Tetraphenylethylene

Base Information

• 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

Synonyms:tetraphenylethylene

Chemical Property of Tetraphenylethylene

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:

99% ^*data from raw suppliers

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

Safty Information:

• 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
• Uses: 1,1,2,2-Tetraphenylethylene is used as a reagent in the synthesis of a dynamic covalent imine gel as a luminescent sensor. Studies show that 1,1,2,2-Tetraphenylethylene (TPE) can assemble into self-luminescent nanoparticles which are part of a drug delivery system that shows aggregation-induced emission and can be easily tracked in cells.

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:

Reference yield: 95.0%

bromobenzene (108-86-1,52753-63-6) + diphenyl acetylene (501-65-5) + bis(pinacol)diborane (73183-34-3) → Triphenylethylene (58-72-0) + 1,1,2,2-tetraphenylethylene (632-51-9)

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

Reference yield: 81.0%

para-iodoanisole (696-62-8) + phenylmagnesium bromide (100-58-3) + diphenyl acetylene (501-65-5) → 4-methoxylbiphenyl (613-37-6) + (2-(4-methoxyphenyl)ethene-1,1,2-triyl)tribenzene (70592-05-1) + 1,1,2,2-tetraphenylethylene (632-51-9)

Guidance literature:

With nickel dichloride; In tetrahydrofuran; water; toluene; at 30 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ja513166w

Reference yield: 72.0%

Dichlorodiphenylmethane (2051-90-3) + (methyllithium)(2-phenyllithium)sulfide → diphenyldisulfane (882-33-7) + 1,1,2,2-tetraphenylethylene (632-51-9)

Guidance literature:

for 48h; Ambient temperature;

DOI:10.3987/COM-88-4551

upstream raw materials:

N-Formylpiperidine

Diethyl disulfide

diethyl ether

1,2-disodiotetraphenylethane

Downstream raw materials:

7-Imino-7H-phenothiazin-3-ylamine

benzophenone

9,10-diphenylphenanthrene

tetraphenyloxirane

Refernces

• 1、 Warner, Kirstin F.,Rehman, Atiq-Ur,Jha, Salil K.,Schnatter, Wayne F. K.. "Coupling of geminal dihalides with disodium tetracarbonyl ferrate: A novel reactivity pattern for Collman's reagent". . p. 514 - 515. Retrieved 1999.
• 2、 Singh,Rivest. "". . p. 1773,1775. Retrieved 1968.
• 3、 Mehrotra,Singh. "". . p. 4949. Retrieved 1972.
• 4、 Barbosa, Frederique,Peron, Vincent,Gescheidt, Georg,Fuerstner, Alois. "Radical ions of crownophanes derived from tetraphenylethene. Solution structures and ion-pairing phenomena". . p. 8806 - 8814. Retrieved 1998.
• 5、 Satoh, Tetsuya,Ogino, Shinji,Miura, Masahiro,Nomura, Masakatsu. "Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes". . p. 5063 - 5065. Retrieved 2004.
• 6、 Zhan, Yingying,Yang, Zhiwen,Tan, Jihua,Qiu, Zhipeng,Mao, Yuanyou,He, Jia,Yang, Qingdan,Ji, Shaomin,Cai, Ning,Huo, Yanping. "Synthesis, aggregation-induced emission (AIE) and electroluminescence of carbazole-benzoyl substituted tetraphenylethylene derivatives". . . Retrieved 2020.
• 7、 Fliszar,Chylinska. "". . p. 783,787. Retrieved 1968.
• 8、 Mohamed, Mohamed Gamal,Elsayed, Mohamed Hammad,Elewa, Ahmed M.,EL-Mahdy, Ahmed F. M.,Yang, Cheng-Han,Mohammed, Ahmed A. K.,Chou, Ho-Hsiu,Kuo, Shiao-Wei. "Pyrene-containing conjugated organic microporous polymers for photocatalytic hydrogen evolution from water". . p. 2229 - 2241. Retrieved 2021/04/09.
• 9、 Bhaumik, Asim,Chakraborty, Debabrata,Chandra, Bijan Krishna,Dam, Tapabrata,Ghosh, Aswini,Majee, Adinath,Modak, Arindam,Pant, Kamal K.. "A novel crystalline nanoporous iron phosphonate based metal-organic framework as an efficient anode material for lithium ion batteries". . p. 15458 - 15468. Retrieved 2021/09/07.