- (DiMeIHeptCl)Pd: A Low-Load Catalyst for Solvent-Free (Melt) Amination
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(DiMeIHeptCl)Pd, a hyper-branched N-aryl Pd NHC catalyst, has been shown to be efficient at performing amine arylation reactions in solvent-free ("melt") conditions. The highly lipophilic environment of the alkyl chains flanking the Pd center serves as lubricant to allow the complex to navigate through the paste-like environment of these mixtures. The protocol can be used on a multi-gram scale to make a variety of aniline derivatives, including substrates containing alcohol moieties.
- Semeniuchenko, Volodymyr,Sharif, Sepideh,Day, Jonathan,Chandrasoma, Nalin,Pietro, William J.,Manthorpe, Jeffrey,Braje, Wilfried M.,Organ, Michael G.
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p. 10343 - 10359
(2021/07/31)
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- Method for synthesizing carbazole derivative
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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.
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Paragraph 0013; 0032-0033
(2021/10/05)
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- Diazine isomer blue-light material
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The invention reveals a diazine isomer blue-light material. The technical scheme of the invention uses a carbazole derivative as an electron donor unit and a diazine isomer as an electron acceptor unit, the photophysical properties of a luminescent materi
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Paragraph 0051-0052
(2019/02/13)
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- Synthesis and structure-property correlation of blue fluorescence isomer emitters based on rigid pyrazine-bridged carbazole frameworks
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Three novel blue fluorescence isomer emitters, namely 2,5-bis(6,9-bis(4-(tert-butyl)phenyl)-9H-carbazol-3-yl)pyrazine (TCz-3PA-TCz), 9-(5-(6,9-bis(4-(tert-butyl)phenyl)-9H-carbazol-3-yl)pyrazin-2-yl)-3,6-bis(4-(tert-butyl)phenyl)-9H-carbazole (TCz-3,9PA-T
- Wei, Lingjuan,Li, Jie,Xue, Kai,Ye, Shanghui,Jiang, Hongji
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p. 16629 - 16638
(2019/11/11)
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- A General Palladium–Phosphine Complex To Explore Aryl Tosylates in the N-Arylation of Amines: Scope and Limitations
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The scope and limitations of the monoselective N-arylation of various amines by using aryl and hetaryl tosylates are presented. The air-stable and easily accessible Pd(OAc)2/CM-phos {CM-phos=2-[2-(dicyclohexylphosphino)phenyl]-1-methyl-1H-indole}catalyst system was able to deal with a wide range of aryl tosylate substrates as well as amine nucleophiles, including primary and secondary cyclic/acyclic aliphatic amines and anilines. NH-Bearing heterocycles such as indole, carbazole, pyrrole, 10-phenothiazine, and 10-phenoxazine were shown to be feasible coupling partners under this catalytic system. The described reaction conditions tolerate a wide range of functional groups and allow an array of aromatic amines as well as unsymmetrical amine products to be easily accessed from the various phenolic derivatives. Interestingly, this catalyst system even offers the opportunity to perform the reaction in water medium. We also report the intermolecular coupling of optically active α-central chiral amines with aryl tosylates without erosion of the enantiomeric purity.
- Choy, Pui Ying,Chung, Kin Ho,Yang, Qingjing,So, Chau Ming,Sun, Raymond Wai-Yin,Kwong, Fuk Yee
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supporting information
p. 2465 - 2474
(2018/09/10)
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- Design, synthesis and biological evaluation of: N -arylsulfonyl carbazoles as novel anticancer agents
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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
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p. 17183 - 17190
(2018/05/28)
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- DIALKYL[2-(PYRENYL)PHENYL]PHOSPHINE, AND CATALYST COMPRISING PALLADIUM COMPOUND AND THE SAME
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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
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Paragraph 0038
(2017/08/16)
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- Thermal activation delayed fluorescence material based on 1,10-phenanthroline and preparing method and application thereof
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The invention discloses a thermal activation delayed fluorescence material based on 1,10-phenanthroline serving as an electron attracting unit and an aryl-substituted amino unit serving as an electron supplying unit. The invention further provides a preparing method for the fluorescence material. The preparing method includes the following steps that 1 a brominated target product containing an aryl-substituted amino unit is prepared; 2, the obtained brominated target product reacts with isopropoxy pinacol borate through n-butyllithium to obtain a target product containing borate; 3, the thermal activation delayed fluorescence material based on 1,10-phenanthroline is generated by the borate-containing target product obtained in the step 2 and 3-bromo-1,10-phenanthroline under the action of a palladium catalyst. The material is easy to synthesize and purify and high in solubility, has good film morphology and high carrier mobility, and has important application value and prospects in organic electroluminescence devices.
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Paragraph 0110-0112
(2016/11/07)
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- Transition-Metal-Free Synthesis of Carbazoles and Indoles by an SNAr-Based "aromatic Metamorphosis" of Thiaarenes
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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
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supporting information
p. 10234 - 10238
(2015/09/01)
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- Charge-transfer-featured materials - Promising hosts for fabrication of efficient OLEDs through triplet harvesting via triplet fusion
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A charge-transfer-featured naphthalimide derivative with a small exchange energy but a lower lying 3ππ* state than 3CT state is found to contribute to triplet harvesting through a P-type rather than an E-type delayed fluorescence, and could act as a quite promising host to achieve highly efficient OLEDs.
- Zhou, Jie,Chen, Ping,Wang, Xu,Wang, Yan,Wang, Yi,Li, Feng,Yang, Minghui,Huang, Yan,Yu, Junsheng,Lu, Zhiyun
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supporting information
p. 7586 - 7589
(2014/07/08)
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- An efficient guest/host fluorescent energy transfer pair based on the naphthalimide skeleton, and its application in heavily-doped red organic light-emitting diodes
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A red aggregation-emission-enhancement guest fluorophor and a green host compound both based upon the naphthalimide skeleton namely, 11-tert-butyl-((E)- 4-(2-(7-(diphenylamino)-9,9-diethyl-9H-fluoren-2-yl)vinyl)-7H-benzimidazo[2,1-a] benzo[de]isoquinolin-
- Wang, Yi,Zhou, Jie,Wang, Xu,Zheng, Xujun,Lu, Zhiyun,Zhang, Wei,Chen, Yunqing,Huang, Yan,Pu, Xuemei,Yu, Junsheng
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- Synthesis of carbazoles via one-pot copper-catalyzed amine insertion into cyclic diphenyleneiodoniums as a strategy to generate a drug-like chemical library
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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
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p. 2172 - 2178
(2013/10/01)
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- Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity
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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
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- High-performance organic materials for dye-sensitized solar cells: Triarylene-linked dyads with a 4-tert-butylphenylamine donor
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A series of organic dyes were prepared that displayed remarkable solar-to-energy conversion efficiencies in dye-sensitized solar cells (DSSCs). These dyes are composed of a 4-tert-butylphenylamine donor group (D), a cyanoacrylic-acid acceptor group (A), a
- Chang, Yuan Jay,Chou, Po-Ting,Lin, Szu-Yu,Watanabe, Motonori,Liu, Zhi-Qian,Lin, Ju-Ling,Chen, Kew-Yu,Sun, Shih-Sheng,Liu, Ching-Yang,Chow, Tahsin J.
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supporting information; experimental part
p. 572 - 581
(2012/05/20)
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- Electrochemical and spectral characterizations of 9-phenylcarbazoles
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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
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scheme or table
p. 331 - 337
(2012/07/03)
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- Palladium-catalyzed amination of aryl mesylates
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(Chemical Equation Presented) Aminated adventures: The new phosphine ligand L in combination with a Pd(OAc)2 precursor provides the first palladium-catalyzed amination of unactivated aryl mesylates. This catalyst system can be applied in an aqueous reaction medium without detrimental effect.
- So, Chau Ming,Zhou, Zhongyuan,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 6402 - 6406
(2009/03/11)
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- Nonconjugated hybrid of carbazole and fluorene: A novel host material for highly efficient green and red phosphorescent OLEDs
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(Chemical Equation Presented) A novel host material for efficient green and red electrophosphorescence devices is obtained by adopting the new molecular strategy of nonconjugated linkage of carbazole and fluorene moieties. The new host combines characteri
- Wong, Ken-Tsung,Chen, You-Ming,Lin, Yu-Ting,Su, Hai-Ching,Wu, Chung-Chih
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p. 5361 - 5364
(2007/10/03)
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