- Hole compound, preparation method thereof and organic electroluminescent device
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The invention discloses a hole compound, a preparation method thereof and an organic electroluminescent device, and belongs to the technical field of chemical and organic luminescent materials. The structural general formula of the hole compound is shown in the specificatoin. In the formula, X and Y are independently any one of O, S and N-R3; a ring A is any one of a substituted or unsubstituted (C6-C30) aryl group and a substituted or unsubstituted (3-membered to 10-membered) heteroaryl group; and L1 and L2 are respectively and independently at least one of a connecting bond, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted 3-membered to 30-membered heteroaryl group. The hole injection layer and/or the hole transport layer of the organic electroluminescent device prepared by using the hole compound can improve the luminous efficiency of the device and reduce the driving voltage of the device, so that the durability of the obtained organic electroluminescent device can be enhanced.
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Paragraph 0058; 0060; 0063-0064
(2021/05/19)
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- Aromatic amine derivative and application thereof
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The invention relates to an aromatic amine derivative and an application thereof, belongs to the technical field of semiconductors, and provides a compound with a structure as shown in a general formula (I). The compound provided by the invention has relatively strong hole transmission capability, and improves hole injection and transmission performance under a proper HOMO energy level; under the appropriate LUMO energy level, the electron blocking effect is achieved, and the recombination efficiency of excitons in a light-emitting layer is improved; when the compound is used as a light-emitting functional layer material of an OLED light-emitting device, the utilization rate of excitons and the radiation efficiency can be effectively improved by matching with the branched chains in the range of the material.
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Paragraph 0049-0051
(2021/10/30)
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- A Three-Phase Four-Component Coupling Reaction: Selective Synthesis of o-Chloro Benzoates by KCl, Arynes, CO2, and Chloroalkanes
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A transition-metal-free three-phase four-component coupling reaction (3P-4CR) involving KCl, arynes, chloroalkanes and CO2 has been reported for the first time, enabling the incorporation of both chloro and CO2 into an aryne simultaneously. The reactions for the synthesis of different types of o-chloro benzoates can be selectively modulated by the chloroalkane utilized. The corresponding products can be alternatively transformed for postsynthetic functionalizations conveniently.
- Jiang, Huanfeng,Zhang, Yu,Xiong, Wenfang,Cen, Jinghe,Wang, Lu,Cheng, Ruixiang,Qi, Chaorong,Wu, Wanqing
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supporting information
p. 345 - 349
(2019/01/24)
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- Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent
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Fluorine is probably another favorite hetero-atom for incorporation into small molecules after nitrogen. Among many fluorine-containing groups, trifluoromethyl aryl ethers (ArOCF3) have unique properties in drug design and are difficult to be synthesized, and many different methods were developed to prepare them. A novel one-pot synthesis of o-iodine-aryl trifluoromethyl ethers (ArOCF3I) was described by the reaction of trifluoromethoxylation and iodination with trifluoromethyl aryl sulfonates (TFMS) in this manuscript. The reaction conditions were optimized by screening different solvents, crown ethers, substrates and the ratios and the yields of products were in moderate to high yields (up to 86%).
- Lei, Meng,Miao, Hang,Wang, Xueyuan,Zhang, Wen,Zhu, Chengjian,Lu, Xiaqiang,Shen, Jian,Qin, Yanru,Zhang, Haoyang,Sha, Sijia,Zhu, Yongqiang
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supporting information
p. 1389 - 1392
(2019/04/30)
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- ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
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This invention discloses novel polycyclic heteroaromatic compound core structures. These compounds can be used as hosts for PHOLEDs
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Paragraph 0014
(2018/04/13)
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- Selective and efficient generation of ortho-brominated para-substituted phenols in ACS-grade methanol
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The mono ortho-bromination of phenolic building blocks by NBS has been achieved in short reaction times (15-20 min) using ACS-grade methanol as a solvent. The reactions can be conducted on phenol, naphthol and biphenol substrates, giving yields of >86% on gram scale. Excellent selectivity for the desired mono ortho-brominated products is achieved in the presence of 10 mol % para-TsOH, and the reaction is shown to be tolerant of a range of substituents, including CH3/ F,and NHBoc.
- Georgiev, David,Saes, Bartholomews W.H.,Johnston, Heather J.,Boys, Sarah K.,Healy, Alan,Hulme, Alison N.
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- Multisubstituted benzo[b]furans through a copper- and/or palladium-catalyzed assembly and functionalization process
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Full details as well as the study of the scope, limitations, and further elaboration of a straightforward approach to the synthesis of 2,5,7-trisubstituted benzo[b]furans from 2-bromo- and 2-chloro-6-iodo-4- substituted phenols through a consecutive copper- and/or palladium-catalyzed assembly and functionalization process is described. Functionalization at the C(7) position is carried out by Suzuki-Miyaura cross-coupling, alkynylation, alkenylation, and C-N bond forming reactions. A one-pot protocol for the synthesis of 2,5,7-trisubstituted benzo[b]furans is also reported.
- Arcadi, Antonio,Blesi, Federico,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Marinelli, Fabio
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p. 1857 - 1871
(2013/04/10)
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- A deacetylation-diazotation-coupling sequence: Palladium-catalyzed C-C bond formation with acetanilides as formal leaving groups
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Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki crosscoupling reactions, and a Pd-catalyzed [2+2+1] cycloaddition hav
- Schmidt, Bernd,Berger, Rene
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supporting information
p. 463 - 476
(2013/05/08)
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- Reversible formation of aryloxenium ions from the corresponding quinols under acidic conditions
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Quinols, 1, are products of the hydration of O-aryloxenium ions, 2, and N-arylnitrenium ions, 3, and they are being investigated for medical uses. Under acidic conditions (pH 1-3) kinetics and products of Br- trapping demonstrate that 1a, 4-phenyl-4-hydroxy-2,5-cyclohexadienone, and 1b, 4-p-tolyl-4-hydroxy-2,5-cyclohexadienone, generate the corresponding oxenium ions 2a and 2b, respectively, as steady-state intermediates. Formation and trapping of the oxenium ions occurs in competition with the acid catalyzed dienone-phenol rearrangement. Because oxenium ion formation is reversible, the ion can only be detected by trapping with a nucleophile. Br- is an efficient trap under acidic conditions because, unlike N3 -, it is not protonated under those conditions. Attempts to detect the oxenium ions 2a and 2b at pH 4.6 and 7.1 with N3- were unsuccessful indicating that oxenium ion formation only occurs under acidic conditions. The oxenium ion 2c could not be detected under acidic conditions from the quinol 1c, 4-(benzothiazol-2-yl)-4-hydroxy-2,5-cyclohexadienone, by Br- trapping methods, even though this ion can be detected during hydrolysis of the corresponding ester, 4c. Although the benzothiazol-2-yl group is a resonance electron donor that is capable of stabilizing an O-aryloxenium ion, it is also a strong inductive electron withdrawing group that hinders the formation of 2c from 1c by decreasing the extent of protonation of 1c to generate 1cH+ and by destabilizing the transition state for ionization of 1cH+. Generation of an oxenium ion from the corresponding quinol is feasible under acidic conditions as long as the 4-substituent of the quinol is both a resonance and inductive electron donor. Copyright
- Chakraborty, Mrinal,Brzozowski, Christopher F.,Novak, Michael
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p. 1236 - 1242
(2013/08/24)
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- 2,5,7-Trisubstituted benzo[b]furans through a copper- and/or palladium-catalyzed assembly and functionalization process
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A straightforward approach to the synthesis of 2,5,7-trisubstituted benzo[b]furans from 2-bromo- and 2-chloro-6-iodo-4-substituted phenols through a consecutive copper- and/or palladium-catalyzed assembly and functionalization process is described. Functionalization at the C(7) position is carried out by Suzuki-Miyaura cross-coupling and C-N bond forming reactions.
- Arcadi, Antonio,Blesi, Federico,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella
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scheme or table
p. 5149 - 5152
(2011/10/12)
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- Suzuki-Miyaura cross coupling reactions with Phenoldiazonium salts
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The Suzuki-Miyaura coupling of phenol diazonium salts and aryl trifluoroborates yields 4-hydroxybiaryls in a protecting group-free synthesis. The Royal Society of Chemistry 2011.
- Schmidt, Bernd,Hoelter, Frank
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supporting information; experimental part
p. 4914 - 4920
(2011/08/06)
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- Synthesis of new type of macrocyclic lactones functionalized with different groups and investigation of their metal binding abilities
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New type of macrocyclic lactones functionalized with different groups were synthesized by reaction of the dihydroxy compounds such as 5a-d with suitable glycolyl chloride such as tri, tetra dicarboxylic acid dichloride derivatives. Their metal complexes with NaClO4.H2O, KCIO4 and Ba(ClO4)2.H2O were studied. Furthermore, their metal-pic-rate extraction studies with metal salts such as Na+, K+, Cu2+, Ni2+ and Hg2+ from aqueous phase to organic phase were attempted. All the structures of the ligands and complexes were confirmed by1H-, 13C-NMR, IR, UV-Vis, MS and elemental analyses methods.
- Ertul,Bayrakci
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experimental part
p. 493 - 502
(2009/10/09)
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- Synthesis of new macrocyclic lactones and their extraction study
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New macrocyclic lactones were synthesized by reaction of 3-bromo-5-(5-tert-butyl-2-hydroxybenzyl)biphenyl-4-ol with appropriate polyethylene glycol-based dicarboxylic acid dichlorides, and their complexes with Mg(ClO4)2·6H2O, Pb(SCN) 2, NaClO4·H2O, and KClO4 were prepared. The macrocyclic ligands were evaluated as extractants in the transfer of Li+, Na+, K+, Cu2+, Ni 2+, and Hg2+ picrates from aqueous to organic phase.
- Bayrakci,Ertul
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experimental part
p. 1384 - 1388
(2009/09/06)
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- The hydrolysis of 4-acyloxy-4-substituted-2,5-cyclohexadienones: Limitations of aryloxenium ion chemistry
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The title compounds serve as potential precursors to aryloxenium ions, often proposed, but primarily uncharacterized intermediates in phenol oxidations. The uncatalyzed and acid-catalyzed decomposition of 4-acetoxy-4-phenyl-2,5-cyclohexadienone, 2a, generates the quinol, 3a. 18O-Labeling studies performed in 16O-H2O, and monitored by LC/MS and1 13C NMR spectroscopy that can detect 18O-induced chemical shifts on 13C resonances, show that 3a was generated in both the uncatalyzed and acid-catalyzed reactions by C alkyl-O bond cleavage consistent with formation of an aryloxenium ion. Trapping with N3- and Br- confirms that both uncatalyzed and acid-catalyzed decompositions occur by rate-limiting ionization to form the 4-biphenylyloxenium ion, 1a. This ion has a shorter lifetime in H2O than the corresponding nitrenium ion, 7a (12 ns for 1a, 300 ns for 7a at 30 °C). Similar analyses of the product, 3b, of acid- and base-catalyzed decomposition of 4-acetoxy-4-methyl-2,5-cyclohexadienone, 2b, in 18O-H2O show that these reactions are ester hydrolyses that proceed by Cacyl-O bond cleavage processes not involving the p-tolyloxenium ion, 1b. Uncatalyzed decomposition of the more reactive 4-dichloroacetoxy-4-methyl-2,5-cyclohexadienone, 2b′, is also an ester hydrolysis, but 2b′ undergoes a kinetically second-order reaction with N3- that generates an oxenium ion-like substitution product by an apparent SN2′ mechanism. Estimates based on the lifetimes of 1a, 7a, and the p-tolylnitrenium ion, 7b, and the calculated relative stabilities of these ions toward hydration indicate that the aqueous solution lifetime of 1b is ca. 3-5 ps. Simple 4-alkyl substituted aryloxenium ions are apparently not stable enough in aqueous solution to be competitively trapped by nonsolvent nucleophiles.
- Novak, Michael,Glover, Stephen A.
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p. 8090 - 8097
(2007/10/03)
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- 1,3,5-Tris[(2-hydroxy-3,5-diphenyl)phenyl]benzene and its phenoxyl radicals
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The title compound 4 was synthesized, starting from 4-hydroxybiphenyl (6), in a search for organic ferromagnets. Electrochemical and chemical oxidation of 4 resulted in a dark green, insoluble solid with the properties of a monoradical rather than the expected trisradical 4a.
- Deckert-Gaudig, Tanja,Huenig, Siegfried,Dormann, Elmar,Kelemen, Marc Tibor
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p. 1563 - 1567
(2007/10/03)
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- The Synthesis of 5-Substituted 2,3-Dihydrobenzofurans
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The preparation of 2,3-dihydrobenzofurans 6 from 2-(2-bromophenoxy)ethyl chlorides 3 by reaction with magnesium in a development of the Parham cyclialkylation reaction is described.A high yielding procedure using phase-transfer catalysis has also been developed for the preparation of the intermediate chloroethyl ethers 3 from bromophenols 2.The 5-hydroxy derivative 15 may be obtained from 2,3-dihydrobenzofuran (6a) by reaction with electrophilic reagents followed by oxidation.
- Alabaster, Ramon J.,Cottrell, Ian F.,Marley, Hugh,Wright, Stanley H. B.
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p. 950 - 952
(2007/10/02)
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- Calixarenes. 7. p-Phenycalixarene
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p-Phenylcalixarene (11), in the cone conformation, is a basket-shaped compound containing a large cavity and, therefore, is of interest for studies of host-guest complexation.Its unequivocal synthesis has been achieved by the stepwise method of Hayes and Hunter, by starting with 2-bromo-4-phenylphenol and adding methylene and p-phenylphenol groups sequentially until a linear tetramer (9) is attained.Removal of the bromine followed by acid-catalyzed cyclization yields the calixarene 11, along with two other materials that are presumed to be the isomeric macrocyclic compounds 12 and 13. p-Phenylcalixarene synthesized in this fashion is different from the compound reported by Zinke from the condensation of p-phenylphenol and formaldehyde in the presence of base, and it appears that 11 is not a major product, and perhaps not even a minor product, of that reaction mixture.
- Gutsche, C. David,No, Kwang Hyun
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p. 2708 - 2712
(2007/10/02)
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