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Usage

Uses

Used in Organic Electronic Materials:
2,5-bis(3-bromophenyl)-1,3,4-oxadiazole is used as a building block for the synthesis of organic electronic materials, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells, due to its favorable properties.
Used in Blue OLEDs:
In the OLED industry, 2,5-bis(3-bromophenyl)-1,3,4-oxadiazole is used as an emitter material for its ability to emit blue light, contributing to the development of high-performance blue OLEDs.
Used in Sensors and Optoelectronic Devices:
2,5-bis(3-bromophenyl)-1,3,4-oxadiazole is studied for its potential application in the field of sensors and optoelectronic devices, leveraging its favorable optical and electronic properties for improved device performance.

Upstream product

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Relevant academic research and scientific papers

IBX/KI promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles

Background: Oxadiazoles are privileged scaffolds in different areas of medicinal, pesticidal, polymer and material science. They act as anticancer, benzodiazepine receptor agonists, antimicrobial, analgesic, diuretic and tyrosinase inhibitors etc. A number of compounds containing an oxadiazole moiety are in late stage clinical trials including zibotentan and furamizole. Despite numerous methods are reported, the majority of them suffer from major drawbacks such as the use of strong alkaline or acidic conditions, highly toxic and corrosive reagents and also involve the use of costly reagents, elevated temperatures and longer reaction times. Inspired by the potential application of hypervalent iodonium reagents in organic synthesis, we would like to explore the readily available IBX and KI reagents for the facile synthesis of 1, 3, 4-oxadiazoles. Method: Oxidative cyclization has successfully been developed for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles. Results: An efficient process for the one-pot synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles has been developed using IBX/KI system at 25°C. The reaction was successful with a wide range of substrates such as aromatic and heterocyclic aldehyde and arylhydrazides to afford the corresponding unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles. The mild reaction conditions, cost-effective reagents and short reaction time are noteworthy advantages of this methodology. Conclusion: We have developed a one-pot strategy for the synthesis of 1, 3, 4-oxadiazioles using a combination of IBX/KI at ambient temperature. This one-pot procedure proved to be quite general and worked well with a wide variety of aryl and heterocyclic aldehydes and variety of acylhydrazides. The advantage of this method lies in the simplicity of experimental procedure and the ready accessibility of the reagents, which render this, an experimentally attractive method for the preparation of unsymmetrical 1, 3, 4-oxadiazoles.

A 1, 2, 4-oxadiazole micromolecule the main body material and its preparation method, application

The invention discloses a 1, 2, 4-oxadiazole micromolecule main body material. The 1, 2, 4-oxadiazole micromolecule main body material contains one or multiple electrophilic 1, 2, 4-oxadiazoles which serve as electron acceptor units, wherein the tail ends of molecules are connected to electron donor units. The invention also discloses a preparation method of the micromolecule main body material. The preparation method is characterized in that a dibromo substituted intermediate, namely a 1, 2, 4-oxadiazole compound is prepared by using bromobenzonitrile as a reaction raw material, and then electron donor units are connected to the dibromo substituted intermediate, namely the 1, 2, 4-oxadiazole compound through Suzuki coupling reaction. The invention also discloses an application of the 1, 2, 4-oxadiazole micromolecule main body material. The 1, 2, 4-oxadiazole micromolecule main body material has relatively good solubility and film-forming property, relatively strong eletrophilicity, relatively low LUMO (Lowest Unoccupied Molecular Orbital) energy level and relatively high electronic mobility.

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.

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.

The tuning of the energy levels of dibenzosilole copolymers and applications in organic electronics

An understanding of the structure-function relationships of conjugated polymers is an invaluable resource for the successful design of new materials for use in organic electronics. To this end, we report the synthesis, characterisation and optoelectronic properties of a range of new alternating copolymers of dibenzosilole. Suzuki polycondensation reactions were used to afford a series of eight conjugated materials by the respective combination of either a 3,6- or 2,7-linked 9,9-dioctyldibenzosilole with 3,6-linked-N- octylcarbazole, triarylamine, oxadiazole and triazole monomers. The copolymers were fully characterised using 1H, 13C{1H} NMR spectroscopy, size exclusion chromatography (SEC), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The photophysical properties were determined using UV-Vis spectroscopy, photoluminescence (PL) measurements, cyclic voltammetry (CV) and photoelectron emission spectroscopy in air (PESA). The spectroscopic and electrochemical measurements were used to determine the materials' HOMO and LUMO energies and the values were correlated with the copolymer composition and structure. A selection of the copolymers (P4, P5 and P8) were evaluated as the active layer within single-layer polymer light emitting diodes (PLEDs), with the configuration: glass/ITO/PEDOT:PSS/emissive layer/Ba/Al, which gave low intensity electroluminescence. The selected copolymers were also evaluated as the organic semiconductor in bottom-gate, bottom-contact organic field effect transistors (OFETs). The best performing devices gave a maximum mobility of 3 × 10-4 cm2 V-1 s-1 and on/off current ratios of 105. The Royal Society of Chemistry 2011.