58775-13-6Relevant academic research and scientific papers
A solution-processable triphenylamine-fluorene host for exciplex based white phosphorescent organic light-emitting diodes
Fan, Zhaokang,Li, Nengquan,Quan, Yiwu,Chen, Qingmin,Ye, Shanghui,Fan, Quli,Huang, Wei,Xu, Hui
, p. 9754 - 9759 (2014)
A novel triphenylamine-fluorene oligomer with macro-spirocyclic structure was designed and prepared as a host for exciplex based white phosphorescent organic light-emitting diodes (white PhOLEDs), in which only iridium(iii)bis(4,6-(difluorophenyl)pyridina
Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls
Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin
supporting information, p. 7445 - 7449 (2021/10/02)
An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.
The Origin of Catalytic Benzylic C?H Oxidation over a Redox-Active Metal–Organic Framework
Carter, Joseph H.,Day, Sarah J.,Han, Xue,Kang, Xinchen,Kimberley, Louis,Li, Jiangnan,McInnes, Eric J. L.,Schr?der, Martin,Sheveleva, Alena M.,Smith, Gemma L.,Tang, Chiu C.,Tuna, Floriana,Yang, Sihai
supporting information, p. 15243 - 15247 (2021/06/08)
Selective oxidation of benzylic C?H compounds to ketones is important for the production of a wide range of fine chemicals, and is often achieved using toxic or precious metal catalysts. Herein, we report the efficient oxidation of benzylic C?H groups in a broad range of substrates under mild conditions over a robust metal–organic framework material, MFM-170, incorporating redox-active [Cu2II(O2CR)4] paddlewheel nodes. A comprehensive investigation employing electron paramagnetic resonance (EPR) spectroscopy and synchrotron X-ray diffraction has identified the critical role of the paddlewheel moiety in activating the oxidant tBuOOH (tert-butyl hydroperoxide) via partial reduction to [CuIICuI(O2CR)4] species.
Amphiphilic ligands for Cu-catalyzed aerobic oxidation to synthesize 9-fluorenones in water
Li, Longjia,Liu, Zibo,Tang, Shanyu,Li, Jiao,Ren, Xuanhe,Yang, Guanyu,Li, Heng,Yuan, Bingxin
, p. 34 - 38 (2019/05/10)
A series of amphiphilic PEG-functionalized nitrogen ligands were developed for the highly efficient copper-catalyzed aerobic oxidation of 9-fluorenes, with molecular oxygen as the sole oxidant in neat water. A broad range of functional groups are well tolerated and thus offer the opportunity for further functionalization.
Method for synthesizing fluorenone ketone compound through molecular oxygen oxidation in water phase
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Paragraph 0062-0065, (2019/08/20)
Aiming at the technical problems that in the prior art a method for synthesizing a fluorenone ketone compound has organic solvent pollution and byproducts can be generated, the invention provides a method for synthesizing a fluorenone ketone compound through molecular oxygen oxidation in a water phase. The method comprises the following steps: by taking a fluorenone compound as a substrate, dispersing into an alkali solution, and at 40-120 DEG C, in the presence of oxygen, and with a water-soluble transition metal compound as a catalyst, stirring to carry out reactions, thereby obtaining the fluorenone ketone compound. By adopting the method, molecular oxygen is adopted as an oxidant, and water is adopted as a solvent, so that an organic solvent is avoided, and the problem that multiple byproducts are generated because of peroxidation can be avoided.
Sodium copper chlorophyllin catalyzed chemoselective oxidation of benzylic alcohols and diarylmethanes in water
Liu, Shi-juan,Zhang, Miao,Lu, Rong,Li, Xiu-ying,Che, Guang-bo
, (2018/08/17)
We report the highly efficient and chemoselective oxidation of benzylic alcohols catalyzed by sodium copper chlorophyllin in water, producing corresponding arylcarbonyl compounds. Importantly, the catalytic system exhibits a wide substrate scope and high functional group tolerance. Moreover, secondary alcohols and even diarylmethanes were smoothly oxidized to the desired aryl ketones with excellent yields.
Immobilization of Keggin polyoxovanadoniobate in crystalline solids to produce effective heterogeneous catalysts towards selective oxidation of benzyl-alkanes
Hu, Jufang,Dong, Jing,Huang, Xianqiang,Chi, Yingnan,Lin, Zhengguo,Li, Jikun,Yang, Song,Ma, Hongwei,Hu, Changwen
, p. 8245 - 8251 (2017/07/10)
Two ionic organic-inorganic hybrid compounds, [CuII(C2N2H8)2]4[CuII(C2N2H8)2(H2O)2]2[PNb12O40VVVIVO2]·(OH)2·11H2O (1) and [CoIII(C2N2H8)3]2[CoIII(C2N2H8)2(H2O)2]0.5[H2.5PNb12O40 VVVIVO2]·20H2O (2), based on P-centered dicapped polyoxoniobates and organometallic cations were isolated and structurally characterized by routine techniques. The trivalent cobalt complex-containing compound exhibits a looser arrangement compared with its divalent copper complex-containing counterpart, with a space volume of 34.9% for the former and 17.0% for the latter. The two compounds were proved to be effective in facilitating the oxidation of benzyl-alkanes to ketone products in a heterogeneous manner, evidencing the feasiblity of the strategy of self-immobilization of catalytically active, readily soluble PNb12O40(VO)2 species in crystalline solids.
Four alkoxohexavanadate-based pd-polyoxovanadates as robust heterogeneous catalysts for oxidation of benzyl-alkanes
Li, Ji-Kun,Huang, Xian-Qiang,Yang, Song,Ma, Hong-Wei,Chi, Ying-Nan,Hu, Chang-Wen
supporting information, p. 1454 - 1461 (2015/04/21)
Four alkoxohexavanadate-based Pd-POVs [Pd(dpa)(acac)]2[V6O13(OMe)6] (1), [Pd(dpa)(acac)]2[V6O11(OMe)8] (2), [Pd(dpa)(acac)]2[V6O11(OMe)8]·H2O (3), and [Pd(DMAP)2(acac)]2[V6O11(OMe)8]·H2O (4) (POV = polyoxovanadate; dpa = 2,2′-dipyridine amine; DMAP = 4-dimethylaminopyridine; acac = acetylacetone anion) have been synthesized and fully characterized by single crystal X-ray diffraction and powder X-ray diffraction analyses, Fourier transform infrared spectroscopy, element analyses, and X-ray photoelectron spectroscopy. In 1-4, Pd complexes and hexavanadate anions are assembled through electrostatic interactions. Interestingly, the [V6O11(OMe)8]2- cores in 2 and 3 are a pair of isomers that can be isolated by controlling crystallization temperature. Moreover, to the best of our knowledge, the {V6} core in 3 represents a new octamethoxyhexavanadates cluster. It is notable that compounds 1-4 exhibit excellent heterogeneous catalytic performance in the oxidation of benzyl-alkanes with t-butylhydroperoxide as oxidant. Among them, the catalytic activity of 1 (conv. and selec. up to 99%, respectively) outperforms others and can be reused without losing its activity.
Tuning HOMO-LUMO levels: Trends leading to the design of 9-fluorenone scaffolds with predictable electronic and optoelectronic properties
Eakins, Galen L.,Alford, Joshua S.,Tiegs, Brandon J.,Breyfogle, Bryan E.,Stearman, Chad J.
experimental part, p. 1119 - 1128 (2012/03/22)
Highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) tuning is an important consideration in the development of organic-based semiconducting materials. A study of the specific effects and overall trends for the HOMO-LUMO tuning of a diverse series of 9-fluorenones by means of extended conjugation and substituent effects is described. Trends were explored in a range of compounds, beginning with structures having highly electron-withdrawing substituents and progressing to structures having highly electron-donating substituents. Compounds with an incremental increase in conjugation were also examined. Electrochemical and optical measurements were used to calculate the HOMO-LUMO levels and HOMO-LUMO bandgap (HLG) for each structure. Results from both methods were compared and correlated with the differences in molecular structure. Increasing the electron-donating character of the substituents was observed to decrease the HLG and increase the energy levels of the HOMO and the LUMO, whereas an increase in the electron-withdrawing character produced the opposite results. Increasing conjugation decreased the HLG, increased the HOMO energy level, but decreased the LUMO energy level. Spectroscopic evidence of substituent influence on the carbonyl suggests that substituents directly impact the HLG by influencing the availability of nonbonding electrons within the carbonyl, which impacts the probability of an nπ* transition. The data presented not only elaborate on the HOMO-LUMO tuning of 9-fluorenone systems but also enable the consideration of 9-fluorenones as analogous models for HOMO-LUMO tuning in other more complex polyaromatic systems such as bifluorenylidenes. These trends may provide insight into developing materials with specifically tuned HLGs and HOMO-LUMO levels for a variety of applications. Copyright
C-9 fluorenyl substituted anthracenes: A promising new family of blue luminescent materials
Wang, Jing,Wan, Wen,Jiang, Haizhen,Gao, Yan,Jiang, Xueyin,Lin, Huaping,Zhao, Weiming,Hao, Jian
supporting information; experimental part, p. 3874 - 3877 (2010/11/18)
Syntheses, optical, and electrochemical properties of novel C-9 fluorenyl substituted anthracenes linked by a tetrahedral sp3-hybridized carbon atom are reported for blue light emitting materials. Remarkably, an unoptimized organic light-emitting diode based on 1-fold fluorene-functionalized anthracene 3 exhibits a radiance of 4100 cd/m2 at 12 V and a maximum EL efficiency of 1.36 cd/A with color purity CIE x, y (0.157, 0.082), which is very close to the National Television System Committee standard blue.
