5243-24-3

Usage

Uses

Used in Organic Light-Emitting Diode (OLED) Industry:
2,3,5,6-TETRAFLUOROIODOBENZENE is used as a hole-transporting material for its relative thermal stabilities and low-lying HOMO (Highest Occupied Molecular Orbital) levels. These properties make it a promising candidate for improving the performance and efficiency of OLEDs, which are widely used in display and lighting technologies.
The unique combination of fluorine and iodine atoms in 2,3,5,6-TETRAFLUOROIODOBENZENE contributes to its potential as a hole-transporting material in OLEDs. The electron-withdrawing fluorine atoms help to stabilize the positive charge on the hole, while the electron-donating iodine atom facilitates the transport of holes within the material. This results in improved charge carrier mobility and overall device performance.

InChI:InChI=1/C6HF4I/c7-2-1-3(8)5(10)6(11)4(2)9/h1H

Upstream product

• 10269-06-4 4-iodotetrafluorophenylhydrazine 
• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 392-57-4 1,4-diiodo-2,3,5,6-tetrafluorobenzene 
• 75-77-4 chloro-trimethyl-silane 
• 652-18-6 2,3,5,6-tetrafluorobenzoic acid 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 

Downstream Products

• 61794-51-2 1-(2,3,5,6-tetrafluorophenyl)-1-propyn-3-ol 
• 61794-52-3 1,4-Bis-(3'-hydroxyprop-1'-inyl)-tetrafluorbenzol. 
• 3883-86-1 2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenyl 
• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 20083-07-2 1-trimethylsilyl-2,3,5,6-tetrafluorobenzene 
• 505058-38-8 3,3′,4,4′,5,5′-hexafluoro-1,1′-biphenyl 
• 220991-61-7 N-(2’3’5’6’-tetrafluorophenyl)-5-ethylindol-2-one 

Relevant academic research and scientific papers

Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.

Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki-Miyaura Cross Coupling with Electron-Poor Substrates

Polyfluorinated biphenyls are interesting and promising substrates for many different applications. Unfortunately, all current methods for the syntheses of these compounds only work for a hand full of molecules or only in very special cases. Thus, many of these compounds are still inaccessible to date. Here we report a general strategy for the synthesis of a wide range of highly fluorinated biphenyls. In our studies we investigated crucial parameters, such as different phosphine ligands and the influence of various nucleophiles and electrophiles with different degrees of fluorination. These results extend the scope of the already very versatile Suzuki-Miyaura reaction toward the synthesis of very electron-poor products, making these more readily accessible. The presented methodology is scalable and versatile without the need for elaborate phosphine ligands or Pd-precatalysts.

Method for producing tetrakis ( fluoroaryl) borate-magnesium compound

Fluoroaryl magnesium halide is reacted with a boron compound so that a molar ratio of the fluoroaryl magnesium halide to the boron compound is not less than 3.0 and not more than 3.7, so as to produce a tetrakis (fluoroaryl) borate·magnesium compound. With this method, there occurs no hydrogen fluoride which corrodes a producing apparatus and requires troublesome waste water treatment.

Reaction of polyfluoroaromatic compounds with electrophilic agents in the presence of tris(dialkylamino)phosphines: 7. * Replacement of a halogen by hydrogen in halogenopolyfluoroaromatic compounds

A method was developed for the replacement of chlorine, bromine, and iodine in halopolyfluoroaromatic compounds by hydrogen under the action of P(NEt2)3 and a proton donor.

Reactions of polyfluoroaromatic compounds with electrophilic agents in the presence of tris(dialkylamino)phosphine: 6. * Reactions of halogenotetrafluorobenzenes RC6F4X (X = Cl, Br, or I) with chlorotrimethylsilane

The rate of replacement of the halogen atom in isomers of RC6F4X (X = Cl, Br, or I) by the SiMe3 group under the action of Me3SiCl and P(NEt2)3 depends on the nature and the mutual arrangement of the substituents X and R. In addition to silyldehalogenation, compounds C6HF4X (X = Br or I) undergo silyldeprotonation and reduction to tetrafluorobenzenes.

C-I STRETCHING VIBRATIONS IN IODOBENZENES

Comparison of the calculated and experimental IR and Raman spectra of a series of iodobenzenes showed that the C-I stretching vibrations for these compounds correspond to a very highly polarized Raman band 150 - 270 cm-1 (ρ = 0.1).The position of this band depends on the mass of the para substituent and relative position of the fluorine and iodine atoms in the molecule.The UV absorption spectral data indicate an interaction of the iodine atom and para substituents through the ?-system.Opposite substituent effects on the change in intensity of the B-band in the UV spectra of iodobenzenes and tetrafluoroiodobenzenes were noted.