942-06-3Relevant academic research and scientific papers
High-efficiency synthesis method of halogenated 1, 3-indanedione compound
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Paragraph 0023-0025, (2020/08/09)
The invention relates to the technical field of new material synthesis, in particular to a novel efficient synthesis method of an organic photoelectric intermediate material. The method is characterized in that the synthesis technology is simple, efficient, easy to operate and good in repeatability. The specific synthesis details are as follows: halogenated phthalic acid which is very easy to obtain in industry is used as a raw material, and a corresponding anhydride is obtained after dehydration treatment; different acid anhydrides are reacted with ethyl acetoacetate or tert-butyl acetoacetate at room temperature, and then carboxyl is mildly removed in a hydrochloric acid aqueous solution to obtain the halogenated 1, 3-indanedione compound. Simple and efficient synthesis of the organic intermediates is achieved through the method, synthesis raw materials are easy to obtain, the synthesis process is simple, the path is short, and the synthesis cost is greatly reduced.
Heterogeneous catalysts for the cyclization of dicarboxylic acids to cyclic anhydrides as monomers for bioplastic production
Rashed, Md. N.,Siddiki,Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Kon, Kenichi,Toyao, Takashi,Shimizu, Ken-Ichi
, p. 3238 - 3242 (2017/07/28)
Cyclic anhydrides, key intermediates of carbon-neutral and biodegradable polyesters, are currently produced from biomass-derived dicarboxylic acids by a high-cost multistep process. We present a new high-yielding process for the direct intramolecular dehydration of dicarboxylic acids using a reusable heterogeneous Lewis acid catalyst, Nb2O5·nH2O. Various dicarboxylic acids, which can be produced by a biorefinery process, are transformed into the corresponding cyclic anhydrides as monomers for polyester production. This method is suitable for the production of renewable polyesters in a biorefinery process.
Design, Synthesis, and Photovoltaic Characterization of a Small Molecular Acceptor with an Ultra-Narrow Band Gap
Yao, Huifeng,Cui, Yong,Yu, Runnan,Gao, Bowei,Zhang, Hao,Hou, Jianhui
supporting information, p. 3045 - 3049 (2017/03/13)
The design of narrow band gap (NBG) donors or acceptors and their application in organic solar cells (OSCs) are of great importance in the conversion of solar photons to electrons. Limited by the inevitable energy loss from the optical band gap of the photovoltaic material to the open-circuit voltage of the OSC device, the improvement of the power conversion efficiency (PCE) of NBG-based OSCs faces great challenges. A novel acceptor–donor–acceptor structured non-fullerene acceptor is reported with an ultra-narrow band gap of 1.24 eV, which was achieved by an enhanced intramolecular charge transfer (ICT) effect. In the OSC device, despite a low energy loss of 0.509 eV, an impressive short-circuit current density of 25.3 mA cm?2 is still recorded, which is the highest value for all OSC devices. The high 10.9 % PCE of the NBG-based OSC demonstrates that the design and application of ultra-narrow materials have the potential to further improve the PCE of OSC devices.
Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal-Free C(sp3)–C(sp3) Cleavage and Allylation/Alkenylation
Zhang, Jing,Li, Yang,Xu, Ruoyu,Chen, Yiyun
supporting information, p. 12619 - 12623 (2017/09/11)
The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor–acceptor complex-enabled alkoxyl radical generation under metal-free reaction conditions induced by visible light. Hantzsch ester forms the key donor–acceptor complex with N-alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments. Selective C(sp3)-C(sp3) bond cleavage and allylation/alkenylation is demonstrated for the first time using this photocatalyst-free approach with linear primary, secondary, and tertiary alkoxyl radicals.
Efficient Semitransparent Organic Solar Cells with Tunable Color enabled by an Ultralow-Bandgap Nonfullerene Acceptor
Cui, Yong,Yang, Chenyi,Yao, Huifeng,Zhu, Jie,Wang, Yuming,Jia, Guoxiao,Gao, Feng,Hou, Jianhui
, (2017/10/18)
Semitransparent organic solar cells (OSCs) show attractive potential in power-generating windows. However, the development of semitransparent OSCs is lagging behind opaque OSCs. Here, an ultralow-bandgap nonfullerene acceptor, “IEICO-4Cl”, is designed and synthesized, whose absorption spectrum is mainly located in the near-infrared region. When IEICO-4Cl is blended with different polymer donors (J52, PBDB-T, and PTB7-Th), the colors of the blend films can be tuned from purple to blue to cyan, respectively. Traditional OSCs with a nontransparent Al electrode fabricated by J52:IEICO-4Cl, PBDB-T:IEICO-4Cl, and PTB7-Th:IEICO-4Cl yield power conversion efficiencies (PCE) of 9.65 ± 0.33%, 9.43 ± 0.13%, and 10.0 ± 0.2%, respectively. By using 15 nm Au as the electrode, semitransparent OSCs based on these three blends also show PCEs of 6.37%, 6.24%, and 6.97% with high average visible transmittance (AVT) of 35.1%, 35.7%, and 33.5%, respectively. Furthermore, via changing the thickness of Au in the OSCs, the relationship between the transmittance and efficiency is studied in detail, and an impressive PCE of 8.38% with an AVT of 25.7% is obtained, which is an outstanding value in the semitransparent OSCs.
Synthesis and biological evaluation of new fluorinated and chlorinated indenoisoquinoline topoisomerase i poisons
Beck, Daniel E.,Lv, Wei,Abdelmalak, Monica,Plescia, Caroline B.,Agama, Keli,Marchand, Christophe,Pommier, Yves,Cushman, Mark
, p. 1469 - 1479 (2016/03/16)
Fluorine and chlorine are metabolically stable, but generally less active replacements for a nitro group at the 3-position of indenoisoquinoline topoisomerase IB (Top1) poisons. A number of strategies were employed in the present investigation to enhance the Top1 inhibitory potencies and cancer cell growth inhibitory activities of halogenated indenoisoquinolines. In several cases, the new compounds' activities were found to rival or surpass those of similarly substituted 3-nitroindenoisoquinolines, and several unusually potent analogs were discovered through testing in human cancer cell cultures. A hydroxyethylaminopropyl side chain on the lactam nitrogen of two halogenated indenoisoquinoline Top1 inhibitors was found to also impart inhibitory activity against tyrosyl DNA phosphodiesterases 1 and 2 (TDP1 and TDP2), which are enzymes that participate in the repair of DNA damage induced by Top1 poisons.
Process for the preparation of eight fluorine substituted phthalocyanine
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Paragraph 0035; 0036; 0043, (2017/04/07)
The invention relates to a method for preparing octafluoro-substituted phthalocyanine. According to the method, easily available 4,5-dichlorophthalic acid serving as a raw material is subjected to five-step reactions, namely acetic anhydride dehydration, aniline imidization, potassium fluoride fluorination, hydrolysis and one-step condensation to obtain a target product, namely an octafluoro-substituted phthalocyanine compound. The method has the advantages of low raw material cost, mild reaction condition, safe experiment operation, simple post-treatment, relatively high target product yield, high purity and the like. A novel method is provided to preparation for synthesizing octafluoro-substituted phthalocyanine compounds, synthesis researches of octafluoro-substituted phthalocyanine compounds are promoted, and more possibility is provided to application of the octafluoro-substituted phthalocyanine compounds serving as semiconductor materials in researches of dye-sensitized solar cells, organic thin-film transistors and other aspects. The method can be easily industrialized, and the obtained product has high purity and stable quality.
Tetrathiafulvalene compound and synthesis method thereof
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Paragraph 0038; 0039; 0040, (2016/10/09)
The invention discloses a tetrathiafulvalene compound and a synthesis method thereof; the synthesis method comprises the following steps: (1) synthesis of 4,5-dichlorophthalic anhydride; (2) synthesis of 5,6-dichloro-2-cyclohexylisoindole-1,3-dione; (3) synthesis of 5,6-dibenzyl methylmercapto-2-cyclohexylisoindole-1,3-dione; (4) synthesis of 6-cyclohexyl-5H-[1,3]dithio-[4,5-f]isoindole-2,5,7(6H)-trione; and (5) synthesis of 6,6'-dicyclohexyl-5H,5'H-[2,2'-di[1,3]dithio[4,5-f]isoindole-5,5',7,7'(6H,6H')tetrone.
Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide
Camelio, Andrew M.,Liang, Yong,Eliasen, Anders M.,Johnson, Trevor C.,Yuan, Changxia,Schuppe, Alex W.,Houk,Siegel, Dionicio
, p. 8084 - 8095 (2015/09/01)
The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.
Discovery of novel dual-action antidiabetic agents that inhibit glycogen phosphorylase and activate glucokinase
Zhang, Lei,Chen, Xiaojie,Liu, Jun,Zhu, Qingzhang,Leng, Ying,Luo, Xiaomin,Jiang, Hualiang,Liu, Hong
, p. 624 - 639 (2013/02/21)
Dual-target-directed agents simultaneously inhibiting glycogen phosphorylase (GP) and activating glucokinase (GK) could decelerate the inflow of glucose from glycogenolysis and accelerate the outflow of glucose in the liver, therefore allow for a better control over hyperglycaemia in a synergetic manner. A series of hybrid compounds were designed by structure-assisted and ligand-based strategies. In vitro bioassays found two novel compounds (1j, 6g) worthy of further optimization on balance of dual action to GP and GK. In addition, for single-target activity, two compounds exhibited more potent GP inhibitory activity and four compounds showed better GK activation than their corresponding references.
