741259-14-3

Usage

Chemical structure

1,1,2,2-tetrakis(4-(2-(trimethylsilyl)ethynyl)phenyl)ethene is a chemical compound consisting of four connected units of 4-(2-(trimethylsilyl)ethynyl)phenyl groups attached to an ethene backbone.

Building block

It is commonly used as a building block in the synthesis of functional materials such as conducting polymers and organic electronic devices.

Chemical stability

The presence of ethynyl and trimethylsilyl groups in the molecule allows for the formation of strong covalent bonds and provides chemical stability.

Electronic and optical properties

1,1,2,2-tetrakis(4-(2-(trimethylsilyl)ethynyl)phenyl)ethene exhibits unique electronic and optical properties, making it a promising candidate for applications in organic electronics, optoelectronics, and photovoltaic devices.

Highly conjugated structure

The compound has a highly conjugated structure, which contributes to its potential use in the development of molecular semiconductors and light-emitting materials.

Rigid backbone

The rigid backbone of the compound also plays a role in its potential applications in molecular semiconductors and light-emitting materials.

Upstream product

• 299914-63-9 1,1,2,2-tetrakis(4-iodophenyl)ethene 
• 1066-54-2 trimethylsilylacetylene 
• 61326-44-1 1,1,2,2-tetrakis(4-bromophenyl)ethene 
• 119-61-9 benzophenone 
• 3988-03-2 bis(4-bromophenyl)methanone 
• 101-81-5 Diphenylmethane 
• 4863-90-5 1,1,2,2-tetrakis(4-ethynylphenyl)ethane 
• 147820-36-8 4,4’-bis(2-trimethylsilylethynyl)benzophenone 
• 632-51-9 1,1,2,2-tetraphenylethylene 

Downstream Products

• 4863-90-5 1,1,2,2-tetrakis(4-ethynylphenyl)ethane 

Relevant academic research and scientific papers

Halogen Bonding Tetraphenylethene Anion Receptors: Anion-Induced Emissive Aggregates and Photoswitchable Recognition

A series of tetraphenylethene (TPE) derivatives functionalized with highly potent electron-deficient perfluoroaryl iodo-triazole halogen bond (XB) donors for anion recognition are reported. 1H NMR titration experiments, fluorescence spectroscopy, dynamic light scattering measurements, TEM imaging and X-ray crystal structure analysis reveal that the tetra-substituted halogen bonding receptor forms luminescent nanoscale aggregates, the formation of which is driven by XB-mediated anion coordination. This anion-coordination-induced aggregation effect serves as a powerful sensory mechanism, capable of luminescence chloride sensing at parts per billion concentration. Furthermore, the doubly substituted geometric isomers act as unprecedented photoswitchable XB donor anion receptors, where the composition of the photostationary state can be modulated by the presence of a coordinating halide anion.

Synthesis and Properties of BODIPY Appended Tetraphenylethylene Scaffolds as Photoactive Arrays

Tetraphenylethylene (TPE) and its derivatives exhibit excellent aggregation-induced emission (AIE) properties. The TPE unit is easily accessible, and many functional groups can be introduced in a facile manner to yield effective luminescent materials in both solution and the solid-state. It is because of this, several TPE-based compounds have been developed and applied in many areas, such as OLEDs and chemical sensors. Boron dipyrromethenes (BODIPYs) are a class of pyrrolic fluorophore of great interest with myriad application in both material science and biomedical applications. Through the combination of Pd-catalyzed cross-coupling reactions and traditional dipyrromethene chemistry, we present the syntheses of novel tetra-BODIPY-appended TPE derivatives with different distances between the TPE and BODIPY cores. The TPE-BODIPY arrays 6 and 9 show vastly differing AIE properties in THF/H2O systems, with 9 exhibiting dual-AIE, along with both conjugates being found to produce singlet oxygen (1O2). We presume the synthesized BODIPY-appended TPE scaffolds to be utilized for potential applications in the fields of light-emitting systems and theranostics.

White-Light Emission from Dual-Way Photon Energy Conversion in a Dye-Encapsulated Metal–Organic Framework

The design of white-light phosphors is attractive in solid-state lighting (SSL) and related fields. A new strategy in obtaining white light emission (WLE) from dual-way photon energy conversion in a series of dye?MOF (LIFM-WZ-6) systems is presented. Besi

Functionalized metal-organic framework compounds, complexes formed therefrom, and methods of preparation and use thereof

The invention discloses a functionalized metal-organic framework compounds, complexes formed therefrom, and methods of preparation and use thereof, wherein the molecular formula of the functionalizedmetal-organic framework compound is C36H22N7O4Zn, and th

Water-soluble Glucosamine-coated AIE-Active Fluorescent Organic Nanoparticles: Design, Synthesis and Assembly for Specific Detection of Heparin Based on Carbohydrate–Carbohydrate Interactions

Two water-soluble carbohydrate-coated AIE-activate fluorescent organic nanoparticles TPE3G and TPE4G were designed and synthesized for the detection of heparin. Different from the reported strategy, we not only utilized the general detection mechanism of

Tetrakis(trialkylsilylethynylphenyl)ethenes: Mechanofluorochromism arising from steric considerations with an unusual crystal structure

Mechanofluorochromism (MFC) arising from extended partial planarization of a conjugated molecular framework through the transfer of mechanical stress by terminal bulky groups is demonstrated. Thus the tetrakis(triisopropylsilyl-4-ethynylphenyl)ethene [TPE-(TIPS)4] luminophore, synthesized for the first time, is shown to exhibit MFC when the threshold pressure exceeds about 1.3 MPa. An analogous luminophore, tetra(trimethylsilyl-4-ethynylphenyl)ethene [TPE-(TMS)4], with smaller bulky groups at the periphery of TPE, synthesized for comparative studies, was also observed to exhibit MFC. MFC is observed under visible and UV light excitation. The color change is reversed upon annealing or under solvent fumigation conditions. The luminophores show high quantum yields in the solid state ranging from 60 to 74%. Very interestingly, TPE-(TMS)4 exhibited quite an unusual crystal structure, where no intermolecular interactions attributed to mechanofluorochromism are observed. The solid state optical absorption and CP-MAS 13C NMR measurements strongly suggested that the mechanism of MFC could have originated from partial planarization of the molecule upon grinding/shearing, facilitated by the bulky peripheral/terminal groups. These high solid state emitting luminophores with MFC properties could find applications in the areas of solid state lighting and sensors. The synthetic design, in principle, should enable MFC as a function of pressure (through variation in steric handle) and temperature (through electronic and conformational handles). The novel and rational synthetic design, in principle, should enable MFC in a family of organic molecules as a function of pressure and temperature.

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.

Mechanoluminescence from pure hydrocarbon AIEgen

We obtained a pure hydrocarbon tetraphenylethene (TPE) derivative with the characteristic of aggregation-induced emission (AIE) and mechanoluminescence (ML). The centrosymmetric crystal in the space group of C2 and the non-polar molecule indicate that the ML property is not related to the piezoelectric effect in the crystal; alternatively, a strong static electric interaction may be responsible for its ML phenomenon.

Conjugated microporous polymer networks with adjustable microstructures for high CO2 uptake capacity and selectivity

A series of phenylene-based conjugated microporous polymers (CMPs) of the A6 + Mx (x = 2, 3, 4, 6) type were synthesized. By tuning the monomer length and geometry, the BET surface area of CMPs can be tuned from 571 to 1115 m2/

BODIPY-containing porous organic polymers for gas adsorption

A series of BODIPY-containing microporous organic polymers was synthesized via a Sonogashira-Hagihara cross-coupling reaction of a BODIPY derivative with triple polymerisable groups and a range of aryl-alkyne monomers. All of the polymers show high isosteric heats of CO2 adsorption (23.3-27.3 kJ mol-1) because the incorporation of heteroatoms (N, B, F) from the BODIPY unit into the polymer skeleton enhanced the binding affinity between the pore wall and CO2 molecules. The aryl-alkyne monomer has a large influence on the surface area and CO2 adsorption performance of the resulting polymers. The polymer BDPCMP-3 shows a high Brunauer-Emmett-Teller specific surface area of up to 725 m2 g-1, while BDPCMP-2 with a low surface area of 582 m2 g-1 shows a high CO2 uptake ability of 2.25 mmol g-1 at 1.13 bar/273 K with a CO2/N2 adsorption selectivity of 32.3.