Tetrathiafulvalene

Structural formula
General
Surname	Tetrathiafulvalene
other names	TTF 1,4,5,8-tetrathiafulvalene Δ2,2-Bi-1,3-dithiol
Molecular formula	C 6 H 4 S 4
Brief description	orange solid
External identifiers / databases
CAS number 31366-25-3 EC number 250-593-7 ECHA InfoCard 100,045,979 PubChem 99451 Wikidata Q2179180
properties
Molar mass	204.35596 g / mol
Physical state	firmly
Melting point	116-119 ° C
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 317 P: 261-280-302 + 352-321-363-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetrathiafulvalene ( TTF ) is an organosulfur compound and organic semiconductor with the chemical formula (H ₂ C ₂ S ₂ C) ₂ . The substance is used as a material in molecular electronics, for example for the construction of organic field effect transistors (OFETs). Together with tetracyanoquinodimethane , TTF forms single crystals with good electrical conductivity .

history

The salt [TTF ⁺ ] Cl ^- was described in 1972 as a semiconductor. The charge-transfer salt [TTF] TCNQ was then shown to be a narrow band gap semiconductor . X-ray diffraction studies of [TTF] [TCNQ] showed stacks of partially oxidized TTF molecules adjacent to anionic stacks of TCNQ molecules. This “segregated stack” pattern was unexpected and is responsible for the characteristic electrical properties, ie high and anisotropic electrical conductivity . Numerous analogs of TTF have been made since these early discoveries. Well-studied analogs include tetramethyltetrathiafulvalene (Me ₄ TTF), tetramethylselenafulvalene (TMTSFs), and bis (ethylenedithio) tetrathiafulvalene (BEDT-TTF, CAS [66946-48-3]). Several tetramethyltetrathiafulvalene salts (also called Fabre salts) are also of some importance as organic superconductors .

Individual evidence

1. ↑ ^{a b} Data sheet Tetrathiafulvalene, 97% from Sigma-Aldrich , accessed on August 12, 2013 ( PDF ).
2. ↑ ^{a b c} Data sheet Tetrathiafulvalene, 97% from AlfaAesar, accessed on August 12, 2013 ( PDF )(JavaScript required) .
3. ↑ M. Bendikov, F. Wudl, DF Perepichka: Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics . In: Chemical Reviews . 104, No. 11, 2004, pp. 4891-4945. doi : 10.1021 / cr030666m . PMID 15535637 .
4. ↑ F. Wudl: From organic metals to superconductors: managing conduction electrons in organic solids . In: Accounts of Chemical Research . tape 17 , no. 6 , 1984, pp. 227-232 , doi : 10.1021 / ar00102a005 .
5. ↑ Fred Wudl, Darold Wobschall, Earl J. Hufnagel: Electrical conductivity by the bis (1,3-dithiole) -bis (1,3-dithiolium) system . In: Journal of the American Chemical Society . tape 94 , no. January 2 , 1972, ISSN  0002-7863 , pp. 670-672 , doi : 10.1021 / ja00757a079 .
6. ↑ John. Ferraris, DO Cowan, V. Walatka, JH Perlstein: Electron transfer in a new highly conducting donor-acceptor complex . In: Journal of the American Chemical Society . tape 95 , no. 3 , February 1973, ISSN  0002-7863 , p. 948-949 , doi : 10.1021 / ja00784a066 .
7. ↑ http://www.orgsyn.org/demo.aspx?prep=cv9p0072. Retrieved May 15, 2018 .