[1,1'-Binaphthalene]-2,2'-dithiol

• CAS: 102555-71-5
• Catalog Number: ACM102555715-1
• Category: Main Products
• Molecular Weight: 318.46
• Molecular Formula: C20H14S2
• Synonyms: 1-(2-Sulfanylnaphthalen-1-yl)naphthalene-2-thiol
• IUPAC Name: 1-(2-sulfanylnaphthalen-1-yl)naphthalene-2-thiol
• InChI: PQTIXYILPGIIHM-UHFFFAOYSA-N
• InChI Key: InChI=1S/C20H14S2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,21-22H
• Appearance: Solid
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC(=C2C3=C(C=CC4=CC=CC=C43)S)S

Case Study

[1,1'-Binaphthalene]-2,2'-Dithiol for the Synthesis of Iron-Sulfur Cluster Compound

Wang X B, et al. Applied organometallic chemistry, 2016, 30(8), 638-644.

A new iron-sulfur cluster compound [(μ-BNT)Fe2 was synthesized using (R)-1,1'-binaphthalene-2,2'-dithiol) (BNT) through self-assembly reaction with [Fe3(CO)12] (CO)6](A). The iron-sulfur cluster compound A can be further used to construct a homogeneous photocatalytic system for hydrogen evolution applications.
Synthesis of iron-sulfur cluster compound
· The ligand BNT, which contains both rigid and tenacious groups, can be synthesized by using (R)-1,1'-binaphthol as the precursor.
· BNT (1.27 g, 4.00 mmol), [Fe3(CO)12] (2.42 g, 4.80 mmol) and toluene (80 ml) were combined in a 250 ml Schlenk vessel.
· The mixture was then refluxed for 3 h, the solution turning from green to red. The resultant solution was allowed to cool to room temperature, filtered and concentrated to dryness using a rotary evaporator.
· The residue was purified using a silica gel column and recrystallized from CH2Cl2-petroleum ether to afford A as a red powder.

[1,1'-Binaphthalene]-2,2'-Dithiol for the Synthesis of Metal Dithiolene Complexes

Rao H, et al. Catalysis Science & Technology, 2015, 5(4), 2332-2339.

Using (R)-1, 1'-binaphthalene-2,2'-dithiol) (BNT) as ligand, two new metal dithiolene complexes were prepared, namely NtBu4[M(BNT)2] (M=Co/Ni). The prepared homogeneous photocatalytic system based on metal dithiolene complexes exhibits good photocatalytic hydrogen evolution activity and can be used as a potential catalyst for converting solar energy into hydrogen.
Preparation of NtBu4[M(BNT)2]
· In a 100 mL Schlenk vessel, Co(BF4)2·6H2O or Ni(BF4)2·6H2O and KOtBu were dissolved in 30 mL of dry MeOH under a N2 atmosphere and allowed to stir at room temperature for 1 h.
· Then, a degassed mixture of BNT in MeOH was added dropwise into the above solution. The mixture was continually stirred for 4 h at room temperature, during which its color darkened to deep blue.
· A solution of NtBu4Br in 5 mL MeOH was added dropwise into the above reaction mixture. Thereafter the N2 atmosphere was removed from the Schlenk vessel, and the mixed solution was allowed to stir under air at room temperature overnight.
· Following vacuum evaporation to remove most of the solvent, a dark blue precipitate was obtained. The crude solid was collected and recrystallized from a mixture of dichloromethane and ether to yield 1 as a blue crystalline solid or blue-black solid.