4,5-Ethylenedioxy-4′,5′-ethylenedithiotetrathiafulvalene (EOET): a new unsymmetrical electron donor

Kini, A. M.; Mori, Takehiko; Geiser, U.; Budz, Sandra M.; Williams, Jack M.

doi:10.1039/c39900000647

Cited by 31 publications

(8 citation statements)

References 13 publications

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“…. These results indicate that the replacement of one sulfur atom with oxygen slightly enhances the electron-donating ability, but scarcely affects the on-site Coulomb repulsion, similar to the electrochemical tendency found among BEDT-TTF and its oxygen-substituted analogues [38,42].…”

Section: Synthesis Molecular Structure and Electrochemical Propertiesupporting

confidence: 57%

Chemical Modifications of BDH-TTP [2,5-Bis(1,3-dithiolan-2-ylidene)-1,3,4,6-tetrathiapentalene]: Control of Electron Correlation

Yamada

Akutsu

2012

Crystals

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Organic molecular conductors with a strongly correlated electron system, in which the itinerancy of electrons (or holes) and the electron correlation (U/W, U, the on-site Coulomb repulsion, W, the bandwidth) compete with each other, are promising candidates for achieving superconductivity and also for exploring remarkable physical properties induced by external stimuli such as pressure, light, voltage and current. Our synthetic approach to the construction of strongly correlated organic electron systems is based on chemical modifications to the donor molecule BDH-TTP [2,5-bis(1,3-dithiolan-2-ylidene)-1,3,4,6-tetrathiapentalene] capable of producing metallic CT (charge-transfer) salts stable down to low temperatures (4.2-1.5 K). This aims at enhancing the electron correlation in the itinerant electron system by decreasing the bandwidth. Chemical modifications of BDH-TTP such as ring expansion of two outer dithiolane rings, replacement of one sulfur atom in an outer dithiolane ring with an oxygen atom and introduction of two methyl substituents into an outer ditiolane ring led to BDA-TTP [2,5-bis(1,3-dithian-2-ylidene)-1,3,4,6-tetrathiapentalene], DHOT-TTP [2-(1,3-dithiolan-2-ylidene)-5-(1,3-oxathiolan-2-ylidene)-1,3,4,6-tetrathiapentalene] and DMDH-TTP [2-(4,5-dimethyl-1,3-dithiolan-2-ylidene)-5-(1,3-dithiolan-2-ylidene)-1,3,4,6-tetrathiapentalene], respectively. In this review, the physical properties and the crystal and electronic structures of molecular conductors derived from these donor molecules will be described. OPEN ACCESSCrystals 2012, 2 813

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Section: Synthesis Molecular Structure and Electrochemical Propertiesupporting

confidence: 57%

Chemical Modifications of BDH-TTP [2,5-Bis(1,3-dithiolan-2-ylidene)-1,3,4,6-tetrathiapentalene]: Control of Electron Correlation

Yamada

Akutsu

2012

Crystals

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“…One of the methods is the introduction of bulky substituents. For example, the substitution of one of the ethylenedioxy groups by an ethylenedithio group affords ethylenedioxyethylenedithio-TTF (EOET), 3 which shows a weak self-assembling ability compared with BO. 4 The radical cation salts of EOET exhibit a variety of donor packing patterns and electronic properties depending on the counter anions.…”

Section: Introductionmentioning

confidence: 99%

Formation of two-dimensional metals by weak intermolecular interactions based on the asymmetric EDO-TTF derivatives

et al. 2008

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Two mono-substituted EDO-TTF derivatives, 4,5-ethylenedioxy-4 0 -methyl-TTF (MeEDO-TTF, 2) and 4,5-ethylenedioxy-4 0 -methylthio-TTF (MeSEDO-TTF, 3), were synthesized in the moderate yields. These two donors showed similar electronic structures of the p-electron systems to that of the parent molecule EDO-TTF, according to the cyclic voltammetry and UV-vis spectroscopy. Despite their different compositions, the radical cation salts of these two donors exhibited similar optical spectra with a low-lying absorption band at around 3.3 Â 10 3 cm À1 , which was consistent with their good conductivities at room temperature. The transport properties of these salts ranged from stable metals, metal-insulator transition systems, to semiconductors. Most of the radical cation salts showed Pauli paramagnetic behavior at around room temperature. The crystal structures of the stable metallic salts, (MeEDO-TTF) 2 X (X ¼ BF 4 , ClO 4 ), exhibited a novel donor packing pattern, and the calculated band structures showed two-dimensional feature, consistent with their transport properties.

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“…Data for 5 'H N M R 6 3.20 (m, 2H), 3.29 (s, 4H), 4.45 (m, 2H); 13C NMR: 826. 8, 31.0, 68.5, 91.6, 109.8, 111.3, 114.3, 114.6, 136.3 The (3) A, p= 93.02(4)", U = 1409.1 (6) A', T = 293i1 K, Z = 4, D, = 1.737 gem-', i = 0.71073 A, p (Mo-Ka) = 1.100 mm. ', analytical absorption correction; transmission range 0.4148-0.7107, (sinf?/A),,,ax = 0.7056 A-', 2171 reflections with I tOo(I), 41 restraints and 17.5 parameters, S = 1.0191, wR2 = 0.1671, R1 (I > 2s(I)) = 0.0565.…”

mentioning

confidence: 99%

Rapid switching solid state electrochromic devices based on complementary conducting polymer films

et al. 1996

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New electrochromic materials (ECMs) must exhibit rapid response times, long‐term stability, and a large difference in percentage transmittance between the bleached and colored states. The design, fabrication, and characterization of fast, solid‐state, dual conducting polymer EC devices that utilize PEDOT (see Figure) as the cathodically coloring material are described, following background information on ECMs. magnified image

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4,5-Ethylenedioxy-4′,5′-ethylenedithiotetrathiafulvalene (EOET): a new unsymmetrical electron donor

Cited by 31 publications

References 13 publications

Chemical Modifications of BDH-TTP [2,5-Bis(1,3-dithiolan-2-ylidene)-1,3,4,6-tetrathiapentalene]: Control of Electron Correlation

Chemical Modifications of BDH-TTP [2,5-Bis(1,3-dithiolan-2-ylidene)-1,3,4,6-tetrathiapentalene]: Control of Electron Correlation

Formation of two-dimensional metals by weak intermolecular interactions based on the asymmetric EDO-TTF derivatives

Rapid switching solid state electrochromic devices based on complementary conducting polymer films

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