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tetrathiafulvalene
Sign in to saveAlso known as Delta(2),(2')-Bi-1,3-dithiole, 1,4,5,8-Tetrathiafulvalene, delta-2,2'-Bi-1,3-dithiole, delta-2:2'-Bis(1,3-dithiazole), TTF
Tetrathiafulvalene (TTF) is an organosulfur compound with the formula . It is the parent of many tetrathiafulvenes. Studies on these heterocyclic compound contributed to the development of molecular electronics, although no practical applications of TTF emerged. Over 10,000 scientific publications discuss TTF and its derivatives.
Chemical data
- Formula
- C6H4S4
- Molecular weight
- 204.4 g/mol
- IUPAC name
- 2-(1,3-dithiol-2-ylidene)-1,3-dithiole
- SMILES
- C1=CSC(=C2SC=CS2)S1
- InChIKey
- FHCPAXDKURNIOZ-UHFFFAOYSA-N
- XLogP
- 2.5
- Polar surface area
- 101 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 203.919584
- Image
- Sample of TTF.jpg
Show 4 more facts
- chemical formula
- C₆H₄S₄
- canonical SMILES
- C1=CSC(=C2SC=CS2)S1
- melting point
- 118.0
- Commons category
- Tetrathiafulvalene
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Preparation
- Redox properties
- History
- See also
- References
- Further reading
Tetrathiafulvalene (TTF) is an organosulfur compound with the formula . It is the parent of many tetrathiafulvenes. Studies on these heterocyclic compound contributed to the development of molecular electronics, although no practical applications of TTF emerged. Over 10,000 scientific publications discuss TTF and its derivatives.
==Preparation== The high level of interest in TTFs spawned many syntheses of TTF and its analogues. Most preparations entail the coupling of cyclic 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 (1,3-dithiole-2-thione), which is S-methylated and then reduced to give (1,3-dithiole-2-yl methyl thioether), which is treated as follows:
Excerpted from Wikipedia’s “tetrathiafulvalene” article, available under the CC BY-SA 4.0 licence.