Names | |
---|---|
Preferred IUPAC name 2,2′-Bi(1,3-dithiolylidene) | |
Other names Δ2,2-Bi-1,3-dithiole | |
Identifiers | |
3D model (JSmol) | |
1282106 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.045.979 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H4S4 | |
Molar mass | 204.34 g·mol−1 |
Appearance | Yellow solid |
Melting point | 116 to 119 °C (241 to 246 °F; 389 to 392 K) |
Boiling point | Decomposes |
Insoluble | |
Solubility in organic solvents | Soluble[ vague ] |
Structure | |
0 D | |
Hazards [1] | |
Occupational safety and health (OHS/OSH): | |
Main hazards | combustible |
GHS labelling: | |
Warning | |
H317 | |
P261, P280, P302+P352, P333+P313, P363, P501 | |
Related compounds | |
Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Tetrathiafulvalene (TTF) is an organosulfur compound with the formula (C3H2S2)2. Studies on this heterocyclic compound contributed to the development of molecular electronics. TTF is related to the hydrocarbon fulvalene, (C5H4)2, by replacement of four CH groups with sulfur atoms. Over 10,000 scientific publications discuss TTF and its derivatives. [2]
The high level of interest in TTFs has spawned the development of many syntheses of TTF and its analogues. [2] Most preparations entail the coupling of cyclic C3S2 building blocks such as 1,3-dithiole-2-thion or the related 1,3-dithiole-2-ones. For TTF itself, the synthesis begins with the cyclic trithiocarbonate H2C2S2C=S (1,3-dithiole-2-thione), which is S-methylated and then reduced to give H2C2S2CH(SCH3) (1,3-dithiole-2-yl methyl thioether), which is treated as follows: [3]
Bulk TTF itself has unremarkable electrical properties. Distinctive properties are, however, associated with salts of its oxidized derivatives, such as salts derived from TTF+.
The high electrical conductivity of TTF salts can be attributed to the following features of TTF:
Each dithiolylidene ring in TTF has 7π electrons: 2 for each sulfur atom, 1 for each sp2 carbon atom. Thus, oxidation converts each ring to an aromatic 6π-electron configuration, consequently leaving the central double bond essentially a single bond, as all π-electrons occupy ring orbitals.
The salt [TTF+
]Cl−
was reported to be a semiconductor in 1972. [5] Subsequently, the charge-transfer salt [TTF]TCNQ was shown to be a narrow band gap semiconductor. [6] X-ray diffraction studies of [TTF][TCNQ] revealed stacks of partially oxidized TTF molecules adjacent to anionic stacks of TCNQ molecules. This "segregated stack" motif was unexpected and is responsible for the distinctive electrical properties, i.e. high and anisotropic electrical conductivity. Since these early discoveries, numerous analogues of TTF have been prepared. Well studied analogues include tetramethyltetrathiafulvalene (Me4TTF), tetramethylselenafulvalenes (TMTSFs), and bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF, CAS [66946-48-3]). [7] Several tetramethyltetrathiafulvalene salts (called Fabre salts) are of some relevance as organic superconductors.
Organic electronics is a field of materials science concerning the design, synthesis, characterization, and application of organic molecules or polymers that show desirable electronic properties such as conductivity. Unlike conventional inorganic conductors and semiconductors, organic electronic materials are constructed from organic (carbon-based) molecules or polymers using synthetic strategies developed in the context of organic chemistry and polymer chemistry.
Conductive polymers or, more precisely, intrinsically conducting polymers (ICPs) are organic polymers that conduct electricity. Such compounds may have metallic conductivity or can be semiconductors. The main advantage of conductive polymers is that they are easy to process, mainly by dispersion. Conductive polymers are generally not thermoplastics, i.e., they are not thermoformable. But, like insulating polymers, they are organic materials. They can offer high electrical conductivity but do not show similar mechanical properties to other commercially available polymers. The electrical properties can be fine-tuned using the methods of organic synthesis and by advanced dispersion techniques.
Polythiophenes (PTs) are polymerized thiophenes, a sulfur heterocycle. The parent PT is an insoluble colored solid with the formula (C4H2S)n. The rings are linked through the 2- and 5-positions. Poly(alkylthiophene)s have alkyl substituents at the 3- or 4-position(s). They are also colored solids, but tend to be soluble in organic solvents.
In chemistry, charge-transfer (CT) complex, or electron-donor-acceptor complex, describes a type of supramolecular assembly of two or more molecules or ions. The assembly consists of two molecules that self-attract through electrostatic forces, i.e., one has at least partial negative charge and the partner has partial positive charge, referred to respectively as the electron acceptor and electron donor. In some cases, the degree of charge transfer is "complete", such that the CT complex can be classified as a salt. In other cases, the charge-transfer association is weak, and the interaction can be disrupted easily by polar solvents.
Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH3CH2−O−C(=O)−N=N−C(=O)−O−CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.
An electron acceptor is a chemical entity that accepts electrons transferred to it from another compound. Electron acceptors are oxidizing agents.
Dithiolene metal complexes are complexes containing 1,2-dithiolene ligands. 1,2-Dithiolene ligands, a particular case of 1,2-dichalcogenolene species along with 1,2-diselenolene derivatives, are unsaturated bidentate ligand wherein the two donor atoms are sulfur. 1,2-Dithiolene metal complexes are often referred to as "metal dithiolenes", "metallodithiolenes" or "dithiolene complexes". Most molybdenum- and tungsten-containing proteins have dithiolene-like moieties at their active sites, which feature the so-called molybdopterin cofactor bound to the Mo or W.
Tetracyanoquinodimethane (TCNQ) is an organic compound with the chemical formula (N≡C−)2C=C6H4=C(−C≡N)2. It is an orange crystalline solid. This cyanocarbon, a relative of para-quinone, is an electron acceptor that is used to prepare charge transfer salts, which are of interest in molecular electronics.
Borohydride refers to the anion [BH4]−, which is also called tetrahydridoborate, and its salts. Borohydride or hydroborate is also the term used for compounds containing [BH4−nXn]−, where n is an integer from 0 to 3, for example cyanoborohydride or cyanotrihydroborate [BH3(CN)]− and triethylborohydride or triethylhydroborate [BH(CH2CH3)3]−. Borohydrides find wide use as reducing agents in organic synthesis. The most important borohydrides are lithium borohydride and sodium borohydride, but other salts are well known. Tetrahydroborates are also of academic and industrial interest in inorganic chemistry.
A molecular solid is a solid consisting of discrete molecules. The cohesive forces that bind the molecules together are van der Waals forces, dipole–dipole interactions, quadrupole interactions, π–π interactions, hydrogen bonding, halogen bonding, London dispersion forces, and in some molecular solids, coulombic interactions. Van der Waals, dipole interactions, quadrupole interactions, π–π interactions, hydrogen bonding, and halogen bonding are typically much weaker than the forces holding together other solids: metallic, ionic, and network solids. Intermolecular interactions typically do not involve delocalized electrons, unlike metallic and certain covalent bonds. Exceptions are charge-transfer complexes such as the tetrathiafulvane-tetracyanoquinodimethane (TTF-TCNQ), a radical ion salt. These differences in the strength of force and electronic characteristics from other types of solids give rise to the unique mechanical, electronic, and thermal properties of molecular solids.
Trimethyl phosphite is an organophosphorus compound with the formula P(OCH3)3, often abbreviated P(OMe)3. It is a colorless liquid with a highly pungent odor. It is the simplest phosphite ester and finds used as a ligand in organometallic chemistry and as a reagent in organic synthesis. The molecule features a pyramidal phosphorus(III) center bound to three methoxy groups.
Charge ordering (CO) is a phase transition occurring mostly in strongly correlated materials such as transition metal oxides or organic conductors. Due to the strong interaction between electrons, charges are localized on different sites leading to a disproportionation and an ordered superlattice. It appears in different patterns ranging from vertical to horizontal stripes to a checkerboard–like pattern , and it is not limited to the two-dimensional case. The charge order transition is accompanied by symmetry breaking and may lead to ferroelectricity. It is often found in close proximity to superconductivity and colossal magnetoresistance.
Organoruthenium chemistry is the chemistry of organometallic compounds containing a carbon to ruthenium chemical bond. Several organoruthenium catalysts are of commercial interest and organoruthenium compounds have been considered for cancer therapy. The chemistry has some stoichiometric similarities with organoiron chemistry, as iron is directly above ruthenium in group 8 of the periodic table. The most important reagents for the introduction of ruthenium are ruthenium(III) chloride and triruthenium dodecacarbonyl.
Oxazoline is a five-membered heterocyclic organic compound with the formula C3H5NO. It is the parent of a family of compounds called oxazolines, which contain non-hydrogenic substituents on carbon and/or nitrogen. Oxazolines are the unsaturated analogues of oxazolidines, and they are isomeric with isoxazolines, where the N and O are directly bonded. Two isomers of oxazoline are known, depending on the location of the double bond.
Croconate violet or 1,3-bis(dicyanomethylene)croconate is a divalent anion with chemical formula C
11N
4O2−
3 or ((N≡C−)2C=)2(C5O3)2−. It is one of the pseudo-oxocarbon anions, as it can be described as a derivative of the croconate oxocarbon anion C
5O2−
5 through the replacement of two oxygen atoms by dicyanomethylene groups =C(−C≡N)2. Its systematic name is 3,5-bis(dicyanomethylene)-1,2,4-trionate. The term croconate violet as a dye name specifically refers to the dipotassium salt K
2C
11N
4O
3.
Rhodocene is a chemical compound with the formula [Rh(C5H5)2]. Each molecule contains an atom of rhodium bound between two planar aromatic systems of five carbon atoms known as cyclopentadienyl rings in a sandwich arrangement. It is an organometallic compound as it has (haptic) covalent rhodium–carbon bonds. The [Rh(C5H5)2] radical is found above 150 °C (302 °F) or when trapped by cooling to liquid nitrogen temperatures (−196 °C [−321 °F]). At room temperature, pairs of these radicals join via their cyclopentadienyl rings to form a dimer, a yellow solid.
Cyclobis(paraquat-p-phenylene) belongs to the class of cyclophanes, and consists of aromatic units connected by methylene bridges. It is able to incorporate small guest molecule and has played an important role in host–guest chemistry and supramolecular chemistry.
1,2,4,5-Tetrabromobenzene is an aryl bromide and a four-substituted bromobenzene with the formula C6H2Br4. It is one of three isomers of tetrabromobenzene. The compound is a white solid. 1,2,4,5-Tetrabromobenzene is an important metabolite of the flame retardant hexabromobenzene.
Transition metal nitrile complexes are coordination compounds containing nitrile ligands. Because nitriles are weakly basic, the nitrile ligands in these complexes are often labile.
Sodium 1,3-dithiole-2-thione-4,5-dithiolate is the organosulfur compound with the formula Na2C3S5, abbreviated Na2dmit. It is the sodium salt of the conjugate base of the 4,5-bis(sulfanyl)-1,3-dithiole-2-thione. The salt is a precursor to dithiolene complexes and tetrathiafulvalenes.
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