- Phenothiazine and carbazole substituted pyrene based electroluminescent organic semiconductors for OLED devices
-
Due to their easy availability, low cost and opportunities for exploiting reactions of bromo substituents, 1,3,6,8-tetrabromopyrene has attracted major attention in the organic electronics community for designing and constructing novel classes of pyrene b
- Salunke, Jagadish K.,Wong,Feron, Krishna,Manzhos, Sergei,Lo, Ming Fai,Shinde, Durgaprasad,Patil, Abhijeet,Lee,Roy,Sonar, Prashant,Wadgaonkar, Prakash P.
-
-
Read Online
- Constructing host-σ-guest structures to optimize the efficiency of non-doped solution-processed OLEDs
-
Two novel host-σ-guest emitters based on a blue emissive thermally activated delayed fluorescence (TADF) unit were designed and synthesized. By grafting 4TCzBN onto common host materials, these neat films (4TCzBN-o-PhCz and 4TCzBN-o-mCP) emit strong fluor
- Liu, Dan,Zhang, Meng,Chen, Haowen,Ma, Daiyu,Tian, Wenwen,Sun, Kaiyong,Jiang, Wei,Sun, Yueming
-
-
Read Online
- Impact of alkoxy chain length on carbazole-based, visible light-driven, dye sensitized photocatalytic hydrogen production
-
Alkoxyphenyl-substituted carbazole-based metal-free organic dyes were synthesized and effectively used for dye-sensitized, visible-light-driven, photocatalytic hydrogen production. Photocatalytic hydrogen production was investigated using a TiO2/dye/Pt structure with triethanolamine as the sacrificial reagent. The dye-loaded TiO2 photocatalyst exhibited a high yield of hydrogen production when the length of the alkoxy chain was long enough to sufficiently improve the hydrophobicity at the interface between the dye-loaded TiO2 and the water medium. In the alkoxyphenyl-substituted carbazole dyes, the dye with the longest alkoxy chain (C22) exhibited the best hydrogen production performance, but it had a yield only slightly better than that of the dye with the second longest chain length (C16). The dye C22 displayed a turnover number (TON) of 3094 after 24 h of visible light irradiation (>420 nm). However, the compound with no hydrophobic substituent (C1), exhibited the lowest hydrogen production performance with a TON of 1497. Thus, a 207% increase in the hydrogen production yield was observed when hydrophobic substituents were present. Analysis of time-resolved absorption spectra, impedance spectra and incident photon conversion efficiency spectra revealed that the alkoxy chain has a hydrophobic effect at the interface between the dye-loaded TiO2 and the water. Specifically, the hydrophobicity of the dye improved the charge-recombination lifetime for electron injection from the dye into the TiO2 surface in the water for hydrogen production.
- Watanabe, Motonori,Hagiwara, Hidehisa,Ogata, Yudai,Staykov, Aleksandar,Bishop, Sean R.,Perry, Nicola H.,Chang, Yuan Jay,Ida, Shintaro,Tanaka, Keiji,Ishihara, Tatsumi
-
-
Read Online
- Highly Efficient Tuning of Ferromagnetic Spin Interactions in High-Spin Arylamine Structures by Incorporation of Spin Bearing Carbazole Units
-
Arylamine moieties oxidized to radical cations are considered promising spin bearing units in high-spin-type compounds. Here, we report the first use of carbazole-3,6-diamine units as efficient, rigid spin containing units. The use of rigid spin bearing u
- Skórka, ?ukasz,Maurel, Vincent,Gosk, Jacek B.,Pu?niak, Roman,Mouesca, Jean-Marie,Kulszewicz-Bajer, Irena
-
-
Read Online
- Red emitting coumarin based 4, 6-disubstituted-3-cyano-2-pyridones dyes – Synthesis, solvatochromism, linear and non-linear optical properties
-
New coumarin fluorescent based D-π-A-π-D dyes are synthesized and studied for their optical properties. Their show absorption and emission respectively are in the range of 471–504 nm and 506–550 nm. Viscosity induced emission intensity increase is examined with 0–100% PEG-400 in ethanol MLK 4 is good FMR as compared to the MLK 1–3 due to the presence of extra-π-conjugation. FMO analysis and Generalized Mulliken Hush analysis show a strong interaction of molecular charge transfer characteristics. The first (α), second (β) and third (γ) order polarizability of MLK 1–4 are calculated by the solvatochromic technique and corroborated by DFT calculations using CAM-B3LYP/6-31G(d) method. The outcomes found by solvatochromic technique are compared theoretically with DFT using B3LYP/6-31G(d) and CAM-B3LYP/6-31G(d) methods. These methods reveal that, CAM-B3LYP/6-31G(d) carry out for calculating α β γ. Photophysical data was also applied to establish the ground and excited state dipole moment ratio using Bakhshiev, Bilot-Kawski, and Liptay functions. Liptay function shows better correlations than the other two functions for all dyes.
- Kadam, Mayuri M.L.,Patil, Dinesh S.,Sekar, Nagaiyan
-
-
Read Online
- Microenvironment modulation of cuprous cluster enables inert aryl chlorides activation in single-molecule metallaphotoredox amination
-
Amination of aryl halides is an important tool in organic synthesis and the activation of inert aryl chlorides is particular difficult. We herein report the first study of aromatic microenvironment modulation of cuprous clusters as single-molecule metalla
- Ji, Wei,Jing, Su,Li, Ai-Min,Qi, Zheng-Hang,Qiu, Wen-Jie,Zha, Guo-Jin,Zhu, Dun-Ru
-
p. 313 - 321
(2022/01/03)
-
- Transition-metal free synthesis of: N -aryl carbazoles and their extended analogs
-
Herein, we describe a facile synthesis of N-arylated carbazoles via ladderization of fluorinated oligophenylenes. The reaction consists of two subsequent nucleophilic substitutions triggered by an electronic transfer from dimsyl anions. The reaction allows the effective one-pot formation of at least six C-N bonds with pronounced selectivity to the C-F bond placement.
- Akhmetov, Vladimir,Amsharov, Konstantin,Feofanov, Mikhail,Takayama, Ryo
-
supporting information
p. 7172 - 7175
(2021/08/30)
-
- Metal-organic frameworks derived CuONPs@C nanocatalysts for synthesizing optoelectronic triarylamine molecules
-
Carbon encapsulated copper oxide nanoparticles (CuONPs@C) fabricated using copper metal organic frameworks (Cu-MOFs) used as reusable nanocatalysts in Ullmann C[sbnd]N coupling reactions for synthesizing optoelectronic triphenylamine (TPA) and carbazole (CBZ) derivatives. The formation of CuONPs in carbon matrix was confirmed by powder X-ray diffraction (PXRD), X-ray photoelectron spectroscopy (XPS) and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of CuONPs@C was performed with diphenylamine/carbazole with substituted aryl halides in presence of mild K2CO3 base that produced triarylamines with 63–83% yields. Carbazole triarylamines exhibited strong solid state fluorescence (Φf = 14.54–36.32%) with λmax between 370 and 420 nm.
- Kundu, Anu,Kumar, Vadivel Vinod,Anthony, Savarimuthu Philip
-
-
- Synthesis of carbazole-based small organic molecule hole transport material and application of carbazole-based small organic molecule hole transport material in perovskite solar cell
-
The invention belongs to the field of perovskite solar cell materials, and discloses a carbazole-based small organic molecule hole transport material. According to the carbazole-based small organic molecule hole transport material, a carbazole intermediate core group fragment is synthesized by utilizing a low-temperature reaction and a bromination reaction; a target product OY1, a target product OY2 and a target product OY3 are obtained by means of synthesis from the carbazole intermediate core group fragment and peripheral triphenylamine micromolecules through an acylation reaction and a coupling reaction; the structures of the target product OY1, the target product OY2 and the target product OY3 are confirmed through a high-resolution mass spectrum characterization means, and the target product OY1, the target product OY2 and the target product OY3 are applied to a perovskite solar cell; the synthesized compound is subjected to photophysic, electrochemical, intrinsic hole mobility and thin film characteristic tests, and in addition, the photovoltaic performance of the perovskite solar cell is represented through tests of output current-voltage, incident monochromatic photon-electron conversion efficiency, long-term stability and the like of the cell device. Due to low cost, easy chemical synthesis and excellent performance, the carbazole-based small organic molecule hole transport material will become a powerful competitor.
- -
-
Paragraph 0024; 0038-0041
(2021/07/31)
-
- Synthesis of hole transport material based on diphenylamine substituted carbazole fluorene hybridization and application of hole transport material in perovskite solar cell
-
The invention relates to the field of hole transport materials in perovskite solar cells, and particularly discloses a hole transport material based on diphenylamine substituted carbazole/fluorene hybridization. Three HTMs (F1A, F2A and F3A) based on carbazole/fluorene hybridization are designed and synthesized through a Friedel-Crafts reaction and a Buchwald-Hartwisting coupling reaction. A peripheral diphenylamine substituted fluorene derivative with relatively strong electron donating ability is introduced into a core group molecule as an end-capping group, so that the spatial confusion degree of the whole molecular structure is improved, the plane conjugacy of the molecular structure is destroyed, and the aggregation phenomenon of HTMs in a solution is reduced, thereby obtaining a relatively excellent film. The film is applied to a perovskite solar cell. The invention relates to the field of hole transport materials of perovskite solar cells. The film has great commercial prospects in the aspects of improving the efficiency and the stability of the perovskite solar cells, reducing the cost of the perovskite solar cells and the like.
- -
-
Paragraph 0025; 0034; 0039-0041
(2021/08/21)
-
- TRIARYL PHOSPHINE LIGANDS, PREPARATION METHOD THEREFOR, AND USE IN CATALYSING COUPLING REACTIONS
-
Provided are triaryl phosphine ligands, as shown in general formulae Ia and Ib, or a mixture thereof, and a preparation method therefor. The invention addresses the deficiencies of biaryl phosphine ligands invented by Buchwald et al. Also provided are a triaryl phosphine coordinated palladium complex, a system composed of triaryl phosphine ligand and a palladium salt or complex, and a use of the triaryl phosphine coordinated palladium complex in catalysing organic reactions, in particular a use in catalysis of coupling reactions involving (pseudo)halogenated aromatic hydrocarbon as substrate.
- -
-
Paragraph 0265
(2021/05/21)
-
- Method for synthesizing carbazole derivative
-
The invention aims to provide a method for synthesizing a carbazole derivative. The method is characterized in that palladium chloride is used as a catalyst, 2, 2' - dibromobiphenyl is used as an electrophilic reagent, primary amine is taken as a nucleophile, and the carbazole derivative is directly cross-coupled under the conditions of toluene as a solvent and an air atmosphere. The method has the advantages of high yield, high selectivity, simplicity and convenience in operation and the like.
- -
-
Paragraph 0013; 0022-0023
(2021/10/05)
-
- Efficient Copper-Catalysed Synthesis of Carbazoles by Double N -Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air
-
An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C-N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.
- Do, Ha Nam,Quan, Nguyen Minh,Van Phuc, Ban,Van Tinh, Dinh,Tien, Nguyen Quyet,Nga, Truong Thi Thanh,Nguyen, Van Tuyen,Hung, Tran Quang,Dang, Tuan Thanh,Langer, Peter
-
supporting information
p. 611 - 615
(2021/01/21)
-
- Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives
-
A simple and cost-effective protocol for the C–N cross coupling of indole derivatives with aryl iodides using CuI/phenanthroline catalytic system in aqueous and DME/H2O solvent mixture is described. The reactions were performed in the absence of phase-transfer catalyst, and afforded N-arylated products in moderate to excellent yields under mild reaction conditions. A systematic tuning of reaction conditions using DME as a co-solvent enables to improve product yields of N-arylation reactions. The broad substrate scope, easy performance, and low loading of catalyst as well as ligand render this approach appropriate for large scale processes. The mechanism of “on water” Cu-catalyzed N-arylation reaction is investigated using kinetic and computational studies, which reveal interesting mechanistic aspects of the reaction. A series of kinetic experiments showed significant rate enhancement for “on water” Cu-catalyzed N-arylation over the reaction performed in the organic solvent (DME). Computational studies corroborated “on water” rate acceleration by delineating the role of water in the reaction. The water induces rate acceleration by stabilizing the transition state of oxidative addition through hydrogen bonding interactions, presumably at the oil-water interface, and thus helps to reduce the free energy of activation of oxidative addition of iodobenzene to the Cu complex, which is identified as the rate-limiting step of reaction.
- Malavade, Vrunda,Patil, Manish,Patil, Mahendra
-
supporting information
p. 561 - 569
(2020/02/05)
-
- CARBAZOLE OXIME ESTER DERIVATIVE COMPOUND, AND PHOTOPOLYMERIZATION INITIATOR AND PHOTOSENSITIVE COMPOSITION CONTAINING THE SAME
-
PROBLEM TO BE SOLVED: To provide a carbazole oxime ester derivative compound having excellent sensitivity, heat resistance, chemical resistance and curability, and a photopolymerization initiator and a photosensitive composition containing the same. SOLUT
- -
-
Paragraph 0093; 0094; 0095-0097
(2019/07/16)
-
- PHOSPHINE COMPOUND AND CATALYST FOR COUPLING CONTAINING THE SAME AS LIGAND
-
PROBLEM TO BE SOLVED: To provide a phosphine ligand providing good yield and selectivity in manufacturing 9-aryl-9H-carbazole using a palladium catalyst. SOLUTION: A palladium catalyst consisting of a palladium compound and a phosphine compound represented by the general formula (1), wherein Ar represents a methyl group, an ethyl group, or a pyrenyl group which may be substituted by a linear or branched alkyl group having 3 to 4 carbon atoms. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPO&INPIT
- -
-
Paragraph 0280-0035; 0041
(2019/03/23)
-
- Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides
-
The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.
- -
-
Page/Page column 116
(2020/01/09)
-
- "on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols
-
The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.
- Chakraborti, Gargi,Paladhi, Sushovan,Mandal, Tirtha,Dash, Jyotirmayee
-
p. 7347 - 7359
(2018/07/29)
-
- A waste-minimized protocol for copper-catalyzed Ullmann-type reaction in a biomass derived furfuryl alcohol/water azeotrope
-
We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines. Furfuryl alcohol (FA) can be mixed with water to form the corresponding azeotrope (20 wt% of FA) and therefore can be easily recovered and reused. This protocol is efficiently applied to substrates with various electronic nature and affords the expected products (27 examples) in generally good to excellent yields. It has also been demonstrated that the protocol is both chemically and environmentally effective as the azeotropic mixture can be easily and almost quantitatively recovered at the end of the process.
- Ferlin, Francesco,Trombettoni, Valeria,Luciani, Lorenzo,Fusi, Soliver,Piermatti, Oriana,Santoro, Stefano,Vaccaro, Luigi
-
supporting information
p. 1634 - 1639
(2018/04/12)
-
- Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
-
A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.
- Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua
-
p. 5578 - 5582
(2018/09/25)
-
- Design, synthesis and biological evaluation of: N -arylsulfonyl carbazoles as novel anticancer agents
-
In this work, a set of structurally diverse synthetic carbazoles was screened for their anticancer activities. According to structure-activity relationship studies, carbazoles with an N-substituted sulfonyl group exhibited better anticancer activity. Moreover, compound 8h was discovered to show the most potent anticancer effects on Capan-2 cells by inducing apoptosis and cell cycle arrest in G2/M phase. Finally, the in vivo study demonstrated that 8h prevented the tumor growth in PANC-1 and Capan-2 xenograft models without apparent toxicity.
- You, Xin,Zhu, Daqian,Lu, Wenhua,Sun, Yichen,Qiao, Shuang,Luo, Bingling,Du, Yongliang,Pi, Rongbiao,Hu, Yumin,Huang, Peng,Wen, Shijun
-
p. 17183 - 17190
(2018/05/28)
-
- Dendron engineering in self-host blue iridium dendrimers towards low-voltage-driving and power-efficient nondoped electrophosphorescent devices
-
Dendron engineering in self-host blue Ir dendrimers is reported to develop power-efficient nondoped electrophosphorescent devices for the first time, which can be operated at low voltage close to the theoretical limit (Eg/e: corresponding to the optical bandgap divided by the electron charge). With increasing dendron's HOMO energy levels from B-POCz to B-CzCz and B-CzTA, effective hole injection is favored to promote exciton formation, resulting in a significant reduction of driving voltage and improvement of power efficiency. Consequently, the nondoped device of B-CzTA achieves extremely low driving voltages of 2.7/3.4/4.4 V and record high power efficiencies of 30.3/24.4/16.3 lm W?1 at 1, 100 and 1000 cd m?2, respectively. We believe that this work will pave the way to the design of novel power-efficient self-host blue phosphorescent dendrimers used for energy-saving displays and solid-state lightings.
- Wang, Yang,Wang, Shumeng,Ding, Junqiao,Wang, Lixiang,Jing, Xiabin,Wang, Fosong
-
supporting information
p. 180 - 183
(2016/12/27)
-
- Nickel-Catalyzed N-Arylation Using N -Trimethylsilyl-carbazole
-
Nickel-catalyzed N-arylation reaction of N -trimethylsilyl-carbazole using aryl bromides is found to proceed in the presence of sodium acetate, giving N -aryl-carbazoles in high yields. Under these conditions, N -trimethylsilyl-carbazole could react with aryl bromides selectively even in the presence of other N -trimethylsilyl-amines or N -H-amines. This arylation reaction was applied to the polymerization to provide a polycarbazole.
- Minami, Yasunori,Komiyama, Takeshi,Shimizu, Kenta,Uno, Shu-Ichi,Hiyama, Tamejiro,Goto, Osamu,Ikehira, Hideyuki
-
supporting information
p. 2407 - 2410
(2017/09/30)
-
- DIALKYL[2-(PYRENYL)PHENYL]PHOSPHINE, AND CATALYST COMPRISING PALLADIUM COMPOUND AND THE SAME
-
PROBLEM TO BE SOLVED: To provide a catalyst which comprises a palladium compound and [2-(pyrenyl)phenyl]phosphine. SOLUTION: The invention uses as a catalyst a complex compound which comprises a palladium compound and [2-(pyrenyl)phenyl]phosphine represen
- -
-
Paragraph 0046
(2017/08/16)
-
- Substituted bisaryloxybiphenyl compounds for use in light-emitting devices
-
Compounds according to Formula 1 may be used as host materials, hole-transfer materials, hole-injecting materials, or for other purposes in electronic devices such as in organic light-emitting devices.
- -
-
-
- SBA-15 Immobilized Phenanthroline-Copper(I) Complex as a Recyclable Efficient Catalyst for N-Arylation of Amides and N-H Heterocycles with Aryl Halides
-
5-(N,N-bis-3-(triethoxysilyl) propyl) ureyl-1,10-phenanthroline was prepared and successively grafted onto mesoporous silica of SBA-15 to get SBA-15 anchored ligand which was then reacted with Cu(I) to get SBA-15 anchored complex as the heterogeneous copper catalyst. This catalyst was characterized by FT-IR, XRD, CHN, AAS, TGA, EDAX, BET, SEM and TEM. The activities of the catalyst were tested in C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. The catalyst showed high catalytic activities for these cross-coupling reactions providing good to excellent yields of desired products. Moreover, the catalyst can be easily recovered by simple filtration and reused several times without significant loss of its catalytic activity.
- Hosseinzadeh, Rahman,Aghili, Nora,Tajbakhsh, Mahmood
-
p. 193 - 203
(2016/03/12)
-
- Single molecular tuning of the charge balance in blue-emitting iridium dendrimers for efficient nondoped solution-processed phosphorescent OLEDs
-
The single molecular tuning of charge balance has been demonstrated here by integrating a p-type dendron, an n-type dendron and a blue emissive Ir core into one dendritic platform. Compared with the commonly used physical blending, not only can the charge
- Wang, Yang,Lu, Yaoming,Gao, Baoxiang,Wang, Shumeng,Ding, Junqiao,Wang, Lixiang,Jing, Xiabin,Wang, Fosong
-
supporting information
p. 11508 - 11511
(2016/10/03)
-
- Novel 2,6-site-substituted BODIPY organic dye sensitizer and preparation method therefor
-
The present invention relates to a novel 2,6-site-substituted BODIPY organic dye sensitizer and a preparation method therefor. The organic dye sensitizer is organic photovoltaic materials with a D-pi-A structure. By taking a meso-site-substituted BODIPY core as a pi bridge framework, the sites 2 and 6 of the BODIPY core is respectively substituted by an electron donor and an electron acceptor. The present invention further discloses a preparation method for the above the dye sensitizer. The preparation method obtains a dye molecule having a general structural formula I by taking 2,4-dimethylpyrrole as an initial reaction raw material, performing a serials of simple synthesis reactions, and finally performing classical Suzuki coupling and Knoevenagel condensation reactions. The dye sensitizer synthesis method is simple, easy to control and high in yield, and has general applicability. When the method is applied to dye sensitized solar cell preparation, a dye sensitized solar cell material with a high fill factor and an ideal photoelectric conversion efficiency can be obtained. The formula I is shown in the description.
- -
-
Paragraph 0084; 0085
(2016/10/09)
-
- Photochemical Synthesis of Carbazoles Using an [Fe(phen)3](NTf2)2/O2 Catalyst System: Catalysis toward Sustainability
-
An increasingly sustainable photochemical synthesis of carbazoles was developed using a catalytic system of Fe(phen)3(NTf2)2/O2 under continuous flow conditions and was demonstrated on gram-scale using a numbering-up strategy. Photocyclization of triaryl and diarylamines into the corresponding carbazoles occurs in general in higher yields than with previously developed photocatalysts.
- Parisien-Collette, Shawn,Hernandez-Perez, Augusto C.,Collins, Shawn K.
-
supporting information
p. 4994 - 4997
(2016/10/14)
-
- Strained dehydrogenative ring closure of phenylcarbazoles
-
What does it take to force a rigid and strained dehydrogenative ring closure, for example, in phenylcarbazoles? Since the works of Buchwald and Fagnou, palladium-catalysed ring-closing dehydrogenative reactions are legion, but will not operate when the st
- Jones, Alexander W.,Louillat-Habermeyer, Marie-Laure,Patureau, Frederic W.
-
supporting information
p. 945 - 949
(2015/03/30)
-
- Copper/β-diketone-catalysed N-arylation of carbazoles
-
A copper-catalysed C-N bond-forming reaction of carbazoles with aryl iodides is described. Several commercially available ligands such as β-diketone and diamine, are tested in the N-arylation of carbazoles. The catalytic system generated in situ from an inexpensive copper salt, simple β-diketone and inorganic base efficiently N-arylated the carbazoles. A wide range of aryl iodides and carbazoles can be coupled to generate N-arylcarbazoles in the presence of various functional groups. However, the sterically hindered effect of aryl iodides is evident in this catalytic system. The selectivity of two iodine atoms on the aromatic ring of diiodobenzene is evaluated in the developed catalytic system. Results showed that the selectivity of diiodobenzene can be tuned by the reaction temperature.
- Chen, Fei,Liu, Ning,Ji, Enhui,Dai, Bin
-
p. 51512 - 51523
(2015/06/25)
-
- Visible Light-Mediated Ullmann-Type C-N Coupling Reactions of Carbazole Derivatives and Aryl Iodides
-
The combined use of an iridium-based photocatalyst and a copper salt under blue light emitting diode irradiation enables the Ullmann-type C-N cross-coupling reaction between carbazole derivatives and aryl iodides to proceed under mild conditions.
- Yoo, Woo-Jin,Tsukamoto, Tatsuhiro,Kobayashi, Shu
-
supporting information
p. 3640 - 3642
(2015/07/28)
-
- Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow
-
An evaluation of both a visible-light- and UV-light-mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous-flow conditions has been conducted. In general, triarylamines bearing electron-rich groups tend to produce higher yields than triarylamines possessing electron-withdrawing groups. The incorporation of nitrogen-based heterocycles, as well as halogen-containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV-light and visible-light (photoredox) methods.
- Hernandez-Perez, Augusto C.,Caron, Antoine,Collins, Shawn K.
-
p. 16673 - 16678
(2015/11/09)
-
- Transition-Metal-Free Synthesis of Carbazoles and Indoles by an SNAr-Based "aromatic Metamorphosis" of Thiaarenes
-
Dibenzothiophene dioxides, which are readily prepared through oxidation of the parent dibenzothiophenes, undergo nucleophilic aromatic substitution with anilines intermolecularly and then intramolecularly to yield the corresponding carbazoles in a single operation. The "aromatic metamorphosis" of dibenzothiophenes into carbazoles does not require any heavy metals. This strategy is also applicable to the synthesis of indoles. Since electron-deficient thiaarene dioxides exhibit interesting reactivity, which is not observed for that the corresponding electron-rich azaarenes, a combination of a thiaarene-dioxide-specific reaction with the SNAr-based aromatic metamorphosis allows transition-metal-free construction of difficult-to-prepare carbazoles.
- Bhanuchandra,Murakami, Kei,Vasu, Dhananjayan,Yorimitsu, Hideki,Osuka, Atsuhiro
-
supporting information
p. 10234 - 10238
(2015/09/01)
-
- An Efficient Synthesis of N-(Hetero)arylcarbazoles: Palladium-Catalyzed Coupling Reaction between (Hetero)aryl Chlorides and N-Carbazolylmagnesium Chloride
-
An efficient method for the synthesis of N-(hetero)arylcarbazoles, useful compounds for functional materials, is reported. Various (hetero)aryl chlorides reacted with N-carbazolylmagnesium chloride in the presence of a palladium catalyst (0.05 to 0.2 mol%) prepared from allylpalladium(II) chloride dimer {[PdCl(allyl)]2} and di-tert-butyl(2,2-diphenyl-1-methylcyclopropan-1-yl)phosphine (cBRIDP) under mild conditions (110°C) in a short period of time (15 min to 2 h) to give N-(hetero)arylcarbazoles in high yields. The reactions of bromochlorobenzenes proceeded in favour of the bromo group to afford N-(chlorophenyl)carbazoles in a highly selective manner. Functional materials for use in organic light-emitting diodes, such as mCP, 26mcPy, CBP and TCB, were also obtained in high yields within 15 min by the reaction of (hetero)aryl polyhalides. Optimization of the reaction conditions and a postulated catalytic cycle for the reaction are also discussed.
- Nakayama, Yuji,Yokoyama, Naota,Nara, Hideki,Kobayashi, Tohru,Fujiwhara, Mitsuhiko
-
supporting information
p. 2322 - 2330
(2015/07/27)
-
- Method for producing hydroxytriarylamine (by machine translation)
-
PROBLEM TO BE SOLVED: To economically provide arylamines such as triarylamine. SOLUTION: An arylamine compound represented by formula (1) and an aryl compound having a leaving group represented by formula (2): X-Ar2-X1, are subjected to an arylamination reaction in the presence of a basic group, an alkaline metal salt and/or an alkaline earth metal salt, and an iron catalyst to thereby obtain arylamines such as triarylamines. In formula (1), Ar and Ar1are identical or different, and denote a substituted or non-substituted aryl group, and may be ring-condensed; and a denotes 1 or 2. In formula (2), X and X1are identical or different, and denote at least one leaving group selected from the group consisting of H or Br, I, CMs (mesylate), OTf (triflate) and OTs (tosylate), provided that X and X1are not simultaneously H, and have at least one leaving group; and Ar2denotes a substituted or non-substituted aryl group. COPYRIGHT: (C)2012,JPO&INPIT
- -
-
Paragraph 0034-0036
(2018/02/24)
-
- Copper-catalyzed N-arylation of 2-arylindoles with aryl halides
-
10 mol% CuI combined with the DMEDA ligand can efficiently catalyze the N-arylation of 2-arylindoles with aryl iodides and aryl bromides in good to excellent yields. The aryl halides bearing electron-rich or electron-deficient functional groups can be wel
- Liu, Wei,Han, Li-Ya,Liu, Rui-Li,Xu, Li-Ge,Bi, Yan-Lan
-
p. 1240 - 1243
(2014/11/07)
-
- 3,6-Bis(indol-1-yl)-9-phenylcarbazoles as electroactive materials for electrophosphorescent diodes
-
Four derivatives of 3,6-bis(indol-1-yl)-9-phenylcarbazole were synthesized by Ullmann-type coupling including those having methoxy groups at the different positions. Thermal, optical and photophysical properties of the synthesized materials were studied.
- Keruckas,Grazulevicius,Volyniuk,Cherpak,Stakhira
-
-
- Efficient synthesis of biscarbazoles by palladium-catalyzed twofold C-N coupling and C-H activation reactions
-
A new and efficient strategy for the synthesis of 3,9′- and 2,9′-biscarbazoles was developed. Our strategy relies on the cyclization of 1,1′-biphenyl-2,2′-diyl bis(trifluoromethanesulfonate) with 4- or 3-anisidine, transformation of the methoxy to a triflate group and subsequent oxidative Pd-catalyzed cyclization with various anilines. This journal is the Partner Organisations 2014.
- Hung, Tran Quang,Thang, Ngo Ngoc,Hoang, Do Huy,Dang, Tuan Thanh,Villinger, Alexander,Langer, Peter
-
p. 2596 - 2605
(2014/04/17)
-
- Synthesis of heteroaromatic derivatives with nitrogen atoms: Tripyrrolyl pyrimidine and tripyrrolyl[1,3,5]triazine
-
As a part of a research program related to the synthetic study of pharmacologically and photoconductively interesting pyrrole derivatives, we have synthesized 1-arylpyrroles (3a-e), 9-arylcarbazoles (4a-e), aminophenylpyrroles (6a,b), dipyrrolylbenzenes (7a-c), 2,4,6-tri-pyrrol-1- yl-pyrimidine (8) and 2,4,6-tri-pyrrol-1-yl[1,3,5]triazine (9). We proposed a plausible mechanism for the formation of 9-arylcarbazole.
- Lee,Lee,Jung,Hahn
-
p. 501 - 504
(2013/02/22)
-
- A versatile approach to ullmann C-N couplings at room temperature: New families of nucleophiles and electrophiles for photoinduced, copper-catalyzed processes
-
The use of light to facilitate copper-catalyzed cross-couplings of nitrogen nucleophiles can enable C-N bond formation to occur under unusually mild conditions. In this study, we substantially expand the scope of such processes, establishing that this approach is not limited to reactions of carbazoles with iodobenzene and alkyl halides. Specifically, we demonstrate for the first time that other nitrogen nucleophiles (e.g., common pharmacophores such as indoles, benzimidazoles, and imidazoles) as well as other electrophiles (e.g., hindered/deactivated/heterocyclic aryl iodides, an aryl bromide, an activated aryl chloride, alkenyl halides, and an alkynyl bromide) serve as suitable partners. Photoinduced C-N bond formation can be achieved at room temperature using a common procedure with an inexpensive catalyst (CuI) that does not require a ligand coadditive and is tolerant of moisture and a variety of functional groups.
- Ziegler, Daniel T.,Choi, Junwon,Munoz-Molina, Jose Maria,Bissember, Alex C.,Peters, Jonas C.,Fu, Gregory C.
-
supporting information
p. 13107 - 13112
(2013/09/24)
-
- A visible-light-mediated synthesis of carbazoles
-
The photosynthetic preparation of N-aryl- and N-alkyl-bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu-based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures. Copyright
- Hernandez-Perez, Augusto C.,Collins, Shawn K.
-
supporting information
p. 12696 - 12700
(2013/12/04)
-
- Synthesis of carbazoles via one-pot copper-catalyzed amine insertion into cyclic diphenyleneiodoniums as a strategy to generate a drug-like chemical library
-
Carbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by cop- per(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfon amides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT-22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.
- Zhu, Daqian,Liu, Qi,Luo, Bingling,Chen, Meihui,Pi, Rongbiao,Huang, Peng,Wen, Shijun
-
p. 2172 - 2178
(2013/10/01)
-
- Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity
-
Carbazole moiety is an important scaffold with a variety of biological applications, for example, anti-oxidative stress. Our previous synthesized carbazoles were screened for their neuroprotective properties against two individual oxidative stresses. Some of the new carbazole derivatives were observed with modest to good neuroprotective effects on neuronal cells HT22 against cell injury induced by glutamate or homocysteic acid (HCA). Substituents introduced to the carbazole ring system play crucial roles in their biological activities. In particular, a bulky group favors the neuroprotective activity of the compounds. One of the new compounds, 6, showed the best neuroprotective effects, which might result from its anti-oxidative activity with a GSH-independent mechanism. These findings might provide an alternative strategy for the development of novel carbazole derivatives for the treatment of CNS diseases such as Alzheimer's disease.
- Zhu, Daqian,Chen, Meihui,Li, Min,Luo, Bingling,Zhao, Yang,Huang, Peng,Xue, Fengtian,Rapposelli, Simona,Pi, Rongbiao,Wen, Shijun
-
-
- PROCESS FOR PRODUCING N-(HETERO)ARYLAZOLES
-
The present invention provides a process for effectively producing an N-(hetero)arylazole with high yield, which is useful as a medical or agrochemical product, an organic photoconductor material, an organic electroluminescent element material, or the like. The present invention relates to a process for producing an N-(hetero)arylazole, which includes reacting a (hetero)aryl (pseudo)halide with an NH-azole in the presence of: a catalyst including a palladium compound and a coordination compound; and a basic magnesium compound.
- -
-
Page/Page column 32; 33
(2013/03/28)
-
- CuI/8-hydroxyquinalidine promoted N-arylation of indole and azoles
-
An efficient catalytic system of CuI/8-hydroxyquinalidine was developed for the coupling of aryl iodides and indole as well as some azoles. The reaction could be carried out at 90°C under the condition of relatively low catalyst loading, affording various
- Zhang, Yihua,Yang, Xinye,Xing, Hui,Zhang, Ye,Lai, Yisheng,Jiang, Yongwen,Ma, Dawei
-
experimental part
p. 875 - 880
(2012/05/21)
-
- N-PHENYL TRISCARBAZOLE
-
The present invention relates to a novel triscarbazole compound having substituent on N-phenyl, which can be represented by Formula (I). wherein R1 is selected from the group consisting of hydrogen, halogen or alkyl or alkoxy group having 1 to 20 carbon atoms wherein at least one hydrogen atom is optionally replaced by halogen; RA, RB, RC, RD and RE are any of substituents other than hydrogen wherein at least two of R1 and RA may further form a fused ring; and i, j, k, l and m are same or different at each occurrence and represent an integer from 0 to 4, with the proviso that when R1 is hydrogen, i is not 0. By introduction of the substituent on N-phenyl, the device efficiency, stability and lifetime can be increased while maintaining the solubility. These compounds can be used in various organic devices such as organic light emitting diodes, photovoltaic cells or organic semiconductor devices.
- -
-
Page/Page column 16-17
(2012/03/26)
-
- N-phenyl triscarbazole
-
The present invention relates to a novel triscarbazole compound having substituent on N-phenyl, which can be represented by Formula (I). wherein R1 is selected from the group consisting of halogen or alkyl or alkoxy group having 1 to 20 carbon atoms wherein one or more hydrogen atom may be replaced by halogen; RA, RB, Rc, RD and RE are any of substituents; and i, j, k, l and m are same or different at each occurrence and represent an integer from 0 to 4. By introduction of the substituent on N-phenyl, the device efficiency, stability and lifetime can be increased while maintaining the solubility. These compounds can be used in various organic devices such as organic light emitting diodes, photovoltaic cells or organic semiconductor devices.
- -
-
Page/Page column 12-13
(2012/04/10)
-
- Electrochemical and spectral characterizations of 9-phenylcarbazoles
-
A series of 9-phenylcarbazoles have been synthesized and characterized for their electrochemical as well as spectral properties. For 3,6-substituted carbazoles, the oxidation is reversible and the potential is affected by the substituents. For 3,6-unprotected carbazoles, on the other hand, the oxidized forms can undergo dimerization. Their corresponding dimers have been independently synthesized by chemical methods and have exhibited identical spectral properties. The para position of the 9-phenyl group is relatively insensitive for redox and chemical reactions. The amino derivatives are unstable in carbazole cation radical form compared with their triphenylamine counterparts.
- Chiu, Ssu-Kai,Chung, Yi-Chun,Liou, Guey-Sheng,Su, Yuhlong Oliver
-
scheme or table
p. 331 - 337
(2012/07/03)
-