82-05-3Relevant articles and documents
Synthesis and Characterization of Polysubstituted Dibenzopyrenes as Charge-Transporting Materials
Kumar, Sushil,Ho, Man-Tzu,Tao, Yu-Tai
, p. 4876 - 4879 (2016)
A new class of benzopyrene-based semiconducting molecules is prepared and characterized. A four-step protocol involving Suzuki coupling and aromatic dehydrogenation reactions renders the new unsymmetrical framework. Introduction of various substituents at the dibenzopyrene framework modulates mainly the optoelectronic properties rather than the packing motif. Single-crystal field-effect transistors fabricated from these materials show a mobility ranging from 0.7 to 3.2 cm2/(V s). The highest mobility, 3.2 cm2/(V s), with an on/off ratio of 104-105 was achieved for 11-methoxy-8-(4-methoxyphenyl)dibenzo[a,e]pyrene.
Novel production method of phenanthrone (by machine translation)
-
Paragraph 0031-0043, (2020/01/25)
The invention relates to the field of, fine chemical engineering, in particular to a, preparation method of phenanthrapyone: and, specifically, relates, to a method for preparing phenylanthrone, in particular, to H the following steps of: transferring a catalyst and a solvent to a pressure reaction kettle through a catalyst and a solvent in an anthraquinone process. 2 After the reaction completion of the reaction was; completed, the reaction solution was, cooled and the reaction solution, was left to H leave the remainder. 2 Compared with the prior, art, the method, disclosed by the invention has second the advantages; that the raw material recycling rate is; high second the process is, easy to control, the cost is; low, and the product quality, is obviously improved . (by machine translation)
Compound with anthrene structure and application of compound in organic light emitting diode devices
-
Paragraph 0065-0067; 0078, (2020/03/16)
The invention discloses a compound with an anthrene structure and application of the compound, and belongs to the technical field of semiconductors. The structure of the compound is represented by a formula (1) as shown in the description. The invention further discloses the application of the compound. The compound takes anthrene as a core and has high carrier mobility and good carrier equilibrium capability. Meanwhile, the compound has relatively high glass transition temperature, high molecular thermal stability and suitable HOMO and LUMO energy levels. The compound serves as a main body material of a luminescent layer and can generate a triplet-triplet coupling effect, and thus a utilization rate of triplet states is effectively increased. By adopting device structures based on the compound, the efficiency of OLED devices can be effectively improved, and the service lives of the OLED devices can be effectively prolonged.
Benzanthrone derivative and preparation method thereof and application thereof in functional pigments
-
, (2020/07/24)
The invention discloses a benzanthrone derivative and a preparation method thereof. The general formula is shown as a formula I or IV, formula I or IV, R1, R2, R3 is independently selected from hydrogen, halogen, an ester group, an acyl group, a branched-chain or straight-chain C1-C20 alkyl group, a straight-chain or branched-chain C1-C20 alkoxy group, a branched-chain or straight-chain perfluoroC1-C20 alkyl group, a branched-chain or straight-chain perfluoroC1-C20 alkoxy group, a substituted or unsubstituted C4-C40 aryl group, and a substituted or unsubstituted C4-C40 heteroaryl group. The benzanthrone derivative with a novel structure provided by the invention is simple in preparation method, non-toxic and harmless, has yellow fluorescence, can be used as a potential organic functional material, and is an important dye intermediate.
Palladium-Catalyzed Site-Selective Benzocyclization of Naphthoic Acids with Diaryliodonium Salts: Efficient Access to Benzanthrones
Xue, Chenwei,Wang, Limin,Han, Jianwei
, p. 15406 - 15414 (2020/12/23)
Dual activation of both C-I and vicinal C-H bonds of diaryliodonium salts allowing for diarylation is a subject of rapid construction of π-extended frameworks. Here, we report palladium-catalyzed cascade of C8-arylation/intramolecular Friedel-Crafts acylation of α-naphthoic acids in the synthesis of benzanthrone derivatives. The step-economical protocol tolerates various substrates, which resulted in a potential molecular library for developing functional polycyclic scaffolds. The approach relies on the synergistic action of strong acid with palladium catalysts to form two bonds in a one-pot procedure.
The linkage between reversible Friedel–Crafts acyl rearrangements and the Scholl reaction
Agranat, Israel,Oded, Yaacov Netanel,Mala’bi, Tahani,Pogodin, Sergey,Cohen, Shmuel
, p. 1579 - 1610 (2019/07/29)
Friedel–Crafts acyl rearrangements in PPA (at 80–240?°C) and Scholl reactions in AlCl3/NaCl (at 140–220?°C) of benzoylnaphthalenes and fluorobenzoylnaphthalenes have been studied experimentally as a function of temperature and time and computationally. 1BzNA, 2BzNA, 1-4FBzNA, 2-4FBzNA, 1-3FBzNA, 2-3FBzNA, 1-2FBzNA, and 2-2FBzNA were synthesized by classical Friedel–Crafts acylations of naphthalene with benzoyl chloride, benzene with 2-naphthoyl chloride,?fluorobenzene with 1- and 2-naphthoyl chlorides and of naphthalene with fluorobenzoyl chlorides, and served as substrates in the investigation. Their structures have been determined by X-ray crystallography and verified by their 1H-, 13C-, and 19F-NMR spectra. 1BzNA, 1-4FBzNA, 1-3FBzNA, and 2-2FBzNA crystallized as the E-diastereomers, whereas 2BzAN, 1-2FBzAN, 2-4FBzAN, and 2-3FBzAN crystallized as the Z-diastereomers. The deviations of the carbonyl group from the naphthyl plane were higher as compared with the deviations from the phenyl plane and were considerably higher in the α-naphthyl ketones than in the β-naphthyl ketones. Intermolecular interactions due to C–H···O and/or C–H···F contacts in the crystal structures of 1E-4FBzNA and 1E1′E-3FBzAN have been revealed. 1BzNA rearranged in PPA under argon to 2BzNA via deacylation to naphthalene (e.g., 140?°C, 10?h) and underwent a regioselective intramolecular cyclodehydrogenation at high temperatures to the Scholl reaction product 7H-benz[de]anthracen-7-one (BdeAN) (e.g., 200?°C, 6?h). At 80?°C, benzene was isolated. 2BzNA underwent in PPA deacylation to naphthalene (e.g., 160?°C, 6?h) and an intramolecular cyclodehydrogenation to BdeAN at high temperatures (e.g., 220?°C, 6?h), necessarily via the putative intermediate 1BzNA. Higher yields of the acyl rearrangement and the Scholl reaction products were obtained under oxygen. 1-4FBzNA and 2-4FBzNA reacted in PPA analogously to 1BzNA and 2BzNA, respectively, with the following exceptions: 2-4FBzNA underwent an acyl rearrangement in PPA to 1-4FBzNA at 260–300?°C, without any formation of the Scholl reaction product 10FBdeAN. 1-4FBzNA also did not yield 10FBdeAN. 1-2FBzNA and 2-2FBzNA behaved similarly. The formation of naphthalene and benzene in the deacylation steps indicated cleavages of both the 1- and 2-naphthyl–benzoyl bonds and the 1- and 2-naphthoyl–phenyl bonds to give naphthalene and benzoylium cation and benzene and 1- and 2-naphthoylium cation, respectively. At 80–100?°C, 1-2FBzNA, 1-3FBzNA, and 1-4FBzNA underwent deacylations to fluorobenzene in PPA, followed by reacylation, each giving a mixture of the three 1-fluorobenzoylnaphthalenes. 2FBzNA, 2-3FBzNA, and 2-4FBzNA behaved similarly, each giving a mixture of the three 2-fluorobenzoylnaphthalenes. The results taken together verified the reversibility of the 1-BzNA?2BzNA acyl rearrangements in PPA. The Scholl reaction (AlCl3/NaCl) of 1BzNA (e.g., at 140?°C) gave BdeAN and 2BzNA, whereas 2BzNA gave only BdeAN (at 200–220?°C). 1-4FBzNA and 2-4FBzNA gave (at 200–220?°C) only 2-4FBzNA and 1-4FBzNA, respectively. All the six FBzNA isomers failed to undergo Scholl reaction cyclodehydrogenations to give any FBdeAN isomer. A linkage between the Friedel–Crafts acyl rearrangements and the Scholl reaction has thus been established. A systematic DFT study at B3LYP/6-311(d,p)/PCM (formic acid)) substantiated the predicted mechanism and the reversibility of the acyl rearrangements of benzoylnaphthalenes, in which 1BzNA and 2BzNA are the kinetically controlled and the thermodynamically controlled products, respectively. The DFT-calculated Gibbs free-energy of the transition-state (1Z-1BzNH+ ?? 2σ-2BzNA) in the Friedel–Crafts acyl rearrangement of 1Z-BzNA is considerably lower than the transition state of the cyclization step in the arenium-cation mechanism of the Scholl reaction, in line with experiment, which indicated higher temperatures for the Scholl reaction. DFT calculations of the dication pathway of the Scholl reaction of the E- and Z-diastereomers/conformers of 1BzNA confirmed the preference of the formation of BdeAN versus BaFL, consistently with experiment.
One-Pot Catalytic Cleavage of C=S Double Bonds by Pd Catalysts at Room Temperature
Zhu, Ting,Wu, Xiaoxi,Yang, Xinzheng,Sharma, Bigyan,Li, Na,Huang, Jiaming,Wang, Wentao,Xing, Wang,Zhao, Zhenwen,Huang, Hui
supporting information, p. 9266 - 9273 (2018/08/17)
The C=S double bonds in CS2 and thioketones were catalytically cleaved by Pd dimeric complexes [(N∧N)2Pd2(NO3)2](NO3)2 (N∧N, 2,2′-bipyridine, 4,4′-dimethylbipyridine or 4,4′-bis(trifluoromethyl)) at room temperature in one pot to afford CO2 and ketones, respectively, for the first time. The mechanisms were fully investigated by kinetic NMR, isotope-labeled experiments, in situ ESI-MS, and DFT calculations. The reaction is involved a hydrolytic desulfurization process to generate C=O double bonds and a trinuclear cluster, which plays a pivotal role in the catalytic cycle to regenerate the dimeric catalysts with HNO3. Furthermore, the electronic properties of catalyst ligands possess significant influence on reaction rates and kinetic parameters. At the same temperature, the reaction rate is consistent with the order of electronegativity of N∧N ligands (4,4′-bis(trifluoromethyl) > 2,2′-bipyridine > 4,4′-dimethylbipyridine). This homogeneous catalytic reaction features mild conditions, a broad substrate scope, and operational simplicity, affording insight into the mechanism of catalytic activation of carbon sulfur bonds.
Aluminum oxide mediated C-F bond activation in trifluoromethylated arenes
Papaianina,Amsharov
supporting information, p. 1505 - 1508 (2016/01/25)
Thermally activated γ-aluminium oxide was found to be very effective for C-F bond activation in trifluoromethylated arenes. Depending on the activation degree the respective arenes can be converted either to cyclic ketones or to the respective carboxylic acids with good to excellent yields.
Chelation-assisted Pd-catalysed ortho-selective oxidative C-H/C-H cross-coupling of aromatic carboxylic acids with arenes and intramolecular Friedel-Crafts acylation: One-pot formation of fluorenones
Sun, Denan,Li, Bijin,Lan, Jingbo,Huang, Quan,You, Jingsong
supporting information, p. 3635 - 3638 (2016/03/05)
Pd-Catalysed ortho-selective oxidative C-H/C-H cross-coupling of aromatic carboxylic acids with arenes and subsequent intramolecular Friedel-Crafts acylation has been accomplished for the first time through a chelation-assisted C-H activation strategy. Starting from the readily available substrates, a variety of fluorenone derivatives are obtained in one pot. The direct use of naturally occurring carboxylic acid functionalities as directing groups avoids unnecessary steps for installation and removal of an extra directing group.
PhI(OAc)2-BF3-OEt2mediated domino imine activation, intramolecular C-C bond formation and β-elimination: New approach for the synthesis of fluorenones, xanthones and phenanthridines
Sarkar, Satinath,Tadigoppula, Narender
, p. 40964 - 40968 (2015/02/05)
PhI(OAc)2-BF3-OEt2mediated domino synthesis of biologically important fluorenones, xanthones and phenanthridines has been developed. The reaction proceeds through imine activation, intramolecular C-C bond formation and β-elimination. This journal is
