70592-06-2

Usage

Type of compound

Derivative of benzene

Contains groups

Methyl group, 1,2,2-triphenylethylene moiety

Usage

Organic synthesis, production of pharmaceuticals, dyes, and other industrial chemicals

Applications

Materials science, building block for synthesis of complex organic compounds

Unique features

Structure and properties useful for various chemical reactions and research purposes

Upstream product

• 125847-08-7 1-(4-methylphenyl)-1,2,2-triphenylethanol 
• 75-36-5 acetyl chloride 
• 859932-96-0 1,1,2-triphenyl-2-p-tolyl-ethanol 
• 134-84-9 4-Methylbenzophenone 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 591-50-4 iodobenzene 
• 2789-88-0 1,2-bis(4-methylphenyl)acetylene 
• 98-80-6 phenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 100-58-3 phenylmagnesium bromide 
• 501-65-5 diphenyl acetylene 
• 106-38-7 para-bromotoluene 
• 1607-57-4 Triphenylvinyl bromide 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 1403677-99-5 (2-(4-(azidomethyl)phenyl)ethene-1,1,2-triyl)tribenzene 
• 1434839-89-0 1-[4-(isothiocyanatomethyl)phenyl]-1,2,2-triphenylethene 
• 1609104-34-8 2-[4-(1,2,2-triphenylvinyl)phenyl]acetonitrile 

Relevant academic research and scientific papers

Multicomponent Polycoupling of Internal Diynes, Aryl Diiodides, and Boronic Acids to Functional Poly(tetraarylethene)s

This paper describes the development of a new three-component polymerization route to functional poly(tetraarylethene)s (PTAEs). The polycoupling reactions of internal diynes, aryl diiodides, and arylboronic acids proceed smoothly in the presence of PdCl2 and NaF at 70 °C in dimethylformamide, generating PTAEs with promising molecular weights in high yields from different monomers. Most of the PTAEs are soluble in common organic solvents and are thermally stable. Some of the PTAEs exhibit the phenomenon of aggregation-induced emission: their light emission in solution is enhanced by aggregate formation. The tetraphenylethene-containing PTAE can function as a fluorescent chemosensor for detecting Ru3+ ions with high sensitivity and specificity. It is also a promising material for the fabrication of fluorescent pattern by photolithography process. All the PTAEs possess good film-forming ability and their thin films exhibit high refractive index (RI = 1.7751-1.6382) at 632.8 nm, whose values are higher than those of commercial polymers such as polycarbonate and polystyrene.

Intermolecular hydrogen-bond interaction to promote thermoreversible 2'-deoxyuridine-based AIE-organogels

Fluorescent supramolecular nucleoside-based organogels or hydrogels have attracted increasing attention owing to their tunable stability, drug delivery, tissue engineering, and inherent biocompatibility for applications in designing sensors. As the temper

Aggregation-induced emission or aggregation-caused quenching? Impact of covalent bridge between tetraphenylethene and naphthalimide

Understanding the physical mechanisms governing aggregation-induced-emission (AIE) and aggregation-caused-quenching plays a vital role in developing functional AIE materials. In this work, tetraphenylethene (TPE, a classical AIEgen) and naphthalimide (NI, a popular fluorophore with ACQ characteristics) were connected through non-conjugated linkages and conjugated linkages. We showed that the nonconjugated-linkage of TPE to NI fragments leads to substantial PET in molecular aggregates and ACQ. In contrast, the conjugated connection between TPE and NI moieties results in the AIE phenomenon by suppressing twisted intramolecular charge transfer. This work provides an important guideline for the rational design of AIE materials.

The aggregation-induced emission of Methyl-bis-(4-triphenylvinyl-benzyl)-amine in solution with torsional and locked stacking effects

Herein, we designed and synthesized a compound, Di-TPE, which has the torsional, locked stacking effect in aggregation with aggregation-induced emission properties in solution. The carbon chain of Di-TPE molecule centered on the nitrogen atom acts as a linker to connect two tetraphenylethylene groups. Di-TPE has a torsional stacking effect in the aggregation state, which is very different from the face-to-face stacking mode of TPE. Under the torsional stacking effect, Di-TPE aggregates will also form intra-locked conformation, resulting in the electron cloud distribution of Di-TPE aggregates with the sandwich biscuit shape. This is completely different from TPE and has a profound effect on the spectral properties of Di-TPE. Di-TPE with aggregation-induced emission properties under torsional stacking effect may provide a beneficial help for researchers to expand the field of fluorescent molecules, luminescent devices and biological fluorescent probes.

TPE-2'-deoxynucleoside, fluorescent gel, and preparation methods and application of TPE-2'-deoxynucleoside and fluorescent gel

The invention discloses TPE-2'-deoxynucleoside, fluorescent gel, and preparation methods and application of the TPE-2'-deoxynucleoside and the fluorescent gel. The preparation method of TPE-2'-deoxynucleoside comprises the following steps: mixing alkyne-m

Synthesis of Tetraarylethene Luminogens by C?H Vinylation of Aromatic Compounds with Triazenes

Tetraarylethenes are obtained by acid-induced coupling of vinyl triazenes with aromatic compounds. This new C?H activation route for the synthesis of aggregation-induced emission luminogens is simple, fast, and versatile. It allows the direct grafting of triarylethenyl groups onto a variety of aromatic compounds, including heterocycles, supramolecular hosts, biologically relevant molecules, and commercial polymers.

Nitrogen-oxygen stable free radical with aggregation-induced emission function, and preparation method thereof

The invention discloses a nitrogen-oxygen stable free radical with an aggregation-induced emission function, and a preparation method thereof. The nitrogen-oxygen stable free radical has a structure represented by a formula shown in the description; and in the formula, R1, R2, R3 and R4 are respectively and independently selected from C1-6 alkyl groups or heterochain groups optionally substitutedwith other elements, and R5 is hydrogen, NH2, a carbonyl group, a hydroxyl group, an oxygen-linked alkyl group, or a heterochain group optionally substituted with other elements. The preparation method comprises the following steps: synthesizing teramethylpiperidinyl-1-oxy with a hydroxyl group from tetramethyl piperidinol, synthesizing a tetraphenylethylene intermediate from 2-bromo-1,1,2-triphenylethylene and 4-methylphenylboronic acid, and brominating the tetraphenylethylene intermediate to obtain tetraphenylethylene with a benzyloxybromo group; carrying out a nucleophilic substitution reaction on a nitrogen-oxygen stable free radical and the tetraphenylethylene with the benzyloxybromo group at room temperature for 2-12 h; and performing purification by adopting a column chromatographyseparation process to obtain a nitrogen-oxygen stable free radical product with the aggregation-induced emission performance.

Catalyst shuttling enabled by a thermoresponsive polymeric ligand: Facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium

A polymeric monophosphine ligand WePhos has been synthesized and complexed with palladium(ii) acetate [Pd(OAc)2] to generate a thermoresponsive pre-catalyst that can shuttle between water and organic phases, with the change being regulated by temperature. The structure of the polymeric ligand was confirmed with matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) mass spectrometry and size-exclusion chromatography (SEC) analysis, as well as nuclear magnetic resonance (NMR) measurements. This polymeric metal complex enables highly efficient Pd-catalyzed cross-couplings and tandem reactions using 50 to 500 ppm palladium, and this can facilitate reactions that are tolerant to a broad spectrum of (hetero)aryl substrates and functional groups, as demonstrated with 73 examples with up to 99% isolated yields. Notably, 97% Pd remained in the aqueous phase after 10 runs of catalyst recycling experiments, as determined via inductively coupled plasma-atomic emission spectrometry (ICP-AES) measurements, indicating highly efficient catalyst transfer. Furthermore, a continuous catalyst recycling approach has been successfully developed based on flow chemistry in combination with the catalyst shuttling behavior, allowing Suzuki-Miyaura couplings to be conducted at gram-scales with as little as 10 ppm Pd loading. Given the significance of transition-metal catalyzed cross-coupling and increasing interest in sustainable chemistry, this work is an important step towards the development of a responsive catalyst, in addition to having high activity, by tuning the structures of the ligands using polymer science.

New method for preparing aggregation-included light emitting materials of tetraphenyl ethylene derivatives

The invention relates to the technical field of fine chemical engineering and discloses a new method for preparing aggregation-included light emitting materials of tetraphenyl ethylene derivatives. The method specifically comprises the steps of taking ary

Luminescent cyclic trinuclear coinage metal complexes with aggregation-induced emission (AIE) performance

A series of AIE active cyclic trinuclear complexes (Au3, Ag3, and Cu3) have been successfully prepared and elucidated by X-ray crystallography. These complexes showed excellent AIE properties and their quantum yields (QYs)