602-55-1

Usage

Chemical Properties

Pale Yellow Plates

Preparation

Phenylboronic acid (2.13 g, 17.49 mmol), 9- bromoanthracene (3 g, 11.66 mmol), Pd(PPh3)4 (140 mg, 0.12 mmol), K2CO3 (16 mL, 2 M), and ethanol (8 mL) were mixed in a 100 mL flask containing anhydrous toluene (32 mL). The mixture was refluxed for 48 h under nitrogen. After cooled to room temperature, the reaction mixture was quenched with dilute hydrochloric acid solution and extracted with CH2Cl2. The organic extracts were dried over anhydrous MgSO4 and concentrated by rotary evaporation. The crude product was further purified by silica gel column chromatography (CH2Cl2/petroleum ether (1:4,v/v)) to get a white powder (2.43 g, 81.9 %). 1H NMR (500 MHz, CDCl3) δ 8.53 (s, 1H), 8.08 (d, J = 8.5 Hz, 2H), 7.70 – 7.67 (m, 2H), 7.63 – 7.54 (m, 3H), 7.50 – 7.45 (m, 4H), 7.37 (ddd, J = 8.7, 6.5, 1.2 Hz, 2H). EI-MS (m/z): Calculated for C20H14: 254.33. Found [M+]: 253.02. Synthesis of 9-phenylanthracene

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 393, 1957 DOI: 10.1021/ja01559a042

Purification Methods

Chromatograph it on alumina in *C6H6 and recrystallise it from AcOH or toluene. [Beilstein 5 H 725, 5 II 639, 5 III 2462.]

InChI:InChI=1/C20H14/c1-2-8-15(9-3-1)20-18-12-6-4-10-16(18)14-17-11-5-7-13-19(17)20/h1-14H

Upstream product

• 90-44-8 anthracen-9(10H)-one 
• 612-35-1 2-Benzylbenzoic acid 
• 591-51-5 phenyllithium 
• 13577-28-1 9-phenyl-9,10-dihydroanthracene 
• 120-12-7 anthracene 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 57835-99-1 triphenylsulphonium hexafluorophosphate 
• 108-88-3 toluene 
• 642-31-9 9-anthracene aldehyde 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 108-90-7 chlorobenzene 
• 98-86-2 acetophenone 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 

Downstream Products

• 1251-77-0 9-(4-nitro-phenyl)-10-phenyl-anthracene 
• 13577-28-1 9-phenyl-9,10-dihydroanthracene 
• 5146-30-5 10-phenyl-10-hydroxy-9-anthracenone 
• 17803-81-5 10-phenyl-9-acetoxyanthracene 
• 23674-20-6 9-bromo-10-phenylanthracene 
• 134450-66-1 9-phenyl-10-nitroanthracene 
• 54440-48-1 9-phenyl-9,10-dihydro-9,10-epidioxido-anthracene 
• 55255-70-4 9-cyclohexyl-tetradecahydro-anthracene 
• 54458-81-0 10-Phenylanthracene-9-carboxaldehyde 
• 116706-33-3 C₂₅H₂₃P 
• 123676-14-2 12-(p-nitrobenzoyl)-1,3-dichloro-6-phenyl-11,12-dihydro-6,11<1',2'>-benzeno-6H-dibenz<1,4>oxazocine 
• 120-12-7 anthracene 
• 203-33-8 benzo[a]fluoranthene 
• 76411-30-8 1,5-Diphenyl-3,4:7,8:9,10:11,12-tetrabenzotricyclo<4.2.2.2^2,5>dodeca-3,7,9,11-tetraen 

Relevant academic research and scientific papers

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Amine-Tagged Fragmented Ligand Installation for Covalent Modification of MOF-74

MOF-74 is one of the most explored metal–organic frameworks (MOFs), but its functionalization is limited to the dative post-synthetic modification (PSM) of the monodentate solvent site. Owing to the nature of the organic ligand and framework structure of MOF-74, the covalent PSM of MOF-74 is very demanding. Herein, we report, for the first time, the covalent PSM of amine-tagged defective Ni-MOF-74, which is prepared by de novo solvothermal synthesis by using aminosalicylic acid as a functionalized fragmented organic ligand. The covalent PSM of the amino group generates metal binding sites, and subsequent post-synthetic metalation with PdII ions affords the PdII-incorporated Ni-MOF-74 catalyst. This catalyst exhibits highly efficient, size-selective, and recyclable catalytic activity for the Suzuki–Miyaura cross-coupling reaction. This strategy is also useful for the covalent modification of amine-tagged defective Ni2(DOBPDC), an expanded analogue of MOF-74.

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A variety of chemical transformations benefit from the use of strong electron-donating ancillary ligands, such as alkylphosphines or N-heterocyclic carbenes when electron-rich metal centers are required. Herein, we describe a facile and highly modular access to monodentate and bidentate imidazolin-2-ylidenamino-substituted phosphines. Evaluation of the phosphine's electronic properties substantiate that the formal replacement of alkyl or aryl groups by imidazolin-2-ylidenamino groups dramatically enhance their donor ability beyond that of alkylphosphines and even N-heterocyclic carbenes. The new phosphines have been coordinated onto palladium(II) centers, and the beneficial effect of the novel substitution patterns has been explored by using the corresponding complexes in the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of non-activated aryl chloride substrates. Upgrading phosphines: A conceptually new approach to a family of extremely electron-rich phosphines is based on the use of imidazolin-2-ylidenamino groups directly attached to the phosphorus atom. The steric and electronic properties of the new ligands can be easily varied owing to the general and modular synthesis, which provides new prospects for phosphine ligands in catalysis.

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Compound, organic luminescent material and organic electroluminescent device

The invention provides a compound as shown in a general formula (I), which has a mother structure of sym-triphenyl substituted anthracene, is high in bond energy among atoms, has good thermal stability, is beneficial to solid-state accumulation among molecules, is large in bandwidth, has a light-emitting region in a blue light region, is high in light-emitting intensity, and has a proper energy level with adjacent levels. And injection and migration of excitons are facilitated. When the compound is used as a blue light host material in a luminescent layer, the driving voltage of an organic electroluminescent device can be effectively reduced, the luminous efficiency is improved, and the service life is prolonged. The invention also provides an organic electroluminescent device and a display device containing the compound of the general formula (I).

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