19264-73-4Relevant articles and documents
Experimental and DFT studies on the vibrational and electronic spectra of 9-p-tolyl-9H-carbazole-3-carbaldehyde
Wang, Yiwei,Zhang, Yu,Ni, Haiwei,Meng, Nana,Ma, Kuirong,Zhao, Jianying,Zhu, Dunru
, p. 296 - 306 (2015)
The compound 9-p-tolyl-9H-carbazole-3-carbaldehyde (HCCD) was synthesized and characterized by X-ray diffraction, FT-IR, FT-Raman and UV-Vis spectra. The X-ray diffraction study showed that HCCD has a Z-configuration. The benzene ring including methyl is twisted from the mean plane of the carbazole group by 59.7(3)°, which is comparable with the calculated result 65° for B3LYP/6-311++G(d, p) method. Vibrational spectra and electronic spectra measurements were made for the compound. Optimized geometrical structure and harmonic vibrational frequencies were computed with B-based DFT (BLYP, B3LYP and cam-B3LYP) methods, and WB-based DFT (WB97, WB97X and WB97XD) methods and ab initio RHF method using 6-311++G(d, p) basis set. Assignments of the observed spectra were proposed. The equilibrium geometries computed by all of the methods were compared with X-ray diffraction results. The absorption spectra of the title compound were computed both in gas phase and in DMF solution using TD-(cam)B3LYP/6-311++G(d, p) and PCM-(cam)B3LYP/6-311++G(d, p) approaches, respectively. The calculated results provide good descriptions of the bands maxima in the observed electronic spectrum. Temperature dependence of thermodynamic parameters in the range of 100-1000 K was determined. The natural atomic hybrids were calculated and discussed.
Experimental and DFT studies on the vibrational and electronic spectra and NBO analysis of 2-amino-3-((E)-(9-p-tolyl-9H-carbazol-3-yl) methyleneamino) maleonitrile
Meng, Nana,Zhang, Yu,Wang, Yiwei,Ma, Kuirong,Zhao, Jianying,Tang, Guodong
, p. 494 - 507 (2014)
2-Amino-3-((E)-(9-p-tolyl-9H-carbazol-3-yl) methyleneamino) maleonitrile (ACMM) was synthesized and characterized by X-ray diffraction, FT-IR, FT-Raman and UV-Vis spectra. The X-ray diffraction study showed that ACMM has a Z-configuration, due to the intramolecular C18H18Aa?N2, N3H3Aa?N2 and C20H20Aa?N4 hydrogen bonds and intermolecular C10H10Aa?N4, N3H3Ba?N9 (2 - x, 2 - y, 2 - z) and N3H8Ca?N4 (2 - x, 1 - y, 2 - z) hydrogen bonds. The benzene ring including methyl is twisted from the mean plane of the carbazole group by 59.7(3). Vibrational spectra and electronic spectra measurements were made for the compound. Optimized geometrical structure and harmonic vibrational frequencies were computed with DFT (B3-based B3P86, B3LYP, B3PW91 and B-based BP86, BLYP, BPW91) methods and ab initio RHF method using 6-311++G(d, p) basis set. Assignments of the observed spectra were proposed. The equilibrium geometries computed by all of the methods were compared with X-ray diffraction results. The absorption spectra of the title compound were computed both in gas phase and in DMF solution using TD-B3LYP/6-311++G(d, p) and PCM-B3LYP/6- 311++G(d, p) approaches, respectively. The calculated results provide a good description of positions of the bands maxima in the observed electronic spectrum. Temperature dependence of thermodynamic parameters in the range of 100-1000 K were determined. The bond orbital occupancies, contribution from parent natural bond orbital (NBO), the natural atomic hybrids was calculated and discussed.
Functionalised carbazole as a cathode for high voltage non-aqueous organic redox flow batteries
Mirle, Chinmaya R.,M., Raja,P., Vasudevarao,S., Sankararaman,R., Kothandaraman
, p. 14401 - 14410 (2020)
Prospective high reduction potential cathode materials have been proposed that can be used in non-aqueous redox flow battery applications. A new class of material, 3,6-dibromo-9-(p-tolyl)-9H-carbazole(3)incorporating a carbazole core, showing a very good reversibility is employed as the cathode material and dissolved oxygen in the solvent mixture is used as the anolyte material. Labile positions of the carbazole have been substituted with electron withdrawing groups, which increases the reduction potential of the redox couple. Apart from substituting the labile positions, we have also explored the possible structural modification responsible for stabilizing the cation radical of the carbazole moiety and obtained the reversible behavior thereafter. From this, it is evident that a free radical is stabilized upon delocalization of the charge in the molecule. The mass-transport and redox parameters, diffusion coefficient and heterogeneous electron transfer rate coefficient values are high enough to realize good battery performance. A solvent mixture of acetonitrile and dichloromethane (4?:?1) has been used in this work in order to increase the solubility of electroactive materials in the medium.
Microenvironment modulation of cuprous cluster enables inert aryl chlorides activation in single-molecule metallaphotoredox amination
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)
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
Method for synthesizing carbazole derivative
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Paragraph 0013; 0018-0019, (2021/10/05)
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.
Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives
Malavade, Vrunda,Patil, Manish,Patil, Mahendra
supporting information, p. 561 - 569 (2020/02/05)
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.
