17938-13-5

Usage

Uses

Used in Chemical Synthesis:
1,4-Bis[(trimethylsilyl)ethynyl]benzene is used as a key intermediate in the synthesis of various organic compounds. Its unique reactivity allows for the formation of new chemical bonds and the creation of complex molecular structures.
Used in Material Science:
In the field of material science, 1,4-Bis[(trimethylsilyl)ethynyl]benzene is utilized as a precursor for the development of advanced materials with specific properties. Its ability to form stable bonds with other elements makes it a valuable component in the design of new materials with tailored characteristics.
Used in Pharmaceutical Research:
1,4-Bis[(trimethylsilyl)ethynyl]benzene is employed as a building block in the design and synthesis of novel pharmaceutical compounds. Its unique structure and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Electronics Industry:
In the electronics industry, 1,4-Bis[(trimethylsilyl)ethynyl]benzene is used as a component in the development of advanced electronic materials, such as semiconductors and conductive polymers. Its electronic properties make it a promising candidate for enhancing the performance of electronic devices.
Used in Nanotechnology:
1,4-Bis[(trimethylsilyl)ethynyl]benzene is utilized in nanotechnology for the fabrication of nanoscale structures and devices. Its ability to form stable bonds with other elements allows for the precise manipulation of materials at the nanoscale, leading to the development of innovative applications in various fields.

InChI:InChI=1/C16H22Si2/c1-17(2,3)13-11-15-7-9-16(10-8-15)12-14-18(4,5)6/h7-10H,1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 624-38-4 para-diiodobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 935-14-8 1,4-diethynylbenzene 
• 106-37-6 1.4-dibromobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 544706-67-4 cis-1,4-diacetoxy-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene 
• 250643-77-7 tris(2-(trimethylsilyl)ethynyl)indium 
• 862801-08-9 1,4-bis[(trimethylsilyl)ethynyl]-2,5-cyclohexadiene-1,4-diol 
• 16029-98-4 trimethylsilyl iodide 

Downstream Products

• 935-14-8 1,4-diethynylbenzene 
• 168762-34-3 1,4-bis(4',4'-dichloro-2'-trimethylsilyl-3'-oxo-1'cyclobutenyl)benzene 
• 1849-27-0 1,4-bis(2-phenylethynyl)benzene 
• 147492-76-0 1-(phenylethynyl)-4-[(trimethylsilyl)ethynyl]benzene 
• 475094-86-1 1,4-bis-[(dimethoxy-methyl-silanyl)-ethynyl]-benzene 
• 849928-05-8 [Fe(C₅H₄Si(CH₃)2C(CHSi(CH₃)3)C₆H₄CCSi(CH₃)3)2] 
• 187849-77-0 dicarbonylbis(trimethyl phosphite)(1,4-bis(trimethylsilylethynyl)benzene)iron⁽⁰⁾ 
• 864448-72-6 (((C₅H₅)MoS₂)2CH₂CCSi(CH₃)3(C₆H₄CCSi(CH₃)3)) 
• 937181-45-8 C₆H₄(CHC(Si(CH₃)3)Ga(C₃H₇)2)2 
• 937181-46-9 C₆H₄(CHC(Si(CH₃)3)Ga(CH(CH₃)2)2)2 
• 926647-01-0 [(Z,E)-(1-(4-(trimethylsilylethynyl)phenyl)-2-(trimethylsilyl)ethenyl)[(2-diphenylphosphino)thiophenyl(S,P)]trimethylphosphine]nickel(II) 
• 937181-41-4 C₆H₄(CHC(Si(CH₃)3)Ga(C₂H₅)2)2 
• 1303613-37-7 C₂₂H₂₂O₄ 
• 1303613-38-8 C₃₀H₃₄O₄ 

Relevant academic research and scientific papers

Pyrazine-based donor tectons: Synthesis, self-assembly and characterization

Two new supramolecular building blocks derived from pyrazine are introduced. These molecules, having pendant pyridine units covalently linked to central pyrazine ring, are structurally rigid with pre-defined bite angles. Therefore they can act as donor tectons in design of supramolecular hexagons using coordination driven self-assembly protocol. Multinuclear NMR (including 1H DOSY) and mass spectrometry have been utilized to confirm the purity and stoichiometry of these self assembled hexagonal ensembles. PM6 molecular modeling studies corroborate their hexagonal shape and nanoscalar dimensions.

A Triazine-Based Analogue of Graphyne: Scalable Synthesis and Applications in Photocatalytic Dye Degradation and Bacterial Inactivation

Graphyne, a theorized carbon allotrope possessing only sp- and sp2-hybridized carbon atoms, holds great potentials in many fields, especially in catalysis and energy-transfer/storage devices. Using a bottom-up strategy, we synthesized a new N-doped graphyne analogue, triazine- and 1,4-diethynylbenzene-based graphyne TA-BGY, in solution in gram-scale. The unique sp/sp2 carbon-conjugated TA-BGY possesses an extended porous network structure with a BET surface area of approximately 300 m2 g?1. Owing to its low optical band gap (1.44 eV), TA-BGY was expected to have many applications, which were exemplified by the photodegradation of methyl orange and photocatalytic bacterial inactivation.

Study on synthesis, characterization, and nonvolatile memory behavior of ferrocene-containing metallopolymers

In this work, two metallopolymers (P1 and P2)were designed and synthesized through coupling of ferrocene-anchored fluorene derivatives with porphyrin and benzene based diethynyl ligand, respectively. The chemical structure and physical properties of these two metallpolymers were fully characterized, which indicate that these two metallopolymers are thermally stable and semiconducting. Then, sandwich-like organic resistive memory based on P1 and P2 for data storage were explored. The memory device testing results manifest that both P1 and P2 are of the stable electric bistability and show write once read many times memory (WORM)characteristics.

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.

Fluorescence and visual sensing of nitroaromatic explosives using electron rich discrete fluorophores

Several π-electron rich fluorescent aromatic compounds containing trimethylsilylethynyl functionality have been synthesized by employing Sonogashira coupling reaction and they were characterized fully by NMR ( 1H, 13C)/IR spectroscop

C-Au Covalently Bonded Molecular Junctions Using Nonprotected Alkynyl Anchoring Groups

We report on an approach to realize carbon-gold (C-Au) bonded molecular junctions without the need for an additive to deprotect the alkynyl carbon as endstanding anchor group. Using the mechanically controlled break junction (MCBJ) technique, we determine the most probable conductance value of a family of alkynyl terminated oligophenylenes (OPA(n)) connected to gold electrodes through such an akynyl moiety in ambient conditions. The molecules bind to the gold leads through an sp-hybridized carbon atom at each side. Comparing our results with other families of molecules that present organometallic C-Au bonds, we conclude that the conductance of molecules contacted via an sp-hybridized carbon atom is lower than the ones using sp3 hybridization due to strong differences in the coupling of the conducting orbitals with the gold leads.

Arene-Inserted Extended Germa[n]pericyclynes: Synthesis, Structure, and Phosphorescence Properties

This report describes the synthesis and characterization of arene-inserted extended (ArEx) germa[n]pericyclynes composed of germanium and 1,4-diethynylbenzene units. These novel cyclic germanium-π unit materials were synthesized with diethynylbenzene and germanium dichloride. X-ray crystallographic analysis revealed their structures, and the planar conformation of ArEx germa[4]pericyclyne along with the regular aromatic rings. UV/Vis absorption spectra and fluorescence emission spectra showed considerably unique and highly improved character compared to previously reported germa[n]pericyclynes. Even in the absence of transition metal components, phosphorescence emissions were observed, and the emission lifetimes were dramatically improved. ArEx germa[n]pericyclynes showed high photoluminescence quantum yields, whereas low photoluminescence quantum yields were observed for acyclic compounds. Density functional theory calculations show delocalized orbitals between skipped alkyne units through a germanium tether, and an increase in the HOMO energy level, leading to a small HOMO–LUMO energy gap.

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

An efficient fragment splicing method for the construction of multiple nucleobase-terminated monomers has been developed. Conformationally fixed rod, trigonal planar and tetrahedral thymine and adenine structures were generated in moderate to good yields,

Microwave-assisted unprotected Sonogashira reaction in water for the synthesis of polysubstituted aromatic acetylene compounds

A microwave-assisted, efficient and rapid Sonogashira reaction was developed for the synthesis of polysubstituted aromatic alkynes. The reaction was made environmentally friendly and easy to perform by replacing the traditional amine solvents with water.

2D arrays of organic qubit candidates embedded into a pillared-paddlewheel metal-organic framework

The creation of ordered arrays of qubits that can be interfaced from the macroscopic world is an essential challenge for the development of quantum information science (QIS) currently being explored by chemists and physicists. Recently, porous metal?organic frameworks (MOFs) have arisen as a promising solution to this challenge as they allow for atomic-level spatial control of the molecular subunits that comprise their structures. To date, no organic qubit candidates have been installed in MOFs despite their structural variability and promise for creating systems with adjustable properties. With this in mind, we report the development of a pillared-paddlewheel-type MOF structure that contains 4,7-bis(2-(4-pyridyl)-ethynyl) isoindoline N-oxide and 1,4-bis(2-(4-pyridyl)-ethynyl)-benzene pillars that connect 2D sheets of 9,10-dicarboxytriptycene struts and Zn2(CO2)4 secondary binding units. The design allows for the formation of ordered arrays of reorienting isoindoline nitroxide spin centers with variable concentrations through the use of mixed crystals containing the secondary 1,4-phenylene pillar. While solvent removal causes decomposition of the MOF, magnetometry measurements of the MOF containing only N-oxide pillars demonstrated magnetic interactions with changes in magnetic moment as a function of temperature between 150 and 5 K. Variable-temperature electron paramagnetic resonance (EPR) experiments show that the nitroxides couple to one another at distances as long as 2 nm, but act independently at distances of 10 nm or more. We also use a specially designed resonance microwave cavity to measure the face-dependent EPR spectra of the crystal, demonstrating that it has anisotropic interactions with impingent electromagnetic radiation.