51501-77-0

Basic information

• Product Name: TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE
• Synonyms: TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE;TMT-TTF;2-[4,5-bis(Methylthio)-1,3-dithiol-2-ylidene]-4,5-bis(methylthio)- 1,3-dithiole;Tetramethylthiotetrathiafulvalene;Tetrakis(methylthio)tetrathiafulvalene [Organic Electronic Material];4,4',5,5'-Tetra(methylthio)-Δ2,2'-bi(1,3-dithiole);4,4',5,5'-Tetrakis(methylthio)-Δ2,2'-bi(1,3-dithiol);Δ2,2'-Bi[4,5-bis(methylthio)-1,3-dithiol]
• CAS NO: 51501-77-0
• Molecular Formula: C₁₀H₁₂S₈
• Molecular Weight: 388.72
• Product Categories: Charge Transfer Complexes for Organic Metals;Donors (Charge Transfer Complexes);Functional Materials;TTF Derivatives
• Mol File: 51501-77-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 96 °C
• Boiling Point: 397.1°C at 760 mmHg
• Flash Point: 186.1°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 3.72E-06mmHg at 25°C
• Refractive Index: 1.808
• CAS DataBase Reference: TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE(51501-77-0)
• EPA Substance Registry System: TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE(51501-77-0)

Safety Data

• Hazardous Substances Data: 51501-77-0(Hazardous Substances Data)

Usage

Description

TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE, also known as Tetrakis(methylthio)tetrathiafulvalene (TMTTF), is a chemical compound characterized by a tetrathiafulvalene core with four methylthio groups attached to its four carbon atoms. TMTTF is recognized for its high stability and long-lived radical donor nature, making it a valuable component in the development of organic conductive materials and molecular electronics.

Uses

Used in Organic Conductive Materials:
TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE is used as a building block for the synthesis of organic conductive materials due to its stable and long-lived radical donor properties, which contribute to the enhanced electrical conductivity of these materials.
Used in Molecular Electronics:
In the field of molecular electronics, TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE is utilized as a key component in the design and construction of molecular-scale electronic devices, leveraging its unique molecular structure and electronic properties.
Used in Organic Photovoltaics:
TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE is employed as a material in organic photovoltaics for its potential to improve the efficiency and performance of solar cells, capitalizing on its ability to facilitate charge transport and generation.
Used in Molecular Magnets:
In the realm of molecular magnets, TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE is used as a component to explore its magnetic properties, with the aim of developing advanced materials with unique magnetic behaviors.
Used in Organic Semiconductors:
TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE is utilized in the development of organic semiconductors, where its electrical and magnetic properties are harnessed to create materials with improved semiconducting characteristics for use in various electronic applications.
Used in Advanced Electronic Devices and Materials:
TETRAKIS(METHYLTHIO)TETRATHIAFULVALENE is used as a promising candidate in the creation of advanced electronic devices and materials, owing to its interesting electrical and magnetic properties that can potentially enhance the performance and capabilities of these technologies.

InChI:InChI=1/C10H12S8/c1-11-5-6(12-2)16-9(15-5)10-17-7(13-3)8(14-4)18-10/h1-4H3

Upstream product

• 61485-46-9 4,5-bis(methylthio)-1,3-dithiol-2-one 
• 128457-00-1 4,5-ethylenedioxy-1,3-dithiole-2-thione 
• 144868-69-9 4,5-bis(p-acetoxybenzylsulfanyl)-1,3-dithiol-2-one 
• 49638-64-4 4,5-bis(methylthio)-1,3-dithiole-2-thione 
• 337533-84-3 5-(4'-bromophenyl)-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one 
• 337533-81-0 5-(4'-methoxyphenyl)-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one 
• 625851-32-3 6-(4'-bromophenyl)thieno[2,3-d][1,3]dithiol-2-one 
• 625851-31-2 6-(4'-methoxyphenyl)thieno[2,3-d][1,3]dithiol-2-one 
• 337533-79-6 5-phenyl-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one 

Relevant articles and documents

Porphyrins fused with strongly electron-donating 1,3-dithiol-2-ylidene moieties: Redox control by metal cation complexation and anion binding

A new class of redox-active free base and metalloporphyrins fused with the 1,3-dithiol-2-ylidene subunits present in tetrathiafulvalene, termed MTTFP (M = H2, Cu, Ni, Zn), have been prepared and characterized. The strong electron-donating properties of MTTFP were probed by electrochemical measurement and demonstrated that oxidation potentials can be tuned by metalation of the free base form, H2TTFP. X-ray crystal structures of H 2TTFP, ZnTTFP, and CuTTFP revealed that a severe saddle-shape distortion was observed with the dithiole rings bent out of the plane toward one another in the neutral form. In contrast, the structure of the two-electron oxidized species (CuTFFP2+) is planar, corresponding to a change from a nonaromatic to aromatic structure upon oxidation. A relatively large two-photon absorption (TPA) cross-section value of H2TTFP 2+ (1200 GM) was obtained for the free base compound, a value that is much higher than those typically seen for porphyrins (- and Br - as revealed by thermal electron-transfer between ZnTTFP and Li +-encapsulated C60 (Li+@C60) in benzonitrile, which was switched on by the addition of either Cl- or Br- (as the tetrabutylammonium salts). The X-ray crystal structure of Cl--bound ZnTTFP was determined and provided support for the strong binding between the Cl- anion and the Zn 2+ cation present in ZnTTFP.

Synthesis of Unsymmetrical Tetrakis(alkylsulfanyl)tetrathiafulvalene Derivatives

The p-acetoxybenzylsulfanyl protecting group is compatible with the triethylphosphite mediated cross-coupling of 4,5-bis(alkylsulfanyl)-1,3-dithiol-2-ones, providing access to bis(protected)tetrathiafulvalenes, and thus to tetrathiafulvalenedithiolate dia

Unsymmetrically Substituted Ethylenedioxytetrathiafulvalenes

Seven new electron donors, 4,5-ethylenedioxytetrathiafulvalenes where 4',5'-substituents are trimethylenedithio, ethylenedithio, methylenedithio, 2-oxatrimethylenedithio, methylthio, hydrogen and methyl carboxylate, are prepared, and their electrochemical properties are investigated.