97094-33-2

Usage

Uses

Used in Organic Synthesis:
2,5-Bis(phenylethynyl)-1,4-dibromobenzene is used as a key intermediate in organic synthesis for the creation of complex organic molecules. Its reactive bromine atoms and ethynyl groups facilitate various chemical reactions, making it a versatile building block for the synthesis of a wide range of organic compounds.
Used in Materials Science:
In materials science, 2,5-Bis(phenylethynyl)-1,4-dibromobenzene is used as a precursor for the development of advanced materials. Its unique structure allows for the creation of materials with specific properties, such as those used in liquid crystals, which are vital for display technologies.
Used in Electronics:
2,5-Bis(phenylethynyl)-1,4-dibromobenzene is used as a component in the development of electronic materials, particularly in the area of light-emitting diodes (LEDs). Its electronic properties contribute to the efficiency and performance of these devices, making it an important material in the electronics industry.
Used in Optoelectronics:
2,5-Bis(phenylethynyl)-1,4-dibromobenzene is also used in optoelectronics, where its optical properties are harnessed for applications such as nonlinear optics. The ability to manipulate light through nonlinear interactions is crucial for various optoelectronic devices, including optical communication systems and photonic devices.
Used in Research:
2,5-Bis(phenylethynyl)-1,4-dibromobenzene is used as a research material for exploring its potential as a building block for organic semiconductor materials. Its unique structure and properties make it a promising candidate for the development of new materials with improved electronic and optoelectronic properties.

Upstream product

• 63262-06-6 1,4-dibromo-2,5-diiodobenzene 
• 536-74-3 phenylacetylene 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 871334-09-7 (2,5-bis(phenylethynyl)-1,4-phenylene)bis(methylsulfane) 
• 97094-34-3 2,5-bis(phenylethynyl)terephthalic acid 
• 1189114-50-8 1,4-bis(phenylethynyl)-2,5-bis(diphenylhydroxymethyl)benzene 
• 791114-86-8 2,2'-(2,5-dibromo-1,4-phenylene)bis(3-phenylquinoxaline) 
• 791114-85-7 1,1'-(2,5-dibromo-1,4-phenylene)bis(2-phenylethanedione) 
• 219597-02-1 2,6-diphenylbenzo[1,2-b:4,5-b']dithiophene 

Relevant academic research and scientific papers

On-Surface Dehydro-Diels-Alder Reaction of Dibromo-bis(phenylethynyl)benzene

On-surface synthesis under ultrahigh vacuum conditions is a powerful tool to achieve molecular structures that cannot be accessed via traditional wet chemistry. Nevertheless, only a very limited number of chemical reactions out of the wide variety known f

“Golden” Cascade Cyclization to Benzo[c]-Phenanthridines

Herein, we describe a gold-catalyzed cascade cyclization of Boc-protected benzylamines bearing two tethered alkyne moieties in a domino reaction initiated by a 6-endo-dig cyclization. The reaction was screened intensively, and the scope was explored, resulting in nine new Boc-protected dihydrobenzo[c]phenanthridines with yields of up to 98 %; even a π-extension and two bidirectional approaches were successful. Furthermore, thermal cleavage of the Boc group and subsequent oxidation gave substituted benzo[c]phenanthridines in up to quantitative yields. Two bidirectional approaches under the optimized conditions were successful, and the resulting π-extended molecules were tested as organic semiconductors in organic thin-film transistors.

Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole-Transport Properties

Thienoacenes and furoacenes are among the most frequent molecular units found in organic materials. The efficient synthesis of morphologically different heteroacenes and the rapid determination of their solid-state and electronic properties are still challenging tasks, which slow down progress in the development of new materials. Here, we report a flexible and efficient synthesis of unprecedented heterotetracenes based on a platinum- and gold-catalyzed cyclization–alkynylation domino process using EthynylBenziodoXole (EBX) hypervalent iodine reagents in the key step. The proof-of-principle in silico estimation of the synthesized tetracenes’ charge transport properties reveals their strong dependence on both the position and nature of the heteroatoms in the ring system. A broad range of mobility is predicted, with some compounds displaying performance potentially comparable to that of state-of-the-art electronic organic materials.

Solution-processable flower-shaped hierarchical structures: Self-assembly, formation, and state transition of biomimetic superhydrophobic surfaced

Superhydrophobic surfaces inspired by biological microstructures attract considerable attention from researchers because of their potential applications. In this contribution, two kinds of microscale flower-shaped morphologies with nanometer petals formed

Modular synthesis of 1H-indenes, dihydro-s-indacene, and diindenoindacene - A carbon-bridged p-phenylenevinylene congener

(Chemical Equation Presented) A variety of 1H-indenes, dihydro-s-indacenes, and diindenoindacenes, carbon-bridged phenylenevinylene derivatives, can be synthesized in good to high yields using as a synthetic module a 3-lithioindene compound made available

Synthesis of silafluorenes by iridium-catalyzed [2 + 2 + 2] cycloaddition of silicon-bridged diynes with alkynes

(Chemical Equation Presented) Silicon-bridged 1,6-diynes underwent [2 + 2 + 2] cycloaddition with alkynes in the presence of an iridium(I)-phosphine catalyst to afford densely substituted silafluorene derivatives. Extended silafluorene skeletons were cons

Linear C2-symmetric polycyclic benzodithiophene: Efficient, highly diversified approaches and the optical properties

Two facile approaches to two new series of the seven-rings fused benzodithiophene-based polycyclic aromatics are developed in good yields.

Copper-free sonogashira coupling reaction with PdCl2 in water under aerobic conditions

(Chemical Equation Presented). A mild protocol for the copper-free Sonogashira coupling of aryl iodides with terminal acetylenes in water under aerobic conditions has been developed. The use of 1 mol % PdCl2 in the presence of pyrrolidine allows the coupling reaction to proceed at room temperature or 50°C with good to excellent yields.

2,6-Diphenylbenzo[1,2-b:4,5-b′]dichalcogenophenes: A New Class of High-Performance Semiconductors for Organic Field-Effect Transistors

2,6-Diphenylbenzo[1,2-b:4,5-b′]dichalcogenophenes including thiophene, selenophene, and tellurophene analogues as organic semiconductors for field-effect transistors were effectively synthesized in three steps from commercially available 1,4-dibromobenzen

Synthesis, photophysics, and electroluminescence of new quinoxaline-containing poly(p-phenylenevinylene)s

Four new soluble poly(p-phenylenevinylene) (PPV) derivatives containing one or two quinoxaline moieties per repeat unit, either in the main chain or as pendants to the main chain, were synthesized, characterized, and explored as emissive and electron transport materials in polymer light-emitting diodes (LEDs). Polymers containing one quinoxaline moiety per repeat unit (QXPV1 and QXPV3) showed low melting transitions (140°C). The polymers emit blue to green light (404-536 nm) in dilute solution and blue-green to yellow light (470-563 nm) in the solid state. The photoluminescence emission was well-described by single-exponential decay with lifetimes ranging from 200 ps to 2.2 ns in both dilute solution and thin film, indicating lack of intermolecular emissive species in the solid state. PPV derivatives with quinoxaline moieties in the main chain (QXPV1 and QXPV2) showed facile reversible electrochemical reductions with electron affinities of 2.63-2.75 eV. As emissive materials in LEDs, greenish-yellow electroluminescence with a brightness of up to 450 cd/m2 was obtained from single-layer diodes of QXPV1 with aluminum cathode in air.