Novel highly extended and sulfur rich tetrathiafulvalene (TTF) derivatives through an unprecedented TTF core building process

Cariou, M.; Gorgues, A.; Boulle, C.; Desmars, O.; Gautier, Nicolas; Hudhomme, Piétrick

doi:10.1039/a805653f

Cited by 41 publications

(32 citation statements)

References 11 publications

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“…[5] The importance of these p-extended bis(1,3-dithiole) compounds has led to systematic studies of their chemical functionalization at both the anthracene [6] and dithiole units, [7] which has enabled the preparation of more sophisticated electron-donor TTF derivatives and novel electroactive donor-acceptor systems. [8] Compounds 3, [9] 4, [10] 5, [11] and 6 [6] are representative examples of combined TTF-exTTF systems, which possess multistage redox behavior. In contrast to the large number of studies on bis-and multi-TTF derivatives, [12] there are only a few recent examples of dimeric exTTF derivatives with quinoid structures, namely 7, [13] 8, [14] 9, [15] and 10.…”

Section: Introductionmentioning

confidence: 99%

Electronic Interactions in a New π‐Extended Tetrathiafulvalene Dimer

Díaz¹,

Illescas²,

Martín³

et al. 2006

Chemistry A European J

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The first pi-extended tetrathiafulvalene (exTTF) dimer in which the two exTTF units are covalently connected by 1,3-dithiole rings has been obtained in a multistep synthetic procedure involving the Ullmann cross-coupling reaction by using copper(I) thiophene-2-carboxylate (CuTC). The electronic spectrum reveals a significant electronic interaction between the exTTF units. The electrochemical study carried out by cyclic voltammetry in solution and in thin-layer conditions, and the electrochemical simulation and spectroelectrochemical (SEC) measurements confirm the electronic communication and show that the oxidation of dimer 14 occurs as two consecutive 2 e(-) processes D(0)-D(0)-->D(2+)-D(0)-->D(2+)-D(2+). Theoretical calculations, performed at the B3P86/6-31G* level, confirm the experimental findings and predict that 14(2+) exists as a delocalized D(.+)-D(.+) species in the gas phase and as a localized D(2+)-D(0) species in solution (CH(3)CN or CH(2)Cl(2)). Oxidation of 14(2+) forms the tetracation 14(4+) which is constituted by two aromatic anthracene units bearing four aromatic, almost orthogonal 1,3-dithiolium cations.

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Section: Introductionmentioning

confidence: 99%

Electronic Interactions in a New π‐Extended Tetrathiafulvalene Dimer

Díaz¹,

Illescas²,

Martín³

et al. 2006

Chemistry A European J

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“…According to our Horner-Wadsworth-Emmons methodology of TTF core building (15), by treatment of the llb with the phosphonate anion of 14, TTF Mono and diquinone C and D were fully characterized by usual methods, and in particular, we have undertaken preliminary electrochemical and spectroscopic studies on them. For instance, in cyclic voltammetry, they present the reversible oxidation and reduction peaks related to the TTF and quinone moieties respectively, at values consistent with those of their conjugated donor and acceptor moieties.…”

Section: Ttf -Quinone Assembliesmentioning

confidence: 99%

New Tetrathiafulvalene (TTF) Derivatives Linked to Various Acceptors for Advanced Materials

Gorgues

Kréher

Gautier

et al. 2002

Molecular Low Dimensional and Nanostructured Materials for Advanced Applications

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“…The reactivity of the vicinal bis(bromomethyl) group has been demonstrated with the possibility of generating the corresponding diene by reductive elimination 18,19 or to perform its transformation into the pyrrolo group. 20 The versatile synthetic reactivity of this group is now extended to the Arbuzov-type reaction to reach bis 15, 16 or tetrakis 17 phosphonate derivatives respectively.…”

Section: Methodsmentioning

confidence: 99%

“…In order to improve its purity, the resulting material was dissolved in CH 2 Cl 2 , filtered on silica gel using CH 2 Cl 2 as the eluent. , 100), 220 (45), 192 (18). Compound (35).…”

Section: 5-bis(dimethylphosphono)methyl-2-thioxo-13-dithiole (15)mentioning

confidence: 99%

“…17 The high reactivity of the phosphonate anion was finally demonstrated with the synthesis of spatial extended fused T-shaped TTF which involved a three-fold HWE olefination process (reaction IV). 18 We were interested in developing new phosphonate reagents derived from 1,3-dithiole or TTF moieties to reach highly sulfur-rich extended TTF-based architectures. Consequently, we now present a new approach to extend the TTF framework using HWE-type reagents (compounds 15-18).…”

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confidence: 99%

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New synthetic routes to highly-extended tetrathiafulvalenes

Hudhomme¹,

Sallé²,

Gautier³

et al. 2006

Arkivoc

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Dedicated to Prof. Armand LATTES on the occasion of his 50th anniversary of teaching and research activities and for his involvement as a President of the "Société Française de Chimie" AbstractVarious synthetic routes to highly extended tetrathiafulvalene (TTF) derivatives are presented. They generally involve a (poly)olefination reaction in the last step, thanks to Wittig-type or Horner-Wadsworth-Emmons (HWE) reactions. Two complementary strategies have been carried out by reacting a (poly)formyl-TTF with a phosphorous (P-ylide or phosphonate) reagent, or on the contrary, by the preparation of (poly)phosphonate-TTF derivatives prone to react with aldehydes. An X-ray structural determination of one of these systems confirms the high π-extension of such resulting TTF derivatives.

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Novel highly extended and sulfur rich tetrathiafulvalene (TTF) derivatives through an unprecedented TTF core building process

Cited by 41 publications

References 11 publications

Electronic Interactions in a New π‐Extended Tetrathiafulvalene Dimer

Electronic Interactions in a New π‐Extended Tetrathiafulvalene Dimer

New Tetrathiafulvalene (TTF) Derivatives Linked to Various Acceptors for Advanced Materials

New synthetic routes to highly-extended tetrathiafulvalenes

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