Bis(ethylenethio)tetrathiafulvalene (BET‐TTF), an organic donor with high electrical conductivity

Rovira, Concepció; Tarrés, Judit; Veciana, Jaume; Rovira, Meritxell; Novoa, Juan J.; Yang, Syaulan; Cowan, D. O.; Canadell, Enric

doi:10.1002/adma.19950071212

Cited by 26 publications

(20 citation statements)

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“…In this type of geometrical arrangement, the shortest S´´´S contacts are expected to be found between S atoms of neighboring molecules of the same stack or between S atoms of one stack and those of the adjacent stack. The other general packing motif is a T-shaped one, which is similar to that found in benzene, although in this case it sometimes involves individual molecules, whereas in other cases, like in the BEDT-TTF neutral crystal, [10] it involves pairs of molecules. From the point of view of the geometrical distribution of the S´´´S contacts, the two motifs are not so different, as in both cases for one atom the shortest contacts are nearly perpendicular to the plane of the other molecule.…”

Section: Resultsmentioning

confidence: 92%

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Strength and Directionality of the S⋅⋅⋅S Intermolecular Interactions Present in TTF-Based Molecular Crystals. A Combined Statistical and Ab Initio Study

Rovira¹,

Novoa²

1999

Chem. Eur. J.

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Abstract:The strength and directionality of the S´´´S interactions have been evaluated by combining the results from the statistical analysis of neutral and charge-transfer molecular crystals of the tetrathiafulvalene (TTF) family with those from Mùller ± Plesset (MP2) calculations on model systems. The model systems have been designed to represent the environment of the S´´´S interactions in these crystals. Our statistical analysis of the geometrical distribution of the S´´´S contacts in these crystals suggests that they are attractive and that there is a maximum probability for collinear S´´´S orientations. Small differences are found between the neutral and charge-transfer distributions. MP2 computations on the H 2 S dimer and functionalized XYS dimers oriented to present short S´´´S contacts show that the S´´´S interactions are attractive and quite anisotropic. Their strength depends significatively on the X and Y functional groups and can be of the order of À 1.5 kcal mol À1 for the p ± p interactions between the five-membered rings of the TTF molecule. Consequently, S´´´S interactions should contribute significantly to the cohesive energy of TTF-based crystals.

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Section: Resultsmentioning

confidence: 92%

“…[10] In the light of these facts, it seems natural to use neutral model dimers as starting models in our study of the intermolecular S´´´S interactions.…”

Section: Abstract In Spanishmentioning

confidence: 99%

Strength and Directionality of the S⋅⋅⋅S Intermolecular Interactions Present in TTF-Based Molecular Crystals. A Combined Statistical and Ab Initio Study

Rovira¹,

Novoa²

1999

Chem. Eur. J.

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“…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. Some selected examples are summarized in Table 4.…”

Section: Neutral Closed Shell Moleculementioning

confidence: 99%

“…Although they are semiconductive, the increased intermolecular interactions give rise to a high carrier mobility of 6-20 cm 2 V À1 s À1 (TOF: time of flight) for TTC n -TTF (n ¼ 8 and 10, single crystals), 68 for DT-TTF (single crystal, FET). 47 It appears that the unusually small band gap of 0.22 eV for 13 75 arises either from increased t owing to the special intermolecular interactions or from some extrinsic cause including impurity. LB films of 14 have been reported to be highly conductive without carrier doping (10 À2 S cm À1 ).…”

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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confidence: 99%

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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Bis(ethylenethio)tetrathiafulvalene (BET‐TTF), an organic donor with high electrical conductivity

Abstract: Scheme 2 range of analyte concentration. Thus, better tuning of hydrogen bond interactions will result in structure-breaking effects at lower analyte concentrations. VCH Rdagsgevell~chuft mhH 0-69469 Weinlirim, 1995 0935-9648/95/1212-1026 $ T 00+ 25,O Adv M a w 1995, 7, No 12

Cited by 26 publications

References 20 publications

Strength and Directionality of the S⋅⋅⋅S Intermolecular Interactions Present in TTF-Based Molecular Crystals. A Combined Statistical and Ab Initio Study

Strength and Directionality of the S⋅⋅⋅S Intermolecular Interactions Present in TTF-Based Molecular Crystals. A Combined Statistical and Ab Initio Study

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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