Preparation and properties of a tetracyanoquinodimethane fused with 1,2,5-thiadiazole units

Yamashita, Yoshiro; Suzuki, Takanori; Mukai, Toshio; Saito, Gunzi

doi:10.1039/c39850001044

Cited by 37 publications

(23 citation statements)

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“…The calculated lattice constants of the SMC unit cell ( a = b =9.9 Å and γ =81.5°) are almost identical to our STM observations, and the calculated distance for the S–N contacts (∼2.80 Å) is also well matched with that of the crystal structure of BTDA-TCNQ (∼3.04 Å; ref. 29 ).…”

Section: Resultsmentioning

confidence: 99%

“…The geometric and electronic structures of the SMC were investigated by means of scanning tunnelling microscopy/spectroscopy (STM/STS) and density functional theory (DFT) calculations. For this work, bis[1,2,5]thiadiazolotetracyanoquinodimethane (BTDA-TCNQ) 29 was used as the key building block with which to realize the SMCs, not only on a single crystal gold (Au) surface but also on a pre-annealed amorphous Au surface. Tetracyanoquinodimethane (TCNQ) is one of the strongest organic electron acceptors to have found wide use in organic devices, and forms a strongly bonded donor–acceptor complex with tetrathiafulvalene (TTF) 17 19 30 31 32 .…”

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confidence: 99%

“…Thus, we used a model system of BTDA-TCNQ, which integrates the structural properties of both TCNQ and TTF in a single molecule, for realizing self-organization into an ordered domain. BTDA-TCNQ is a TCNQ derivative fused with 1,2,5-thiadiazole rings, exerting strong intermolecular interactions in a planar fashion to form network structures in the single crystal 29 and even in its charge-transfer crystals 33 34 . The rhombic structure of BTDA-TCNQ exhibits twofold symmetry with two mirror planes, allowing perpendicular alignment of two electrostatically opposite symmetry axes consisting of electronegative and electropositive end groups, respectively.…”

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Seamless growth of a supramolecular carpet

et al. 2016

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Organic/metal interfaces play crucial roles in the formation of intermolecular networks on metal surfaces and the performance of organic devices. Although their purity and uniformity have profound effects on the operation of organic devices, the formation of organic thin films with high interfacial uniformity on metal surfaces has suffered from the intrinsic limitation of molecular ordering imposed by irregular surface structures. Here we demonstrate a supramolecular carpet with widely uniform interfacial structure and high adaptability on a metal surface via a one-step process. The high uniformity is achieved with well-balanced interfacial interactions and site-specific molecular rearrangements, even on a pre-annealed amorphous gold surface. Co-existing electronic structures show selective availability corresponding to the energy region and the local position of the system. These findings provide not only a deeper insight into organic thin films with high structural integrity, but also a new way to tailor interfacial geometric and electronic structures.

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Seamless growth of a supramolecular carpet

et al. 2016

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“…Formation of their 1:1 CT complexes with para -xylene, durene, 2,6- and 2,7-dimethylnaphthalene has been observed and their crystal structures have been studied in detail [96]. Later, a number of CT complexes of 65a with tetrathiatetracene (TTT; IUPAC name: tetraceno[5,6-cd:11,12-c’d’]bis[1,2]dithiole), TTF and its derivatives, and aromatic amines were prepared [179,180].…”

Section: Charge-transfer Complexes and Radical-ion Saltsmentioning

confidence: 99%

Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen π-Heterocycles as Electron Acceptors

et al. 2013

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Recent progress in the design, synthesis and characterization of chalcogennitrogen π-heterocycles, mostly 1,2,5-chalcogenadiazoles (chalcogen: S, Se and Te) and their fused derivatives, possessing positive electron affinity is discussed together with their use in preparation of charge-transfer complexes and radical-anion salts-candidate building blocks of molecule-based electrical and magnetic functional materials.

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“…2 The redox cycle of BTDA-TCNQ, including hydrogen and proton transfer, is considered to be as shown in Scheme 1. Dihydro-BTDA-TCNQ (H2BTDA) is a derivative of benzo[ 1,2-c : 4,5-c']bis [ 1,2,5]thiadiazole (l), an interesting hypervalent sulphur-nitrogen heterocycle. In order to clarify the redox cycle to discover the effect of the novel heterocyclic skeleton of (l), we have prepared BTDA2-and H2BTDA, and investigated their properties.…”

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Preparation and properties of the dianion and the dihydro derivative of the bis[1,2,5]thiadiazolo derivative of tetracyanoquinodimethane

Yamashita¹,

Suzuki²,

Mukai³

1987

J. Chem. Soc., Chem. Commun.

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The dianion of the bis[l,2,5]thiadiazolo derivative of tetracyanoquinodimethane (BTDA-TCNQ) was isolated as a stable sodium salt; the dihydro derivative of BTDA-TCNQ, containing the benzo[l,2-c: 4,5-~']bis[l,2,5]thiadiazole skeleton, was found to be a strong dibasic acid.Recently we have prepared the bis[ 1,2,5]thiadiazolo derivative of tetracyanoquinodimethane (BTDA-TCNQ) ,i. a new acceptor which forms highly conductive complexes with donors. 1 The presence of thiadiazole rings enlarges the n-electron system and reduces Coulombic repulsion, which is reflected in the smaller log K,,, value (8.10) as compared with that of TCNQ (9.31).1 Therefore, the dianion of BTDA-TCNQ (BTDA2-) was expected to be persistent, in contrast t Benzo[l,2-c : 4,5-c']bis[ 1,2,5]thiadiazole-4,8-diylidenedi(malononitrile).

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Preparation and properties of a tetracyanoquinodimethane fused with 1,2,5-thiadiazole units

Abstract: Bis[l,2,5]thiadiazolo-tetracyanoquinodimethane (1) was prepared and found to form a highly conductive complex with tetrathianaphthacene.

Cited by 37 publications

References 2 publications

Seamless growth of a supramolecular carpet

Seamless growth of a supramolecular carpet

Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen π-Heterocycles as Electron Acceptors

Preparation and properties of the dianion and the dihydro derivative of the bis[1,2,5]thiadiazolo derivative of tetracyanoquinodimethane

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