Nickel bis(stilbenedithiolate)

Nickel bis(stilbenedithiolate)
Names
	Other names bis[1,2-diphenyl-1,2-ethenedithiolato]nickel
Identifiers
CAS Number	28984-20-5;
3D model (JSmol)	Interactive image;
ChemSpider	44211332;
ECHA InfoCard	100.044.853
PubChem CID	5374634;
CompTox Dashboard (EPA)	DTXSID5067427;
	InChI InChI=1S/2C14H12S2.Ni/c215-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12;/h21-10,15-16H;/p-4/b2*14-13-; Key: LJISAPFYPQSNRX-DEWSNNOYSA-J;
	SMILES C1=CC=C(C=C1)/C(=C(/[S-])\C2=CC=CC=C2)/[S-].C1=CC=C(C=C1)/C(=C(/[S-])\C2=CC=CC=C2)/[S-].[Ni];
Properties
Chemical formula	C28H20NiS4
Molar mass	543.40 g·mol−1
Appearance	black-green solid
Density	1.466 g/cm3
Melting point	260 °C (500 °F; 533 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Nickel bis(stilbenedithiolate) is a coordination complex with the formula Ni(S₂C₂Ph₂)₂ (where Ph = phenyl). It exists as a black solid that gives green solutions in toluene. The complex is a prototype of a large family of bis(dithiolene) complexes or the formula Ni(S₂C₂R₂)₂ (R = H, alkyl, aryl). These complexes have attracted much attention as dyes. They are of academic interest because the dithiolenes are noninnocent ligands.^[1] The lengths of the C-S and C-C bonds in the backbone, respectively 1.71 and 1.39 Å, are intermediate between double and single bonds.^[2]

Limiting resonance structures of a R₂C₂S₂M ring

The complex was prepared originally by treating nickel sulfide with diphenylacetylene.^[3] High yielding syntheses involve treating nickel salts with sulfided benzoin. The complex reacts with ligands to form monodithiolene complexes of the type Ni(S₂C₂Ph₂)L₂.^[4]

References[]

^ Karlin, K. D.; Stiefel, E. I., Eds. “Progress in Inorganic Chemistry, Dithiolene Chemistry: Synthesis, Properties, and Applications” Wiley-Interscience: New York, 2003. ISBN 0-471-37829-1
^ Miao, Qingqing; Gao, Junxiong; Wang, Zeqing; Yu, Hang; Luo, Yi; Ma, Tingli (2011). "Syntheses and Characterization of Several Nickel Bis(dithiolene) Complexes with Strong and Broad Near-IR Absorption". Inorganica Chimica Acta. 376: 619–627. doi:10.1016/j.ica.2011.07.046.
^ Schrauzer, G. N.; Mayweg, V. (1962). "Reaction of Diphenylacetylene with Nickel Sulfides". Journal of the American Chemical Society. 84 (16): 3221. doi:10.1021/ja00875a061.
^ Obanda, Antony; Martinez, Kristina; Schmehl, Russell H.; Mague, Joel T.; Rubtsov, Igor V.; MacMillan, Samantha N.; Lancaster, Kyle M.; Sproules, Stephen; Donahue, James P. (2017). "Expanding the Scope of Ligand Substitution from [M(S2C2Ph2] (M = Ni²⁺, Pd²⁺, Pt²⁺) to Afford New Heteroleptic Dithiolene Complexes" (PDF). Inorganic Chemistry. 56 (17): 10257–10267. doi:10.1021/acs.inorgchem.7b00971. PMID 28820242.

[1] Karlin, K. D.; Stiefel, E. I., Eds. “Progress in Inorganic Chemistry, Dithiolene Chemistry: Synthesis, Properties, and Applications” Wiley-Interscience: New York, 2003. ISBN 0-471-37829-1

[2] Miao, Qingqing; Gao, Junxiong; Wang, Zeqing; Yu, Hang; Luo, Yi; Ma, Tingli (2011). "Syntheses and Characterization of Several Nickel Bis(dithiolene) Complexes with Strong and Broad Near-IR Absorption". Inorganica Chimica Acta. 376: 619–627. doi:10.1016/j.ica.2011.07.046.

[3] Schrauzer, G. N.; Mayweg, V. (1962). "Reaction of Diphenylacetylene with Nickel Sulfides". Journal of the American Chemical Society. 84 (16): 3221. doi:10.1021/ja00875a061.

[4] Obanda, Antony; Martinez, Kristina; Schmehl, Russell H.; Mague, Joel T.; Rubtsov, Igor V.; MacMillan, Samantha N.; Lancaster, Kyle M.; Sproules, Stephen; Donahue, James P. (2017). "Expanding the Scope of Ligand Substitution from [M(S2C2Ph2] (M = Ni²⁺, Pd²⁺, Pt²⁺) to Afford New Heteroleptic Dithiolene Complexes" (PDF). Inorganic Chemistry. 56 (17): 10257–10267. doi:10.1021/acs.inorgchem.7b00971. PMID 28820242.

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