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Usage

Uses

Used in Organic Electronics:
2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole is used as a component in the development of organic light-emitting diodes (OLEDs) for its electronic and optical properties that contribute to the efficiency and performance of these devices.
Used in Photovoltaic Devices:
In the photovoltaic industry, 2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole is utilized as a material in the construction of solar cells, leveraging its unique properties to enhance the conversion of light into electricity.
Used in Organic Semiconductors:
2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole is employed as a semiconductor material in the field of organic electronics, where its properties are harnessed to improve the performance of electronic devices.
Used in Pharmaceuticals:
Due to its biological activity, 2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole is used as a potential active pharmaceutical ingredient, with ongoing research exploring its therapeutic applications.
Used in Agrochemicals:
In the agrochemical industry, 2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole is investigated for its potential as a biologically active compound, which could be utilized in the development of new pesticides or other agricultural chemicals.
2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole's diverse range of potential applications has made it a subject of significant research and development, with the aim of fully realizing its capabilities across various industries.

Upstream product

• 456-06-4 4-fluorobenzoyl hydrazide 
• 459-57-4 4-fluorobenzaldehyde 
• 1194-02-1 4-fluorobenzonitrile 
• 456-22-4 4-Fluorobenzoic acid 
• 403-43-0 4-fluorobenzoyl chloride 
• 50907-21-6 5-(4-fluorophenyl)-1H-1,2,3,4-tetrazole 
• 138570-93-1 C₁₈H₁₆F₂N₄O₄ 
• 582-91-2 N,N′-bis(4-fluorobenzoyl)hydrazine 

Downstream Products

• 146898-59-1 3,5-bis(4-fluorophenyl)-4-phenyl-4H-1,2,4-triazole 
• 1448013-59-9 C₂₆H₂₀N₄OS₂ 
• 146898-62-6 3,5-bis(4-fluorophenyl)-4-(3-(trifluoromethyl)phenyl)-1,2,4-triazole 
• 144029-01-6 2,5-bis[4-(m-aminophenoxy)phenylene]-1,3,4-oxadiazole 
• 22915-81-7 2,5-bis[4-(p-aminophenoxy)phenylene]-1,3,4-oxadiazole 

Relevant academic research and scientific papers

Specific spectral characteristics of some phenylquinoxaline derivatives

Absorption and emission spectral characteristics of a bis(hydroxyphenylquinoxaline) Q, and two aromatic polyethers containing phenylquinoxaline rings, Q-DBF and Ox-Q, were studied in various solvents. Q, Q-DBF and Ox-Q display two absorption bands, while a poly(1,3,4-oxadiazole-ether) Ox-BisA, exhibits a single absorption band. Their fluorescence spectra (2.5 × 10- 6 mol L- 1) were characterized by an emission band between 380 and 520 nm. At slightly lower concentrations (6.4 × 10- 7 mol L- 1) and under excitation with light corresponding to the highest energy absorption band, Q-DBF and Ox-Q in ethyl acetate and cyclohexane solutions exhibited simultaneously dual emission bands in the near-UV (≈ 355 nm) and blue region (≈ 432 nm). The emission characteristics were quantified by CIE indices (in x, y color coordinates) for the investigated systems. Values of fluorescence quantum yields ranging from 15.93 to 49.83% in chloroform media were obtained.

One pot solvent-free solid state synthesis, photophysical properties and crystal structure of substituted azole derivatives

A solvent-free solid state method has been developed to synthesize three series of substituted azole derivatives (including 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole) in high yields by condensation cyclization of N,N′-bishydrazide derivatives with corresponding cyclization agents, respectively. This general method avoids the use of organic solvents, saves cost and resources, simplifies post-processing and increases reaction rates. These compounds have been fully characterized by 1H NMR, 13C NMR, elemental analysis and MS. The structure of 2,5-di (4-tertbutylphenyl)-1,3,4-oxadiazole has been determined by single crystal X-ray diffraction analysis. The cell parameters are as follows: monoclinic crystal system, Cc space group, a = 18.735 (2) ?, b = 6.3375 (8) ?, c = 16.824 (2) ? and α = γ = 90°; β = 98.292 (2). The electronic absorption and fluorescent properties of these compounds have been systematically investigated for the first time. The relationships between heterocyclic structures and photophysical properties have been discussed. The alteration of emission and absorption wavelengths can be elucidated by hybrid atoms' electronegativity and Substituents' Hammett constants. This approach proposes a novel insight to provide a great number of novel substituted azole derivatives with good photophysical properties by a general green method.

Electrochemical oxidation of aldehyde-N-arylhydrazones into symmetrical-2,5-disubstituted-1,3,4-oxadiazoles

A convenient, efficient and one-pot synthesis of chemically and pharmaceutically interesting symmetrical-2,5-disubstituted-1,3,4-oxadiazoles is reported. The protocol involves anodic oxidation of aldehyde-N-arylhydrazones in anhyd. MeCN-LiClO4. Constant potential electrolysis carried out in an undivided cell and platinum electrodes leads to the formation of the corresponding oxadiazoles under ambient condition and the mechanism was deduced from voltammetry studies. The reaction proceeded smoothly with high atom economy. Springer Science+Business Media Dordrecht 2013.

Influence of conformational rigidity on physical properties of some poly(1,3,4-oxadiazole-ether)s containing trifluoromethyl groups

A series of fluorinated poly(1,3,4-oxadiazole-ether)s was synthesized by the reaction of some aromatic bisphenols containing trifluoromethyl groups, such as 4,4′-(hexafluoroisopropylidene) diphenol, 1a, 1,1-bis(4′-hydroxyphenyl)-1-(3′-trifluoro-methylphenyl)-2,2,2-trifluoroethane, 1b, and 1,1-bis(4′-hydroxy-phenyl)- 1-(3′,5′-ditrifluoromethylphenyl)-2,2,2-trifluoroethane, 1c , with an activated difluorinated aromatic compound incorporating an oxadiazole ring, namely 2,5-bis(p-fluorophenyl)-1,3,4-oxadiazole, 2. Copoly(1,3,4-oxadiazole-ether)s were prepared by reacting the same compound 2 with mixtures of equimolar amounts of 1b or 1c and 9,9-bis(4-hydroxyphenyl)-fluorene, 3. The polymers were easily soluble in organic solvents and showed high thermal stability having initial decomposition temperature above 400°C and glass transition temperature in the range of 193-237°C. The conformational rigidity parameters of polymers were calculated by Monte Carlo method with allowance for hindered rotation. Conformational parameters and free and Van der Waals volume values have been correlated with some physical properties such as solubility and glass transition temperature. The presence of trifluoromethyl groups led to an increase of free volume due to the repulsion of these groups belonging to different chains. (Chemical Equation Presented).

Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents

The electrochemical oxidation of aldehyde-N-aroylhydrazone has been studied in the presence of NaClO4 as supporting electrolyte in MeOH solution using cyclic voltammetry and controlled potential electrolysis. The results indicate that intramolecular cyclization of aldehyde-N-aroylhydrazone has been successfully performed at a platinum electrode in an undivided cell with good yields of the corresponding 1,3,4-oxadiazoles at ambient conditions. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The antifungal activity of the synthesized compounds was evaluated on Fusarium oxysporum, Alternaria solani, Candida albicans and Aspergillus niger. The results revealed that all the synthesized compounds have significant antifungal activity against the tested fungi. Among the synthesized derivatives 7b, 7d, 7g, 7h, 7i, 7j and 7r were found to be the most effective antifungal compounds. The Royal Society of Chemistry 2013.

Synthesis and properties of sulfonated poly(arylene ether)s containing azole groups

Random and multiblock sulfonated poly(arylene ether sulfone)s (SPEs) containing various azole groups such as oxadiazole and triazole were synthesized and characterized for fuel cell application. Successful preparation of SPE membranes depended on the stru

Copoly(peryleneimide)s containing 1,3,4-oxadiazole rings: Synthesis and properties

New copolyimides containing perylenediimide, oxadiazole and hexafluoroisopropylidene moieties were prepared by one-step polycondensation reaction in solution at high temperature of aromatic diamines containing preformed oxadiazole ring with a mixture of a dianhydride having a perylene ring and another dianhydride with hexafluoroisopropylidene unit. The thermal stability and glass transition temperatures of these copolyimides were measured and compared with those of related polyimides. The solid polymers were also studied by polarized light microscopy and X-ray diffraction which revealed a semicrystalline state consisting of face-to-face arranged columns of perylenediimide units. The film-forming ability and properties of the resulting thin films were investigated by using atom force microscopy and scanning electron microscopy which showed that the films were organized into selfassembled rod-like structures. The UV-Vis and photoluminescence properties in solution and in solid state were also investigated.

Fluorinated heterocyclic polyperyleneimides

New polyperyleneimides containing 1,3,4-oxadiazole rings and hexafluoroisopropylidene linkages were synthesized by solution polycondensation reaction at high temperature of aromatic diamines having oxadiazole rings with a mixture of perylenetetracarboxylic dianhydride and hexafluoroisopropylidene diphthalic dianhydride. The solubility and thermal stability of these polymers were studied and compared with those of related polyimides and polyoxadiazoles. The film-forming ability and the quality of the resulting thin films were investigated by using atom force microscopy and scanning electron microscopy, which showed that the films were organized into self-assembled rod-like structures. The photoluminescence of the polymers, both in solution and in solid state, after irradiation with light of different wavelengths, were also studied.

Synthesis and properties of iridium complexes based 1,3,4-oxadiazoles derivatives

A series of iridium complexes with 2,5-diaryl-[1,3,4]-oxadiazole ligands were synthesized and their electrochemical, photophysical, and electroluminescent (EL) properties studied. It was found that electron-withdrawing or donating substituents on the phenyl ring affected the emission maxima. Complex 3, iridium(III) bis(2,5-bis-(2-hydroxyphenyl)-[1,3,4]oxadiazolato-C2′,N3) (acetyl acetonate), was characterized by single-crystal X-ray structural determination. Three organic light emitting diodes devices were fabricated, which showed stable green-yellow luminescence.

Aromatic polyoxadiazoles with silicon in the main chain

This article presents a review on aromatic polymers which contain 1,3,4-oxadiazole rings and diphenylsilylene units in the main chain. These polymers have been synthesized by polycondensation reactions of certain monomers containing silicon, such as dicarboxylic acids, diacid chlorides, diesters or dihydrazides, with conventional aromatic dihydrazides or with aromatic diamines containing preformed oxadiazole rings. The properties of these polymers, such as solubility, film forming ability, thermal stability, electrochemical behavior and photoluminescence properties, and their potential applications are discussed.