Trimethylenetetrathiafulvalenedithiolate

Trimethylenetetrathiafulvalenedithiolate (tmdt) is a ligand used in the making of metal organic electric conductors. It normally has a charge of −2.[1] Known compounds include Ni(tmdt)2,[2] Pt(tmdt)2,[3] Pd(tmdt)2,[2] Au(tmdt)2,[4]

Trimethylenetetrathiafulvalene­dithiolate
Names
IUPAC name
2-(5,6-dihydro-4H-cyclopenta[d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-dithiolate
Identifiers
3D model (JSmol)
  • InChI=1S/C9H8S6/c10-6-7(11)15-9(14-6)8-12-4-2-1-3-5(4)13-8/h10-11H,1-3H2/p-2
    Key: DQTKCIVHDDGAFK-UHFFFAOYSA-L
  • [S-]C1=C([S-])SC(S1)=C2SC3=C(S2)CCC3
Properties
C9H6S6−2
Molar mass 306.51 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The tmdt2− ion is based on fulvalene, but with the four atoms adjacent to the bridging double bond replaced with sulfur yielding tetrathiafulvalene, at one end of the pair of rings is another five-member ring attached by adding three carbon atoms (the trimethylene part), and the other side of the fulvalene has two sulfur atoms, that bond to the metal ion.[5]

The gold compound has an antiferromagnetic transition at 100 K (−173 °C).[6]

Some of the sulfur atoms can be replaced by selenium to yield similar conducting compounds.[6]

List
formula comment CAS ref
Ni(tmdt)2 [2]
Pd(tmdt)2 [2]
Pt(tmdt)2 1196461-89-8 [3]
Au(tmdt)2 852955-03-4 [6]

References
  1. Devillanova, Francesco A.; Mont, Woolf-Walther Du (2013). Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium. Royal Society of Chemistry. p. 155. ISBN 9781849736244.
  2. Tanaka, Hisashi; Kobayashi, Hayao; Kobayashi, Akiko (January 2002). "Syntheses and physical properties of metal complex conductors with extended ttf ligands". Molecular Crystals and Liquid Crystals. 380 (1): 197–202. doi:10.1080/713738705. S2CID 94758687.
  3. Zhou, Biao; Kobayashi, Akiko; Okano, Yoshinori; Nakashima, Takeshi; Aoyagi, Shinobu; Nishibori, Eiji; Sakata, Makoto; Tokumoto, Madoka; Kobayashi, Hayao (18 September 2009). "Single-Component Molecular Conductor [Pt(tmdt)2] (tmdt = trimethylenetetrathiafulvalenedithiolate) - An Advanced Molecular Metal Exhibiting High Metallicity". Advanced Materials. 21 (35): 3596–3600. doi:10.1002/adma.200803116.
  4. Suzuki, Wakako; Fujiwara, Emiko; Kobayashi, Akiko; Fujishiro, Yuichi; Nishibori, Eiji; Takata, Masaki; Sakata, Makoto; Fujiwara, Hideki; Kobayashi, Hayao (February 2003). "Highly Conducting Crystals Based on Single-Component Gold Complexes with Extended-TTF Dithiolate Ligands". Journal of the American Chemical Society. 125 (6): 1486–1487. doi:10.1021/ja0292243. PMID 12568602.
  5. Bruce, Duncan W.; O'Hare, Dermot; Walton, Richard I. (2011). Molecular Materials. John Wiley & Sons. ISBN 9781119972952.
  6. Saito, Gunzi; Enoki, Toshiaki; Wudl, Fred; Haddon, Robert C.; Tanigaki, Katsumi (2007). Multifunctional Conducting Molecular Materials. Royal Society of Chemistry. ISBN 9780854044962.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.