57114-80-4

Upstream product

• 690958-91-9 ethyl benzoylnaphthoyl acetate 
• 93-58-3 benzoic acid methyl ester 
• 93-08-3 methyl 2-naphthyl ketone 
• 98-88-4 benzoyl chloride 
• 16736-88-2 1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-one 
• 170166-53-7 methyl 2'-naphthoylformate 
• 70-11-1 α-bromoacetophenone 
• 2459-25-8 methyl naphthalene-2-carboxylate 
• 144-55-8 sodium hydrogencarbonate 
• 98-86-2 acetophenone 
• 2243-83-6 2-naphthaloyl chloride 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 93-89-0 benzoic acid ethyl ester 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 

Downstream Products

• 690958-56-6 C₁₉H₁₃BF₂O₂ 
• 65648-94-4 1-(naphthalen-2-yl)-2-phenylethane-1,2-dione 
• 273736-18-8 4,4-dimethyl-3-(2'-naphthyl)-5-phenyl-4H-pyrazole 
• 273736-16-6 2,2-dimethyl-1-(2'-naphthyl)-3-phenylpropane-1,3-dione 
• 1157-94-4 5-(naphthalene-2-yl)-3-phenylisoxazole 
• 57114-95-1 3-(naphthalen-2-yl)-5-phenyl-1,2-oxazole 

Relevant academic research and scientific papers

Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils

The conversion of 1,3-diaryl-2-diazo-1,3-diketones to 1,2-daryl-1,2-diketones (benzils) is reported based on a rhodium(II)-catalyzed aerobic decomposition process. The reaction occurs at ambient temperatures and can be catalyzed by a few dirhodium carboxylates (5 mol %) under a balloon pressure of oxygen. Moreover, an oxygen atom from the O2 reagent is shown to be incorporated into the product, and this is accompanied by the extrusion of a carbonyl unit from the starting materials. Mechanistically, it is proposed that the decomposition may proceed via the interaction of a ketene intermediate resulting from a Wolff rearrangement of the carbenoid, with a rhodium peroxide or peroxy radical species generated upon the activation of molecular oxygen. The proposed mechanism has been supported by the results from a set of controlled experiments. By using this newly developed strategy, a large array of benzil derivatives as well as 9,10-phenanthrenequinone were synthesized from the corresponding diazo substrates in varying yields. On the other hand, the method did not allow the generation of benzocyclobutene-1,2-dione from 2-diazo-1,3-indandione because of the difficulty of inducing the initial rearrangement.

Method of preparing 1,3-diketone compound by acetyenic ketone

The invention relates to a preparation method of preparing a 1,3-diketone compound by acetyenic ketone. The preparation method comprises the following steps: S1, putting alpha-alkynyl ketone compound,water, gold salt and silver salt in a reaction solvent to obtain a precursor mixture, wherein the molar ratio of the alpha-alkynyl ketone compound, water, gold salt and silver salt is 1: (1-50): (0.001-0.10): (0.002-0.15); and S2, putting the precursor mixture obtained in the S1 to react at a reaction temperature of 0-50 DEG C to obtain the 1,3-diketone compound, wherein the reaction time is 5 min to 48 h. The method is simple in reaction condition, free of acid or alkaline additives and high in yield, and can be applied to modern production on a large scale.

Phosphorescence Tuning through Heavy Atom Placement in Unsymmetrical Difluoroboron β-Diketonate Materials

Difluoroboron β-diketonates (BF2bdks) show both fluorescence (F) and room-temperature phosphorescence (RTP) when confined to a rigid matrix, such as poly(lactic acid). These materials have been utilized as optical oxygen sensors (e.g., in tumors, wounds, and cells). Spectral features include charge transfer (CT) from the major aromatic donor to the dioxaborine acceptor. A series of naphthyl–phenyl dyes (BF2nbm) (1–6) were prepared to test heavy-atom placement effects. The BF2nbm dye (1) was substituted with Br on naphthyl (2), phenyl (3), or both rings (4) to tailor the fluorescence/phosphorescence ratio and RTP lifetime—important features for designing O2 sensing dyes by means of the heavy atom effect. Computational studies identify the naphthyl ring as the major donor. Thus, Br substitution on the naphthyl ring produced greater effects on the optical properties, such as increased RTP intensity and decreased RTP lifetime compared to phenyl substitution. However, for electron-donating piperidyl-phenyl dyes (5), the phenyl aromatic is the major donor. As a result, Br substitution on the naphthyl ring (6) did not alter the optical properties significantly. Experimental data and computational modeling show the importance of Br position. The S1 and T1 states are described by two singly occupied MOs (SOMOs). When both of these SOMOs have substantial amplitude on the heavy atom, passage from S1 to T1 and emission from T1 to S0 are both favored. This shortens the excited-state lifetimes and enhances phosphorescence.

Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones

A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.

Mechanochromic luminescent difluoroboron beta-diketonates

The invention provides luminescent solid-state compositions comprising difluoroboron beta-diketonates wherein the compositions can exhibit mechanochromic luminescence. The mechanochromic effect on the luminescence can be reversible, such as thermally reversible. Various solid-state forms of the invention can have emission spectra that differ from the properties of the respective difluoroboron beta-diketonate in solution. The mechanochromic effect can be stimulated by pressure such as handwriting, and can be reversed over a period of minutes to hours at room temperature. The invention also provides methods of making and methods of using the solid-state compositions, such as for sensors and for information displays for use in biological sensing, and in art, design, and consumer products. Compositions of the invention, such as compositions in nanoparticulate form, or contained within a matrix material, can be used in conjunction with fluorescence microscopy to provide information concerning pressures and tensions within and external to living cells, tissues, or organisms.

Arene effects on difluoroboron β-diketonate mechanochromic luminescence

Difluoroboron β-diketonate (BF2bdk) dyes display reversible mechanochromic luminescence (ML) in the solid state. A series of BF 2bdk dyes with methyl, phenyl, naphthyl and anthracyl groups (i.e. arene substituents and bdk ligands: Me-Ph = mbm, Ph-Ph = dbm, Np-Ph = nbm, An-Ph = abm) were prepared to test the effects of π conjugation length and arene size on ML properties. Solid-state emission spectra were recorded for powders, spin-cast films, and dye coated weighing paper. The materials emit at various wavelengths from blue to red, depending on the conjugation length. Additionally, emission spectra were recorded for smeared solids and their recovery was tracked at room temperature over time. All dyes except for BF2mbm show emission changes upon mechanical perturbation, with increasing π conjugation correlating with more dramatic, redshifted fluorescence, however, their recovery is significantly affected by the aromatic substituents. The thermal and structural properties of the dyes in the solid state were also investigated by differential scanning calorimetry (DSC) and atomic force microscopy (AFM).

Diaroyl(methanato)boron Difluoride Compounds as Medium-Sensitive Two-Photon Fluorescent Probes

This paper evaluates the use of diaroyl(methanato)boron difluoride compounds for designing efficient fluorescent probes through two-photon absorption. Three different pathways allowing for the syntheses of symmetrical and dissymmetrical molecules are reported. The stable diaroyl(methanato)-boron difluoride derivatives can be easily obtained in good yields. They exhibit a large one-photon absorption that is easily tuned in the near-UV range. Their strong fluorescence emission covers the whole visible domain. In addition to these attractive linear properties, several diaroyl(methanato)-boron difluoride derivatives possess significant cross sections for two-photon absorption. The derived structure-property relationships are promising for designing new generations of molecules relying on the diaroyl(methanato)boron difluoride backbone.

Metal chelates and methods of using them for time-resolved fluorescence

β-diketone fluorescent tags are disclosed, particularly those enabling the use of excitation energy in the near visible or visible spectrum. In some cases, these tags allow the use of cost-effective excitation devices such as LED's. The compounds form flu