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

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

Uses

Used in Organic Synthesis:
3,4-Dicyanothiophene is used as a building block for the synthesis of various organic compounds due to its strong electron-accepting properties, which facilitate the formation of new chemical bonds and structures.
Used in Electronic Materials:
In the Electronics Industry, 3,4-Dicyanothiophene is used as a component for the production of high-performance semiconductors and polymers, contributing to the advancement of electronic devices with improved efficiency and performance.
Used in Organic Electronic Devices:
3,4-Dicyanothiophene is used as a key material in the development of organic light-emitting diodes (OLEDs) for its ability to enhance the efficiency and brightness of these devices.
Used in Organic Photovoltaic Cells:
In the Renewable Energy Industry, particularly in solar power, 3,4-Dicyanothiophene is utilized in the fabrication of organic photovoltaic cells (OPVs) to improve their light absorption and energy conversion capabilities.
Used in Medicinal Chemistry:
3,4-Dicyanothiophene is used as a starting material in the development of new pharmaceuticals and biologically active molecules, leveraging its unique chemical properties to create novel therapeutic agents.

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

Upstream product

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

Downstream Products

• 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 
• 1260428-76-9 2-bromo-3,4-dicyanothiophene 
• 1056841-63-4 2,5-dibromo-3,4-dicyanothiophene 
• 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.

New regiosymmetrical dioxopyrrolo- and dihydropyrrolo-functionalized polythiophenes

(Chemical Equation Presented) We present the synthesis of two N-alkylated poly(dioxopyrrolothiophene)s and two N-alkylated poly(dihydropyrrolothiophene)s with potential application in the field of conducting polymers. The polymers are synthesized from the corresponding 2,5-dibromothiophenes by an Ullmann-type polymerization and a Stille-type polymerization, respectively. The two N-alkylated poly(dihydropyrrolothiophene)s are the first examples of amino-functionalized polythiophenes built from regiosymmetrical thiophene monomers.

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.

CRYSTAL FORMS OF THIOPHENE DERIVATIVES

Disclosed is crystal form I of compound (S)—N-[5-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-4,6-dioxo-5,6-dihydro-4H-thieno[3,4-c]pyrrole-1-yl]acetamide.

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.

A versatile approach to organic photovoltaics evaluation using white light pulse and microwave conductivity

State-of-the-art low band gap conjugated polymers have been investigated for application in organic photovoltaic cells (OPVs) to achieve efficient conversion of the wide spectrum of sunlight into electricity. A remarkable improvement in power conversion efficiency (PCE) has been achieved through the use of innovative materials and device structures. However, a reliable technique for the rapid screening of the materials and processes is a prerequisite toward faster development in this area. Here we report the realization of such a versatile evaluation technique for bulk heterojunction OPVs by the combination of time-resolved microwave conductivity (TRMC) and submicrosecond white light pulse from a Xe-flash lamp. Xe-flash TRMC allows examination of the OPV active layer without requiring fabrication of the actual device. The transient photoconductivity maxima, involving information on generation efficiency, mobility, and lifetime of charge carriers in four well-known low band gap polymers blended with phenyl-C61-butyric acid methyl ester (PCBM), were confirmed to universally correlate with the PCE divided by the open circuit voltage (PCE/Voc), offering a facile way to predict photovoltaic performance without device fabrication.

THIOPHENE DERIVATIVES

Disclosed is a compound of formula (1), wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the present application.

OLIGOTHIOPHENES DERIVATIVES

The present invention is directed to new oligothiophene derivatives and their use as a semiconductor material in electronic devices. More specifically, the present invention relates to new 3,4-dicyanooligothiophenes derivatives, processes for manufacturing thereof, and to their use as organic n-type (electron-transporting) semiconductors, in particular, in field-effect transistors (FET).

Preparation and characterization of nonclassical tetraazaporphyrin, bis(4-methylpyridine)[1,3,5,7,9,11,13,15-octaphenyltetra(3,4-thieno) tetraazaporphyrinato]ruthenium(II)

The tetramerization reaction of 2,5-diphenyl-3,4-dicyanothiophene (2) proceeded on treatment with ruthenium(III) trichloride, DBU, and 4-methylpyridine in 2-ethoxyethanol at 135 °C to give bis(4-methylpyridine) [1,3,5,7,9,11,13,15-octaphenyltetra(3,4-thie

Synthesis of soluble oligothiophenes bearing cyano groups, their optical and electrochemical properties

The synthesis and the characterization of twelve new soluble oligothiophenes, possessing two to four 3,4-dicyanothiophene units in their backbone, are described. These semiconductors are prepared through Stille coupling and/or homo-coupling reactions. Cyclic voltammetry studies have been performed to evaluate their stability as n-type semiconducting materials under ambient conditions. The measured electrochemical and optical properties are fully supported by quantum-chemical calculations.