ona prkpark un complexe cristallin du tttrathiafulvalbne et dup-dinitrobenzene et onl'a caracttrist par la rpe, la spectroscopie ir, la susceptibilitk magnktique de groupe, la conductivitk cd, et par l'analyse de diffraction de rayons X. C'est un complexe neutre 1: 1 qui est un isolant 2 la temptrature ambiante, o , , = 2,s x ohm-' cm-I. Le complexe cristallise dans le systkme triclinique et appartienta~grouped'es~ace P i a v e c a = 6,915

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“…Averaged values (mmm molecular symmetry) for the TMTTF cation are compared with those for neutral TTF (Cooper, Kenney, Edmonds, Nagel, Wudl & Coppens, 1971;Cooper, Edmonds, Wudl & Coppens, 1974) and the TTF cation in TTF-TCNQ (Kistenmacher, in Table 4. Several distinctive trends are observed in the sequence TTF ° to TTF-TCNQ to (TMT-(F)~.3(TCNQ)2" (1) a general increase of about 0.02 A per step in the bridging carbon-carbon bond [C(3)-C(3)']; (2) an increase of about the same order of magnitude in the exterior carbon-carbon bond [C(1 j-C(2)]; (3) a decrease in the S-C (bridging) distance and an increase in the S-C (exterior) bond.…”

Section: Discussion Of the Crystal Structure (A) Molecular Geometry Omentioning

confidence: 99%

Crystal structure and diffuse X-ray scattering of the 1.3:2 salt of 4,4',5,5'-tetramethyl-Δ^2,2-bis-1,3-dithiole [TMTTF] and 7,7,8,8-tetracyano-p-quinodimethane [TCNQ], a nonstoichiometric quasi one-dimensional organic conductor

Kistenmacher¹,

Phillips²,

Cowan³

et al. 1976

Acta Crystallogr Sect B

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The diffraction properties of an unusual radical cation-radical anion salt of composition (TMTTF)I.a(TCNQ)2 [(CIoHI2S4)l.a(C12H4N4)2] have been studied by single-crystal X-ray methods.The diffraction patterns show a strong subcell of monoclinic symmetry, space group P2~/n, with a= 3-819(1), b= 13.021 (6), c= 34.827 (14)/~, fl= 91"68 (3) °, V= 1731.1 ,~a, Z= 2 (for the empirical formula 1.3:2), Dm = 1"43 (1), De= 1"433 g cm -3. Intensities for 2731 reflections with l>a(I)were collected by counter methods in this subcell. The structure was solved by conventional heavy-atom Patterson and Fourier methods and has been refined by full-matrix least-squares calculations to a final R value of 0.127. The final weighted R value and goodness-of-fit are 0.114 and 2.5, respectively. The subcell structure is dominated by homologous columns of cations and anions running parallel to the short a axis. The interplanar spacing in the TCNQ columns is small, 3.24 /~, while the spacing in the TMTTF columns is 3.59/~ and corresponds to about the expected van der Waals separation. Among the columns of molecular cations and anions are channels of TMTTF residues (0.6 per subcell). The end-to-end alignment of the TMTTF residues in these channels approximately parallels the a axis and the stacks of cations and anions. Oscillation photographs about the a axis show a set of diffuse layer lines with a period corresponding to 10/3a. These are interpreted as arising from an incipient Peierls distortion of the columns, the first observed in an organic system. The material is a semiconductor with a room temperature conductivity of order 10 .Q-~ cm-~

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Crystal and molecular structure of the aromatic sulphur compound 2,2′-bi-1,3-dithiole. Evidence for d-orbital participation in bonding

Cited by 130 publications

References 0 publications

First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties

First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties

Preparation, properties, and X-ray crystal structure of a 1:1 complex of tetrathiafulvalene and p-dinitrobenzene

Crystal structure and diffuse X-ray scattering of the 1.3:2 salt of 4,4',5,5'-tetramethyl-Δ^2,2-bis-1,3-dithiole [TMTTF] and 7,7,8,8-tetracyano-p-quinodimethane [TCNQ], a nonstoichiometric quasi one-dimensional organic conductor

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Crystal and molecular structure of the aromatic sulphur compound 2,2′-bi-1,3-dithiole. Evidence for d-orbital participation in bonding

Cited by 130 publications

References 0 publications

First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties

First charge-transfer complexes between tetrathiafulvalene and 1,2,5-chalcogenadiazole derivatives: Design, synthesis, crystal structures, electronic and electrical properties

Preparation, properties, and X-ray crystal structure of a 1:1 complex of tetrathiafulvalene and p-dinitrobenzene

Crystal structure and diffuse X-ray scattering of the 1.3:2 salt of 4,4',5,5'-tetramethyl-Δ2,2-bis-1,3-dithiole [TMTTF] and 7,7,8,8-tetracyano-p-quinodimethane [TCNQ], a nonstoichiometric quasi one-dimensional organic conductor

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Crystal structure and diffuse X-ray scattering of the 1.3:2 salt of 4,4',5,5'-tetramethyl-Δ^2,2-bis-1,3-dithiole [TMTTF] and 7,7,8,8-tetracyano-p-quinodimethane [TCNQ], a nonstoichiometric quasi one-dimensional organic conductor