Tetramethyltetraselenafulvalene
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| Names | |
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| IUPAC name
2-(4,5-dimethyl-1,3-diselenol-2-ylidene)-4,5-dimethyl-1,3-diselenole | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.152.166 |
| EC Number |
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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: | |
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| 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).
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Tetramethyltetraselenafulvalene is the organoselenium compound with the chemical formula ((CH3)2C2Se2C)2.[1] It is one of the heterofulvalenes.[2][3]
Structure
[edit]TMTSF is a planar molecule with C2v symmetry. It is structurally analogous to tetramethyltetrathiafulvalene (TMTTF).[4] This structure is suitable for the role of TMTSF as an electron donor and the formation of some charge-transfer salts. A notable family of derivatives are the Bechgaard salts, e.g., (TMTSF)2PF6, the first organic superconductor.[5][6]
Synthesis
[edit]TMTSF is prepared from 3-chloro-2-butanone via a triselenocarbonate. Diethylselenocarbamate is a source of Se.[7]
- CH3C(O)CHClCH3 + (CH3CH2)2NCSe−2 → (CH3CH2)2NC(Se)SeCHC(O)(CH3)2 + Cl−
- (CH3CH2)2NC(Se)SeCHC(O)(CH3)2 + 2H+ → (CH3CH2)2N=CSe2C2(CH3)+2 + H2O
- (CH3CH2)2N=CSe2C2(CH3)+2 + SeH− → Se=CSe2C2(CH3)2 + (CH3CH2)2NH
- 2 Se=CSe2C2(CH3)2 + 2 P(OCH3)3 → (CH3)2C2Se2C=CSe2C2(CH3)2 + 2 SeP(OCH3)3
References
[edit]- ↑ "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.
- ↑ 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.
- ↑ 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.