Showing papers on "Fluorenone published in 2012"
TL;DR: A decarboxylative radical cyclization reaction has been developed for the synthesis of fluorenones and undergoes cyclization to afford fluorenone products in good yield.
111 citations
TL;DR: This method provides a concise and effective route toward the synthesis of fluorenone derivatives, which shows outstanding functional group compatibility.
96 citations
TL;DR: N-Vinyl nitrones derived from fluorenone have been prepared via a copper-mediated coupling between fluore None oxime and vinyl boronic acids and undergo subsequent rearrangement and addition reactions that are distinct from the traditional [3 + 2] cycloaddition reactivity of nitrones.
64 citations
TL;DR: In this paper, two new organic dyes based on a donor-acceptor-π-bridge/anchor configuration were synthesized, characterized, and successfully employed in dye-sensitized solar cells.
Abstract: Two new organic dyes based on a donor–acceptor–π–bridge–acceptor/anchor (D–A–π–A) configuration, HIQF1 and HIQF2, were synthesized, characterized, and successfully employed in dye-sensitized solar cells. The incorporation of the weakly electron-withdrawing fluorenone group as an additional acceptor enhanced the dyes' properties for solar energy conversion in several ways. First, the absorption spectra of the dyes were broadened, covering a large range of sunlight. Second, the absorption spectra observed upon dye adsorption on TiO2 were only slightly blue-shifted as compared to the spectra of the dyes in solution. Third, the orbital energy levels and electron distributions of the D–A–π–A backbone were ideal for highly efficient electron transport and injection. The incorporation of long electron-donating alkoxy groups in the donor unit of HIQF1 further increased the dye's short-circuit photocurrent density (Jsc), open-circuit voltage (Voc), and overall conversion efficiency (η), but had little negative effect on the fill factor (FF). Solar cells sensitized with HIQF1 showed excellent current–voltage characteristics; the Jsc, Voc, and FF values were 12.26 mA cm−2, 0.70 V, and 0.73, corresponding to a η value of 6.26%.
60 citations
TL;DR: A solution-processable acceptor-acceptor conjugated copolymer (P1) based on perylene diimide (PDI) incorporating planar electron-deficient fluorenone was synthesized by palladium(0)-catalyzed Suzuki coupling reaction as discussed by the authors.
Abstract: A new solution-processable acceptor-acceptor conjugated copolymer (P1) based on perylene diimide (PDI) incorporating planar electron-deficient fluorenone was synthesized by palladium(0)-catalyzed Suzuki coupling reaction. Relative to the donor-acceptor conjugated copolymer (P2) of PDI and dithienothiophene, polymer P1 exhibits 0.1 eV down shift of lowest unoccupied molecular orbital (LUMO) level, 70 nm blue shift of low-energy absorption band, and 0.36 eV increase of optical band gap. Polymer P1 in top-contact bottom-gate organic field-effect transistors exhibits a saturation electron mobility of 0.01 cm2/(V s) in air, while P2 does not function in the same device in air. The better air stability of P1 is attributed to a more dense packing of the polymer chains excluding oxygen or water and lower LUMO level of P1. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012
40 citations
TL;DR: Electrochemical and spectral data combined in a modular electronic analysis model show how the donor HOMO and acceptor LUMO act as major determinants of the frontier molecular orbital energy levels.
Abstract: Push–pull organic molecules composed of electron donor diarylamines at the 2- and 2,7-positions of fluorenone exhibit intramolecular charge-transfer behaviour in static absorption and emission spectra. Electrochemical and spectral data combined in a modular electronic analysis model show how the donor HOMO and acceptor LUMO act as major determinants of the frontier molecular orbital energy levels.
34 citations
TL;DR: Improved charge transport properties of melt-processed crystalline films were obtained for the isomer exhibiting a highly ordered mesophase below its disordered smectic phase.
33 citations
TL;DR: A donor-acceptor-donor dye consisting of a 2,7-disubstituted fluorenone with diethylaminophenyl moieties present as strong electron donating groups was designed and synthesized and switched between twisted intramolecular charge transfer emission and excimer emission by simply changing the solvent used.
Abstract: We designed and synthesized a donor-acceptor-donor dye consisting of a 2,7-disubstituted fluorenone with diethylaminophenyl moieties present as strong electron donating groups. Switching between twisted intramolecular charge transfer (TICT) emission and excimer emission was achieved, with no ground state changes, by simply changing the solvent used. In a nonpolar solvent, excimer emission was observed; with increasing polarity, the emission gradually disappeared, and the TICT emission appeared.
26 citations
TL;DR: Two fluorene-based copolymers (PF-33F and PF-50F ) with p-difluorophenylene units in the backbone were synthesized in this paper.
20 citations
TL;DR: The trifluoromethylphenylene unit was introduced into the copolymer backbone and its content ratio was varied from 10 −mol% to 50 −mol%. In contrast to pure polyfluorene, the deep-blue fluorescence of these copolymers is quite stable and not contaminated by the well-known green emission associated with fluorenone defects.
9 citations
TL;DR: The DSFO-doped 3B2B microspheres (DMPs) exhibited significantly reduced fluorescence from 3B 2B (donor) and strongly enhanced emission from DSFO (acceptor), which is highly sensitive to the concentration of metalloprotein.
Patent•
03 Oct 2012
TL;DR: In this article, a method for producing 9-fluorenone by oxidizing industrial fluorine is described, which includes the following steps of dissolving industrial fluorines as a raw material in to a halogenated hydrocarbon solvent at the temperature of 30-80 DEG C, adding sodium hydroxide and a quaternary ammonium salt which are cheaper than potassium hyroxide for serving as catalysts, reacting in a reaction kettle for 05-5 hours, separating a liquid, and distilling an organic phase under reduced pressure for removing the solvent to obtain an
Abstract: The invention discloses a method for producing 9-fluorenone by oxidizing fluorine The method comprises the following steps of: dissolving industrial fluorine as a raw material in to a halogenated hydrocarbon solvent at the temperature of 30-80 DEG C, adding sodium hydroxide and a quaternary ammonium salt which are cheaper than potassium hydroxide for serving as catalysts, reacting in a reaction kettle for 05-5 hours, separating a liquid, and distilling an organic phase under reduced pressure for removing the solvent to obtain an intermediate substance; adding an intermediate and an alcohol solvent into the reaction kettle, heating to 40-80 DEG C for dissolving, introducing air at the speed of 1-10m /h into every kilogram of industrial fluorine, and reacting for 05-5 hours; and after the reaction, removing the solvent under reduced pressure, cooling and crystallizing simultaneously, and filtering a crystal product to obtain fluorenone The equipment investment is low, process operation is easy, the solvent can be recycled, and cost is effectively saved; an obtained fluorenone product has high purity and high yield; in an entire process, an industrial grade organic solvent is adopted, so that operation and running costs are low; and an entire device is controlled automatically, so that operation conditions are improved, and the product quality stability is ensured simultaneously
Patent•
06 Jun 2012
TL;DR: In this article, a novel novolac prepared by acid catalyzed condensation between biphenols or bisphenofluorenes and fluorenone is presented, which exhibits excellent oxidative thermal stability and high carbon content, suitable for dielectric, etch stop applications as spin-on material.
Abstract: A novel novolac prepared by acid catalyzed condensation between biphenols or bisphenofluorenes and fluorenone is presented. The polymers exhibit excellent oxidative thermal stability and high carbon content, suitable for dielectric, etch stop applications as spin-on material.
Patent•
06 Jun 2012
TL;DR: In this paper, a novel novolac prepared by acid catalyzed condensation between biphenols or bisphenofluorenes and fluorenone is presented, which exhibits excellent oxidative thermal stability and high carbon content, suitable for dielectric, etch stop applications as spin-on material.
Abstract: A novel novolac prepared by acid catalyzed condensation between biphenols or bisphenofluorenes and fluorenone is presented. The polymers exhibit excellent oxidative thermal stability and high carbon content, suitable for dielectric, etch stop applications as spin-on material.
Patent•
28 Mar 2012
TL;DR: In this paper, a method for the preparation of 9-fluorenone is described. But the method is not suitable for the use of industrial fluorene, benzene series solvent, sodium hydroxide and quaternary ammonium salt, and the solvent is toluene or dimethylbenzene.
Abstract: The invention relates to the technical field of production of an aromatic compound 9-fluorenone, in particular to a preparation method of the 9-fluorenone. The preparation method includes the steps as follows: 1) taking industrial fluorene, benzene series solvent, sodium hydroxide and quaternary ammonium salt, and adding the four components in a four-mouth bottle; 2) stirring the mixture in normal pressure, increasing the temperature to above 90 DEG C, reacting, and introducing air for oxidization; 3) conducting reduced-pressure distillation and allowing concentrate to crystallize, thus obtaining yellow fluorenone crystals; and 4) washing the fluorenone crystals for one time and then drying the fluorenone crystals, thus obtaining the 9-fluorenone product. The benzene series solvent is toluene or dimethylbenzene. Compared with the prior art, the preparation method has the benefits as follows: 1) the reaction temperature is low, the operation is simple and convenient and the reaction conditions are moderate; 2) the cheap sodium hydroxide is taken as a catalyst, so the cost is low; 3) the benzene series solvent can be recycled by reduced-pressure distillation, washing water is little in quantity, treatment is easy and pollution to environment is small; and 4) the gas chromatographic purity of the product is higher than 99.2%, the yield is higher than 86.7% and the production requirements are met.
Patent•
17 Oct 2012
TL;DR: In this article, a method for coarse fluorene and fluorenone by taking wash oil as a raw material is presented. But the method is not suitable for the high energy consumption and high cost, environment pollution and the like.
Abstract: The invention discloses a method for preparing coarse fluorene and fluorenone by taking wash oil as a raw material. The method comprises the following steps of: firstly, carrying out acid and alkali treatment on wash oil fraction obtained by fractionating coal tar, and enriching in a rectifying way to obtain coarse fluorene; secondly, converting fluorene in the coarse fluorene into fluorenone by an air liquid phase catalytic oxidation method; and based on ethylene glycol as entrainer, carrying out azeotropic distillation on reaction mixture to separate the fluorenone in the reaction mixture. The method has the advantages that a process route of first reaction and second separation is adopted, so that the fluorenone can be directly prepared by taking the coarse fluorene as the raw material, therefore, the fluorenone can be more easily separated from the reaction mixture; and the conventional preparation method of the fluorenone by firstly separating the fluorene from the coarse fluorene can be replaced, as the conventional method has the problems such as large material loss, high energy consumption, high cost, environment pollution and the like since the fluorene is very hard to separate.
Patent•
15 Aug 2012
TL;DR: In this article, a "vertically" unsymmetrical spirobifluorene compound derived from conversion of methyl on a fluorene loop is presented, which has a spiral conjugation effect, high dissolubility and high heat stability.
Abstract: The invention relates to a 'vertically' unsymmetrical spirobifluorene compound derived from conversion of methyl on a fluorene loop. A structural formula of the compound is (I) shown in the source text, wherein R1 and R2 in the formula can be various electron withdrawing and donating groups such as alkyl, substituted aryl, substituted heterocyclic radical, substituted alkylene, substituted amino, chlorine, bromine, iodine and the like, and the R1 and R2 are different. 4,4'-dimethyl diphenyl which is cheap and easy to obtain is used as a raw material to be bromized and reacted with fluorenone or 2,7-substituted fluorenone to covert the methyl on the fluorine loop into various fluctional groups and the like to obtain the compound (I). The 'vertically' unsymmetrical spirobifluorene compound derived from conversion of methyl on the fluorene loop is low in cost, simple in synthetic route, high in yield and easy in industrial production, has special spiral conjugation effect, high dissolubility and high heat stability, and is widely applicable to fields of organic luminous display, organic nonlinear materials, fluorescent probes and the like.
TL;DR: A series of polymers were synthesized by incorporating low contents of fluorenone (FO) and 4,7-bis(2-thienyl)-2,1,3-benzothiadiazole (DBT) into the main chain of poly(9,9-dioctylfluorene) as discussed by the authors.
Abstract: A series of polymers were synthesized by incorporating low contents of fluorenone (FO) and 4,7-bis(2-thienyl)-2,1,3-benzothiadiazole (DBT) into the main chain of poly(9,9-dioctylfluorene). White-light emission was obtained from a single polymer by adjusting the FO and DBT contents. All polymers showed good thermal stability with 5% weight loss up to 410 °C and good solubility in common organic solvents. Electroluminescence devices with indium tin oxide/poly(3,4-ethylenedioxythiophene): poly(styrenesulfonate)/emission layer/Ca/Al structure were found to emit white light with Commission Internationale de l’Eclairage coordinate of (0.37, 0.34). These devices exhibited a maxium brightness of 3414 cd/m2 and a maximum current efficiency of 2.79 cd/A.
Patent•
28 Mar 2012
TL;DR: In this paper, a method for the production of 2, 7-binitro fluorenone is described, which is characterized by comprising the following steps: (1), adding industrial 2,7-binito fluorenos, benzene series resolvent, sodium hydroxide and quaternary ammonium salt into four bottles; (2), carrying out air oxidation under the temperature of 90 to 100 DEGC, and reacting for 6 to 7 hours: (3), recovering solvent through reduced pressure distillation and crystallizing condensate; and (4),
Abstract: The invention relates to the technical field of the production of aromatic compound 2, 7-binitro fluorenone, particularly to a method for producing 2, 7-binitro fluorenone. The method for producing 2, 7-binitro fluorenone is characterized by comprising the following steps: (1), adding industrial 2, 7-binitro fluorenone, benzene series resolvent, sodium hydroxide and quaternary ammonium salt into four bottles; (2), carrying out air oxidation under the temperature of 90 to 100 DEGC, and reacting for 6 to 7 hours: (3), recovering solvent through reduced pressure distillation and crystallizing condensate; and (4), washing, alkali removing and drying so as to obtain the product of 2, 7-binitro fluorenone. The benzene series resolvent is toluene or xylene. Compared with the prior art, the invention has the benefits as follows: (1), the reaction temperature is low, the operation is simple and convenient, and the reaction conditions are moderate; (2), sodium hydroxide is taken as the catalyst, and the cost is low; (3), the benzene series resolvent can be depressurized, distilled, recovered and recycled, the wash water is easy to be treated, and pollutions to the environment are small; and (4), the purity of the gas phase chromatography of the product is higher than 99.1 percent, the yield is higher than 84.8 percent, and the production requirements are met.
Patent•
07 Nov 2012
TL;DR: In this article, a vertically asymmetrical methyl spirobifluorene compound is described, where the structural formula of the product provided by the invention is as shown in the formula (I), wherein R1 can be various electron-withdrawing and electro-donating groups such as various alkyl groups, substituted aryl group, substituted heterocyclic radical group, substituting alkylene group, substitute amino group, chlorine, bromine, iodine and the like, but is not methyl.
Abstract: The invention relates to a vertically asymmetrical methyl spirobifluorene compound. The structural formula of the product provided by the invention is as shown in the formula (I), wherein R1 can be various electron-withdrawing and electro-donating groups such as various alkyl groups, substituted aryl group, substituted heterocyclic radical group, substituted alkylene group, substituted amino group, chlorine, bromine, iodine and the like, but is not methyl. Cheap and easily available 4,4'-dimethyl biphenyl is used as a raw material and undergoes bromination and reaction with 2,7-diX(X represents substituent)fluorenone, and the Xsubstituent on the fluorine ring is changed into various function groups so as to obtain the compound (I). The vertically asymmetrical methyl spirobifluorene compound provided by the invention has advantages of low product cost, simple synthetic route and high yield, is easy for industrial production, has a special spiro-conjugation effect, good dissolvability and high thermal stability, and can be widely applied in fields of organic electroluminesence display, organic non-linear materials, fluorescent probe and the like.
Patent•
30 May 2012
TL;DR: A noble metal/TiO2-C catalyst for removing p-carboxybenzaldehyde, 2,6-dicarboxyl anthraquinone, and other colored impurities from crude p-phthalic acid was proposed in this paper.
Abstract: The invention discloses a noble metal/TiO2-C catalyst for removing p-carboxybenzaldehyde, 2,6-dicarboxyl anthraquinone, 2,6-dicarboxyl fluorenone, and other colored impurities from crude p-phthalic acid. The noble metal/TiO2-C catalyst of the present invention can be used for the hydrogenation refinement process of the crude p-phthalic acid. With the noble metal/TiO2-C catalyst of the present invention, the contents of the p-carboxybenzaldehyde, the 2,6-dicarboxyl anthraquinone, the 2,6-dicarboxyl fluorenone, and other colored impurities can be significantly reduced.
Patent•
12 Sep 2012
TL;DR: In this article, a synthesizing process for 9-fluorenone derivatives is described, and the product has the advantages of low melting point, high stacking density, good fluidity, convenience in operation and easiness in implementation.
Abstract: The invention discloses a synthesizing process for fluorenone derivatives. In the presence of concentrated sulfuric acid and a 3-mercaptoacetic acid catalyst, 9-fluorenone and ethylene glycol phenyl ether react at certain temperature, are washed and recrystallized to prepare 9,9-bi[(4-(2- hydroxy ethoxy) phenyl] fluorene, the purity of the product is larger than 97%, the melting point of the product ranges from 106 DEG C to 161 DEG C, a low-melting-point portion accounts for 85% at least, and the volume density of the product is larger than 0.5g/cm . The 9,9-bi[(4-(2- hydroxy ethoxy) phenyl] fluorene synthesized by the process has the advantages of low melting point, high stacking density, good fluidity, convenience in operation and easiness in implementation, and is favorable for popularization and application.
TL;DR: In this paper, a decarboxylative radical cyclization reaction was developed for the synthesis of fluorenones, which uses Ag(I)/K2S2O8 to oxidatively decompose an aroylbenzoic acid to an aryl radical, which undergoes cyclization to afford fluorenone products.
Abstract: A decarboxylative radical cyclization reaction has been developed for the synthesis of fluorenones. The reaction uses Ag(I)/K2S2O8 to oxidatively decarboxylate an aroylbenzoic acid to an aryl radical, which undergoes cyclization to afford fluorenone products in good yield.
Patent•
20 Apr 2012
TL;DR: In this article, a synthesis method of indenofluorene derivatives, isotruxene and mono-substituted isotruixene derivatives, is described, which can be used in the field of organic electroluminescence and organic micromolecule solar cells.
Abstract: The invention discloses a synthesis method of indenofluorene derivatives, isotruxene and mono-substituted isotruxene derivatives. The synthesis method of indenofluorene derivatives is characterized in that ester-group-containing compounds are formed through Diels-Alder reaction of methyl propiolate and indenocyclopentadienone, ethyl substituted indenofluorene derivatives are formed through hydrolysis, acid catalytic ring closing, carbonyl reduction and introduction of ethyl onto methylene, diketone compounds produced after ring closing react with lithium salt of 4, 4'-di-tert-butyl-2-brominated biphenyl, and then acidification and ring closing are conducted to obtain indenofluorene derivatives with spirofluorene. The synthesis method of isotruxene is characterized in that 1, 4-diphenyl-2, 3-di (carbalkoxy) fluorenone products are formed through the Diels-Alder reaction of indenocyclopentadienone and dimethyl acetylenedicarboxylate, isotruxene ketone is obtained through hydrolysis and acid catalytic ring closing and finally isotruxene is obtained; dibenzyl alcohol products are formed through the Diels-Alder reaction of 1, 4-butynediol and indenocyclopentadienone, and isotruxene is obtained through acetone protection, carbonyl reduction, acetone removal and polyphosphoric acid (PPA) ring closing; and oriented oxy substituted products, i.e. isotruxene ketone which is derived from isotruxene with methylene at a No.5 position being substituted, and corresponding diethyl substituted products are additionally obtained. The indenofluorene derivatives, the isotruxene and the mono-substituted isotruxene derivatives disclosed by the invention can be used in the field of organic electroluminescence and organic micro-molecule solar cells.
Patent•
21 Mar 2012
TL;DR: In this article, a method for extracting and purifying fluorenone from industrial wastes generated in production of benzoic acid, which includes steps of obtaining crude solid fluore none by means of reaction of crude benzyl ester, water and sodium hydroxide according to a certain proportion after rectification of benzosic acid.
Abstract: The invention provides a method for extracting and purifying fluorenone from industrial wastes generated in production of benzoic acid, which includes steps of obtaining crude solid fluorenone by means of reaction of crude benzyl ester, water and sodium hydroxide according to a certain proportion after rectification of benzoic acid, and recrystallizing the crude solid fluorenone by ethyl acetate and petroleum ether Purification of the fluorenone is higher than 98%, and separation efficiency ranges from 60% to 75% A new technical scheme is provided for further expansion in recycling of industrial wastes generated in production of benzoic acid and for reduction of environment pollution
Patent•
11 Apr 2012
TL;DR: In this paper, a method for 2,7-dibromo fluorenone is described, which is characterized by comprising of the following steps of: (1) taking industrial 2.7-dimbromo fluorine, a benzene series solvent, potassium hydroxide, quaternary ammonium salts, and adding the constituents in a four-opening bottle; (2) heating to a temperature of 80-90 DEG C for reaction, and inletting air for oxidization; (3) depressurizing and distilling, and obtaining
Abstract: The invention relates to the field of the production of aromatic compound 2,7-dibromo fluorenone and particularly relates to a method for preparing the 2,7-dibromo fluorenone, which is characterized by comprising the following steps of: (1) taking industrial 2,7-dibromo fluorine, a benzene series solvent, potassium hydroxide, quaternary ammonium salts, and adding the constituents in a four-opening bottle; (2) heating to a temperature of 80-90 DEG C for reaction, and inletting air for oxidization; (3) depressurizing and distilling, and obtaining a yellow 2,7-dibromo fluorenone crystal after condensate is crystallized; and (4) carrying out once washing by water, and drying to obtain the product, i.e. the 2,7-dibromo fluorenone. The benzene series solvent is toluene or xylene. Compared with the prior art, the method for preparing the 2,7-dibromo fluorenone has the beneficial effects that: the reaction temperature is low, and the operation is simple and convenient; the low-cost potassium hydroxide is taken as a catalyst, thus, the cost is low; the benzene series solvent can be recovered and recycled through depressurizing and distilling, the amount of washing water is little and the treatment is easy, and the pollution to the environment is little; and the gas-phase chromatographic purity of the product is higher than 99.2%, the yield is higher than 85%, and thus, the production requirements are met.