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Chemical Structure| 1849-27-0 Chemical Structure| 1849-27-0

Structure of 1,4-Bis(phenylethynyl)benzene
CAS No.: 1849-27-0

Chemical Structure| 1849-27-0

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Adhikari, Santosh ; Torres, Xavier Malachi ; Stockdale, John Robert ; Legett, Shelbie A. ; Bezek, Lindsey B. ; Guajardo, Jesus A. , et al.

Abstract: Porous silicone polymer composites (elastomeric foams) with tunable properties and multifunctionalities are of great interest for several applications. However, the difficulties in balancing functionality and printability of silicone polymer based composite resins hinder the development of 3D printed multifunctional porous silicone materials. Here, the direct ink write (DIW) technique and NaCl filler as a sacrificial template were utilized to develop 3D printed porous silicone composites. Three different fillers (hydrophilic and hydrophobic fumed silica, and carbon nanofibers (CNF)) were used to impart additional functionality and to explore their effects on the rheology of the DIW resin, and the mechanical properties of the 3D printed elastomeric foams. While hydrophilic silica was effective in modulating the rheology of the resin, CNFs were effective in improving the tensile strength of the elastomeric foam. Unlike tensile strength, which was found to be dependent on filler type, the uniaxial compressive behavior was found to be more dependent on the porosity of the elastomeric foams. A hyperelastic constitutive model (the Compressive, Hyperelastic, Isotropic, Porosity-based Foam model) was used to simulate the uniaxial compressive behavior of the elastomeric foams, and the model accurately reproduced the experimental stress–strain profiles. The expanded design flexibility of tunable porosity in DIW parts enables the foams to be utilized in a wider variety of applications. For example, the foam with CNF filler demonstrated excellent oil/water separation capacity, with absorbing efficiencies of 450% and 330% respectively for chloroform and toluene. Similarly, a foam with hydrogen getter capacity was developed using the CNF filled foam with hydrogen getter as an additional functional filler, and high performance of the 3D printed hydrogen getter composite was demonstrated.

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Santosh Adhikari ; Douglas J. Safarik ; John R. Stockdale ; Xavier M. Torres ; Adam Pacheco ; Shelbie A. Legett , et al.

Abstract: Hydrogen getters consisting of 1,4-bis[phenylethynyl] benzene (DEB) and a carbon-supported palladium catalyst (Pd/C) have been used to mitigate the accumulation of unwanted hydrogen gas in a sealed system. Here, we report the formulation of a composite resin consisting of silicone polymer plus DEB-Pd/C as an active getter material and the additive manufacturing of silicone getter composites with a high getter content (up to 50 wt %). NMR and DSC studies suggest no reaction between the silicone polymer resin and DEB even at elevated curing temperatures (75 °C). Getter composites with varying amounts of getter and filler were formulated, and their rheological properties were studied. The two composite resins with good printability parameters and different getter contents were chosen to make 3D-printed samples. The hydrogen absorption capacity of these samples was studied at a low hydrogen pressure of 750 mTorr of pure hydrogen. The getter composite with 50 wt% of getter showed normalized DEB conversion of 83%, with the hydrogen adsorption capacity of 100.2 mL of H2 per gram of polymer getter composite.

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Product Details of [ 1849-27-0 ]

CAS No. :1849-27-0
Formula : C22H14
M.W : 278.35
SMILES Code : C1(C#CC2=CC=CC=C2)=CC=C(C#CC3=CC=CC=C3)C=C1
MDL No. :MFCD00160829
InChI Key :FPVSTPLZJLYNMB-UHFFFAOYSA-N
Pubchem ID :624226

Safety of [ 1849-27-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of [ 1849-27-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1849-27-0 ]

[ 1849-27-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 106-37-6 ]
  • [ 536-74-3 ]
  • [ 1849-27-0 ]
  • [ 886-66-8 ]
  • [ 13667-12-4 ]
  • 3
  • [ 589-87-7 ]
  • [ 536-74-3 ]
  • [ 1849-27-0 ]
  • [ 13667-12-4 ]
YieldReaction ConditionsOperation in experiment
68%; 32% With [N-benzyl DABCO]+[Cu4Cl5]-; potassium carbonate; In N,N-dimethyl-formamide; at 135℃;Inert atmosphere; General procedure: Aryl halide (0.2 mmol) and K2CO3 (0.4 mmol) were added to a mixture of DMF (2 mL) and catalyst A (5 mol %) in a round-bottom flask equipped with a condenser and under an N2 atmosphere. The mixture was heated in an oil bath at 135 C and then phenylacetylene (0.22 mmol) was added in two portions. The mixture was stirred continuously during the reaction and monitored by thin-layer chromatography (TLC) and gas chromatography (GC). After the reaction was complete, the mixture was cooled to room temperature and diluted with EtOAc and H2O. The product was extracted with EtOAc and the organic phase dried over MgSO4, filtered, and concentrated. The arylalkynes obtained could be purified by silica gel column chromatography (hexane:EtOAc). The arylalkyne products were known compounds and were characterized from their IR, 1H NMR, and GC-MS.
  • 4
  • [ 1849-27-0 ]
  • [ 59046-72-9 ]
  • C38H26 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 200℃; for 0.5h;Microwave irradiation; General procedure: A solution of <strong>[59046-72-9]2-(phenylethynyl)benzaldehyde</strong> (1) (0.60 mmol, 124 mg), alkyne 2 (0.30 mmol), and TsOH.H2O(0.90 mmol, 171 mg) in ClCH2CH2Cl (2.0 mL) was treated at 200 Cfor 30 min under microwave condition (Biotage INITIATOR; Allreactions were carried out under temperature-constant operation). Thereaction mixture was diluted with CHCl3 and washed with saturatedNaHCO3 (aq) and brine. The organic layer was dried over MgSO4.After removal of the solvent under reduced pressure, the residue waspurified by chromatography on SiO2 to give the naphthalene derivatives. Further purification was carried out a recyclable preparativeHPLC, if necessary. The structures of the products were assigned bytheir NMR spectra. The product was characterized by comparing itsspectral data with previous report.8a
 

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