177546-04-2

Basic information

• Product Name: 5-(2,6-Diphenyl-tetrahydro-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one
• Synonyms: 5-(2,6-Diphenyl-tetrahydro-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one
• CAS NO: 177546-04-2
• Molecular Weight: 444.687
• Mol File: 177546-04-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-(2,6-Diphenyl-tetrahydro-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2,6-Diphenyl-tetrahydro-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one(177546-04-2)
• EPA Substance Registry System: 5-(2,6-Diphenyl-tetrahydro-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-one(177546-04-2)

Safety Data

• Hazardous Substances Data: 177546-04-2(Hazardous Substances Data)

Upstream product

• 37014-01-0 4-oxo-2,6-diphenyl-thiane 
• 177546-03-1 5-(2,6-Diphenyl-tetrahydro-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiole-2-thione 

Downstream Products

• 177546-10-0 2-[5-(2,6-Diphenyl-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-ylidene]-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester 
• 177546-11-1 2-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-5-(2,6-diphenyl-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiole 
• 177546-13-3 2-(2,6-Diphenyl-thiopyran-4-ylidene)-5-[1,3]dithiol-2-ylidene-[1,3]dithiolo[4,5-d][1,3]dithiole 
• 177546-06-4 2-[5-(2,6-Diphenyl-tetrahydro-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-ylidene]-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester 
• 177546-07-5 2-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-5-(2,6-diphenyl-tetrahydro-thiopyran-4-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiole 

Relevant articles and documents

Novel bis-fused π-electron donors for organic metals: 2-(1,3-dithiol-2-ylidene)-5-(thiopyran-4-ylidene)-1,3,4,6-tetrathiapentalene

Bis-fused π-electron donors composed of tetrathiafulvalene (TTF) and 2-(thiopyran-4-ylidene)-1,3-dithiole (TPDT), 2-(1,3-dithiol-2-ylidene)-5-(thiopyran-4-ylidene)-1,3,4,6-tetrathiapentalene (1a, TPDT-TTP), and its derivatives (1b-d, 2a-d) have been synthesized as donor components for organic conductors. An X-ray structure analysis of bis(methylthio)-1 (1c) revealed that the TPDT-TTP skeleton is almost planar except for the outer 1,3-dithiole ring, and that the crystal has a two-dimensional "θ-type" arrangement of molecules. The cyclic voltammograms of TPDT-TTPs exhibit four pairs of single-electron redox waves. The first oxidation potential (E1) of 1a (+0.37 V vs SCE, in PhCN) is comparable to that of TTF (+0.35 V) and is higher by 0.1 V than that of TPDT (+0.27 V). The observed substituent effect on E1 values suggests that the first one-electron oxidation mainly occurs in the 2-(thiopyran-4-ylidene)-1,3-dithiole (TPDT) moiety. On the other hand, on-site coulombic repulsion estimated from the E2 - E1 value is lower than in TTF and TPDT. MNDO MO calculations reveal that all the sulfur atoms in the 1,3-dithiole rings have the same phase in the HOMO, a condition necessary for realization of effective transverse intermolecular interaction. The present donors have produced many charge-transfer complexes and cation radical salts showing relatively high conductivity (σrt = 10-1-101 S cm-1), several of which display metallic temperature dependence.