Tetramethyltetraselenafulvalene
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| IUPAC name
2-(4,5-dimethyl-1,3-diselenol-2-ylidene)-4,5-dimethyl-1,3-diselenole
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.152.166 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C10H12Se4 | |
| Molar mass | 448.090 g·mol−1 |
| Appearance | purple powder |
| Density | g/cm3 |
| Melting point | 275 °C (527 °F; 548 K) |
| Boiling point | 338.8 °C (641.8 °F; 612.0 K) |
| Hazards | |
| GHS labelling: | |
| Danger | |
| H301, H331, H373, H410 | |
| P260, P264, P273, P301, P304, P310, P311, P314, P340 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Tetramethyltetraselenafulvalene is an organic compound of selenium, carbon, and hydrogen with the chemical formula C10H12Se4.[1] The compound belongs to the group of organoselene compounds and heterofulvalenes.[2][3]
Structure
TMTSF features a central fulvalene core where each of the two five-membered rings contains two selenium atoms in 1,3-positions—analogous to the sulfur atoms in tetramethyltetrathiafulvalene (TMTTF). The selenium atoms form C=Se double bonds within the heterocyclic rings, with methyl groups at the 4,5-positions of each ring.[4]
This structure enables TMTSF's electron donor properties in charge-transfer salts.
Synthesis
TMTSF can be obtained by substituting the hydrogen atoms of tetraselenafulvalene with methyl groups.[5] Other methods avoiding the use of gaseous hydrogen selenide are also known.[6]
Physical properties
Tetramethytetraselenafulvalene is a toxic, solid compound generally used in molecular electronics. The compound forms purple powder.[7]
Uses
The compound is used as an electron donor to form charge-transfer salts, most notably conducting Bechgaard salts. It is known for creating the first organic superconductors (e.g., (TMTSF)2PF6) and functions as a semiconductor.[8][9]
References
- ^ "Tetramethyltetraselenafulvalene". Sigma Aldrich. Retrieved 16 March 2026.
- ^ Fraxedas, Jordi (27 April 2006). Molecular Organic Materials: From Molecules to Crystalline Solids. Cambridge University Press. p. 6. ISBN 978-0-521-83446-9. Retrieved 16 March 2026.
- ^ Graja, Andrzej (1992). Low-dimensional Organic Conductors. World Scientific. p. 64. ISBN 978-981-02-0477-8. Retrieved 16 March 2026.
- ^ Wosnitza, J. (November 2019). "Superconductivity of Organic Charge-Transfer Salts". Journal of Low Temperature Physics. 197 (3–4): 250–271. doi:10.1007/s10909-019-02230-6.
- ^ Bockshecker, Michael (1 December 2015). "Chalkogenanthrene und Übergangsmetallhalogenide – Komplexbildung und Redox-Reaktionen". Universitäts- und Landesbibliothek Bonn. Retrieved 16 March 2026.
- ^ Moradpour, A.; Peyrussan, V.; Johansen, I.; Bechgaard, K. (1 February 1983). "High-yield synthesis of tetramethyltetraselenafulvalene (TMTSF) avoiding the use of gaseous hydrogen selenide". The Journal of Organic Chemistry. 48 (3): 388–389. doi:10.1021/jo00151a024. ISSN 0022-3263. Retrieved 16 March 2026.
- ^ "Tetramethyltetraselenafulvalene | CAS 55259-49-9 | SCBT - Santa Cruz Biotechnology". scbt.com. Retrieved 16 March 2026.
- ^ Martorell, B.; Fraxedas, J.; Clotet, A. (1 January 2011). "Tetrathia- and tetraselenafulvalene adsorbed on Ag(110): A theoretical study". Surface Science. 605 (1): 187–192. doi:10.1016/j.susc.2010.10.018. ISSN 0039-6028. Retrieved 16 March 2026.
- ^ Parkin, S S P; Ribault, M; Jerome, D; Bechgaard, K (10 December 1981). "Superconductivity in the family of organic salts based on the tetramethyltetraselenafulvalene (TMTSF) molecule: (TMTSF)2X (X=ClO4, PF6, AsF6, SbF6, TaF6)". Journal of Physics C: Solid State Physics. 14 (34): 5305–5326. doi:10.1088/0022-3719/14/34/011. ISSN 0022-3719. Retrieved 16 March 2026.