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Showing papers on "Fluorenone published in 2018"


Journal ArticleDOI
Wei Sun1, Nonglin Zhou1, Yin Xiao1, Shirong Wang1, Xianggao Li1 
TL;DR: In this article, three carbazolyl-substituted blue emitters, namely SAF-CzB, SAF-2CzBs, and F-2czB were designed and synthesized.

33 citations


Journal ArticleDOI
TL;DR: A series of novel pyrroles fused with pharmacologically important chromone, flavone, coumarin, fluorenone, and anthraquinone moieties were synthesized under metal-free reaction conditions in good to very good yields within a short reaction time.
Abstract: The reaction of arylglyoxals, 4-hydroxycoumarin, and aromatic amines such as 7-amino-2-methylchromone, 6/7-aminoflavone, 7-amino-4-methylcoumarin, 1-amino-9-fluorenone, 1-aminoanthraquinone and aniline derivatives in acetic acid medium under microwave conditions provides the corresponding regioselective fused pyrroles having hydroxycoumarin and aryl substituents. Alternatively, we have developed another method using in situ arylglyoxals from acetophenone derivatives by I2/DMSO promoted C–H oxidation followed by one-pot three component cyclization reactions to provide similar fused pyrroles. Using both the methods a series of novel pyrroles fused with pharmacologically important chromone, flavone, coumarin, fluorenone, and anthraquinone moieties were synthesized under metal-free reaction conditions in good to very good yields within a short reaction time. The structures of the synthesized fused pyrroles have been unambiguously confirmed by spectroscopic techniques, mass analysis and single crystal XRD.

28 citations


Journal ArticleDOI
TL;DR: Two donor–acceptor–donor (D–A–D)-type orange TADF materials based on fluorenone and acridine exhibited a maximum external quantum efficiency of 8.9%, which is higher than the theoretical efficiency of the OLEDs based on conventional fluorescent materials.
Abstract: The design of orange-light emitting, thermally activated, delayed fluorescence (TADF) materials is necessary and important for the development and application of organic light-emitting diodes (OLEDs). Herein, two donor-acceptor-donor (D-A-D)-type orange TADF materials based on fluorenone and acridine, namely 2,7-bis(9,9-dimethylacridin-10(9H)-yl)-9H-fluoren-9-one (27DACRFT, 1) and 3,6-bis(9,9-dimethylacridin-10(9H)-yl)-9H-fluoren-9-one (36DACRFT, 2), were successfully synthetized and characterized. The studies on their structure-property relationship show that the different configurations have a serious effect on the photoluminescence and electroluminescence performance according to the change in singlet-triplet splitting energy (ΔEST) and excited state geometry. This indicates that a better configuration design can reduce internal conversion and improve triplet exciton utilization of TADF materials. Importantly, OLEDs based on 2 exhibited a maximum external quantum efficiency of 8.9%, which is higher than the theoretical efficiency of the OLEDs based on conventional fluorescent materials.

22 citations


Journal ArticleDOI
TL;DR: Diels-Alder reaction of 1,3-diarylbenzo[c]furan/cyclopentadienone with TTF followed by triflic acid mediated cleavage of the resulting adducts led to the formation of the respective 1,4- diaryl substituted naphthalenes, fluoranthenes, and fluorenones.

12 citations


Journal ArticleDOI
TL;DR: In this article, the arrangement for the two side chains which differ from each other only by one carbon atom was discussed from the viewpoint of thermodynamics and kinetics, and the alkyl chain in the same length was speculated to show selective identification during the self-assembly process.
Abstract: Structural diversity induced by the chain-length effect in the field of two-dimensional self-assembly has gained immense attention because of its potential application in nanoscience and crystal engineering. By modifying the two side chains in a certain molecule by one carbon atom and gradually increasing the alkyl chain length, seven fluorenone derivatives (F–CnCn+1, n = 11–17) were synthesized. At the 1-octanoic acid/graphite interface, diverse nanostructures of hexamer-I, tetramer, dimer, alternate-I, hexamer-II, and alternate-II were recorded. The arrangement for the two side chains which differ from each other only by one carbon atom was discussed from the viewpoint of thermodynamics and kinetics. The alkyl chain in the same length was speculated to show selective identification during the self-assembly process, which was favored in consideration of dense packing and maximizing the molecular interplay. Three forces such as dipole–dipole, hydrogen bonding, and van der Waals (vdWs) interactions coopera...

11 citations



Journal ArticleDOI
TL;DR: In this article, three donor-π−acceptor-π-donor multichromophore fluorenone-centered compounds are analyzed by means of experimental and density functional theory methods.
Abstract: Three donor–π−acceptor–π-donor multichromophore fluorenone-centered compounds are presented. The π-bridges between the fluorenone and carbazole donors contain ethynyl moieties linked to various branched spacing moieties, such as triphenylamine, 1,3,5-triphenylbenzene and 9-phenylcarbazole. Differences in the photophysical, photoelectrical, thermal and charge-transporting characteristics of the three compounds are analyzed by means of experimental and density functional theory (DFT) methods. The investigated compounds exhibit good ambipolar charge transport behavior with mobility values exceeding 10−3 cm2 V−1 s−1. The compounds exhibit interesting photoluminescence properties, which are strongly influenced by the important tendency of these compounds in solution to form strongly bound ground state aggregates. Photoluminescence emission of these materials is found to originate predominantly from intramolecular transitions of π–πCT* nature which experience a strong redshift and an intensity decrease from the aggregation and intermolecular H-bonds. A slowly evolving equilibrium between strongly aggregated molecules and free ones is observed in THF solutions, resulting in the emission color swapping gradually from yellow to blue with a drastic intensity increase. The correlation of the aggregation strength with the absorption and emission properties, photoluminescence quantum yield, and the time needed for color swapping is discussed. Furthermore, seldom observed photoluminescence intensity enhancement with temperature increase was detected in non-polar media.

10 citations


Journal ArticleDOI
TL;DR: The first Pd-based heterogeneous homo-and cross-coupling reactions for the synthesis of fluorenones were reported in this article, where the palladium supported SBA-functionalizd 1,2-dicarboxylic acid (Pd@DCA-SBA) was prepared and characterized by the FT-IR, TGA, AAS, TEM, and EDS measurements.

9 citations


Journal ArticleDOI
TL;DR: In this article, 2,7-bi-(N-penothiazinyl)fluorenone was employed as photocatalyst and EBP as atom transfer radical polymerization (ATRP) initiator.
Abstract: In this study, 2,7-bi-(N-penothiazinyl)fluorenone was employed as photocatalyst (PC), ethyl α-bromophenylacetate (EBP) as atom transfer radical polymerization (ATRP) initiator, and photo-induced me...

9 citations


Journal ArticleDOI
TL;DR: In this paper, a 2-butyl octyl (BO) substituted phthalimide (PI) end-capped fluorenone [PI-FN-PI (BO)] non-fullerene electron acceptor for organic photovoltaics has been designed and synthesized to study the effect of endcapping groups on the optoelectronic properties.

8 citations


Journal ArticleDOI
TL;DR: In this article, an efficient and environmentally benign process was developed for the synthesis of fluorenone and 1-tetralone derivatives using cyclic 1,3-dione, malononitrile and dialkylacetylenedicarboxylate as starting materials in aqueous medium.

Journal Article
TL;DR: In this article, a spectrophotometric method applied for the study of (colored charge transfer complexes) CTC of PVK with TNF reveals the formation of 1:1 (A:D) complex, and formation of CTC with PVK and TNF.
Abstract: Carbazole based polymers are materials of considerable scientific and industrial interest due to their attractive features, such as hole-transporting, high charge-carrier mobility, and electroluminescent properties. Among carbazole polymers, a central place is reserved for poly (N-vinyl carbazole) (PVK) because it is easily synthesized, is soluble in common organic solvents and as the poly (N-vinyl carbazole)/2,4,7-trinitro-9- fluorenone (PVK/TNF) charge transfer complex is one of the bestknown organic photos conducting materials for application in electrophotography. it’s an electroluminescent material and emits strong fluorescence and long phosphorescence when excited with UV light. In the present research a spectrophotometric method applied for the study of (colored charge transfer complexes) CTC of PVK with TNF reveals the formation of 1:1 (A:D) complex, and formation of CTC with PVK and TNF, From the conductivity of the CT Complex, it is obtained that the concentration of the donor is affected when it reacts with the acceptor and that when we increase the concentration of the donor.

Patent
06 Apr 2018
TL;DR: In this article, a fluorenone-containing phenothiazine solar dye sensitizer is described, which can serve as the dye sensizer to be applied to a dye-sensitized solar cell.
Abstract: The invention discloses a fluorenone-containing phenothiazine solar dye sensitizer as well as preparation and application thereof. The fluorenone-containing phenothiazine solar dye sensitizer is shownas a formula I, a formula II or a formula III. A synthetic method of the dye sensitizer disclosed by the invention comprises the following steps: mixing a compound of a formula IV and cyanoacetic acid with an organic solvent, heating and performing reflux agitation reaction for 6-8 hours in the presence of piperidine under nitrogen protection, spin-drying the solvent after the reaction is complete, and performing silica gel column chromatography on the residues with an eluent solvent, thereby obtaining the fluorenone-containing phenothiazine solar dye sensitizer shown as the formula I, the formula II or the formula III. The phenothiazine compound disclosed by the invention can serve as the dye sensitizer to be applied to a dye-sensitized solar cell, and a novel applicable substance is added for screening of dye sensitizers. The structural formula is as shown in the specification.

Journal ArticleDOI
TL;DR: An efficient and regioselective synthesis of functionalized benzenes via the cascade reactions of 1,2-allenic ketones with 4-sulfonyl crotonates under mild reaction conditions has been established as mentioned in this paper.

Patent
15 Feb 2018
TL;DR: In this paper, a new method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystal which shows a melting peak by a differential scan calorimetry in a temperature region of 115-125°C and has a bulk density of 0.60-0.75 g/cm.
Abstract: PROBLEM TO BE SOLVED: To provide a new method for producing 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystal which shows a melting peak by a differential scan calorimetry in a temperature region of 115-125°C and has a bulk density of 0.60-0.75 g/cm.SOLUTION: A method for preparing purified crystal of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene includes reacting fluorenone and phenoxy ethanol to obtain rough crystal of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, and purifying the rough crystal to enhance a degree of purity to at least 99%. A method for obtaining 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystal includes: dissolving the purified crystal in a mixed solvent of acetonitrile and methanol of which a temperature is controlled to -20°C to 5°C to prepare a solution; precipitating the crystal in the solution; and separating and drying the precipitated crystal to obtain the 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystal.SELECTED DRAWING: Figure 2

Journal ArticleDOI
TL;DR: Dinuclear Pd(II) halides that contain bridging π-conjugated groups, trans,trans-[(PR3)2(X)Pd-Y-Pd(X)(PR3)-2] (X = Br; YH2 = terpyridine, fluorenone, benzil, benzthiadiazole), were prepared by the ox...
Abstract: Dinuclear Pd(II) halides that contain bridging π-conjugated groups, trans,trans-[(PR3)2(X)Pd–Y–Pd(X)(PR3)2] (X = Br; YH2 = terpyridine, fluorenone, benzil, benzthiadiazole), were prepared by the ox...

01 Jan 2018
TL;DR: In this paper, the microwave assisted Lawesson's reagent mediated one-pot one-step solventless synthesis of 9,9'-bifluorenylidene from two equivalents of fluorenone is described.
Abstract: The ambition of this work is to start a path to the a priori rational design of high yield production for electron acceptors with finely tuned band gaps, from the comfort of an armchair. To this end, organic photovoltaics offer a cheap and sustainable means of manufacture using readily available materials and avoids the toxicity of some of the heavy metals used in first and second-generation solar cells such as cadmium. The microwave assisted Lawesson’s reagent mediated one-pot one-step solventless synthesis takes less than 3 minutes and results in an 84% yield of 9,9’-bifluorenylidene from two equivalents of fluorenone. While fullerenes have traditionally been the most widely used electron acceptors in organic photovoltaics, bifluorenylidenes have been gaining attention due to their superior absorption in the visible spectrum, highly tunable band gap and cheap/efficient synthesis. Using an analog system to study the reaction divided into two parts; intermediate formation and sulfur extrusion, a molecular pathway has been devised that fits the reaction conditions and explains differences in % yields of substituted 9,9’bifluorenylidenes reported in a manner readily conducive to making predictions based on the substituents chosen in the 9-fluorenylidene scaffold.

Patent
28 Dec 2018
TL;DR: In this article, the authors proposed a new catalyst for preparing fluorenone through gas phase oxidation of fluorene, which comprises seven compounds including V2O5, KOH, MnSO4, Fe2(SO4)3, K2SO4 and NH4H2PO4 in the mass ratio being 1:1.5:1:0.03:2.
Abstract: The invention relates to a catalyst used for preparing fluorenone through gas phase oxidation of fluorene. The catalyst comprises seven compounds including V2O5, KOH, MnSO4, Fe2(SO4)3, K2SO4, FeSO4 and NH4H2PO4 in the mass ratio being 1:1.1:0.03:2.5:1:0.05:0.08. The catalyst can make the conversion rate of fluorene reach 99.5% or above in the gas phase oxidation process, has the fluorenone selectivity reaching 98% or above and is low in cost and long in service life.

Patent
07 Sep 2018
TL;DR: The polyimide material is prepared by adopting a high-planarity aromatic diamine containing a fluorene or fluorenone structure and various tetracarboxylic dianhydrides as raw materials.
Abstract: The invention discloses polyimide containing a fluorene or fluorenone structure as well as a preparation method and application of the polyimide The polyimide material is prepared by adopting a high-planarity aromatic diamine containing a fluorene or fluorenone structure and various tetracarboxylic dianhydrides as raw materials, and performing thermal imidization or chemical imidation to preparethe polyimide powdery material or film A lowest energy state structure of the diamine monomer has high planarity and stronger rigidity, and molecular chains of the prepared polyimide are closely packed, so that the prepared polyimide film has excellent barrier properties, higher glass-transition temperature and thermal stability and a lower coefficient of thermal expansion The synthetic method disclosed by the invention has a simple and diverse process and is suitable for industrial production; and the polyimide disclosed by the invention can be widely used in the fields of high and new technology industry such as microelectronics, military industry, aerospace, high-performance packaging and protection, and electronic device packaging

Patent
06 Nov 2018
TL;DR: In this article, the application of fluorenone compounds in dendrobe for preparing a drug for treating diabetes, and particularly providing application of a fluoreone compound shown in a formula IThe compound can be used for a hypoglycemic drug, a hypo-cemic healthcare food or a hypocorrelated food, and can be adopted as the active ingredient and prepared into the drug compound with pharmaceutically acceptable carriers or accessories.
Abstract: The invention provides application of fluorenone compounds in dendrobe for preparing a drug for treating diabetes, and particularly provides application of a fluorenone compound shown in a formula IThe compound can be used for a hypoglycemic drug, a hypoglycemic healthcare food or a hypoglycemic food In the formula I, R1 and R2 are -H or -OH or -OCH3 The fluorenone compound is a natural compound existing in dendrobe and has the high alpha-glucosidase inhibitory activity, and the compound is adopted as the active ingredient and prepared into the hypoglycemic drug or the drug compound with pharmaceutically-acceptable carriers or accessories

Journal ArticleDOI
TL;DR: A butterfly shaped orange-red thermally activated delayed fluorescent (TADF) emitter, named ACFO, was developed by integrating electron-donating (D) 9,9-dimethyl-9,10-dihydroacridine units into γ-positions of an electron-accepting (A) fluorenone core to form a D-A-D configuration as mentioned in this paper.
Abstract: A butterfly shaped orange–red thermally activated delayed fluorescent (TADF) emitter, named ACFO, is developed by integrating electron-donating (D) 9,9-dimethyl-9,10-dihydroacridine units into γ-positions of an electron-accepting (A) fluorenone core to form a D-A-D configuration. ACFO emits intense orange–red light peaking at 600 nm in toluene solution, which is significantly red-shifted compared with its benzophenone-based counterpart. Imparted with a small singlet–triplet splitting energy of 0.13 eV, ACFO exhibits distinct TADF feature with a short delayed fluorescent lifetime of 3.8 μs and displays a moderate photoluminescence quantum yield of 31%. Consequently, employing ACFO as an emitter results in orange–red organic light-emitting diodes that exhibit a maximum external quantum efficiency of nearly 11%, corresponding to a nearly 100% exciton utilization efficiency in electroluminescence process. Our finding demonstrates for the first time that fluorenone derivatives can be employed as TADF emitters for high-efficiency fluorescent organic light-emitting diodes.

Patent
15 Feb 2018
TL;DR: In this article, a mixture of fluorenone and phenoxy ethanol was used to obtain a rough 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystal with a bulk density of 0.60-0.75 g/cm.
Abstract: PROBLEM TO BE SOLVED: To produce 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystal which shows a melting peak by a differential scan calorimetry in a temperature region of 115-125°C and has a bulk density of 0.60-0.75 g/cm.SOLUTION: Fluorenone and phenoxy ethanol are reacted to obtain rough crystal of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene, and the rough crystal is purified to prepare purified crystal of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene having the enhanced degree of purity to at least 99%. The purified crystal is dissolved in a mixed solvent of acetonitrile and methanol of which a temperature is controlled to -20°C to 5°C to prepare a solution, and crystal is precipitated in the solution. When the precipitated crystal is separated and dried, the target 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene crystal is obtained.SELECTED DRAWING: None