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Tetraphenylethylene

Base Information Edit
  • Chemical Name:Tetraphenylethylene
  • CAS No.:632-51-9
  • Molecular Formula:C26H20
  • Molecular Weight:332.445
  • Hs Code.:2902909090
  • European Community (EC) Number:211-179-1
  • NSC Number:52243,40472
  • UNII:MT243CE29P
  • DSSTox Substance ID:DTXSID1060895
  • Nikkaji Number:J103.650E
  • Wikipedia:Tetraphenylethylene
  • Wikidata:Q7706652
  • Mol file:632-51-9.mol
Tetraphenylethylene

Synonyms:tetraphenylethylene

Suppliers and Price of Tetraphenylethylene
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • 1,1,2,2-Tetraphenylethylene
  • 1g
  • $ 312.00
  • TRC
  • 1,1,2,2-Tetraphenylethylene
  • 5g
  • $ 200.00
  • TCI Chemical
  • Tetraphenylethylene >98.0%(GC)
  • 10g
  • $ 93.00
  • TCI Chemical
  • Tetraphenylethylene >98.0%(GC)
  • 1g
  • $ 19.00
  • SynQuest Laboratories
  • Tetraphenylethylene
  • 5 g
  • $ 42.00
  • Sigma-Aldrich
  • 1,1,2,2-Tetraphenylethylene 98%
  • 5g
  • $ 59.50
  • Medical Isotopes, Inc.
  • 1,1,2,2-Tetraphenylethene 95+%
  • 5 g
  • $ 372.00
  • Crysdot
  • 1,1,2,2-Tetraphenylethene 97%
  • 5g
  • $ 90.00
  • Crysdot
  • 1,1,2,2-Tetraphenylethene 97%
  • 10g
  • $ 140.00
  • Crysdot
  • 1,1,2,2-Tetraphenylethene 97%
  • 25g
  • $ 215.00
Total 91 raw suppliers
Chemical Property of Tetraphenylethylene Edit
Chemical Property:
  • Appearance/Colour:white to light beige crystalline powder 
  • Vapor Pressure:7.04E-07mmHg at 25°C 
  • Melting Point:222-226 °C 
  • Refractive Index:1.637 
  • Boiling Point:420.117 °C at 760 mmHg 
  • Flash Point:206.202 °C 
  • PSA:0.00000 
  • Density:1.088 g/cm3 
  • LogP:6.69400 
  • Storage Temp.:Sealed in dry,Room Temperature 
  • Solubility.:Soluble in hot toluene 
  • Water Solubility.:insoluble 
  • XLogP3:8
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:0
  • Rotatable Bond Count:4
  • Exact Mass:332.156500638
  • Heavy Atom Count:26
  • Complexity:353
Purity/Quality:

97% *data from raw suppliers

1,1,2,2-Tetraphenylethylene *data from reagent suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
  • Safety Statements: 22-24/25 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Other Classes -> Aromatic Hydrocarbons
  • Canonical SMILES:C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
  • General Description 1,1',1'',1'''-(1,2-Ethenediylidene)tetrakisbenzene, also known as tetraphenylethylene (TPE), is a versatile compound exhibiting aggregation-induced emission (AIE) properties, making it valuable for applications such as fluorescence turn-on sensors and efficient blue emitters in OLEDs. Its AIE behavior allows for selective detection of hydrogen peroxide and D-glucose through aggregation-driven fluorescence enhancement, as well as specific interactions with proteins like cholera toxin. Additionally, TPE serves as a core structure in designing deep-blue luminogens for OLEDs, where its incorporation enhances charge injection and emission efficiency without compromising color purity. The compound's reactivity in carbenoid reactions further underscores its utility in synthetic chemistry.
Technology Process of Tetraphenylethylene

There total 490 articles about Tetraphenylethylene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
diphenyl acetylene; bis(pinacol)diborane; With tetrakis(triphenylphosphine)platinum; In 1,4-dioxane; at 180 ℃; for 0.5h; microwave irradiation;
bromobenzene; With palladium diacetate; potassium hydroxide; triphenylphosphine; In 1,4-dioxane; at 140 ℃; for 0.5h; Further stages.; microwave irradiation;
DOI:10.1016/j.tetlet.2008.06.017
Guidance literature:
With nickel dichloride; In tetrahydrofuran; water; toluene; at 30 ℃; for 2h; Inert atmosphere; Schlenk technique;
DOI:10.1021/ja513166w
Refernces Edit

A highly selective fluorescence turn-on detection of hydrogen peroxide and d-glucose based on the aggregation/deaggregation of a modified tetraphenylethylene

10.1016/j.tetlet.2014.01.056

The research presents a study on a selective fluorescence turn-on detection method for hydrogen peroxide (H2O2) and D-glucose, utilizing a tetraphenylethylene (TPE)-based molecule, compound 1. The detection mechanism relies on the aggregation-induced emission (AIE) behavior of the TPE unit and the reaction of H2O2 with the arylboronic ester group in compound 1. Upon reaction with H2O2, compound 1 transforms into compound 2, which is less soluble in water, leading to aggregation and a consequent fluorescence turn-on due to AIE properties. The study also demonstrates the application of compound 1 for the selective detection of D-glucose in aqueous solutions, leveraging the enzymatic oxidation of D-glucose by glucose oxidase (GOx) to produce H2O2, which then reacts with compound 1. The experiments involved the synthesis of compound 1, its characterization using 1H NMR, 13C NMR, and mass spectra, and fluorescence spectroscopy to monitor the reaction with H2O2 and the detection of D-glucose. The results showed high selectivity and sensitivity for H2O2 detection, with a low detection limit of 180 nM, and successful D-glucose detection down to a concentration of 3.0 μM. The selectivity was confirmed by testing the fluorescence response of compound 1 to other reactive oxygen species and sugars, with significant enhancement observed only in the presence of H2O2 and D-glucose.

A new approach to prepare efficient blue AIE emitters for undoped OLEDs

10.1002/chem.201303522

The research focuses on the development of new aggregation-induced emission (AIE) active luminogens, specifically targeting the synthesis of efficient blue AIE emitters for undoped organic light-emitting diodes (OLEDs). The purpose of this study was to address the challenges associated with blue OLEDs, which often suffer from inferior performance due to the large band gap in blue luminogens. The researchers successfully synthesized two deep-blue fluorophores, TPE–pTPA and TPE–mTPA, along with six other compounds for comparison. These luminogens were designed to restrict the π-conjugation length, ensuring blue emission, by incorporating hole-dominated triphenylamine (TPA) and fluorene groups with high luminous efficiency, connected through unconjugated linkages. The study concluded that TPE–pTPA and TPE–mTPA exhibited the best electroluminescence performance with low turn-on voltages and high efficiencies, demonstrating that it is possible to enhance the OLED performance without sacrificing deep-blue emission through rational molecular design. Key chemicals used in the synthesis process included tetraphenylethene (TPE), triphenylamine (TPA), fluorene, and various other aromatic compounds. The researchers also utilized palladium-catalyzed Suzuki coupling reactions for the final product formation, with yields ranging from 60.4 to 85.9%. The compounds were purified and characterized using column chromatography and spectroscopic techniques.

An efficient AIE-active blue-emitting molecule by incorporating multifunctional groups into tetraphenylsilane

10.1002/chem.201402152

The research aims to design and synthesize a highly efficient blue-emitting molecule with aggregation-induced emission (AIE) characteristics for organic light-emitting diodes (OLEDs). The study introduces a multifunctional AIE-active molecule, CzPySiTPE, which incorporates carbazole (Cz) and pyridine (Py) groups attached to a tetraphenylsilane core to facilitate carrier injection, while tetraphenylethene (TPE) is used to maintain efficient blue emission. The purpose is to enhance the performance of TPE-based OLEDs without sacrificing blue emission, addressing the challenge of developing efficient blue emitters. The results show that CzPySiTPE exhibits typical AIE properties, high thermal stability, and appropriate energy levels, achieving blue electroluminescence with CIE coordinates of (0.16, 0.17) and an external quantum efficiency of 1.12%. The study concludes that the incorporation of carbazole and pyridine groups enhances charge injection and carrier transport, leading to improved device efficiency, and demonstrates a new method for designing efficient solid-state bipolar blue materials.

CARBENOID REACTION: THE REACTION OF DIBROMODIPHENYLMETHANE, 9,9-DIBROMOFLUORENE AND 9,9-DICHLORO-9H-TRIBENZO[a.c.e]CYCLOHEPTENE WITH ALKYLLITHIUM IN THE PRESENCE OF OLEFINS

10.1016/0040-4020(67)80009-7

The study investigates the carbenoid reaction of various compounds with alkyllithium in the presence of olefins. Dibromodiphenylmethane reacts with methyllithium in the presence of ethyl vinyl ether to produce 1,1-diphenyl-2-ethoxycyclopropane and tetraphenylethylene. However, 9,9-dibromofluorene and 9,9-dichloro-9H-tribenzo[a.c.e]cycloheptene do not yield cyclopropane derivatives under similar conditions but instead produce compounds like 9,9'-bifluorenylidene and 9-methylene-9H-tribenzo[a.c.e]cycloheptene. The study explores the mechanisms behind these reactions, suggesting that the formation of cyclopropane derivatives is influenced by the stability of intermediates and the steric hindrance around the reaction centers. The results indicate that the reactivity of these compounds with olefins cannot be fully explained by existing hypotheses and may involve different transition states and intermediates.

Tetraphenylethylene-based glycoconjugate as a fluorescence "turn-on" sensor for cholera toxin

10.1002/asia.201100141

The study investigates the development of a fluorescence sensor for cholera toxin (CT) using tetraphenylethylene (TPE)-based glycoconjugates. The researchers synthesized TPE derivatives bearing lactosyl (Lac-TPE) and cellobiose (Cel-TPE) moieties through copper(I)-catalyzed "click reactions." Lac-TPE, due to its aggregation-induced emission (AIE) characteristics, exhibited a significant increase in fluorescence upon interaction with the cholera toxin B subunit (CTB), making it a potential sensor for CT detection. In contrast, Cel-TPE did not show any response to the toxin, highlighting the specificity of the interaction. The study demonstrates that the multivalent interactions between Lac-TPE and CTB enhance the binding affinity and specificity, leading to a "turn-on" fluorescence signal. This work provides a promising platform for detecting cholera toxin and investigating carbohydrate–protein interactions.

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