Tetrakis(methyltelluro)tetrathiafulvalene (TTeC1TTF), a high-mobility organic semiconductor

Inokuchi, Hiroo; Imaeda, Kenichi; Enoki, Toshiaki; Mori, Toshisada; Maruyama, Yusei; Saito, Gunzi; Okada, Naoko; Yamochi, Hideki; Seki, Kazuhiko; Higuchi, Yoshiki; Yasuoka, Noritake

doi:10.1038/329039a0

Cited by 76 publications

(23 citation statements)

References 8 publications

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“…Indeed, previous studies dealing with the tetrakis(telluromethyl)tetrathiafulvalene (MeTe) 4 TTF reported interesting results concerning the semiconducting properties of the compound in neutral state, very likely due to zigzag chains formed by Te···Te contacts. [32] The calculated band structure for complex 2, represented in Figure 5, shows a valence-band built up from the HOMO of the EDT fragment, with a dispersion of about 0.2 eV. …”

Section: Electrochemical and Theoretical Studiesmentioning

confidence: 99%

Electron‐Rich Organoantimony(III) Dithiolate Complexes

2004

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Electron‐rich dithiolene complexes of the antimony(III) PhSb moiety, formulated as [SbPh(dddt)] (1) (dddt: 5,6‐dihydro‐1,4‐ditthine‐2,3‐dithiolate) and [SbPh(EDT‐TTFS2)] (2) (EDT‐TTFS2: 4,5‐ethylenedithio‐tetrathiafulvalene‐4′,5′‐dithiolate), have been prepared by deprotection of the corresponding precursors and trapping of the intermediate dithiolates with PhSbCl2. Both complexes have been structurally characterized. The analysis of their single‐crystal X‐ray structures shows original supramolecular organizations governed by secondary Sb···S contacts, with distorted octahedral coordination geometries around the Sb center. Band‐structure calculations for complex 2 reveal only weak dispersion of the valence and conduction bands, with an energy gap of 1.68 eV. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Electrochemical and Theoretical Studiesmentioning

confidence: 99%

Electron‐Rich Organoantimony(III) Dithiolate Complexes

2004

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“…61 A use of heteroatomic contacts (chalcogenÁÁÁchalcogen, chalcogenÁÁÁnitrogen) is effective to increase conductivity as observed for TTeN by Yagubskii, Neilands, Balodis, et al, 28 TTeC 1 -TTF (Fig. 8) by Inokuchi, Saito, et al, 72 BTQBT (Fig. 2) and BTDA-TCNQ (11) by Yamashita et al, 26,27,73 2,5-bis(methylthio)TCNQ (12) by Zambounis et al, 74 and bis-(ethylenethio)-TTF (13) by Rovira et al 75 An extension of the %-moiety for TTP compounds is also effective to improve conductivity.…”

Section: Neutral Closed Shell Moleculementioning

confidence: 99%

Development of Conductive Organic Molecular Assemblies: Organic Metals, Superconductors, and Exotic Functional Materials

Saito¹,

Yoshida²

2007

Bulletin of the Chemical Society of Japan

370

127

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“…The transport properties of a few single crystals of neutral TTF derivatives have been measured, showing semiconductor character with a roomtemperature conductivity on the order of 10 -5 S/cm. [8][9][10] Additionally, organic thin films of TTF derivatives have been grown by vacuum deposition techniques, but only their morphology and nanomechanical properties have been studied. 11 However, TTF derivatives have never been used for the preparation of OFETs despite the fact that they are soluble in various solvents, easily chemically modified, and good electron donors.…”

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High Mobility of Dithiophene-Tetrathiafulvalene Single-Crystal Organic Field Effect Transistors

et al. 2004

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The processing characteristics of organic semiconductors make them potentially useful for electronic applications where low-cost, large area coverage, and structural flexibility are required. 1 Charge carrier mobility is a measure of the quality of organic semiconductors and is a primary factor that determines the performance of organic field effect transistors (OFETs). The highest mobilities are found in single crystals due to molecular ordering that permits good overlapping of the π-π orbitals. A mobility of 1.5 cm 2 /Vs was reported for pentacene, 2 and recently a mobility of 8 cm 2 /Vs was reported for rubrene. 3 These organic crystals were grown from the vapor phase in long and complex experiments. To progress in this field toward device applications, it is very important to search for new molecules that are able to act as organic semiconductors 4 and also to develop easy methods to grow single crystals or films. In this communication, we report on the clear observation of field effect hole mobility in single crystals of the organic semiconductor dithiophene-tetrathiafulvalene (DT-TTF, Figure 1a) grown by drop casting, a very simple method. The maximum mobility observed in these crystals was 1.4 cm 2 /Vs.Tetrathiafulvalene (TTF) and its derivatives are successfully used as building blocks for charge-transfer salts, giving rise to a multitude of organic conductors and superconductors. These conducting salts are prepared mainly as single crystals but also as thin films of nanocrystals supported on dielectric polymers. [5][6][7] The driving force in the crystallization of the salts is the π-π stacking, which permits, together with the S‚‚‚S interactions, an intermolecular electronic transfer responsible for their transport properties. The transport properties of a few single crystals of neutral TTF derivatives have been measured, showing semiconductor character with a roomtemperature conductivity on the order of 10 -5 S/cm. 8-10 Additionally, organic thin films of TTF derivatives have been grown by vacuum deposition techniques, but only their morphology and nanomechanical properties have been studied. 11 However, TTF derivatives have never been used for the preparation of OFETs despite the fact that they are soluble in various solvents, easily chemically modified, and good electron donors.DT-TTF is a particularly promising molecule because it is rigid and completely conjugated, having a low conformational freedom that favors stronger intermolecular interactions and, thus, higher carrier mobilities. Cyclic voltammetry measurements of DT-TTF show two separate reversible one-electron oxidations with E 1/2 1 and E 1/2 2 of 0.78 and 0.96 V, respectively (in DMF/0.1 M TBAPF 6 vs SCE). X-ray studies reveal that the DT-TTF molecules stack uniformly along the b axis in a herringbone pattern ( Figure 1a). 12 Moreover, it is seen that the sulfur atoms also promote interactions between the different DT-TTF stacks within the layer which can lead to electronic dimensionality enhancing 5 (d(S‚‚‚S) ) 3.55 and 3.61 Å). This cr...

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Tetrakis(methyltelluro)tetrathiafulvalene (TTeC1TTF), a high-mobility organic semiconductor

Abstract: ChemInform Abstract The title compound (V) is prepared by consecutive treatment of tetrathiafulvalene (I) with LDA, tellurium powder (II), and methyl iodide (IV).

Cited by 76 publications

References 8 publications

Electron‐Rich Organoantimony(III) Dithiolate Complexes

Electron‐Rich Organoantimony(III) Dithiolate Complexes

Development of Conductive Organic Molecular Assemblies: Organic Metals, Superconductors, and Exotic Functional Materials

High Mobility of Dithiophene-Tetrathiafulvalene Single-Crystal Organic Field Effect Transistors

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