New long-chain tetrathiafulvalene derivatives with a diacetylene group

Khodorkovsky, Vladimir; Tormos, Gregory V.; Neilands, O.; Kolotilo, N. V.; Il'chenko, A. Y.

doi:10.1016/s0040-4039(00)91591-0

Cited by 18 publications

(10 citation statements)

References 4 publications

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“…The solution electrochemistry of these new TTF derivatives was investigated using cyclic voltammetry in dichloromethane, at a platinum electrode (see Table ). The cyclic voltammograms of all four compounds ( 6a−d ) showed behavior typical of TTF derivatives, in which two reversible, or quasi reversible, redox waves were present. These waves corresponded to the sequential oxidation of the TTF core to form the radical−cationic (TTF •+ ) and dicationic (TTF 2+ ) species, respectively.…”

Section: Resultsmentioning

confidence: 99%

Thiophene-Functionalized TTF π-Electron Donors as Potential Precursors to Conducting Polymers and Organic Metals: Synthesis, Properties, Structure, and Electropolymerization Studies

Charlton

Underhill²,

Williams

et al. 1997

J. Org. Chem.

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The synthesis and physical properties of a series of novel thiophene-substituted TTF electron donors (6a-d) are described. The cyclic voltammograms of 6a-d exhibited two reversible one-electron redox waves, characteristic of TTF derivatives. Electropolymerization studies on compound 6a in nitrobenzene indicate that no polymer formed on the working electrode, but a blue-colored intermediate was observed diffusing away from the electrode. In addition, the single-crystal X-ray structure of compound 6d indicates that the central five-membered C(3)S(2) rings are buckled and the ethylenedithiolo fragment adopts a twisted chair conformation. The pendant thiophene moieties are highly flexible, and short intermolecular interactions of 3.49 Å (S.S) and 3.45 Å (S.C) exist in the unit cell, resulting in the formation of a chain structure along the c-axis.

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Section: Resultsmentioning

confidence: 99%

Thiophene-Functionalized TTF π-Electron Donors as Potential Precursors to Conducting Polymers and Organic Metals: Synthesis, Properties, Structure, and Electropolymerization Studies

Charlton

Underhill²,

Williams

et al. 1997

J. Org. Chem.

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“…For comparison, we have given a cyclic voltammogramm for tetrathiafulvalene obtained under the same conditions. The E 1 ox value for TTF is 0.51 V. For substituted tetrathiafulvalens, these values vary between 0.28 and 0.86 V. (vs. SCE) [17] . Thus, diazadiphosphapentalenes are not inferior to classical TTP‐based donors in terms of electron‐donating ability, but the oxidation processes of the studied DDPs are irreversible.…”

Section: Cyclic Voltammetrymentioning

confidence: 89%

3 a,6 a‐Diaza‐1,4‐Diphosphapentalenes: Synthesis and Complexation with the Organic π‐Acceptor 1,2,4,5‐Tetracyanobenzene

et al. 2023

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The reaction of PCl 3 with diethyl ketazine and 4-phenylcyclohexanone azine results in the formation of 1,4-dichloro-3a,6a-diaza-1,4-diphosphapentalenes which were reduced by magnesium in THF to give corresponding diazadiphosphapentalenes EtMeDDP and PhcHexDDP, containing two-coordinate phosphorus atoms. According to the CVA data, the new diazadiphosphapentalenes are strong electron donors showing oxidation peak potentials at 0.34 and 0.10 V, respectively, (vs. Ag/AgCl). Interaction of 1,2,4,5-tetracyanobenzene (TCNB) with the obtained diazadiphosphapentalenes in any stoichiometry produces sandwich complexes of the composition DDP-TCNB-DDP. Black-purple crystals of π-complexes contain infinite molecular chains with short P•••P contacts between DDP molecules and short (Csp 2 À H•••N) contacts between TCNB molecules. Calculations showed that each TCNB molecule is an acceptor of ~0.3e from two DDP molecules. Estimation of the HOMO-LUMO gap from the onset of optical absorption give values of 1.25 eV and 1.31 eV for [(EtMeDDP) 2 (TCNB)] and [(PhcHexDDP) 2 (TCNB)] respectively.

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“…Crystallization from toluene gave red needles of 1; yield: 0.743 g (62%). 1 Bis[2-(trimethylsilyl)ethynyl]-3,7-diphenyltetrathiafulvalene (2): 1 (0.600 g, 0.986 mmol) was dissolved in anhyd THF (20 mL). CuI (5 mol%; 9.37 mg, 0.0494 mmol), Pd(PPh 3 ) 4 (5 mol%; 57.0 mg, 0.0494 mmol) and NEt 3 (20 mL) were added, and then the mixture was stirred for a few minutes.…”

Section: Preparation Of New Tetrathiafulvalene (Ttf) Derivatives Withmentioning

confidence: 99%

“…Flash column chromatography (silica gel, toluene) and crystallization (toluene) gave red plates of 2; yield: 0.142 g (27%). 1…”

Section: Preparation Of New Tetrathiafulvalene (Ttf) Derivatives Withmentioning

confidence: 99%

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Preparation of New Tetrathiafulvalene (TTF) Derivatives with Two Functional Groups at Symmetrical Positions: 2,6-Diiodo-3,7-diphenyl-TTF, 2,6-Bis[2-(trimethylsilyl)-ethynyl]-3,7-diphenyl-TTF, and 2,6-Diethynyl-3,7-diphenyl-TTF

Shimizu¹,

Koizumi²,

Yamaguchi³

et al. 1998

Synthesis

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New long-chain tetrathiafulvalene derivatives with a diacetylene group

Cited by 18 publications

References 4 publications

Thiophene-Functionalized TTF π-Electron Donors as Potential Precursors to Conducting Polymers and Organic Metals: Synthesis, Properties, Structure, and Electropolymerization Studies

Thiophene-Functionalized TTF π-Electron Donors as Potential Precursors to Conducting Polymers and Organic Metals: Synthesis, Properties, Structure, and Electropolymerization Studies

3 a,6 a‐Diaza‐1,4‐Diphosphapentalenes: Synthesis and Complexation with the Organic π‐Acceptor 1,2,4,5‐Tetracyanobenzene

Preparation of New Tetrathiafulvalene (TTF) Derivatives with Two Functional Groups at Symmetrical Positions: 2,6-Diiodo-3,7-diphenyl-TTF, 2,6-Bis[2-(trimethylsilyl)-ethynyl]-3,7-diphenyl-TTF, and 2,6-Diethynyl-3,7-diphenyl-TTF

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