3432-73-3

Usage

Uses

Used in Materials Science:
2,4-Cyclopentadien-1-one, 3,3'-(1,4-phenylene)bis[2,4,5-triphenylis used as a building block for the synthesis of new materials due to its potential reactivity and stability. Its unique molecular structure allows for the creation of novel materials with specific properties tailored for various applications.
Used in Pharmaceutical Research:
2,4-Cyclopentadien-1-one, 3,3'-(1,4-phenylene)bis[2,4,5-triphenylis used as a starting material or intermediate in the development of new pharmaceuticals. Its complex structure and potential for electronic and steric interactions make it a promising candidate for the design of new drugs with unique mechanisms of action.
Used in Organic Chemistry:
2,4-Cyclopentadien-1-one, 3,3'-(1,4-phenylene)bis[2,4,5-triphenylis used as a reagent or catalyst in various organic reactions. Its potential reactivity and the presence of the phenylene group can facilitate specific chemical transformations, contributing to the advancement of organic synthesis methods.

Upstream product

• 3363-97-1 1,4-bis(phenylglyoxalyl)benzene 
• 102-04-5 1,3-Diphenylpropanone 
• 6921-34-2 benzylmagnesium chloride 
• 624-38-4 para-diiodobenzene 
• 1849-27-0 1,4-bis(2-phenylethynyl)benzene 
• 3363-92-6 1,4-bis (phenylacetyl)benzene 

Downstream Products

• 61794-71-6 C₆₄H₄₆O₂ 
• 3364-01-0 2',2''',3',3''',5',5''',6',6'''-octaphenyl-p-quinquephenyl 
• 59907-73-2 1,4-Bis-(2,3,4,5,6,7-hexaphenylcycloheptatri-1,3,6-enyl)-benzol 
• 61794-87-4 1,4-Bis-(3-bromo-2,3,4,5-tetraphenyl-cyclopenta-1,4-dienyl)-benzene 
• 67973-04-0 1,4-Bis(5-chlor-1,3,4-triphenyl-1,3-cyclopentadien-2-yl)benzol 
• 67973-05-1 1,4-Bis(1,3,4-triphenyl-1,3-cyclopentadien-2-yl)benzol 
• 67973-02-8 1,4-Bis(1,3,4-triphenyl-5-hydroxy-1,3-cyclopentadien-2-yl)benzol 

Relevant academic research and scientific papers

Highly Stable, Low Gas Crossover, Proton-Conducting Phenylated Polyphenylenes

Two classes of novel sulfonated phenylated polyphenylene ionomers are investigated as polyaromatic-based proton exchange membranes. Both types of ionomer possess high ion exchange capacities yet are insoluble in water at elevated temperatures. They exhibit high proton conductivity under both fully hydrated conditions and reduced relative humidity, and are markedly resilient to free radical attack. Fuel cells constructed with membrane-electrode assemblies containing each ionomer membrane yield high in situ proton conductivity and peak power densities that are greater than obtained using Nafion reference membranes. In situ chemical stability accelerated stress tests reveal that this class of the polyaromatic membranes allow significantly lower gas crossover and lower rates of degradation than Nafion benchmark systems. These results point to a promising future for molecularly designed sulfonated phenylated polyphenylenes as proton-conducting media in electrochemical technologies.

Sulfo-Phenylated Polyphenylenes Containing Sterically Hindered Pyridines

We systematically investigated the effect of incorporating a sterically hindered pyridyl group into a sulfo-phenylated polyphenylene to control the polymer's physicochemical properties through acid-base interactions. Homopolymers with similar molecular weights and comparable structures that vary by only one atom (N- vs C-) per repeat unit along the polymer chain were prepared. Compared to a non-pyridyl reference membrane, incorporation of a pyridyl group improves the oxidative stability against free radicals, increases the elongation at break to 55% (from 37%), and enhances the thermal stability to 326 °C (from 246 °C). In an accelerated fuel cell degradation test, polymeric membranes containing the sterically encumbered pyridyl unit exhibited exceptional stability (0.16 mV h-1 degradation rate over 1000 h) and retained ～80% of their peak power density over this time.

Structurally-Defined, Sulfo-Phenylated, Oligophenylenes and Polyphenylenes

We report the synthesis and molecular characterization of structurally defined, sulfo-phenylated, oligo- and polyphenylenes that incorporate a novel tetra-sulfonic acid bistetracyclone monomer. The utility of this monomer in the [4 + 2] Diels-Alder cycloaddition to produce well-defined, sulfonated oligophenylenes and pre-functionalized polyphenylene homopolymers is demonstrated. Characterization of the oligophenylenes indicates formation of the meta-meta and para-para adducts in a ～ 1:1 ratio. These functionalized monomers and their subsequent coupling provide a route to prepare novel, sterically encumbered, sulfonated polyphenylenes possessing unprecedented structural control.

Hyperbranched pyridylphenylene polymers based on the first-generation dendrimer as a multifunctional monomer

An A6 + B2 approach was applied for the first time to synthesize novel hyperbranched pyridylphenylene polymers by Diels-Alder cyclocondensation reaction. For this, the first-generation pyridylphenylene dendrimer with six ethynyl functionalities (A6) was used as a branching core for the molecule growth. The phenyl-substituted bis(cyclopentadienone)s (B2) of different structures were used as co-monomer in the reaction. A careful choice of reaction conditions allowed us to obtain high molecular weight polymers without undesirable gelation. The molecular weight of the polymers varied in the range of 10800-80100 with a polydispersity degree of 1.69 to 4.07 according to SEC analysis. The 1H and inverse-gated decoupling 13C NMR combined with heteronuclear single quantum correlation and heteronuclear multiple bond correlation measurements were used to estimate the branching degree of the polymers synthesized.

Synthesis and properties of sulfonated poly(phenylene sulfone)s without ether linkage by Diels-Alder reaction for PEMFC application

A new sulfonated poly(phenylene sulfone) polymer (SPPS) was synthesized by Diels-Alder polymerization from 1,4-bis(2,4,5-triphenylcyclopentadienone)benzene (BTPCPB) and 4,4′-diethynylphenylsulfone, and followed by sulfonation reaction with chlorosulfuric