1227040-87-0

Basic information

• Product Name: [4-(1,2,2-triphenylethenyl)phenyl]boronic acid
• Synonyms: [4-(1,2,2-triphenylethenyl)phenyl]boronic acid;4-(1,2,2-triphenylvinyl)phenylboronic acid
• CAS NO: 1227040-87-0
• Molecular Formula: C₂₆H₂₁BO₂
• Molecular Weight: 376.25474
• Mol File: 1227040-87-0.mol

Chemical Properties

• Melting Point: 126-131°C
• Boiling Point: 513.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.65±0.16(Predicted)
• CAS DataBase Reference: [4-(1,2,2-triphenylethenyl)phenyl]boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [4-(1,2,2-triphenylethenyl)phenyl]boronic acid(1227040-87-0)
• EPA Substance Registry System: [4-(1,2,2-triphenylethenyl)phenyl]boronic acid(1227040-87-0)

Safety Data

• Hazardous Substances Data: 1227040-87-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
[4-(1,2,2-triphenylethenyl)phenyl]boronic acid is utilized as a reagent in Suzuki-Miyaura cross-coupling reactions, a widely used method in organic chemistry for the formation of carbon-carbon bonds. Its role in these reactions is crucial for the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, [4-(1,2,2-triphenylethenyl)phenyl]boronic acid is employed as a building block for the development of new pharmaceutical compounds. Its unique structure allows for the creation of molecules with specific biological activities, contributing to the discovery of potential therapeutic agents.
Used in Materials Science:
[4-(1,2,2-triphenylethenyl)phenyl]boronic acid is also studied for its potential applications in the development of fluorescent sensors and organic electronic materials. Its molecular structure provides opportunities for the creation of materials with tailored properties, such as sensitivity to specific analytes or improved electronic performance.
Used in the Development of Fluorescent Sensors:
[4-(1,2,2-triphenylethenyl)phenyl]boronic acid is used as a component in the development of fluorescent sensors due to its unique molecular structure. These sensors can be designed to detect specific chemical or biological targets, with potential applications in environmental monitoring, medical diagnostics, and other fields.
Used in Organic Electronic Materials:
In the realm of organic electronics, [4-(1,2,2-triphenylethenyl)phenyl]boronic acid is used as a constituent in the creation of materials with enhanced electronic properties. These materials can be employed in various electronic devices, such as organic light-emitting diodes (OLEDs), organic solar cells, and organic field-effect transistors (OFETs), where their unique characteristics can improve device performance and functionality.

Upstream product

• 121-43-7 Trimethyl borate 
• 34699-28-0 1-(4-bromophenyl)triphenylethene 
• 101-81-5 Diphenylmethane 
• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 1391632-33-9 C₂₆H₂₁BrO 
• 881-42-5 diphenylmethyllithium 
• 119-61-9 benzophenone 
• 150-46-9 triethyl borate 
• 7732-18-5 water 
• 5419-55-6 Triisopropyl borate 
• 688-74-4 boric acid tributyl ester 

Downstream Products

• 1260865-91-5 4,4,5,5–tetramethyl–2–(4–(1,2,2–triphenylvinyl)phenyl)–1,3,2–dioxaborolane 
• 1332644-19-5 4,7-bis(4-(1,2,2-triphenylvinyl)phenyl)benzo[c][1,2,5]thiadiazole 
• 1332644-20-8 4,7-bis{5-[4-(1,2,2-triphenylvinyl)phenyl]-2-thienyl}-2,1,3-benzothiadiazole 
• 1332830-69-9 4'-[4'-(1,2,2-triphenylvinyl)-(1,1'-biphenyl)-4-yl]-2,2':6',2''-terpyridine 
• 1365542-76-2 N,N'-dicyclohexyl-1,7-bis(4'-(1',2',2'-triphenyl)vinyl)phenylperylene-3,4:9,10-tetrcarboxylic bisimide 
• 1365541-05-4 2-bromo-9,9-dioctyl-7-(4-(1,2,2-triphenylethylenyl)phenyl)-9H-fluorene 
• 1365541-06-5 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9,9-dioctyl-7-(4-(1,2,2-triphenylethylenyl)phenyl)-9H-fluorene 
• 1365541-02-1 9,9-dioctyl-2,7-bis(4-(1,2,2-triphenylvinyl)phenyl)-9H-fluorene 
• 1365541-03-2 C₁₁₀H₁₁₈ 
• 1365534-67-3 1-[4'-(2-phenyl-5-1,3,4-oxadiazolyl)biphenyl-4-yl]-1,2,2-triphenylethene 
• 1361123-18-3 9-[4'-(1,2,2-triphenylvinyl)biphenyl-4-yl]-9H-carbazole 
• 1361123-19-4 9-phenyl-3,6-bis[4-(1,2,2-triphenylvinyl)phenyl]-9H-carbazole 
• 1391632-32-8 2-(2-(2-hydroxyethoxy)ethyl)-6-(4-(1,2,2-triphenylvinyl)phenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 1416785-73-3 1,5-bis[4-(1,2,2-triphenylvinyl)phenyl]naphthalene 

Relevant articles and documents

Aggregation-Induced Emission-Based Chemodosimeter Approach for Selective Sensing and Imaging of Hg(II) and Methylmercury Species

Methylmercury (CH3Hg+) is the common form of organic mercury and is more toxic than its inorganic or elemental forms. Mercury is emanated in the course of various natural events and human activities and converts to methylmercury by anaerobic organisms. CH3Hg+ are ingested by fish and subsequently bioaccumulated in their tissue and, eventually, enter the human diet, causing serious health issues. Therefore, selective and sensitive detection of bioaccumulated CH3Hg+ in fish samples is essential. Herein, the development of a simple, highly sensitive and selective aggregation-induced emission (AIE)-based turn-on probe for both inorganic mercury ions and organicmercury species is reported. The probe's function is based on mercury ion-promoted transmetalation reaction of aryl boronic acid. The probe, a tetraphenylethylene (TPE)-monoboronic acid (1), was successfully utilized for AIE-based fluorescence imaging study on methylmercury-contaminated live cells and zebrafish for the first time. Both Hg(II) and CH3Hg+ ensued a fast transmetalation of TPE-boronic acid causing drastic reduction in the solubility of the resulting product (TPE-HgCl/TPE-HgMe) in the working solvent system. At the dispersed phase, the aggregated form of TPE-mercury ions recovers planarity because of restricted rotational freedom promoting aggregation-induced emission. Simple design, cost-effective synthesis, high selectivity, inexpensive instrumentation, fast signal transduction, and low limit of detection (0.12 ppm) are some of the key merits of this analytical tool.

A new ligand and its complex with multi-stimuli-responsive and aggregation-induced emission effects

A new ligand containing tetraphenylethylene and terpyridine moieties, and its zinc ion complex were synthesized. Both of them exhibit an aggregation-induced emission effect. Their colors and emissions can be smartly switched by various external stimuli in

Specific detection of D-glucose by a tetraphenylethene-based fluorescent sensor

A conceptually new "light-up" biosensor with a high specificity for D-glucose (Glu) in aqueous media has been developed. The emission from a tetraphenylethene (TPE)-cored diboronic acid (1) was greatly boosted when the fluorogen was oligomerized with Glu because of restriction of the intramolecular rotations of the aryl rotors of TPE by formation of the oligomer. Little change in the light emission was observed when 1 was mixed with D-fructose, D-galactose, or D-mannose, as these saccharides are unable to oligomerize with the fluorogen.

A facile approach to highly efficient and thermally stable solid-state emitters: Knitting up AIE-active TPE luminogens by aryl linkers

A facile approach to thermally stable and efficient solid-state emitters is proposed. By hooking up tetraphenylethene (TPE) units through aryl linkers under Suzuki coupling conditions, a series of arylene bis(tetraphenylethene)s (TPE-Ar-TPE Ar = 2, 5-dime

Novel thieno-[3,4-b]-pyrazine derivatives for non-doped red organic light-emitting diodes

Two novel red fluorescent thieno-[3,4-b]-pyrazine-cored molecules containing tetraphenylethylene as peripheral groups, T-TP and T-TP1, are designed and synthesized. Their photophysical, electrochemical and electroluminescent properties are investigated. T

pH-Responsive dye with dual-state emission in both visible and near infrared regions

A new dual-state emission (DSE) dye comprised of tetraphenylethene (TPE), triphenylamine (TPA), and indoline groups has been synthesized, which showed efficient fluorescence in both solution and solid. The dye is comprised of three parts and these parts s

A multifunctional aggregation-induced emission (AIE)-active fluorescent chemosensor for detection of Zn2+ and Hg2+

An aggregation-induced emission (AIE)-active fluorescent chemosensor based on a tetraphenylethene (TPE) unit has been successfully designed and synthesized. Interestingly, the luminogen could detect Zn2+ selectively in a THF solution with the d

Creation of highly efficient solid emitter by decorating pyrene core with AIE-active tetraphenylethene peripheries

Turning stone into gold : pyrene, a faint fluorophore in the solid state, is transformed into a bright emitter by decorating it with tetraphenylethene units; the new luminogen is thermally and morphologically stable and its light-emitting diode shows excellent performance, with external quantum efficiency and current efficiency up to 4.95% and 12.3 cd A-1, respectively.

Impacts of intramolecular B-N coordination on photoluminescence, electronic structure and electroluminescence of tetraphenylethene-based luminogens

N,C-Chelate four-coordinate organoborons are a new class of luminogenic materials but the impacts of intramolecular B-N coordination on the optoelectronic properties of the luminogens are not fully understood. In this work, B-N coordination is grafted onto two tetraphenylethene (TPE)-based luminogens and the thermal stabilities, optical properties and electronic structures of the generated organoborons are investigated and compared with those of counterparts without B-N coordination. Both luminogens are thermally stable and show aggregation-induced emission. The presence of B-N coordination not only improves photoluminescent property of the luminogens, affording excellent solid-state fluorescence quantum yields up to unity, but also lowers the LUMO energy levels, owing to pπ-π* conjugation. The application of both organoborons as emitters for organic light-emitting diodes is evaluated. The devices of them exhibit superior electroluminescent efficiencies to the devices of counterparts, demonstrating that B-N coordination is conducive to electroluminescent property of the luminogens.

New Organometallic Tetraphenylethylene?Iridium(III) Complexes with Antineoplastic Activity

Iridium(III) complexes have attracted more and more attention in the past few years because of their potential antineoplastic activity. In this study, four IrIII complexes of the types [(η5-Cpx)Ir(N^N)Cl]PF6 (co