10075-85-1

Basic information

• Product Name: 9,10-Bis(phenylethynyl)anthracene
• Synonyms: 9,10-bis(phenylethynyl)-anthracen;BIS(9,10-)(PHENYLETHYNYL) ANTHRACENE;BPEA;9,10-BIS(PHENYLETHYNYL)ANTHRACENE;9,10-bis(phenylvinyl)anthracene;9,10-bis(phenylthynyl)anthracene (yellow) BPEA;9,10-BIS(PHENYLETHYNL)ANTHRACENE;Anthracene, 9,10-bis(phenylethynyl)-
• CAS NO: 10075-85-1
• Molecular Formula: C₃₀H₁₈
• Molecular Weight: 378.46
• EINECS: 233-210-8
• Product Categories: Acetylenes;Acetylenic Hydrocarbons having Benzene Ring;Anthracenes
• Mol File: 10075-85-1.mol

Chemical Properties

• Melting Point: 248-250 °C(lit.)
• Boiling Point: 441.55°C (rough estimate)
• Flash Point: 325.6 °C
• Appearance: /Crystalline
• Density: 1.1846 (estimate)
• Vapor Pressure: 2.3E-14mmHg at 25°C
• Refractive Index: 1.6290 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: It is insoluble in water but is soluble in most organic solvents such as carbon disulfide, alcohols, benzene, chloroform, and hy
• Sensitive: Light Sensitive
• Merck: 14,1299
• BRN: 1891432
• CAS DataBase Reference: 9,10-Bis(phenylethynyl)anthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Bis(phenylethynyl)anthracene(10075-85-1)
• EPA Substance Registry System: 9,10-Bis(phenylethynyl)anthracene(10075-85-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 8-10
• TSCA: Yes
• Hazardous Substances Data: 10075-85-1(Hazardous Substances Data)

Usage

Uses

Used in Scintillator Industry:
9,10-Bis(phenylethynyl)anthracene is used as a scintillator additive for its fluorescence properties. It enhances the light output and detection efficiency of scintillator materials, making it valuable in applications such as radiation detection and imaging.
Used in Chemiluminescence Research:
9,10-Bis(phenylethynyl)anthracene is used as a chemiluminescent fluorophore with high quantum efficiency. It is a reagent for chemiluminescence research, where it plays a crucial role in studying the mechanisms and applications of chemiluminescent reactions.
Used in Lightstick Industry:
In the lightstick industry, 9,10-Bis(phenylethynyl)anthracene is used as a fluorophor, producing a ghostly green light when combined with a suitable chemiluminescent reaction. This makes it useful for emergency lighting, recreational activities, and other applications requiring a portable light source.
Used in Organic Semiconductor Industry:
9,10-Bis(phenylethynyl)anthracene is used as a dopant for organic semiconductors in OLEDs (Organic Light Emitting Diodes). Its fluorescence properties contribute to the overall performance and efficiency of these devices, making it a valuable component in the development of advanced display and lighting technologies.
Used in Peroxyoxalate Chemiluminescence:
9,10-Bis(phenylethynyl)anthracene has been extensively studied as a fluorescence emitter for peroxyoxalate chemiluminescence. Its use in this area allows for the development of new methods and applications in the field of chemiluminescence, further expanding its utility in research and practical applications.

InChI:InChI=1/C30H18/c1-3-11-23(12-4-1)19-21-29-25-15-7-9-17-27(25)30(28-18-10-8-16-26(28)29)22-20-24-13-5-2-6-14-24/h1-18H

Upstream product

• 14825-85-5 9,10-bis(phenylethynyl)-9,10-dihydroanthracene-9,10-diol 
• 859331-73-0 9-(α,β-dichloro-styryl)-10-phenylethynyl-anthracene 
• 523-27-3 9,10-Dibromoanthracene 
• 6928-78-5 Bis(phenylethynyl)magnesium 
• 10273-82-2 (E,E)-9,10-Bis(styryl)anthracene 
• 536-74-3 phenylacetylene 
• 1122-79-8 potassium phenylacetylide 
• 4440-01-1 lithium phenylacetylide 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 71-41-0 pentan-1-ol 
• 3757-88-8 tributylstannylethynylbenzene 
• 115198-11-3 9-bromo-10-(2-phenylethynyl)anthracene 
• 3112-88-7 Benzyl phenyl sulfone 

Downstream Products

• 178388-68-6 [Co2(CO)6]2(μ-9,10-bis(phenylethynyl)anthracene) 
• 32287-35-7 9,10-bis(phenylethynyl)-9,10-dihydro-9,10-epidioxidoanthracene 
• 1166380-82-0 9,10-bis(2-(phenyl)naphthalen-3-yl)anthracene 
• 1006709-42-7 3,4-diphenyl-5-[10-(phenylethynyl)anthracen-9-yl]-3H-1,2,3-diselenaphosphole 3-selenide 
• 1006709-43-8 5,5'-anthracene-9,10-diylbis(3,4-diphenyl-3H-1,2,3-deselenaphosphole) 3,3'-diselenide 
• 875246-61-0 9,10-bis-(α-hydroxy-phenethyl)-anthracene 
• 18532-00-8 9-cis-styryl-10-trans-anthracene 
• 10273-82-2 (E,E)-9,10-Bis(styryl)anthracene 
• 80364-60-9 9-phenylacetyl-10-(phenylethynyl)anthracene 
• 115097-75-1 9,10-bis(phenylacetyl)anthracene 

Relevant articles and documents

Catalytic activities of NHC-PdCl2 species based on functionalized tetradentate imidazolium salt in three types of C-C coupling reactions

A functionalized tetradentate imidazolium salt 9,10-bis{di[2′-(N-ethylimidazolium-1-yl)ethyl]aminomethyl}anthracene tetrakis(hexafluorophosphate) (1) has been synthesized and characterized. The catalytic activity of the NHC-PdCl2 species formed by compound 1 and PdCl2 was tested in Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions. The results showed that this catalytic system was effective for above three types of C-C coupling reactions.

Why triple bonds protect acenes from oxidation and decomposition

An experimental and computational study on the impact of functional groups on the oxidation stability of higher acenes is presented. We synthesized anthracenes, tetracenes, and pentacenes with various substituents at the periphery, identified their photooxygenation products, and measured the kinetics. Furthermore, the products obtained from thermolysis and the kinetics of the thermolysis are investigated. Density functional theory is applied in order to predict reaction energies, frontier molecular orbital interactions, and radical stabilization energies. The combined results allow us to describe the mechanisms of the oxidations and the subsequent thermolysis. We found that the alkynyl group not only enhances the oxidation stability of acenes but also protects the resulting endoperoxides from thermal decomposition. Additionally, such substituents increase the regioselectivity of the photooxygenation of tetracenes and pentacenes. For the first time, we oxidized alkynylpentacenes by using chemically generated singlet oxygen (1O2) without irradiation and identified a 6,13-endoperoxide as the sole regioisomer. The bimolecular rate constant of this oxidation amounts to only 1 × 10 5 s-1 M-1. This unexpectedly slow reaction is a result of a physical deactivation of 1O2. In contrast to unsubstituted or aryl-substituted acenes, photooxygenation of alkynyl-substituted acenes proceeds most likely by a concerted mechanism, while the thermolysis is well explained by the formation of radical intermediates. Our results should be important for the future design of oxidation stable acene-based semiconductors.

PALLADIUM CATALYZED C-C COUPLING FOR SYNTHESIS OF pi -CONJUGATED POLYMERS COMPOSED OF ARYLENE AND ETHYNYLENE UNITS.

Palladium compounds such as Pd(PPh//3)//4 and Pd(OAc)//2 catalyze polycondensation between dihalo aromatic compounds, X-Ar-X (Ar equals p-phenylene, 2,5-thiophenediyl, 9,10-anthracenediyl, 2,6-pyridinediyl, p-benzene-dicarbonyl, p-xylene- alpha , alpha prime -diyl), and acetylenic compounds (p-C//6H//4(C EQUVLNT CH)//2 or p-C//6H//4(C EQUVLNT CMgBr)//2). The polymers obtained have high thermal stabilities and most of them show fluorescence. One of the polymers is converted into semiconductors by doping with electron acceptors.

Synthesis and photophysical properties of 9,10-Bis(3-aryl-2-naphthyl)anthracenes

The 9,10-bis(3-aryl-2-naphthyl)anthracenes 3 were prepared by the benzannulation reaction of 2-(phenylethynyl)benzaldehyde (1) and the corresponding 9,10-bis(arylethynyl)anthracenes 2 in the presence of Cu or Re catalyst and trichloroacetic acid. The photophysical properties of 3 in solutions were investigated.

Palladium-Catalyzed Arylation of Polar Organometallics Mediated by 9-Methoxy-9-Borabicyclononane: Suzuki Reactions of Extended Scope

An alternative way for performing Suzuki reactions is presented.The necessary borate is the actual nucleophile in these palladium catalyzed C-C-bond formations is prepared from 9-methoxy-9-borabicyclononane (9-OMe-9-BBN) and a polar organometallic reagent RM, and not as usually from a borane and a base.This approach allows cross couplings of aryl halides with e.g. alkynyl-, methyl-, or TMSCH2-groups, which were beyond the scope of the conventional Suzuki reaction.The method is highly chemoselective and turned out to be compatible with aldehyde-, amide-, ketone-, ester- and cyano functions as well as with basic nitrogen atoms in the substrates.It was applied to the synthesis of the acetylenic natural products junipal (9a) and eutypine methyl ether (10).Since 11B NMR studies revealed that the 9-OMe-9-BBN only serves as a shuttle for delivering the RM reagent but remains unchanged during the course of the reaction, it has been possible to device the first Suzuki-type reaction sub-stoichiometric in boron.This "catalytic" protocol was used to prepare compound 8 which is highly valuable for its chemoluminescence properties.

Luminescent assays for ketones and aldehydes employing catalytic signal amplification

Herein we report the first use of transition metal catalytic signal enhancement for the analysis of small organic analytes. Two assays using Sonogashira and Suzuki cross-couplings have been used in the detection of ketones and aldehydes produce highly luminescent markers. The latter analysis utilizing the Suzuki coupling demonstrates the first use of peroxyoxalate initiated chemiluminescence in a sensing application. Chemiluminescent measurement revealed much higher sensitivity than fluorescence. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Phenyleneanthracene derivatives as triplet energy acceptor/emitter in red light excitable triplet-triplet-annihilation upconversion

A series of anthracene derivatives with 9,10-substituents were prepared as triplet acceptors/emitters for triplet-triplet-annihilation (TTA) upconversion. Different linkages of C[sbnd]C single bonds and C[tbnd]C triple bonds were used to tune the singlet and triplet state energy levels, which may enhance the TTA upconversion. The study of the photophysical properties of the compounds indicates that the C[sbnd]C linker does not alter the T1 state energy level substantially, whereas the C[tbnd]C linker significantly reduced the T1 state energy levels. With nanosecond transient absorption spectroscopy, the intermolecular triplet-triplet-energy-transfer (TTET) process was studied. The lack of the upconversion for some anthracene derivatives was attributed to the inappropriate T1 energy levels thus the lack of TTET. On the other hand, different upconversion quantum yields were observed for some acceptors, although the TTET processes are similar. This result is due to the different TTA. These studies will be useful for future development of the TTA upconversion and for study of the triplet state properties of organic chromophores.

Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions

Two bis-imidazolium salts LH2·Cl2 and LH2·(PF6)2 with acylated piperazine linker and two N-heterocyclic carbene (NHC) silver(I) and palladium(II) complexes [L2Ag2](PF6)2 (1) and [L2Pd2Cl4] (2) were prepared. The crystal structures of LH2·Cl2 and 1 were confirmed by X-ray analysis. In 1, one 26-membered macrometallocycle was generated through two silver(I) ions and two bidentate ligands L. The catalytic activity of 2 was investigated in Sonogashira, Heck-Mizoroki and Suzuki-Miyaura reactions. The results displayed that these C—C coupling reactions can be smoothly carried out under the catalysis of 2.

Synthesis, one/two-photon optical and electrochemical properties and the photopolymerization-sensitizing effect of anthracene-based dyes: Influence of the donor groups

Four anthracene-based dyes (ANDs) with different donor groups, namely 9,10-bis(phenylethynyl)anthracene (A1), 9,10-bis((9-dodecyl-9H-carbazol-3-yl)ethynyl) anthracene (A2), 9,10-bis((10-dodecyl-10H-phenothiazin-3-yl)ethynyl)anthracene (A3), and 4,4′-(anthracene-9,10-diylbis(ethyne-2,1-diyl))bis(N,N-diphenylaniline) (A4) were synthesized and characterized. The ANDs showed considerable absorption in blue/green regions and strong fluorescence emission in the green to red region. Besides, the ANDs possess large two-photon absorption cross-sections at 780-880 nm. Electrochemical studies revealed that these electron donors possess different donating abilities which in turn influence the redox potential and excited intramolecular charge transfer intensity of the ANDs. The conjugation degree among the donor groups and anthracene also has a significant impact on the redox potential of the ANDs. Moreover, compounds A1, A2, and A3 are able to couple with iodonium salt to initiate radical photopolymerization under blue and green LED irradiation. In summary, the structure-property relationships were investigated in detail in this work, which may provide useful guidance for further research.

Conjugated alkynyl anthracene derivative as well as preparation method and application thereof

The invention discloses a conjugated alkynyl anthracene derivative. The structural formula of the conjugated alkynyl anthracene derivative is as shown in the description, wherein R1 and R2 are any oneof the following structural formulas; and R represents H or one of C1-C30 alkyl groups or one of C1-C30 alkoxy groups. The invention also discloses a preparation method and application of the conjugated alkynyl anthracene derivative. The conjugated alkynyl anthracene derivative has the advantages of being rigid in structure and stable in photochemical property.