Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)

Dautel, Olivier; Larsen, Jan; Fourmigué, Marc

doi:10.1039/b001996h

Cited by 10 publications

(8 citation statements)

References 12 publications

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“…The value calculated for b, the folding angle of the dithiin rings, is 48.1u in good agreement with the average X-ray value (46.2u). These values are slightly larger than the X-ray value reported for the 1,4-dithiine molecule (43u), 45 and are similar to those observed for related TTF derivatives such as bis(vinylenedithio)tetrathiafulvalene (BVDT-TTF: 48.7u) 46 and vinylenedithiotetrathiafulvalene (VDT-TTF: 48.6u), 47 for which the TTF nucleus is fused to 1,4-dithiin rings.…”

Section: Theoretical Calculationssupporting

confidence: 76%

A new series of π-extended tetrathiafulvalene derivatives incorporating fused furanodithiino and thienodithiino units: a joint experimental and theoretical study

et al. 2004

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Section: Theoretical Calculationssupporting

confidence: 76%

A new series of π-extended tetrathiafulvalene derivatives incorporating fused furanodithiino and thienodithiino units: a joint experimental and theoretical study

et al. 2004

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“…[20c, 26] Molecule G has a chair-like TTF core (Figure 7 c) and its symmetry conforms to pseudo-C 2h , resembling those of BVDT-TTF and VDT-TTF. [27] Although C 2v and C 2h symmetries of aryl-fused TTFs have been separately observed in the solid state, [20c, 26, 27] the co-existence of both conformations is only postulated in solution. [20c] To the best of our knowledge, this is the first observation of the coexistence of both C 2v and C 2h conformations in one crystal of an aryl-fused TTF in the neutral state.…”

Section: Ttf-34mentioning

confidence: 99%

Molecular and Crystal Structure Diversity, and Physical Properties of Tetrathiafulvalene Derivatives Substituted with Various Aryl Groups through Sulfur Bridges

Sun

Shao

et al. 2013

Chemistry A European J

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A library of tetrathiafulvalene (TTF) derivatives (TTF-1-TTF-47) bearing aryl groups attached through sulfur bridges has been created. The peripheral aryl groups exert a significant influence on both the electronic and crystallographic properties of the resulting TTFs. These TTFs display broad absorption bands at 400-500 nm caused by intramolecular charge-transfer transitions between the aryl groups and central TTF core, and their first redox potentials increase with increasing electron-withdrawing ability of the aryl groups. In their crystal structures (22 examples), the central TTF cores adopt various conformations, including chair, half-chair, boat, and planar conformations. Moreover, the peripheral aryl groups exhibit multiple alignment modes with respect to the central TTF core, caused by their rotation about the two C-S bonds of the sulfur bridges. The packing motifs of these TTFs depend on both the nature of the aryl groups and their spatial alignment modes. Driven by intermolecular van der Waals forces and π-π interactions between the aryl groups and between the aryl groups and the TTF core, these TTFs adopt various packing structures. As a typical example, TTF-14, an achiral molecule, adopts a helical chain stack through intermolecular atomic close contacts. Moreover, the molecular geometries and packing motifs of these TTFs are sensitive to environmental variation, as exemplified by TTF-28, which adopts three distinct crystal modifications with diverse molecular geometries and stacking modes under different crystallization conditions. This work indicates that these TTFs are potential candidates as electronic materials, as well as functional building blocks for supramolecular assembly.

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“…Fourmigue ´et al prepared the mono-and trans-dichloro substituted oxo compounds 91 and 92 in very good yields by treatment of the unsubstituted oxo compound 90 with one or two equivalents of sulfuryl chloride in carbon tetrachloride. 55 Homocoupling of oxo compounds gave the diand tetra-chloro functionalised ET derivatives 94 and 95 as mixtures of isomers in high yields (Scheme 12). 56 2 salt is strongly one dimensional.…”

Section: Halo-substituted Et Derivativesmentioning

confidence: 99%

Substituted BEDT-TTF derivatives: synthesis, chirality, properties and potential applications

Wallis

Griffiths

2005

J. Mater. Chem.

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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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Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)

Cited by 10 publications

References 12 publications

A new series of π-extended tetrathiafulvalene derivatives incorporating fused furanodithiino and thienodithiino units: a joint experimental and theoretical study

A new series of π-extended tetrathiafulvalene derivatives incorporating fused furanodithiino and thienodithiino units: a joint experimental and theoretical study

Molecular and Crystal Structure Diversity, and Physical Properties of Tetrathiafulvalene Derivatives Substituted with Various Aryl Groups through Sulfur Bridges

Substituted BEDT-TTF derivatives: synthesis, chirality, properties and potential applications

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