18853-32-2

Basic information

• Product Name: 3,4-DICYANOTHIOPHENE,
• Synonyms: 3,4-Thiophenedicarbonitrile;3,4-DICYANOTHIOPHENE;Thiophene-3,4-dicarbonitrile
• CAS NO: 18853-32-2
• Molecular Formula: C₆H₂N₂S
• Molecular Weight: 134.15848
• EINECS: 200-110-4
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Heterocycles;Building Blocks;Cyano;Thiophene
• Mol File: 18853-32-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 225.5-227.5 °C
• Boiling Point: 338.962 °C at 760 mmHg
• Flash Point: 158.799 °C
• Appearance: /
• Density: 1.342 g/cm³
• Vapor Pressure: 9.49E-05mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 3,4-DICYANOTHIOPHENE,(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DICYANOTHIOPHENE,(18853-32-2)
• EPA Substance Registry System: 3,4-DICYANOTHIOPHENE,(18853-32-2)

Safety Data

• Hazardous Substances Data: 18853-32-2(Hazardous Substances Data)

Usage

General Description

3,4-DICYANOTHIOPHENE is a chemical compound with the molecular formula C8H4N2S. It is a heterocyclic aromatic compound that is commonly used as a building block in organic synthesis and as a component of electronic materials. 3,4-DICYANOTHIOPHENE is known for its strong electron-accepting properties, making it useful in the production of high-performance semiconductors and polymers. It is also used in the development of organic electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs). Additionally, it has potential applications in the field of medicinal chemistry, particularly in the development of new pharmaceuticals and biologically active molecules. However, it is important to handle 3,4-DICYANOTHIOPHENE with caution, as it is considered hazardous if not properly handled and managed.

InChI:InChI=1/C6H2N2S/c7-1-5-3-9-4-6(5)2-8/h3-4H

Upstream product

• 3141-26-2 3,4-dibromothiophene 
• 544-92-3 copper(I) cyanide 
• 557-21-1 dicyanozinc 

Downstream Products

• 1260428-76-9 2-bromo-3,4-dicyanothiophene 
• 1056841-63-4 2,5-dibromo-3,4-dicyanothiophene 
• 1255909-03-5 (S)-N-(5-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-4,6-dioxo-5,6-dihydro-4H-thiophene[3,4-c]pyrrole-1-yl)acetamide 
• 566939-56-8 1,3-dibromo-5-(n-hexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 
• 927177-49-9 (4-tert-butylphenoxy)boronsubphthalocyanine 
• 53229-47-3 diethyl thiophene-3,4-dicarboxylate 
• 1255908-96-3 5-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1-methylamino-5H-thiopheno[3,4-c]pyrrole-4,6-dione 
• 1255908-83-8 5-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-5H-thiopheno[3,4-c]pyrrole-4,6-dione 
• 1255908-82-7 N-(5-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-4,6-dioxo-5,6-dihydro-4H-thiopheno[3,4-c]pyrrol-1-yl)acetamide 
• 1255908-81-6 5-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1-amino-5H-thiopheno[3,4-c]pyrrole-4,6-dione 
• 1255908-80-5 5-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1-nitro-5H-thiopheno[3,4-c]pyrrole-4,6-dione 
• 1073-31-0 3,4-thiophene dicarboxaldehyde 
• 33527-20-7 4,9-Dihydronaphtho<2,3c>thiophen-4,9-dion 
• 33527-26-3 thiophene-3,4-dicarboxylic acid chloride 

Relevant articles and documents

Towards novel thieno-fused subporphyrazines via functionalized thiophene precursors

Thieno-fused subporphyrazines (TPs) containing a central and axially substituted boron atom are a class of compounds with interesting optical and redox properties. Here we present our efforts towards expanding this class of compounds using various thiophene substrates that were prepared by cyanation or nitration of 3,4-dibromothiophene. Moreover, we show that one TP derivative forms a 2:1 complex in the solid state with C70.

From Red to Green Luminescence via Surface Functionalization. Effect of 2-(5-Mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4- c]pyrrole-4,6-dione Ligands on the Photoluminescence of Alloyed Ag-In-Zn-S Nanocrystals

A semiconducting molecule containing a thiol anchor group, namely 2-(5-mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4-c]pyrrole-4,6-dione (abbreviated as D-A-D-SH), was designed, synthesized, and used as a ligand in nonstoichiometric quaternary nanocrystals of composition Ag1.0In3.1Zn1.0S4.0(S6.1) to give an inorganic/organic hybrid. Detailed NMR studies indicate that D-A-D-SH ligands are present in two coordination spheres in the organic part of the hybrid: (i) inner in which the ligand molecules form direct bonds with the nanocrystal surface and (ii) outer in which the ligand molecules do not form direct bonds with the inorganic core. Exchange of the initial ligands (stearic acid and 1-aminooctadecane) for D-A-D-SH induces a distinct change of the photoluminescence. Efficient red luminescence of nanocrystals capped with initial ligands (λmax = 720 nm, quantum yield = 67%) is totally quenched and green luminescence characteristic of the ligand appears (λmax = 508 nm, quantum yield = 10%). This change of the photoluminescence mechanism can be clarified by a combination of electrochemical and spectroscopic investigations. It can be demonstrated by cyclic voltammetry that new states appear in the hybrid as a consequence of D-A-D-SH binding to the nanocrystals surface. These states are located below the nanocrystal LUMO and above its HOMO, respectively. They are concurrent to deeper donor and acceptor states governing the red luminescence. As a result, energy transfer from the nanocrystal HOMO and LUMO levels to the ligand states takes place, leading to effective quenching of the red luminescence and appearance of the green one.

Synthesis and characterization of an A2BC type phthalocyanine and its visible-light-responsive photocatalytic H2 production performance on graphitic carbon nitride

A highly asymmetric A2BC type zinc phthalocyanine (Zn-di-PcNcTh) has been designed and synthesized. The Zn-di-PcNcTh used a π electron rich thiophene ring in place of the benzenoid rings of phthalocyanine which acted as an electron donor, diphenylphenoxy substituents to retard aggregation and a carboxyl-naphthalene unit as an electron acceptor. The asymmetric phthalocyanine shows a strongly split Q-band and wide spectral absorption in the visible/near-IR light region, which can extend the spectral response region of graphitic carbon nitride (g-C3N4) from ～450 nm to more than 800 nm. By using it as a sensitizer of 1.0 wt% Pt-loaded graphitic carbon nitride (g-C3N4), the experimental results indicate that Zn-di-PcNcTh-Pt/g-C3N4 shows a H2 production efficiency of 249 μmol h-1 with an impressive turnover number (TON) of 9960.8 h-1 under visible light (λ ≥ 420 nm) irradiation, much higher than that of pristine Pt/g-C3N4. Owing to the introduction of a highly bathochromic shift of 3,4-dicyanothiophene and the valuable "push-pull" effect from the thiophene (electron donor) to the carboxyl-naphthalene (electron acceptor) unit, Zn-di-PcNcTh/g-C3N4 gives an extremely high apparent quantum yield (AQY) of 2.44%, 3.05%, and 1.53% under 700, 730, and 800 nm monochromatic light irradiation, respectively, under optimized photocatalytic conditions.