177991-01-4

Basic information

• Product Name: tetrakis(4-ethynylphenyl)Methane
• Synonyms: tetrakis(4-ethynylphenyl)Methane;tetra(4-acetylenylphenyl)methane
• CAS NO: 177991-01-4
• Molecular Formula: C₃₃H₂₀
• Molecular Weight: 416.5119
• EINECS: -0
• Mol File: 177991-01-4.mol

Chemical Properties

• Melting Point: 300°C(dec.)(lit.)
• Boiling Point: 537.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• CAS DataBase Reference: tetrakis(4-ethynylphenyl)Methane(CAS DataBase Reference)
• NIST Chemistry Reference: tetrakis(4-ethynylphenyl)Methane(177991-01-4)
• EPA Substance Registry System: tetrakis(4-ethynylphenyl)Methane(177991-01-4)

Safety Data

• Hazardous Substances Data: 177991-01-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry and Materials Science:
TEPM is utilized as a building block for the synthesis of innovative organic materials and polymers, leveraging its unique structure and properties.
Used in the Design and Fabrication of Functional Materials:
Due to its rigid and symmetrical structure, TEPM is employed as a valuable component in designing and fabricating materials with specific electronic and optical properties, contributing to the advancement of material science.
Used in the Development of Advanced Electronic Devices:
TEPM has potential applications in the development of cutting-edge electronic devices such as organic light-emitting diodes (OLEDs) and organic semiconductors, where its thermal stability and structural attributes are advantageous.

Upstream product

• 177991-00-3 tetrakis(4-((trimethylsilyl)ethynyl)phenyl)methane 
• 105309-59-9 tetrakis(4-bromophenyl)methane 
• 134080-67-4 tetrakis(4-iodophenyl)methane 
• 630-76-2 tetraphenylmethane 
• 1066-54-2 trimethylsilylacetylene 
• 76-83-5 trityl chloride 
• 62-53-3 aniline 
• 76-84-6 triphenylmethyl alcohol 

Downstream Products

• 1190592-61-0 8,8',8'',8'''-[methanetetrayl-tetrakis(benzene-4,1-diyl-ethyn-2,1-diyl)]tetrauracil 
• 1616282-37-1 C₅₇H₂₈S₁₆ 
• 1593194-23-0 tetrakis(4-(1-(4-methyl-3,5-bis((triisopropylsilyl)ethynyl)phenyl)-1H-1,2,3-triazol-4-yl)phenyl)methane 
• 359647-86-2 tetrakis[4-(pyridin-4-ylethynyl)phenyl]methane 
• 1287733-04-3 tetraethyl 4,4',4'',4'''-[methanetetrayltetrakis(4,1-phenyleneethyne-2,1-diyl)]tetrabenzoate 
• 1287733-05-4 octamethyl 5,5',5'',5'''-[methanetetrayltetrakis(4,1-phenyleneethyne-2,1-diyl)]tetraisophthalate 
• 1287732-98-2 tetrakis[4-(4-methoxyphenylethynyl)phenyl]methane 
• 1287733-02-1 tetrakis[4-(4-acetylphenylethynyl)phenyl]methane 
• 1287733-11-2 tetrakis[4-(3,5-dimethylisoxazol-4-ylethynyl)phenyl]methane 
• 1287733-10-1 tetrakis[4-(3-pyridylethynyl)phenyl]methane 
• 1287733-09-8 tetrakis[4-(2-pyridylethynyl)phenyl]methane 

Relevant articles and documents

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Synthesis of Rigid Rod, Trigonal, and Tetrahedral Nucleobase-Terminated Molecules

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Tetrahedral Tetrakis(p-ethynylphenyl) Group IV Compounds in Microporous Polymers: Effect of Tetrel on Porosity

Three Sonogashira–Hagihara polymerization protocols were applied for the synthesis of conjugated microporous polymers (CMPs) by using group IV tetra(p-ethynylphenyl) monomers with 1,4-diiodobenzene or 1,4-dibromobenzene. The optical properties and surface areas of the CMPs were compared and related to the preparation conditions and the geometry of the tetrahedral building block as obtained after X-ray analysis. In each series, surface areas decreased—independently from the chosen parameters of catalyst, base, and solvent—from carbon-centered CMPs (1595 m2 g?1) to silicon-, germanium-, and tin-centered (649 m2 g?1) networks.

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Microporous organic polymers involving thiadiazolopyridine for high and selective uptake of greenhouse gases at low pressure

A new core of [1,2,5]-thiadiazolo-[3,4-c]-pyridine was employed for the fabrication of microporous organic polymers exhibiting a very high CO2 uptake of 5.8 mmol g-1 (25.5 wt%) at 273 K and 1 bar. The presence of CO2-philic active sites and microporosity confer the high uptake and superior selectivity (61) towards CO2 over N2.

A Triazole-Containing Metal-Organic Framework as a Highly Effective and Substrate Size-Dependent Catalyst for CO2 Conversion

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Electrochemically active porous organic polymers based on corannulene

For the first time, porous organic polymers (POPs) based on the smallest buckybowl, corannulene (BB-POPs) have been synthesized. Three POPs were synthesised via Sonogashira co-polymerization of 1,2,5,6-tetrabromocorannulene and alkyne linkers. BB-POP-3 exhibits the highest surface area (SABET = 560 m2 g-1) and CO2 adsorption of 11.7 wt%, while they retain the redox properties of corannulene.

Tetrahedral rigid core antenna chromophores bearing bay-substituted perylenediimides

Two new representative methane- and adamantane-centered 'antenna' tetramers bearing bay-substituted π-conjugated phenylethynyl-perylenediimides (PDICCPh) as chromophoric subunits, tetrakis-[1-(4-ethynylphenyl)-N,N′-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide]-methane (1) and tetrakis-1,3,5,7-[1-(4-ethynylphenyl)-N,N′-bis(1-hexylheptyl)-perylene-3,4:9,10-tetracarboxylic diimide]-adamantane (2), have been synthesized and their structural aspects have been thoroughly investigated by NMR spectroscopy. These PDI tetramers (1 and 2) represent the first successful example of incorporating the bay-substituted phenylethynyl-perylenediimides into the large rigid core tetrahedral frameworks. In these PDI tetramers, dynamic NMR experiments revealed the existence of perylene-centered conformational dynamic equilibrium (ΔG≠=15-17 kcal/mol), the primary cause of the observed spectral broadening in conventional 1H NMR spectra (295 K). In addition, PDI tetramers 1 and 2 were found to possess exceptional (photo)chemical stability, and their corresponding photophysical properties (εmax～180,000; τFL=6.9 ns; ΦFL～60%) make them viable candidates for various photonic applications and are in good agreement with other related multichromophoric PDI-based systems.

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