Novel Dissymmetric Tetrathiafulvalenes as Precursors of Organic Metals: Synthesis, X-ray Crystal Structures, Electrochemical Properties and Study of Their Radical Cations

Ribera, E.; Veciana, Jaume; Molins, Elı́es; Mata, Ignasi; Wurst, Klaus; Rovira, Concepció

doi:10.1002/1099-0690(200008)2000:16<2867::aid-ejoc2867>3.0.co;2-w

Cited by 24 publications

(29 citation statements)

References 36 publications

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“…The low energy absorption of methylthio TTF + • (MeSTTF + •) is predicted at 729 nm in a reasonable agreement with the experimental value of 785 nm for the dihydrothieno-fused analog. 13 Noteworthy, this band was also ascribed to the p-dimer solely on the grounds of concentration dependence that might stem from any other kind of intermolecular interaction rather than from p-dimerization, as soon as no temperature/concentration anomalies of the EPR signal and appearance of the new p-dimer absorption bands were reported. Concentrated solutions ( > 10 23 M) of the cation radicals exhibit features of aggregation (intensities of additional absorption bands are counteranion and concentration dependent).…”

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confidence: 98%

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Do π-dimers of tetrathiafulvalene cation radicals really exist at room temperature?

et al. 2001

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The longest wave absorption band of the tetramethylthiotetrathiafulvalene cation radical, which is usually interpreted as a p-dimer band, is shown to be the intrinsic cation radical absorption, all studied cation radicals in solution at room temperature exist as paramagnetic monomers and only tetrathiafulvelene and tetramethyltetrathiafulvalene cation radicals undergo p-dimerization at low temperatures.

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confidence: 98%

“…§ For TTF• + and ET• + g-factors of 2.0081 and 2.0074 were determined in methylene chloride at 233 K 18 and rt. 13…”

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confidence: 99%

Do π-dimers of tetrathiafulvalene cation radicals really exist at room temperature?

et al. 2001

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“…In fact, it has been reported that the strongly acidic TFA could oxidize the TTF moiety to give its radical cation. 43 To prove this point, the isotropic solution electron paramagnetic resonance spectrum of the radical cation system was recorded at 298 K. As shown in Fig. 11, only one set of electron spin resonance signals was evidently observed at g = 1.9949 mT, which was in the region characteristic of the TTF radical cation.…”

Section: Multiple-stimulus-responsivenessmentioning

confidence: 88%

Monopyrrolotetrathiafulvalene–succinamide conjugates and their TCNQ charge transfer complex based supramolecular gels with multiple stimulus responsiveness

et al. 2014

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A series of monopyrrolotetrathiafulvalene-succinamide conjugates and their 7,7,8,8-tetracyano-p-quinodimethane (TCNQ) charge transfer (CT) complexes have been synthesized and investigated as new low-molecular mass organogelators. The gelation capability of these conjugates is highly dependent on the length of the alkyl chain of the terminal amide. Thus, only the short alkyl chain derivatives and could efficiently gelate cyclohexane and methylcyclohexane (MCH). Surprisingly, these gelators react with TCNQ to form stable CT complex gels in both cyclohexane and MCH. The FE-SEM images of the native gels reveal the characteristic gelation morphologies of microporous or fibrous structures, whereas the morphologies of CT complex gels show the fibrillar and globular aggregates in cyclohexane and MCH, respectively. SAXS study of the native gel and the CT complex gel of in cyclohexane suggests that the molecules maintain rectangular and hexagonal columnar molecular packing models in the gel phase, respectively. The native gels undergo a reversible gel-sol phase transition upon exposure to external stimuli, such as temperature and chemical oxidation/reduction. Alternatively, the corresponding CT complex gels exhibit a complicated response to external stimuli. Chemical oxidation by I2 results in the destruction of the gel state. However, neither Fe(3+) nor Cu(2+) can induce the collapse of the gel phase. Interestingly, all the gels show an irreversible gel-sol transition on successively triggering with trifluoroacetic acid and triethylamine. The reformation of the gel from the sol state is achieved just by the addition of water, showing the phase-selective gelation of the solvents from their mixtures with water.

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“…Theoretical calculation showed that molecule 134 had very low reorganization energy ( reorg ) values, helping to explain the high mobilities in FETs [83]. A series of TTF derivatives 135-140 were prepared [84], [85] and their single-crystal FETs were fabricated [86]. The FET performance significantly depended on the molecular packing in the crystals as well as the molecular reorganization energy.…”

Section: Tetrathiafulvalene Derivativesmentioning

confidence: 99%

Polycyclic Aromatic Compounds for Organic Field-effect Transistors:Molecular Design and Syntheses

2007

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This review is focused on current state of materials design and syntheses of organic semiconductors for thinfilm field effect transistors (FETs). Recently, high performance p-or n-type organic FETs with high charge carrier mobility, high ON-OFF current ratios and high stability have been achieved due to the improvement of materials syntheses. Intrinsic electronic properties, solid-state packing, stability, and the capability of easy processing are the main issues of molecular design of these semiconductors. Various polycyclic aromatic compounds such as oligoarenes, oligoacenes, tetrathiafulvalenes and disc-like polycyclic aromatic hydrocarbons are qualified as good candidates for FETs after accurate chemical tailoring. We will give an overview of most recent progress in the materials synthesis and the consequential device properties.Dedicated to Professor J. Fraser Stoddart on the occasion of his 65 th birthday.

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Novel Dissymmetric Tetrathiafulvalenes as Precursors of Organic Metals: Synthesis, X-ray Crystal Structures, Electrochemical Properties and Study of Their Radical Cations

Cited by 24 publications

References 36 publications

Do π-dimers of tetrathiafulvalene cation radicals really exist at room temperature?

Do π-dimers of tetrathiafulvalene cation radicals really exist at room temperature?

Monopyrrolotetrathiafulvalene–succinamide conjugates and their TCNQ charge transfer complex based supramolecular gels with multiple stimulus responsiveness

Polycyclic Aromatic Compounds for Organic Field-effect Transistors:Molecular Design and Syntheses

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