386-23-2

Upstream product

• 441-36-1 2-benzyl-4'-trifluoromethyl-benzophenone 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 1564-64-3 9-Bromoanthracene 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 100622-34-2 anthracene-9-boronic acid 

Relevant academic research and scientific papers

When Anthracene and Quinone Avoid Cycloaddition: Acid-Catalyzed Redox Neutral Functionalization of Anthracene to Aryl Ethers

Benzoquinone and 9-phenylanthracene barely undergo anticipated cycloaddition under acid catalysis. Instead, 9-anthracenyl aryl ethers are obtained as unexpected products. Mechanistic studies indicate that the reaction likely undergoes an ionic mechanism between protonated anthracene species and nucleophilic oxygen of 1,4-benzoquinone or 1,4-hydroquinone. A variety of 9-anthracenyl aryl ethers are constructed with this method. Produced anthracenyl aryl ethers are potential scaffolds for new fluorescent molecules.

Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study

Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodynamic stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature. These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium bromide and are characterized by high regioselectivity and expanded substrate scope that includes tetracene, tetraphene, pentacene, and perylene, which have rarely been reduced. The approach provides a cost-effective catalytic protocol for hydrogenation, is scalable, and can be utilized in the synthesis of tetrabromo- and carboxyl-substituted motifs through functionalization of the hydrogenation product. The systematic theoretical mechanistic modelings suggest that low-valent Cr and Co monohydride species, most likely from zerovalent transition metals, are capable of mediating these hydrogenations of fused PAHs.

Substituted aromatic compound, a blue light-emitting materials, the organic EL element

PROBLEM TO BE SOLVED: To provide a substituted aromatic compound, a blue light-emitting material using the same and having high color reproducibility, high color purity and high efficiency, and an organic electroluminescent (EL) element.SOLUTION: The substituted aromatic compound is represented by the general formula [1], where Rto Rare each independently hydrogen or a C1-C4 linear or branched alkyl group; A is hydrogen, a C1-C4 linear or branched alkyl group, or a C1-C4 linear or branched alkoxy group; and EWG is a cyano group or a trifluoromethyl group.

Invisible Chelating Effect Exhibited between Carbodicarbene and Phosphine through π-π Interaction and Implication in the Cross-Coupling Reaction

Palladium complexes supported with the mixed ligands carbodicarbene (CDC) and different phosphine ligands (PPh3, PTol3, and PCy3) were prepared, and their molecular structures were characterized. Examination of the structures of 2-PPh3 and 2-PTol3 with cis configuration discloses the existence of an unexpected π-π interaction between one phenyl group of the phosphine and the benzimidazole ring of a CDC. The palladium complex 2-PPh3 is an active Suzuki-Miyaura catalyst with a wide scope of substrates containing various functional groups and steric demands. In contrast to electron-withdrawing aryl bromide, the yield of product for electron-rich substrates was improved by adding a catalytic amount of DMSO under aerobic conditions. The solution NMR and structural analysis has revealed that the intramolecular π-π interaction between CDC and phosphine ligands has a positive influence on the activity of the reaction, which is further supported by quantum chemical calculations.

Suzuki-Miyaura cross-coupling of bulky anthracenyl carboxylates by using pincer nickel N-heterocyclic carbene complexes: An efficient protocol to access fluorescent anthracene derivatives

A series of fluorescent (hetero)-aryl substituted anthracene derivatives were readily accessible from the corresponding bulky anthracen-9-yl carboxylates via Suzuki-Miyaura cross-coupling reactions by using pincer nickel N-heterocyclic carbene complex 1 even at the catalyst loading as low as 0.1 mol% in the presence of catalytic amounts of PCy3.

METHOD FOR SYNTHESIZING ANTHRACENE DERIVATIVE AND ANTHRACENE DERIVATIVE, LIGHT EMITTING ELEMENT, LIGHT EMITTING DEVICE, ELECTRONIC DEVICE

It is an object to provide a novel method for synthesizing an anthracene derivative with the small number of steps. It is another object to provide a novel anthracene derivative. It is further another object to provide a light-emitting element, a light-emitting device, and an electronic device, each using the anthracene derivative. A method for synthesizing an anthracene derivative represented by a general formula (1) is provided by coupling a 9-arylanthracene derivative having an active site at a 10-position with a 9-arylcarbazole derivative having an active site in an aryl group using metal, a metal compound, or a metal catalyst.

Remote substituent effects on the reactivity of 9-aryl- and 9,10-diarylanthracene radical cations with anions and amines

Radical cations of 9-aryl- and 9,10-diarylanthracenes with substituents on the 4 position of the aryl rings (PA-X?+ and DPA-X?+, respectively) have been generated by photoionization in acetonitrile. Their reactivity with n-butylamine (n-BuNH2) and 1,4-diazabicyclo[2.2.2]octane (DABCO) and a number of anions (CH3CO2-, Br-, CN-, N3-) has been studied using nanosecond laser flash photolysis. Reactions proceed by electron transfer and/or nucleophilic addition. Using PA-X and DPA-X as chemical probes, simple criteria are established that allow one mechanistic pathway to be distinguished from another. When electron transfer is thermodynamically feasible, this pathway dominates (e.g., DABCO and azide). For endothermic electron transfer, addition is not necessarily the preferred ultimate reaction pathway and an inner sphere process (addition/ homolysis) can compete. In these cases other, criteria including steric factors and the strength of the incipient bond become important. Simple kinetic criteria and an approach to estimate the thermochemistry of the addition process are developed. It is clear from these studies that reactivity trends in the radical cation chemistry cannot be generalized as easily as those in carbocation chemistry. This has some implications concerning the development and utility of "clock" reactions in radical cation chemistry.