Showing papers on "Fluorenone published in 2015"

Design and synthesis of fluorenone-based dyes: two-photon excited fluorescent probes for imaging of lysosomes and mitochondria in living cells

Abstract: Three fluorenone-derived two-photon fluorescent probes (TK) targeting the lysosomes (TK-Lyso) and mitochondria (TK-Mito1 and TK-Mito2) were synthesized by introducing different diphenylamine moieties into the fluorenone core. The TK dyes showed high biocompatibility and long-term retention, low cytotoxicity, large Stokes shift and good fluorescence quantum yield. The results of the present work disclose a class of organic dyes with potential wide applications as specific and efficient probes for lysosomes and mitochondria in the study of various biological processes.

Self-assembly polymorphism of 2,7-bis-nonyloxy-9-fluorenone: solvent induced the diversity of intermolecular dipole-dipole interactions.

Abstract: In this present work, a scanning tunneling microscope (STM) operated under ambient conditions was utilized to probe the self-assembly behavior of 2,7-bis-nonyloxy-9-fluorenone (F–OC9) at the liquid–solid (l/s) interface. On the highly oriented pyrolytic graphite (HOPG) surface, two-dimensional (2D) polymorphism with diversity of intermolecular dipole interactions induced by solvent was found. Solvents ranged from hydrophilic solvating properties with high polarity, such as viscous alkylated acids, to nonpolar alkylated aromatics and alkanes. 1-Octanol and dichloromethane were used to detect the assembly of F–OC9 at the gas–solid (g/s) interface. The opto-electronic properties of F–OC9 were determined by UV-vis and fluorescence spectroscopy in solution. Our results showed that there were tremendous solvent-dependent self-assemblies in 2D ordering for the surface-confined target molecules. When a homologous series of alkanoic acids ranging from heptanoic to nonanoic acid were employed as solvents, the self-assembled monolayer evolved from low-density coadsorbed linear lamellae to a semi-circle-like pattern at relatively high concentrations, which was proven to be the thermodynamic state as it was the sole phase observed at the g/s interface after the evaporation of solvent. Moreover, by increasing the chain length of the alkylated acids, the weight of the carboxylic group, also being the group responsible for the dielectric properties, diminished from heptanoic to nonanoic acid, which could make the easier/earlier appearance of a linear coadsorption effect. However, this was not the case for nonpolar 1-phenyloctane and n-tetradecane: no concentration effect was detected. It showed a strong tendency to aggregate to generate coexistence of separate domains of different phases due to the fast nucleation sites. Furthermore, thermodynamic calculations indicated that the stable structural coexistence of the fluorenone derivative was attributed to synergistic intermolecular dipole–dipole and van der Waals (vdWs) forces at l/s interface. It is believed that the results are of significance to the fields of solvent induced polymorphism assembly and surface science.

Coordination complex of boron subphthalocyanine (BSubPc) with fluorenone pinacolate: effective π–π interaction of concave BSubPc macrocycle with fullerene C60

Abstract: Coordination assembly of dimeric fluorenone ketyl (pinacolate, C26H16O22−) with boron subphthalocyanine (BSubPc) was obtained in the complex with fullerene, {(BSubPc)2(C26H16O2)}·C60, featuring an effective π–π interaction between concave-shaped BSubPc macrocycle and spherical C60 molecules.

Oxidative Ring-Opening of Aromatics: Decomposition of Biphenyl Carboxylic Acids and Zinc Biphenyl Carboxylates

Abstract: Ring-opening conversion of multinuclear aromatics can be used to upgrade heavy aromatic oils to lighter products, and it is usually performed reductively with H2. Oxidative ring-opening is an alternative strategy that involves three steps: (i) oxidation of multinuclear aromatics to quinonoids, (ii) further oxidation and ring-opening to produce aromatic carboxylic acids, and (iii) decarboxylation of aromatic carboxylic acids. In the last step, decomposition by ketonization is an undesirable side reaction that leads to a ring-closed product. Selectivity control during aromatic carboxylic acid decomposition was investigated using biphenyl-2-carboxylic acid, biphenyl-2,2′-dicarboxylic acid, zinc(II) biphenyl-2-carboxylate, and zinc(II) biphenyl-2,2′-dicarboxylate. The reaction networks of thermal decomposition of the aromatic carboxylic acids were determined. Decomposition of biphenyl-2-carboxylic acid took place mainly by decarboxylation to produce biphenyl, dehydration and ring-closure to produce fluorenone...

Synthesis of π-Conjugated Polymers Containing Benzodipyrrole Moieties in the Main Chain through Cleavage of C–H Bonds in 1,4-Bis(acetylamino)benzene

Abstract: Rhodium-catalyzed copolymerization between 1,4-bis(acetylamino)benzene and diynes through C–H bond cleavage afforded π-conjugated polymers containing benzodipyrrole moieties. The polymers with substituted benzene units exhibited nearly the same absorption peaks and HOMO levels. Fluorenone and benzothiadiazole moieties can be also introduced as electron-acceptor units to the main chain by polymerization in tert-amyl alcohol and tetrahydropyran as mixed solvent, leading to absorption at longer wavelength.

Fluorenone derivative, preparation method of fluorenone derivative and redox method of synthetic fluorenone

Abstract: The invention relates to a fluorenone derivative, a preparation method of the fluorenone derivative and a redox method of synthetic fluorenone The preparation method includes a, performing precursor synthesis; b, performing target product synthesis; c, performing purifying The fluorenone derivative is obtained by the redox method of four alkyne and polyenynes and serves as non-silver sensitive material applied widely The fluorenone serving as a medical intermediate is used for synthesis of various drugs

Efficient and eco-friendly synthesis of fluorenone Azines by using sulphated titania acid catalyst

Abstract: Conjugated unsymmetrical azines have been synthesized in the presence of acid catalyst sulphated-titania (TiO 2-SO 4 2- ) from fluorenone hydrazone with substituted aldehydes and acetophenones by using mortar and pestle. The scope of present synthetic route avoid in solvents, simple operating method and shorter reaction time. Special feature of synthetic method is recyclable catalyst for all in reactions.

Accurate spectroscopy of polycyclic aromatic compounds: From the rotational spectrum of fluoren-9-one in the millimeter wave region to its infrared spectrum

Abstract: The rotational spectrum of fluoren-9-one, a small oxygenated polycyclic aromatic hydrocarbon, has been recorded and assigned in the 52-74.4 GHz region. The determined small negative value of the inertia defect (−0.3 u A2) has been explained in terms of vibrational-rotational coupling constants calculated at the B3LYP/cc-pVTZ level of theory. Vibrational anharmonic analysis together with second-order vibrational perturbation theory approximation was applied both to fluorenone and its reduced form, fluorene, to predict the mid- and near-infrared spectra. The data presented here give precise indication on the fluorenone ground state structure, allow for an accurate spectral characterization in the millimeter wave and infrared regions, and hopefully will facilitate extensive radio astronomical searches with large radio telescopes.

Two Closely Related Organic Charge-Transfer Complexes Based on Tetrathiafulvalene and 9H-fluorenone Derivatives. Competition between Hydrogen Bonding and Stacking Interactions

Abstract: Two 1:1 charge-transfer organic complexes were formed using tetrathiafulvalene as a donor and a 9H-fluorenone derivative as acceptor: 4,5,7-trinitro-9H-fluoren-9-one-2-carboxylic acid (complex 1) or 4,5,7-trinitro-9H-fluoren-9-one-2-carboxylic acid methyl ester (complex 2). Both systems crystallize with alternated donor and acceptor stacks. However, the crystal structure of 1 is influenced by classical hydrogen bonds involving carboxylic acid groups, which force to arrange acceptors as centrosymmetric dimers in the crystal, via R2 2(8) ring motifs, while such a restriction is no longer present in the case of 2, affording thus a different crystal structure. This main difference is reflected in stacking interactions, and, in turn, in the degree of charge transfer observed in the complexes. The degree of charge transfer, estimated using Raman spectroscopy, is δ1 = 0.07 for 1 and δ2 = 0.14 for 2. It thus seems that, at least for the studied complexes, hydrogen bonding is an unfavorable factor for charge transfer.

Double-furofluorenone as well as derivative and preparation method thereof

Abstract: The invention discloses double-furofluorenone and a derivative thereof. The double-furofluorenone adopts the structure as shown in the specification. The preparation method comprises the following steps: by taking 2,7-dihydroxy fluorenone as a raw material, enabling 2,7-dihydroxy fluorenone to react with bromo-acetadehyde diethylacetal so as to obtain ether, and performing direct ring closure by using polyphosphoric acid so as to obtain double-furofluorenone; by taking 2,7-dihydroxy fluorenone as a raw material, enabling 2,7-dihydroxy fluorenone to react with bromo-acetadehyde diethylacetal so as to obtain ether, reducing fluorenone by using a Huang-ming-long method, further enabling reaction with 1-bromohexane under the action of sodium hydride, and finally performing polyphosphoric acid ring closure, thereby obtaining 9,9-dihexyl double-furofluorenone. Due to the adoption of the compound disclosed by the invention, novel option can be provided for a predecessor of an organic field effect crystal tube material, and the range of an organic electroluminescence material is widened.

Metal oxide supported palladium catalyst for hydrocarbon oxidation

Abstract: A metal oxide supported palladium catalyst comprised of a β-Bi 2 O 3 /Bi 2 Sn 2 O 7 hetero-junction catalyst support and palladium was developed. The catalyst was synthesized using a sol-gel technique as a nanocrystalline structure. In the presence of fluorene, an oxidant and ultraviolet irradiation, the catalyst converts the hydrocarbon to a mixture of fluorenol/fluorenone oxidation products. The close proximity between β-Bi 2 O 3 and Bi 2 Sn 2 O 7 heterojunction phases in the catalyst is thought to be responsible for the efficient charge separation and catalytic activity. An indirect chemical probe method using active species scavengers elucidated that the photo-oxidation mechanism proceeds via holes and superoxide radical (O 2 . − ) moieties.

Method of producing fluorenone derivative

Abstract: PROBLEM TO BE SOLVED: To provide an efficient method of producing 9,9-bis(4-(4-hydroxyphenyloxy)phenyl)fluorene which is useful as a raw material for polyesters, polyurethanes, polycarbonates, epoxy resins and modified acrylic resins, etc.SOLUTION: A method of producing 9,9-bis(4-(4-hydroxyphenyloxy)phenyl)fluorene comprises reacting fluorenone with p-phenoxyphenol in the presence of an acid so as to obtain the fluorenone derivative, so far synthesized through a plurality of reaction stages from expensive raw materials, easily in a high yield.

Photodetachment spectroscopy of fluorenone radical anions microsolvated with methanol: Rationalizing the anomalous solvatochromic behavior due to hydrogen bonding

Abstract: The attribution of the extraordinary blue shift for the intramolecular charge-transfer absorption band of fluorenone radical anion solvated in protic media was investigated by means of photodetachment spectroscopy of the gas-phase anions microsolvated with methanol, in conjunction with quantum chemical calculations based on density functional theory. Sequential shifts of the vertical detachment energy as a function of the cluster size are consistent with theoretical predictions, where up to two methanol molecules can directly attach to the carbonyl group. In the photodetachment excitation spectra as alternatives to the photoabsorption spectra, with increasing cluster size, a new absorption band grows in the higher-energy region, which coincides with the blue-shifted band in protic media. Spectral simulations using time-dependent density functional theory with the CAM-B3LYP functional reproduced the feature of the phenomenon. Analyses on the electronic configuration elucidated that the extraordinarily blue...

Delayed fluorescence light emitting substance, and organic el element

Abstract: PROBLEM TO BE SOLVED: To provide a fluorescence light emitting substance and a thermally activated delayed fluorescence light emitting substance exhibiting a high internal quantum yield, and to provide an organic EL element exhibiting a high external light emitting efficiency obtained by using the fluorescence light emitting substance and the thermally activated delayed fluorescence light emitting substance for a light emitting layer of the organic EL element.SOLUTION: A delayed fluorescence light emitting substance is aromatic hydrocarbon having a substituent Xn in either one of aromatic ring among a benzene ring, a naphthalene ring, a biphenyl ring and a fluorene ring, and the substituent Xn is selected from either one of residues of benzothiazole, coumarin, fluorenone, acridone, quinacridone, acridine, anthraquinone, thioxanthone, phthalimide, naphthyl dicarboimide and pyrene, or a residue of a derivative of the either one, and the number of the substituent is 1 or more. There is also provided an organic EL element containing the delayed fluorescence light emitting substance in a light emitting layer.

Synthesis technique of 9-fluorenone

Abstract: The invention relates to a synthesis technique of 9-fluorenone, which comprises the following steps: by using industrial fluorene as the raw material, sodium hydroxide as a catalyst and dimethylsulfoxide as a solvent, heating and dissolving the material in a reaction kettle, carrying out reaction kettle external circulation, passing through a microbubble generator, returning to the reaction kettle to react, cooling the reaction material to crystallize, separating, washing and recrystallizing to obtain the fluorenone The solvent adopts a non-benzene pyridine solvent, and thus, has the advantages of low toxicity and environment friendliness The catalyst adopts the industrial common catalyst which is cheap and accessible, thereby optimizing the production technique and greatly lowering the consumptions of the catalyst and solvent The solvent can be recovered, thereby implementing reuse The technique has the advantages of mild reaction conditions, simple and effective reactor, sufficient reaction, high speed and high fluorenone yield The purity is greater than 99%, and the yield can reach 85% above

[RuCl2(p-cymene)2]2 Catalyzed Cross Dehydrogenative Coupling (CDC) toward Xanthone and Fluorenone Analogs Through Intramolecular C—H Bond Functionalization Reaction.

Abstract: The route to biologically active xanthone and fluorenone analogs proceeds smoothly for substrates equipped with electron-donating substituents, but leads to no reaction or trace amounts of products for substrates with electron-withdrawing groups.

Synthesis method of 9,9'-spirobifluorene-4-boric acid

Abstract: The invention discloses a preparation method of 9,9'-spirobifluorene-4-boric acid, and belongs to the field of organic chemical synthesis. The 9,9'-spirobifluorene-4-boric acid can be applied to design and synthesis of organic optoelectronic materials. The method is achieved by the following steps: with o-bromoiodobenzene as a raw material, preparing a grignard reagent from magnesium powder, catalyzing with lithium bromide, so as to generate 2-bromobiphenyl-2'-magnesium bromide, and then reacting 2-bromobiphenyl-2'-magnesium bromide with fluorenone; and preparing 9,9'-spirobifluorene-4-boric acid by catalytic closed-loop reaction of p-toluene sulfonic acid and n-butyllithium boration. The method is good in reaction selectivity, few in side reaction, mild in reaction condition, easy to control, low in cost, simple to operate and suitable for industrialized production; and the total yield is over 76%.

Preparation method of 3-halogenated fluorenone compound

Abstract: The invention relates to a preparation method of a 3-halogenated fluorenone compound. According to the method, 2-bromine-4-nitrobenzoic acid methyl ester is used as a starting material, and through Suzuki reaction, reduction reaction, diazotization reaction and ring closing reaction, the 3-halogenated fluorenone compound is prepared. When the method is adopted for synthesizing the 3-halogenated fluorenone, the cost is low; the condition is mild; the operation is simple; the preparation method is suitable for laboratories and industrial large-scale preparation.