10273-82-2

Basic information

• Product Name: 9,10-Bis[(E)-2-(phenyl)ethenyl]anthracene
• Synonyms: 9,10-Bis[(E)-2-(phenyl)ethenyl]anthracene
• CAS NO: 10273-82-2
• Molecular Formula: C₃₀H₂₂
• Molecular Weight: 382.5
• Mol File: 10273-82-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9,10-Bis[(E)-2-(phenyl)ethenyl]anthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Bis[(E)-2-(phenyl)ethenyl]anthracene(10273-82-2)
• EPA Substance Registry System: 9,10-Bis[(E)-2-(phenyl)ethenyl]anthracene(10273-82-2)

Safety Data

• Hazardous Substances Data: 10273-82-2(Hazardous Substances Data)

Upstream product

• 875246-61-0 9,10-bis-(α-hydroxy-phenethyl)-anthracene 
• 7044-91-9 9,10-diformylanthracene 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 121676-73-1 9,10-trans-Dihydroxy-9,10-bis-(trans-styryl)-9,10-dihydro-anthracen 
• 10273-81-1 anthracene-9,10-bis(methyltriphenylphosphonium chloride) 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 523-27-3 9,10-Dibromoanthracene 
• 34373-96-1 9,10-dibromomethylanthracene 
• 10387-13-0 9,1-bis(chloromethyl)anthracene 
• 6921-34-2 benzylmagnesium chloride 
• 90764-27-5 9,10-anthracenedicarboxylic acid chloride 
• 115097-75-1 9,10-bis(phenylacetyl)anthracene 
• 14825-85-5 9,10-bis(phenylethynyl)-9,10-dihydroanthracene-9,10-diol 

Downstream Products

• 10075-85-1 9,10-diphenylethynylanthracene 

Relevant articles and documents

A magnetic palladium nickel carbon nanocomposite as a heterogeneous catalyst for the synthesis of distyrylbenzene and biphenyl derivatives

A magnetic palladium nickel carbon (Fe3O4@Pd@Ni/C) nanocomposite has been synthesized using a simple one-pot procedure via a hydrothermal approach. Ferric nitrate, palladium acetate, and nickel nitrate were dissolved in water together with glucose, and the mixture was heated in an autoclave. The Fe3O4@Pd@Ni/C nanocomposite was characterized via XRD, TEM, FE-SEM, VSM, EDS, and XPS studies. The catalytic abilities of the Fe3O4@Pd@Ni/C nanocomposite were investigated for the synthesis of distyrylbenzene and 9,10-distyrylanthracene derivatives. This method shows obvious advantages, such as the recyclability of the catalyst, simple experimental operation, and the obtaining of good to excellent yields.

A Bidentate Ru(II)-NC Complex as a Catalyst for Semihydrogenation of Alkynes to (E)-Alkenes with Ethanol

Four Ru(II)-NC complexes were tested as catalysts for semihydrogenation of internal alkynes to (E)-alkenes with ethanol, and the complex {(C5H4N)(C6H4)}RuCl(CO)(PPh3)2 (1a) showed the highest activity. The reactions proceeded well with 1 mol % catalyst loading and 0.1 equiv of t-BuONa at 110 °C for 1 h, and 32 alkenes were synthesized with excellent E:Z selectivity. This is the first ruthenium-catalyzed semihydrogenation of internal alkynes to (E)-alkenes using ethanol as the hydrogen donor.

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.

Tuning the structures and photophysical properties of 9,10-distyrylanthrance (DSA): via fluorine substitution

Because of the differences in the position and degree of fluorine substitution, four fluorinated DSA (9,10-distyrylanthracene) derivatives, namely 9,10-bis(4-fluorostyryl)anthracene (4-BFSA), 9,10-bis(3-fluorostyryl)anthracene (3-BFSA), 9,10-bis(3,5-difluorostyryl)anthracene (BDFSA) and 9,10-bis(3,4,5-trifluorostyryl)anthracene (BTFSA), display different crystal packing and photophysical properties in the solid state. Furthermore, the photophysical properties in solution have been investigated. The results show that all the four compounds exhibit tunable aggregation-induced enhanced emission (AIEE) properties. Notably, DSA, 4-BFSA, 3-BFSA and BDFSA display solvatochromic properties. The relationship between their structures and photophysical properties was further discussed. This work has demonstrated that depending on the amount and position, fluorine substitution can tune the structures and photophysical properties of DSA effectively.

Synthesis, structure and catalysis of a NHC-Pd(II) complex based on a tetradentate mixed ligand

Bis-benzimidazolium salt (S)-2,2′-bis[2′′-(N-picolyl-benzimidazoliumyl)ethoxy]-1,1′-binaphthyl hexafluorophosphate [(S)-LH2]·(PF6)2 and its NHC palladium(ii) complex [(S)-LPd](PF6)2 (1) have been prepared and characterized. Complex 1 is formed by one tetradentate mixed ligand (S)-L and one Pd(ii) ion, in which one 15-membered ring and two 6-membered rings are present. In this complex, intramolecular π-π interactions between naphthalene rings and benzimidazole rings are observed. Additionally, the catalytic activity of complex 1 in three types of C-C coupling reactions (Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions) was investigated. The results show that complex 1 is an effective catalyst in these coupling reactions.

Silica-supported PEI capped nanopalladium as potential catalyst in Suzuki, Heck and Sonogashira coupling reactions

We present the use of amine-functionalized silica (NH2-SiO 2) as support for palladium nanoparticles (PdNPs) and the use of heterogeneous catalysts (Pd/NH2-SiO2) for the Suzuki, Heck and Sonogashira coupling reactions. The synthesized Pd catalyst is well characterized by XRD, HRTEM, BET, SEM-EDX, FT-IR, and UV-vis spectral techniques. It exhibits efficient catalytic activity for these coupling reactions without the assistance of ligand and copper salts.

Palladium-catalyzed arylation of styrene and acrylic acid in water

Palladium-catalyzed arylations of styrene and acrylic acid are shown to occur in the presence of base (Na2CO3 or K2CO3) in pure water using simple palladium compounds as catalyst precursors.Keywords: Palladium; Catalysis; Water; Solvent; Aryl

Triplet-State 1- and 2-fold Cis-Trans Isomerization of Bisstyrylarenes: Balance between Diabatic and Adiabatic Mechanisms

The mechanism for triplet-sensitized cis-trans photoisomerization of three bisstyrylarenes, 1-3, has been studied by quantum yield measurements and laser flash photolysis.The triplet-state lifetimes for all three molecules are long enough to give an isomerization pattern essentially determined by the thermodynamics of the triplet excited-state surface, that is, equilibration processes are much faster than decay processes.Decay from the triplet excited-state surface occurs to various degrees from two equilibrated states, the planar 3E,E* and another with one double bond twisted, 3E,p*.Extension of ?-conjugation gives more 2-fold cis-trans isomerization, from the Z,Z isomer to the E,E isomer, due to a more facile adiabatic than diabatic pathway for the isomerization reaction.For one of the molecules, 9,10-bisstyrylanthracene, 3, the Z,Z isomer undergoes exclusively 2-fold isomerization to yield the E,E isomer. 1,4-Bis(3,5-di-tert-butylstyryl)naphthalene, 2, shows mainly 2-fold isomerization from the Z,Z isomer, but there is also a diabatic contribution to this isomerization giving a photostationary state, ZE:EE, 18:82.For 4,4'-bis(3,5-di-tert-butylstyryl)biphenyl, 1, the isomerization is still partly adiabatic.There is no decay from the 3Z,p* but all decay occurs from 3E,p*, giving a photostationary state ZE:EE, ca. 50:50.The photostationary states for the bisstyrylnaphthalene and the bisstyrylbiphenyl can be affected by the addition of a triplet quencher, azulene or perylene, to give almost pure E,E.

Synthesis and Absorption/Emission Spectral Properties of Styrylstilbene and Distyrylanthracene Derivatives

A series of para-substituted styrylstilbenes I and 9,10-distyrylanthracenes II was synthesized by Wittig or Arbusov-Horner reaction as a key step.Subsequently, systematic investigations were carried out on their absorption and fluorescence spectra, and th