868847-75-0

Usage

Chemical structure

A benzene ring with two vinyl groups and two bromine atoms attached at the 1 and 4 positions.

Common use

As a building block in organic synthesis for constructing various functionalized aromatic compounds.

Cross-coupling reactions

Utilized in these reactions to form new carbon-carbon bonds.

Polymerization processes

Involved in various types of polymerization, contributing to the formation of polymers.

Applications

Production of polymers, pharmaceuticals, and agrochemicals.

Versatility

Serves as a valuable building block for different industries due to its diverse applications.

Thermal stability

Exhibits high thermal stability, making it suitable for use in various industrial applications.

Chemical stability

Demonstrates high chemical stability, further enhancing its value in industrial applications.

Upstream product

• 50-00-0 formaldehyd 
• 35335-16-1 1,4-bis(bromomethyl)-2,5-dibromobenzene 
• 106-42-3 para-xylene 
• 1074-24-4 2,5-dibromo-p-xylene 

Downstream Products

• 1166111-31-4 1,4-dipiperidino-2,5-divinylbenzene 
• 1201908-83-9 2,2'-(2,5-dibromo-1,4-phenylene)diethanol 
• 53-70-3 dibenzo[a,h]anthracene 

Relevant academic research and scientific papers

Nonplanar Tub-Shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes

A novel tandem Ru-catalyzed [2+2+2] cycloaddition of arylenynes to dihydrobiphenylenes followed by halogen-radical ring opening has been developed for the construction of tub-shaped halogenated benzocyclooctatetraenes (bCOT's). Cross-couplings and Diels-Alder reactions of the brominated bCOT's allow the formation of the corresponding eight-membered ring-fused PAH's. The halogen-radical ring opening probably occurs via a selective formation of a bis-allyl radical at the 1,3-cyclohexadiene moiety, halogenation at the bridgehead carbon, and finally electrocyclic ring opening.

A high efficiency pure organic room temperature phosphorescence polymer PPV derivative for OLED

For the purpose of improving device efficiency and reducing cost, it is necessary to develop pure organic molecules with room temperature phosphorescence (RTP). A high efficiency pure organic RTP polymer, poly-p-phenylene vinylene (PPV) derivative (Br-PPV-CHO), was designed and synthesized, which possesses a blue emission at 496 nm, an emission lifetime of 14.1 μs, and a photoluminescence quantum yield of 12.2%, and the HOMO and LUMO of ?5.35 eV and ?2.75 eV, respectively, showing a great potential application in the emitting layer of OLED. A device fabricated with the PPV derivative as the emitting material layer shows a max luminance of 194 cd/m2 when the Br-PPV-CHO content was 0.5 wt %, demonstrating the best RTP performance. The good properties of Br-PPV-CHO come from the substituent groups of bromine and aromatic aldehyde, and the molecular structure design strategy in the PPV derivative supplies a useful guidance for the design and syntheses of organic RTP materials.

Aromatizing olefin metathesis by ligand isolation inside a metal- organic framework

The aromatizing ring-closing metathesis has been shown to take place inside an extended porous framework. Employing a combination of solvent-assisted linker exchange and postsynthesis modification using olefin metathesis, the noninterpenetrated SALEM-14 was formed and converted catalytically into PAH-MOF-1 with polycyclic aromatic hydrocarbon (PAH) pillars. The metal-organic framework in SALEM-14 prevents "intermolecular" olefin metathesis from occurring between the pillars in the presence of the first generation Hoveyda-Grubbs catalyst, while favoring the production of a PAH, which can be released from the framework under acidic conditions in dimethylsulfoxide.

Poly(pyridinium phenylene)s: Water-soluble N-type polymers

(Chemical Equation Presented) Poly(pyridinium phenylene) conjugated polymers are synthesized by a cross-coupling and cyclization sequence. These polyelectrolytes are freely soluble in water and display high degrees of electroactivity. When reduced (n-doped) these materials display in situ conductivities as high as 160 S/cm. The high conductivity is attributed to the planar structure that is enforced by the cyclic structures of the polymer. The electron affinities are compared to PCBM, a C60 based n-type material. We find that these polymers undergo excited state electron transfer reactions with other donor conjugated polymers and hence may find utility in photovoltaic devices.

Polycyclic aromatic hydrocarbons by ring-closing metathesis

A strategy for the synthesis of polycyclic aromatic hydrocarbons (PAHs) by the ring-closing olefin metathesis (RCM) of pendant olefins on a phenylene backbone has been developed. RCM of 2,4′,6′,2″-tetravinyl-[1, 1′;3′,1″]terphenyl and 2,2′,5′,2″- tetravinyl-[1,1′;4′,1′]terphenyl affords in high yield the isomeric [a,j] and [a,h] dibenzanthracenes, respectively. In contrast with other intramolecular annulation methods, such as Friedel-Crafts acylations, this reaction is completely regioselective. Since RCM is reversible and PAHs are often thermodynamic sinks, this strategy is an effective and general method for the preparation of PAHs. Density functional theory calculations support these results. Carbon disulfide is a suitable solvent for these reactions.