5216-31-9

Usage

Uses

Used in Organic Synthesis:
4,4'-DIFLUORODIPHENYLACETYLENE is used as a building block in organic synthesis for its ability to form a variety of complex organic compounds, contributing to the development of new materials and chemical entities.
Used in Organic Electronic Materials Production:
In the industry of organic electronic materials, 4,4'-DIFLUORODIPHENYLACETYLENE is used as a key component in the production of OLEDs (organic light-emitting diodes) and OLED displays, due to its unique electronic properties that enhance the performance and efficiency of these devices.
Used in Biochemical and Medical Research:
4,4'-DIFLUORODIPHENYLACETYLENE serves as a fluorescent probe in biochemical and medical research, where its optical properties allow for the tracking and imaging of biological processes at the molecular level, aiding in the understanding of disease mechanisms and the development of therapeutic strategies.
Used in Polymer and Pharmaceutical Production:
4,4'-DIFLUORODIPHENYLACETYLENE is also utilized in the production of polymers and pharmaceuticals, where its chemical structure can be tailored to achieve specific properties and functions, such as improved drug delivery systems or advanced polymer materials with unique characteristics.

Upstream product

• 565-04-8 α,α,α',α'-tetrachloro-4,4'-difluoro-bibenzyl 
• 5676-81-3 4-fluorobenzalaniline 
• 865-47-4 potassium tert-butylate 
• 148004-78-8 (4-fluorophenyl)methyl-2H-benzotriazole 
• 148004-76-6 (4-Fluorophenyl)methyl-1H-benzotriazole 
• 23349-10-2 4,4'-(2-bromoethene-1,1-diyl)bis(fluorobenzene) 
• 459-57-4 4-fluorobenzaldehyde 
• 73584-06-2 diethyl α-chloro-4-fluorobenzylphosphonate 
• 352-34-1 4-fluoro-1-iodobenzene 
• 74-86-2 acetylene 
• 569-74-4 1,1-dichloro-2,2-bis-(4-fluoro-phenyl)-ethene 
• 1066-54-2 trimethylsilylacetylene 
• 345-92-6 4,4'-Difluorobenzophenone 
• 1693-26-1 1,1,1,2-tetrachloro-2,2-bis-(4-fluoro-phenyl)-ethane 

Downstream Products

• 946090-26-2 (bis(di-t-butylphosphino)ethane)Pt(η2-(di(p-fluorophenyl))acetylene) 
• 1015757-82-0 [(C₅H₅)Co(C₄(4-fluorophenyl)4)] 
• 1015757-86-4 [(C₅H₅)Co(C₄(4-fluorophenyl)4CO)] 
• 1064663-67-7 5,8-dimethyl-1,2,3,4-tetra(4-fluorophenyl)naphthalene 
• 588-56-7 (Z)-1,2-bis(4-fluorophenyl)ethylene 
• 1181219-04-4 (E)-2-[1,2-bis(4-fluorophenyl)vinyl]-5-phenyl-1,3,4-oxadiazole 
• 1181219-11-3 (E)-2-[1,2-bis(4-fluorophenyl)vinyl]-5-phenethyl-1,3,4-oxadiazole 
• 1185863-80-2 1,2,3,4-tetrakis(4-fluorophenyl)-9-methyl-9H-carbazole 
• 1185863-96-0 5,6-bis(4-fluorophenyl)indolo[1,2-a]quinoline 
• 1223047-72-0 (E)-1-(2-m-methoxyphenyl-2-p-fluorophenylvinyl)-4-fluorobenzene 
• 1217677-84-3 4,4',4''-(4-phenylbut-1-en-3-yne-1,1,2-tryl)tris(fluorobenzene) 
• 1217677-82-1 4,4',4'',4'''-(but-1-en-3-yne-1,1,2,4-tetrayl)tetrakis(fluorobenzene) 
• 1255383-29-9 diethyl (2E,4Z)-4,5-bis(4-fluorophenyl)-2,4-octadienedioate 
• 1263195-47-6 (2E,4Z)-2-hydroxyethyl 5-acetoxy-4,5-bis(4-fluorophenyl)penta-2,4-dienoate 

Relevant academic research and scientific papers

Mechanochemical Synthesis of Diarylethynes from Aryl Iodides and CaC 2

A mechanochemical synthesis of diarylethynes from aryl iodides and calcium carbide as acetylene source is reported. The reaction is catalyzed by a palladium catalyst in the presence of copper salt, base, and ethanol as liquid assisting grinding (LAG) additive. Various aryl and heteroaryl iodides have been converted in up to excellent yields.

Nickel-Catalyzed Decarbonylative Cycloaddition of Benzofuran-2,3-diones with Alkynes to Flavones

Using dppe as the ligand, the Nickel-catalyzed decarbonylative cycloaddition of benzofuran-2,3-diones with alkynes was established, and a variety of functional flavones were synthesized in 65–99% yields. Terminal alkynes with substituted phenyl groups and internal alkynes such as aryl acyl acetylenes and diphenylacetylenes are suitable for this reaction. The effects of bases on the reactions of different types of alkyne substrates were also investigated and discussed. (Figure presented.).

Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C-H Annulation and Their Application to Pd-Catalyzed Aerobic C-H Alkenylation

A new class of bidentate ligands was prepared by a modular approach involving Rh-catalyzed C-H annulation reactions. The resulting conformationally constrained ligands enabled the Pd-catalyzed C-H alkenylation at electron-rich and sterically less hindered positions of electron-rich arenes while promoting the facile oxidation of Pd(0) intermediates by oxygen. This newly introduced ligand class is complementary to the ligands developed for Pd-catalyzed oxidative reactions and may find broad application in transition-metal-catalyzed reactions.

Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations

Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.

Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents

A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or aryltitanium substrates gave cross-coupling products good yields. This process was simple and easily performed, which provides an efficient method for the synthesis of 1,2-disubstituted acetylenes derivatives.

Palladium-Catalyzed Cascade Dearomative Spirocyclization and C?H Annulation of Aromatic Halides with Alkynes

Described herein is a palladium-catalyzed intermolecular dearomative annulation of aryl halides with alkynes, which provides a rapid approach to a class of structurally unique spiroembedded polycyclic aromatic compounds. The cascade process is accomplished by a sequential alkyne migratory insertion, Heck-type dearomatization, and C-H bond annulation. Further optoelectronic study indicated this fused spirocyclic scaffold could be a potential host material for OLEDs, as exemplified by a fabricated red PhOLED device with a maximum external quantum efficiency of 23.0%.

Synthesis of Diarylethynes from Aryldiazonium Salts by Using Calcium Carbide as an Alkyne Source in a Deep Eutectic Solvent

An efficient method for the synthesis of diarylethynes from aryldiazonium salts by using calcium carbide as an alkyne source at room temperature in a deep eutectic solvent is described. The salient features of this protocol are an inexpensive and easy-to-handle alkyne source, a nonvolatile and recyclable solvent, mild conditions, and a simple workup procedure.

Selective Synthesis of Non-Aromatic Five-Membered Sulfur Heterocycles from Alkynes by using a Proton Acid/N-Chlorophthalimide System

A multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H2O with a proton acid/N-chlorophthalimide (NCPI) system is described to selectively obtain non-aromatic five-membered sulfur heterocycles (1,3-oxathiol-2-imines/thiazol-2(3H)-one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional-group tolerance, high regio- and chemo- selectivities, gram-scale synthesis and late-stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H2O and isothiocyanate, free-radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3-oxathiol-2-imine derivatives possess unique fluorescence characteristics and can be used as Pd2+ sensors with a “turn-off” response, demonstrating potential applications in environmental and biological fields.

Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid

A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.