- Synthesis and Characterization of Two Novel Oxazol-5-ones Derivatives and Their Multifunctional Properties; pH Sensitivity, Electropolymerizability and Antiproliferative Activity
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The aim of this study is to synthesize oxazol-5-one derivatives, which have multi-functional properties. Nomenclatures of newly synthesized molecules are 4-(4-N,N-diethylaminophenylmethylene)-2-(3-thienyl)oxazol-5-one (4a) and 4-(4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)phenylmethylene)-2-(3-thienyl)oxazol-5-one (4b). These two novel derivatives contain pH sensitive and polymerizable groups. 3-Thienyl group was attached to position-2 of the oxazol-5-one ring to provide electrochemical polymerization capability. pH sensing properties were provided by attaching p-N,N-diethylaminophenylmethylene and p-aza-15-crown-5-phenylmethylene groups to the arylmethylene moiety at position-4 of the ring. Target molecules were synthesized by classical process known as Erlenmeyer-Pl?chl Azlactone Synthesis Erlenmeyer (Justus Liebigs Ann Chem 275:1-12, 1893), Rodrigues et al. (J Chem Educ 92:1543-1546, 2015). After structural characterization of 4a and 4b, absorption and emission characteristics were determined in solvents that have different polarities. Difference in maximum absorption and emission wavelengths of the molecules related to solvent polarities were observed at around 6–7 nm and 35–36 nm respectively. In pH studies of the target derivatives in PVC polymer matrix, ratiometric changes were observed at isosbestic point around 398 nm. Polymeric depositions of the molecules (4a, 4b) were proved by using cyclic voltammetry, electrochemical impedance spectrometry studies and scanning electron microscope images. MTT assay studies showed significant results like, 4b derivative’s strong cytotoxic activity on PC-3 (cancerous cell line) with IC50 value of 12.57 ± 0.41 μg/ml without exhibiting any cytotoxic effect on HEK293 (healthy cell line).
- Nazl?, ?brahim Hanif,Alp, Serap,Topkaya, Derya,Güney Afacan, ?mran,Nalbantsoy, Ay?e
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- 2-(2,2-DIARYLETHYL)-CYCLIC AMINE DERIVATIVE OR SALT, SYNTHESIS THEREOF, AND APPLICATION AND COMPOSITION THEREOF
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The disclosure relates to a 2-(2,2-diarylethyl)-cyclic amine derivative or salt, a synthesis method, an application and a composition thereof. Biological activity test shows that this kind of 2-(2,2-diarylethyl)-cyclic amine derivative has good M-receptor antagonistic activity; and can be used as an active component of drugs for the treatment of the diseases mediated or regulated by muscarinic receptors, such as asthma, chronic obstructive pulmonary disease (COPD), overactive bladder (OAB), bronchospasm with chronic obstructive pulmonary disease, visceral spasm, irritable bowel syndrome, Parkinson's disease, depression or anxiety, schizophrenia and related mental diseases.
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Paragraph 0408-0409
(2021/05/28)
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- Metal organic coordination compound and preparation method and application thereof
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The invention provides a metal organic coordination compound as well as a preparation method and application thereof. According to the metal organic coordination compound, the organic coordination compound with a simple structure can be prepared through two steps, namely acylating chlorination and amidation; the organic coordination compound can be used for preparing an organic coordination compound of a conductive conjugated polymer; an experimental scheme is simple and convenient, and raw materials are cheap and widely available; and besides preparation of coordination compounds containing thiophene groups, the method can be expanded to synthesis of coordination compounds containing pyrrole groups, fluorene groups and the like.
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Paragraph 0072-0075; 0080-0083; 0086-0089; 0092-0095
(2021/04/28)
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- Pine Rosin as a Valuable Natural Resource in the Synthesis of Fungicide Candidates for Controlling Fusarium oxysporum on Cucumber
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To improve the effect of pine rosin in plant fungicides, four series of dehydroabietyl-1,3,4-thiadiazole derivatives from the natural product rosin were synthesized. Based on the evaluation of the in vitro antifungal activity against Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium oxysporum, and Magnaporthe oryzae, rosin-based 1,3,4-thiadiazole compounds containing thiophene heterocycles were screened. Notably, compound 3e [dehydroabietyl-(1,3,4-thiadiazol-2-yl)-5-nitrothiophene-2-carboxamide] exhibited excellent antifungal property against F. oxysporum with an EC50 of 0.618 mg/L, which was lower than that of the positive control carbendazim (0.649 mg/L). The in vivo antifungal activity results showed that 3e exerted a protective effect on cucumber plants. Physiological and biochemical studies showed that the primary mechanism of action of compound 3e on F. oxysporum was it changed the mycelial morphology, increased the cell membrane permeability, and inhibited the synthesis of ergosterol in the mycelia. Furthermore, the quantitative structure-activity relationship studies revealed that the frontier orbital energy in the molecule had a key role in the antifungal activity through the conjugation and electrostatic interaction between compound 3e and the receptors of the target. Thus, the present study highlighted the application of rosin-based fungicidal candidates and exploited efficient plant pesticides for sustainable crop production.
- Mao, Shiying,Wu, Chengyu,Gao, Yanqing,Hao, Jin,He, Xiaohua,Tao, Pan,Li, Jian,Shang, Shibin,Song, Zhanqian,Song, Jie
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p. 6475 - 6484
(2021/06/28)
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- Chalcogen bonding mediates the formation of supramolecular helices of azapeptides in crystals
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To explore whether chalcogen bonding was able to drive the formation of supramolecular helices, alanine-based azapeptides containing a β-turn structure, with a thiophene group, respectively, incorporated in theN- orC-terminus, were employed as helical building blocks. While the former derivative formed a supramolecularM-helixviaintermolecular S?S chalcogen bonding in crystals, the latter formedP-helixviaintermolecular S?O chalcogen bonding.
- Cao, Jinlian,Jiang, Yun-Bao,Li, Zhao,Shi, Di,Weng, Peimin,Yan, Xiaosheng
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supporting information
p. 6397 - 6401
(2021/08/03)
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- Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction
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A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.
- Isshiki, Ryota,Kurosawa, Miki B.,Muto, Kei,Yamaguchi, Junichiro
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supporting information
p. 10333 - 10340
(2021/07/21)
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- Visible-Light-Driven Dehydrogenative Coupling of Primary Alcohols with Phenols Forming Aryl Carboxylates
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A preparative method for obtaining aryl esters from aliphatic primary alcohols and phenols was developed. The reaction proceeds under the irradiation of visible light at ambient temperature, dispensing with any oxidant or hydrogen acceptor. Primary alcohols having a variety of functional groups are successfully esterified with phenols. The produced esters can be utilized as the precursor of various carbonyl compounds.
- Ishida, Naoki,Kawasaki, Tairin,Murakami, Masahiro,Tosaki, Tomohiro
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supporting information
p. 7683 - 7687
(2021/10/12)
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- Synthesis of N-trifluoromethyl amides from carboxylic acids
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Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.
- Flavell, Robert R.,Liu, Jianbo,Parker, Matthew F. L.,Toste, F. Dean,Wang, Sinan,Wilson, David M.
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supporting information
p. 2245 - 2255
(2021/08/12)
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- BODIPY based A-D-A molecules: Effect of CF3 group substitution at meso phenyl group
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Two pairs of A-D-A molecules have been synthesized with fluorene and benzodithiophene as the central donor subunits and terminal BODIPY units, functionalized with either a 4-methylphenyl or 4-trifluoromethylphenyl group at the meso position. The effect of the para substituent of the meso phenyl group on the photophysical properties of these molecules is studied through steady state absorption and fluorescence spectroscopy as well as femtosecond transient absorption and time resolved fluorescence spectroscopy techniques. Applicability of these molecules as donors in solution processed solar cell active layers was investigated through time resolved microwave conductivity measurements on blends with PC60BM acceptor, which shows a varying yield of charge transfer with choice of substituent. Transient absorption spectroscopy is then employed to investigate the role of the 4-trifluoromethylphenyl group in altering the efficiency of charge transfer from these A-D-A molecules to PC60BM. The results show a consistent picture of picosecond charge transfer and a component of a few hundred ps geminate recombination that results in a small yield of long-lived free charges optimized for the methylphenyl derivatives.
- Johnson, Justin C.,Larson, Bryon W.,Ramamurthy, Praveen C.,Tarafdar, Gourav
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- Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters
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We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.
- Lee, Minhan,Jung, Hoimin,Kim, Dongwook,Park, Jung-Woo,Chang, Sukbok
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supporting information
p. 11999 - 12004
(2020/08/06)
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- Design, synthesis and agricultural evaluation of derivatives of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin
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ABTRACT: This study aims to design and synthesize a series of N-Acyl-N-(m-fluoro- benzyl)-6- amino-coumarins through the principle of active substructure stitching, which are based on the core structure of N-(m-fluoro-benzyl)-6-amino-coumarin. The structures of target compounds e1–e25 have been characterized by 1H NMR, 13C NMR, ESI-MS and elemental analysis. Meanwhile, their agricultural activity have been evaluated in two weeds (Amaranth and Crabgrass) and four widespread noxious pathogens (V.mali, B.cinerea, F.axysporium and C.bacteria). The herbicidal activity results showed that almost all synthetic molecules have a greater impact on the stem system than on the root. Excellent inhibition rates were discovered from compounds e2–e5 and e20–e23 against Amaranth on stems, which were above 58percent(20 mg/L), 68percent(100 mg/L) respectively. Compounds e2 and e21 also exhibited striking inhibition on stems growth of both weeds. Anti-pathogenic activity showed that all the compounds exerted a better inhibitory activity on B.cinerea at 20 ppm compared to control carbendazim. All the heterocyclic substituted compounds (e17–e24, >57percent) made a better influence than the control (54.1percent) at the100 ppm. This research provides promising herbicidal and anti-pathogenic agents that have the better effects and can be potential for further development.
- Ding, Yin-hao,Dong, Jing-jing,Feng, Bai-cheng,Hao, Shuang-hong,Jin, Yan,Wei, Yan
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supporting information
(2020/08/19)
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- On the role of the vinylsulfoxide side chain of dirchromone towards its bioactivities
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Analogs of dirchromone were prepared to shed light on the pivotal role of its peculiar vinylsulfoxide side chain towards its cytotoxic and antimicrobial properties, especially dependant upon the presence and oxidation state of sulfur. The reaction of dirchromone with cysteamine revealed a surprising Michael acceptor behavior with elimination of the methylsulfinyl moiety and redox transformation of the sulfur atom that could be involved in the mode of action of dirchromone within cells.
- Alsarraf, Jér?me,Legault, Jean,Mihoub, Mouadh,Pichette, André,St-Gelais, Alexis
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supporting information
p. 9700 - 9705
(2020/12/28)
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- Electroluminescent material containing anthracene derivative with polar substituent group and preparation method and application of electroluminescent material
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The invention belongs to the technical field of organic optoelectronics and discloses an electroluminescent material containing an anthracene derivative with a polar substituent group and a preparation method and application of the electroluminescent material. A structural formula of the electroluminescent material is as shown in the specification. By introduction of parallel ring structures at 9and 10 sites of anthracene, a plane structure is expanded while anthracene unit advantages are kept, the material is less prone to crystallization, and the carrier transmission performance of the material can be improved beneficially; by introduction of a solubilizing group, solubility of a novel monomer of the anthracene derivative can be evidently improved; an appropriate unit with steric hindrance and the monomer of the anthracene derivative are coupled to obtain the electroluminescent material, fluorescence quenching caused by intermolecular gathering in a solid state can be effectively avoided, efficient and stable luminescent device performances are achieved, light emitting efficiency of devices is improved, service lives are prolonged, and the requirement on full-color display is met. The electroluminescent material is dissoluble in various polar solvents, a preparation process is green and environmentally friendly, and a huge development potential and a promising prospect in the field of organic electronic displaying are achieved.
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Paragraph 0086-0089
(2019/01/23)
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- Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus
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Influenza A virus is an enveloped negative single-stranded RNA virus that causes febrile respiratory infection and represents a clinically challenging threat to human health and even lives worldwide. Even more alarming is the emergence of highly pathogenic avian influenza (HPAI) strains such as H5N1, which possess much higher mortality rate (60%) than seasonal influenza strains in human infection. In this study, a novel series of heteroaromatic-based benzenesulfonamide derivatives were identified as M2 proton channel inhibitors. A systematic investigation of the structure-activity relationships and a molecular docking study demonstrated that the sulfonamide moiety and 2,5-dimethyl-substituted thiophene as the core structure played significant roles in the anti-influenza activity. Among the derivatives, compound 11k exhibited excellent antiviral activity against H5N1 virus with an EC50 value of 0.47 μM and selectivity index of 119.9, which are comparable to those of the reference drug amantadine.
- Yu, Yongshi,Tazeem,Xu, Zhichao,Du, Liaoqi,Jin, Mengyu,Dong, Chune,Zhou, Hai-Bing,Wu, Shuwen
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- Identification of Phenylpyrazolone Dimers as a New Class of Anti-Trypanosoma cruzi Agents
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Chagas disease is becoming a worldwide problem; it is currently estimated that over six million people are infected. The two drugs in current use, benznidazole and nifurtimox, require long treatment regimens, show limited efficacy in the chronic phase of infection, and are known to cause adverse effects. Phenotypic screening of an in-house library led to the identification of 2,2′-methylenebis(5-(4-bromophenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one), a phenyldihydropyrazolone dimer, which shows an in vitro pIC50 value of 5.4 against Trypanosoma cruzi. Initial optimization was done by varying substituents of the phenyl ring, after which attempts were made to replace the phenyl ring. Finally, the linker between the dimer units was varied, ultimately leading to 2,2′-methylenebis(5-(3-bromo-4-methoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (NPD-0228) as the most potent analogue. NPD-0228 has an in vitro pIC50 value of 6.4 against intracellular amastigotes of T. cruzi and no apparent toxicity against the human MRC-5 cell line and murine cardiac cells.
- Sijm, Maarten,Siciliano de Araújo, Julianna,Ramos Llorca, Alba,Orrling, Kristina,Stiny, Lydia,Matheeussen, An,Maes, Louis,de Esch, Iwan J. P.,de Nazaré Correia Soeiro, Maria,Sterk, Geert Jan,Leurs, Rob
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supporting information
p. 1662 - 1668
(2019/08/30)
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- Regioisomeric BODIPY Benzodithiophene Dyads and Triads with Tunable Red Emission as Ratiometric Temperature and Viscosity Sensors
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Regioisomeric acceptor-donor (AD) molecular rotors (p-AD, m-AD and m-ADA) were synthesized and characterized, wherein dyads p-AD and m-AD, and triad m-ADA contained 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) and benzodithiophene (BDT) as electron-acceptor and electron-donor, respectively. In all the compounds, the donor and acceptor moieties are electronically decoupled by a phenyl spacer, either through a para coupling or through a meta coupling. The dyad counterparts p-AD and m-AD showed distinct photophysical characteristics in which dyad p-AD showed TICT band at ca. 654 nm characterized by a Stokes shift of ca. 150 nm and prominent solvatochromism. However, meta regioisomeric triad m-ADA showed well-defined aggregation in solution. Notably, because of the temperature-tunable and solvent-viscosity-dependent emission, efficient ratiometric temperature sensing with positive and negative temperature coefficients and viscosity sensing was observed for all compounds. Interestingly, the fluorescence of dyad m-AD (in 10/90 v/v THF/water) revealed a near-white light emission with CIE chromaticity coordinates (x, y) of (0.32, 0.29). Furthermore, the fluorescence emission of p-AD in THF at 0 °C also showed a near-white light emission with chromaticity coordinates (x, y) of (0.34, 0.27). Such multifunctional rotors with readily tunable emission in the red region and prominent temperature- and viscosity-sensing abilities are promising for sensing and bioimaging applications.
- Aswathy,Sharma, Sushil,Tripathi, Narendra Pratap,Sengupta, Sanchita
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supporting information
p. 14870 - 14880
(2019/11/13)
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- Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides
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Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.
- Lee, Yong Ho,Morandi, Bill
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p. 1016 - 1022
(2018/09/06)
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- Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis
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We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.
- De La Higuera Macias, Maximiliano,Arndtsen, Bruce A.
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supporting information
p. 10140 - 10144
(2018/08/23)
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- Diaryl vinyl cyclic amine derivatives and preparation method thereof
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The invention provides diaryl vinyl cyclic amine derivatives and a preparation method thereof. The aryl substituted groups of the diaryl vinyl cyclic amine derivatives have a hydroxyl or hydroxy derivative functional groups in the ortho positions of vinyl groups. The bioactivity test shows that the compounds have anticholinergic activity, and the ortho-hydroxy groups can significantly enhance theantagonistic activity; the compounds can be used as active pharmaceutical ingredients for treating asthma, chronic obstructive pulmonary disease (COPD), rhinorrhea caused by allergic rhinitis and cold, urinary incontinence, Parkinson's disease, and the like.
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Paragraph 0356; 0358-0361
(2018/09/08)
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- Palladium-catalyzed intramolecular C-H arylation of 2-halo-: N -Boc- N -arylbenzamides for the synthesis of N-H phenanthridinones
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A palladium catalyzed synthesis of N-H phenanthridinones was developed via C-H arylation. The protocol gives phenanthridinones regioselectively by one-pot reaction without deprotection. It exhibits broad substrate scope and affords targets in up to 95% yields. Importantly, it could be applied for the less reactive o-chlorobenzamides.
- Hu, Quan-Fang,Gao, Tian-Tao,Shi, Yao-Jie,Lei, Qian,Yu, Luo-Ting
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p. 13879 - 13890
(2018/04/25)
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- Synthesis of phthalic acid derivatives: Via Pd-catalyzed alkoxycarbonylation of aromatic C-H bonds with alkyl chloroformates
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A Pd(ii)-catalyzed alkoxycarbonylation of aromatic C-H bonds with alkyl chloroformates has been developed. A broad range of benzamides and alkyl chloroformates are compatible with this protocol. The reaction is operationally simple and scalable. The direct group could be readily removed to access substituted phthalic acid esters (PAEs), 1,2-dibenzyl alcohols and phthalamides. Besides alkoxycarbonylation of benzamide β-C-H bonds, γ-alkoxycarbonylation of 2-phenylacetamide is also feasible.
- Liao, Gang,Chen, Hao-Ming,Shi, Bing-Feng
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supporting information
p. 10859 - 10862
(2018/10/02)
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- Urea Derivatives of 2-Aryl-benzothiazol-5-amines: A New Class of Potential Drugs for Human African Trypanosomiasis
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A previous publication from this lab (Patrick, et al. Bioorg. Med. Chem. 2016, 24, 2451-2465) explored the antitrypanosomal activities of novel derivatives of 2-(2-benzamido)ethyl-4-phenylthiazole (1), which had been identified as a hit against Trypanosoma brucei, the causative agent of human African trypanosomiasis. While a number of these compounds, particularly the urea analogues, were quite potent, these molecules as a whole exhibited poor metabolic stability. The present work describes the synthesis of 65 new analogues arising from medicinal chemistry optimization at different sites on the molecule. The most promising compounds were the urea derivatives of 2-aryl-benzothiazol-5-amines. One such analogue, (S)-2-(3,4-difluorophenyl)-5-(3-fluoro-N-pyrrolidylamido)benzothiazole (57) was chosen for in vivo efficacy studies based upon in vitro activity, metabolic stability, and brain penetration. This compound attained 5/5 cures in murine models of both early and late stage human African trypanosomiasis, representing a new lead for the development of drugs to combat this neglected disease.
- Patrick, Donald A.,Gillespie, J. Robert,McQueen, Joshua,Hulverson, Matthew A.,Ranade, Ranae M.,Creason, Sharon A.,Herbst, Zackary M.,Gelb, Michael H.,Buckner, Frederick S.,Tidwell, Richard R.
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supporting information
p. 957 - 971
(2017/02/19)
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- Dehydrative Nazarov-type electrocyclizations of alkenyl (hetero)aryl carbinols via calcium catalysis: Access to cyclopenta[b]thiophenes and indene derivatives
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A general approach to the understudied cyclopenta[b]thiophenes is reported. The products were directly generated from calcium-catalyzed, dehydrative, Nazarov-type electrocyclizations of alkenyl thienyl carbinols in up to 82% yield. The thienyl carbinols demonstrated good tolerance for aryl and heteroaryl substituents on the alkene. Aryl carbinols were also amenable to the calcium-catalyzed conditions and afforded indene derivatives in good yields. In most cases, the reaction was selective for the thermodynamic alkene isomer; however, substituent effects played a role in determining product outcomes. Mechanistically, the calcium catalyst initiated formation of alkenyl (hetero)aryl carbinyl cations which subsequently underwent a 4π electrocyclization and elimination that is reminiscent of the Nazarov reaction. This transformation is significant for two main reasons: 1) it represents one of the only examples of catalysis for dehydrative, Nazarov-type electrocyclizations in which thiophene was compatible; 2) it allowed for the direct formation of cyclopenta[b]thiophenes while circumventing the need for cyclopenta[b]thiophenones as precursors.
- Martin, M. Cynthia,Sandridge, Matthew J.,Williams, Corey W.,Francis, Zola A.,France, Stefan
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p. 4093 - 4108
(2017/06/29)
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- Merging gold catalysis, organocatalytic oxidation, and Lewis acid catalysis for chemodivergent synthesis of functionalized oxazoles from: N -propargylamides
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Novel catalytic systems consisting of cationic gold complexes, N-hydroxyphthalimide (NHPI), and transition-metal-based Lewis acids have been developed for the one-pot synthesis of functionalized oxazoles from N-propargylamides with excellent functional group tolerance. These transformations demonstrated the excellent compatibility of homogeneous gold catalysis with organocatalytic oxidative carbon-nitrogen bond formations using tert-butyl nitrite as the terminal oxidant. Moreover, oxazolecarbonitriles or carboxamides can be easily synthesized in a one-pot protocol according to the different synthetic requirements.
- Mai, Shaoyu,Rao, Changqing,Chen, Ming,Su, Jihu,Du, Jiangfeng,Song, Qiuling
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supporting information
p. 10366 - 10369
(2017/09/25)
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- Design, Synthesis, and Biological Evaluation of Novel Type I1/2 p38α MAP Kinase Inhibitors with Excellent Selectivity, High Potency, and Prolonged Target Residence Time by Interfering with the R-Spine
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We recently reported 1a (skepinone-L) as a type I p38α MAP kinase inhibitor with high potency and excellent selectivity in vitro and in vivo. However, as a type I inhibitor, it is entirely ATP-competitive and shows just a moderate residence time. Thus, the scope was to develop a new class of advanced compounds maintaining the structural binding features of skepinone-L scaffold like inducing a glycine flip at the hinge region and occupying both hydrophobic regions I and II. Extending this scaffold with suitable residues resulted in an interference with the kinase's R-Spine. By synthesizing 69 compounds, we could significantly prolong the target residence time with one example to 3663 s, along with an excellent selectivity score of 0.006 and an outstanding potency of 1.0 nM. This new binding mode was validated by cocrystallization, showing all binding interactions typifying type I1/2 binding. Moreover, microsomal studies showed convenient metabolic stability of the most potent, herein reported representatives.
- Walter, Niklas M.,Wentsch, Heike K.,Bührmann, Mike,Bauer, Silke M.,D?ring, Eva,Mayer-Wrangowski, Svenja,Sievers-Engler, Adrian,Willemsen-Seegers, Nicole,Zaman, Guido,Buijsman, Rogier,L?mmerhofer, Michael,Rauh, Daniel,Laufer, Stefan A.
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supporting information
p. 8027 - 8054
(2017/10/18)
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- C10H4O2S2/graphene composite as a cathode material for sodium-ion batteries
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Organic electroactive materials are promising candidates for next generation sodium ion batteries (SIBs) due to their low cost, sustainability and environmental benignity. It is of great interest to develop organic compounds with multifunctional groups to be used as electrode materials for SIBs owing to their light weight, multi-electron reactions, redox stability and structural diversity. The organic compound 4,8-dihydrobenzo[1,2-b:4,5-b′] dithiophene-4,8-dione (BDT) was prepared by a facile solution method, and its graphene composite (BDT-G) was synthesized by a simple dispersion-deposition process. BDT-G as a cathode material demonstrated much enhanced electrochemical performance, including higher reversible capacity (217 mA h g-1vs. 145 mA h g-1), better cycling performance (~175 mA h g-1vs. ~100 mA h g-1 after 70 cycles at 0.2C), and higher rate capabilities (1.7 times better than BDT at 2C) compared with BDT. It is revealed that these improved electrochemical properties should be mainly attributed to the excellent electronic conductivity and ionic transport efficiency promoted by graphene. Furthermore, the fast electrode reaction of BDT with the help of unlimited electron transport via the two-dimensional graphene network results in enhanced usage of materials, and BDT in the composite with graphene could be inhibited from dissolution in the organic electrolyte.
- Chen, Xiaoju,Wu, Yiwen,Huang, Zhongkang,Yang, Xiaoyun,Li, Weijie,Yu, Laura Chuan,Zeng, Ronghua,Luo, Yifan,Chou, Shu-Lei
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p. 18409 - 18415
(2016/12/07)
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- A highly selective and sensitive probe based on benzo[1,2-b:4,5-b′]dithiophene: Synthesis, detection for Cu(II) and self-assembly
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A novel turn-off probe for copper(II) containing benzo[1,2-b:4,5-b′]dithiophene (BDT) and two picolinamide units was synthesized. In this probe, two picolinamide units complex with one Cu2+ ion and two nitrogen atoms in each picolinamide unit coordinate with Cu2+, which is verified by DFT calculation. Its fluorescence quantum yield is 0.43 and the detection limit is as low as 2.4×10-8 mol/L. The results show that the probe displays good selectivity for Cu2+ over other ions (Mn2+, Pb2+, Cr3+, Zn2+, Ni2+, K+, Ca2+, Ag+, Mg2+, Fe3+, Fe2+, Hg2+, Al3+, Cd2+, Pd2+, Co2+). Furthermore, the probe induced by Cu2+ and the π-π interaction of the aromatic unit can also form rod structure assembly, which can be observed by scanning electron microscopy (SEM).
- Ma, Yuwen,Leng, Taohua,Lai, Guoqiao,Li, Zhifang,Xu, Xiaojia,Zou, Jianwei,Shen, Yongjia,Wang, Chengyun
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p. 2219 - 2225
(2016/04/09)
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- Rh(III)-Catalyzed Redox-Neutral Annulation of Primary Benzamides with Diazo Compounds: Approach to Isoquinolinones
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Reported herein is a Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds, representing an efficient and economic protocol to isoquinolinones. The procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released. Further utilization of the method provided an alternative route to functionalized isoquinolines.
- Wu, Youzhi,Sun, Peng,Zhang, Kaifan,Yang, Tie,Yao, Hequan,Lin, Aijun
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p. 2166 - 2173
(2016/03/15)
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- Nickel(II)-Mediated Regioselective C H Monoiodination of Arenes and Heteroarenes by using Molecular Iodine
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The 8-aminoquinoline-directed, nickel(II)-mediated ortho-iodination of benzamides using molecular iodine has been developed. The process is highly regioselective and furnishes only monoiodinated products. A broad range of arenes and heteroarenes with diverse functional groups provided monoiodinated products in good to excellent yields. (Figure presented.) .
- Khan, Bhuttu,Kant, Ruchir,Koley, Dipankar
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supporting information
p. 2352 - 2358
(2016/07/28)
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- 2,6-bis(triphenylamine)-4,8-bis(alkoxy)benzo[1,2-b:4,5-b']bithiophene and preparation for same
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The invention discloses a hole transport material 2,6-bis(triphenylamine)-4,8-bis(alkoxy)benzo[1,2-b:4,5-b']bithiophene for a perovskite solar cell. The hole transport material has a simple molecular structure, a lateral group to which an aromatic functional group can be introduced, high hole mobility, high efficiency, high electrical conductivity and high dissolubility, and the perovskite solar cell prepared from the hole transport material can be matched with a perovskite energy level. The invention also discloses a preparation method for the hole transport material. The hole transport material for the perovskite solar cell is prepared by an SUZUKI reaction step from raw materials 2,6-dibromo-4,8-bis(alkoxy)benzo[1,2-b:4,5-b']dithiophene and 4-(diphenylamino)phenylboronicacid. The preparation method has the characteristics of simplicity in operation, readily available raw materials, easiness for separation and high yield.
- -
-
Paragraph 0011; 0012
(2017/07/21)
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- Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides
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We report a palladium-catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon-halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products. The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri-tert-butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon-halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles.
- Quesnel, Jeffrey S.,Kayser, Laure V.,Fabrikant, Alexander,Arndtsen, Bruce A.
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supporting information
p. 9550 - 9555
(2015/06/30)
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- Correlation of structure and photovoltaic performance of benzo[1,2-b:4,5-b′]dithiophene copolymers alternating with different acceptors
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Four π-conjugated benzo[1,2-b:4,5-b′]dithiophene (BDT) based polymers were synthesized for application in polymer solar cells. These polymers possessed desirable HOMO/LUMO levels for polymer photovoltaic applications. PBDTT-TTz and PBDTT-DTBT displayed strong absorption in the range of 300-650 nm, while PBDTT-DPP and PBDTT-TTDPP showed a further 100 nm extended absorption band. The lowest unoccupied molecular orbital energy levels of polymers were tuned effectively from -3.34 eV to -3.81 eV by fusing with different accepting units. A maximum power conversion efficiency of 2.60% was obtained from photovoltaic cells with a PBDTT-TTz:PC61BM (1:2, w/w) blend film as the active layer, with a short circuit current density of 8.37 mA cm-2, an open circuit voltage of 0.70 V, and a fill factor of 44.3%. This journal is
- Yu, Jiangsheng,Zhao, Baofeng,Nie, Xuemei,Zhou, Baojin,Li, Yang,Hai, Jiefeng,Zhu, Enwei,Bian, Linyi,Wu, Hongbin,Tang, Weihua
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supporting information
p. 2248 - 2255
(2015/03/18)
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- organic semiconductor compound, manufacturing method thereof, and organic electronic device that contains it
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The present invention relates to an organic semiconductor compound, a method for manufacturing the same, and an organic electronic device comprising the same and, more specifically, to an organic semiconductor compound including quinoxaline, a method for manufacturing the same, and an organic electronic device comprising the same. In addition, by having a low band gap by synthesizing and copolymerizing a thiophene derivative containing sulfur (S) with a quinoxaline-based compound, the organic electronic device comprising the same has a higher efficiency with an innovative combination with a fullerene derivative, which is a photoactive layer, with the organic semiconductor compound of the present invention. The organic semiconductor compound of the present invention has high thermal stability and high solubility and the organic electronic device comprising the same has excellent electric characteristics, thereby can be valuably used as a n-type material of the organic electronic device, especially an organic solar cell or an organic thin film transistor.
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-
Paragraph 0183-0186
(2016/10/09)
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- Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles
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The Rh(III)-catalyzed selective bromination and iodination of electron-rich heterocycles is reported. Kinetic investigations show that Rh plays a dual role in the bromination, catalyzing the directed halogenation and preventing the inherent halogenation of these substrates. As a result, this method gives highly selective access to valuable halogenated heterocycles with regiochemistry complementary to those obtained using uncatalyzed approaches, which rely on the inherent reactivity of these classes of substrates. Furans, thiophenes, benzothiophenes, pyrazoles, quinolones, and chromones can be applied.
- Schr?der, Nils,Lied, Fabian,Glorius, Frank
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supporting information
p. 1448 - 1451
(2015/02/19)
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- Cobalt-promoted dimerization of aminoquinoline benzamides
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A method for aminoquinoline-directed, cobalt-promoted dimerization of benzamides has been developed. Reactions proceed in ethanol solvent in the presence of Mn(OAc)2 cocatalyst and Na2CO3 base and use oxygen as a terminal oxidant. Bromo, iodo, nitro, ether, and ester moieties are compatible with the reaction conditions. Cross-coupling of electronically dissimilar aminoquinoline benzamides proceeds with modest yields and selectivities.
- Grigorjeva, Liene,Daugulis, Olafs
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supporting information
p. 1204 - 1207
(2015/05/20)
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- Carboxylate Assisted Ni-Catalyzed C-H Bond Allylation of Benzamides
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A one-step synthetic method was developed for allylation of benzamides using Ni(COD)2/RCO2H and [Ni(μ-H2O)(OOCCMe3)2(HOOCCMe3)2]2 (A′) catalytic system. Efficient, well-defined, air and moisture-stable Ni-pivalate complex was isolated and employed in catalytic allylation. The influence of solvent on product selectivity was also investigated. Nickel-back: A one-step synthetic method was developed for the allylation of benzamides using in situ formed nickel carboxylate Ni(COD)2/RCO2H catalyst (see scheme). The air and moisture stable Ni-pivalate complex was isolated and employed in catalytic allylation. The influence of solvent on product selectivity is discussed.
- Barsu, Nagaraju,Kalsi, Deepti,Sundararaju, Basker
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supporting information
p. 9364 - 9368
(2015/06/30)
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- Dithieno[3,2-b:2′,3′-d]pyridin-5(4H)-one-based polymers with a bandgap up to 2.02 eV for high performance field-effect transistors and polymer solar cells with an open-circuit voltage up to 0.98 v and an efficiency up to 6.84%
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A new electron donor, 4-(2-octyldodecyl)-dithieno[3,2-b:2′,3′-d]pyridin-5(4H)-one (DTPO), for polymer semiconductors is reported. Its homopolymer PDTPO reveals a high hole mobility of 0.19 cm2 V-1 s-1 in field-effect transistors. Its copolymers with benzodithiophenes (BDTO and BDTT), namely PDTPO-BDTO and PDTPO-BDTT, not only show wide optical bandgaps of 2.02 and 1.95 eV, but also possess deep HOMO levels of -5.38 and -5.44 eV, respectively. The polymer solar cell based on PDTPO-BDTO with an inverted architecture achieves a power conversion efficiency (PCE) of 6.84% with a high open-circuit voltage (Voc) of 0.93 V, while the one with PDTPO-BDTT realizes the same PCE with conventional architecture and a reasonably high Voc of 0.96 V. The PCEs are among the highest ever reported for wide bandgap PSCs. Compared to the blend with PDTPO-BDTO having the 2-ethylhexyloxy group, the one with PDTPO-BDTT having the 5-(2-ethylhexyl)thiophene-2yl- group is demonstrated to be superior as a result of faster exciton separation into free charge carriers and larger driving force for exciton dissociation, which results in high short-circuit current and Voc, respectively. The wide optical bandgaps and the excellent device performances make these polymers good candidates for boosting the PCE of the PSCs with a ternary blend layer or tandem structures.
- Hao, Minghui,Luo, Guoping,Shi, Keli,Xie, Guohua,Wu, Kailong,Wu, Hongbin,Yu, Gui,Cao, Yong,Yang, Chuluo
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p. 20516 - 20526
(2015/10/28)
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- Synthesis of Amphiphilic RuII Heteroleptic Complexes Based on Benzo[1,2-b:4,5-b′]dithiophene: Relevance of the Half-Sandwich Complex Intermediate and Solvent Compatibility
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The detailed synthesis and characterization of four ruthenium(II) complexes [RuLL′(NCS)2] is reported, in which L represents a 2,2′-bipyridine ligand functionalized at the 4,4′ positions with benzo[1,2-b:4,5-b′]dithiophene derivatives (BDT) and L′ is 2,2′-bipyridine-4,4′-dicarboxylic acid unit (dcbpy) (NCS=isothiocyanate). The reaction conditions were adapted and optimized for the preparation of these amphiphilic complexes with a strong lipophilic character. The photovoltaic performances of these complexes were tested in TiO2 dye-sensitized solar cell (DSSC) achieving efficiencies in the range of 3-4.5 % under simulated one sun illumination (AM1.5G).
- Urbani, Maxence,Medel, María,Kumar, Sangeeta Amit,Ince, Mine,Bhaskarwar, Ashok N.,González-Rodríguez, David,Gr?tzel, Michael,Nazeeruddin, Mohammad Khaja,Torres, Tomás
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supporting information
p. 16252 - 16265
(2015/11/03)
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- Structural design of benzo[1,2- b:4,5- b ′]dithiophene-based 2D conjugated polymers with bithienyl and terthienyl substituents toward photovoltaic applications
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In this contribution, six conjugated polymers consisting of benzo[1,2-b:4,5-b′]dithiophene-bithiophene (BDT-BT) and benzo[1,2-b:4,5-b′]dithiophene-benzothiadiazle (BDT-BTD) as building blocks in the main chain were synthesized by coupling polymerization and utilized for photovoltaic applications. By directly attaching three kinds of alkylthienyl side chains to the conjugated main chain, the resulted two-dimensional configuration revealed a broader absorption range due to the ground state electron transition of their corresponding alkylthienyl units and polymer backbone. Temperature-dependent absorbance, emission spectra, and thermal annealing further verify that the shoulder band(s) were originated from the aggregated (crystalline) species of polymers. The photovoltaic properties of the donor-acceptor polymers revealed well-defined side chain geometries, physical, and electronic structures and showed the highest power conversion efficiency of 4.25% among polymer solar cells based on two-dimensional (2-D) bithienyl- or terthienyl-substituted benzodithiophene.
- Kuo, Cheng-Yu,Nie, Wanyi,Tsai, Hsinhan,Yen, Hung-Ju,Mohite, Adytia D.,Gupta, Gautam,Dattelbaum, Andrew M.,William, Darrick J.,Cha, Kitty C.,Yang, Yang,Wang, Leeyih,Wang, Hsing-Lin
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p. 1008 - 1020
(2014/03/21)
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- C-H activation by amide chelation control: Ruthenium-catalyzed direct synthesis of 2-Aryl-3-furanamides
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A new, catalytic methodology for the synthesis of heterobiaryls by the ruthenium-catalyzed C-H activation/cross-coupling of heterocyclic amides with aryl boroneopentylates is surveyed. From this survey, the highly regioselective reaction of furan-3-carboxamide to give 2-aryl-3-furanamides is optimized and generalized in scope with respect to the aryl boroneopentylate coupling partners. Established thereby is a one-step synthetic method which may supercede the broadly applied two-step directed ortho metalation (DoM)-cross coupling reaction involving cryogenic and strong base conditions and which has potential for further ortho and remote metalation chemistry.
- Zhao, Yigang,Snieckus, Victor
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supporting information
p. 1527 - 1532
(2014/06/09)
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- Triazole-assisted ruthenium-catalyzed C-H arylation of aromatic amides
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Site-selective ruthenium(II)-catalyzed direct arylation of amides was achieved through C-H cleavages with modular auxiliaries, derived from easily accessible 1,2,3-triazoles. The triazolyldimethylmethyl (TAM) bidentate directing group was prepared in a highly modular fashion through copper(I)-catalyzed 1,3-dipolar cycloaddition and allowed for ruthenium-catalyzed C-H arylations on arenes and heteroarenes, as well as alkenes, by using easy-to-handle aryl bromides as the arylating reagents. The triazole-assisted C-H activation strategy was found to be widely applicable, to occur under mild reaction conditions, and the catalytic system was tolerant of important electrophilic functionalities. Notably, the flexible triazole-based auxiliary proved to be a more potent directing group for the optimized ruthenium(II)-catalyzed direct arylations, compared with pyridyl-substituted amides or substrates derived from 8-aminoquinoline. Assisting activation: Ruthenium(II)-catalyzed C-H arylations of (hetero)arenes and alkenes have been achieved with aryl halides through removable bidentate auxiliaries derived from modular 1,2,3-triazoles (see scheme; TAM=triazolyldimethylmethyl).
- Al Mamari, Hamad H.,Diers, Emelyne,Ackermann, Lutz
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supporting information
p. 9739 - 9743
(2014/08/18)
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- Synthesis, structural and mesophase characterization of three ring based thiophene liquid crystals
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Thiophene based calamitic mesogens are receiving paramount importance due to their applications in functional organic materials. The insertion of thiophene in the core unit favours a large change in mesophase characteristics as well as application properties in contrast to those mesogens with phenyl ring core alone. In this work, we report the structural as well as mesophase characterization of six mesogens which are built with a core of three phenyl rings and thiophene ring. The thiophene ring is placed at one end of the core and varied the other end with alkyl/alkoxy chains to investigate the mesophase characteristics. The molecular structures of representative mesogens are confirmed by means of FT-IR and Two-dimensional solution NMR techniques. An enantiotropic nematic phase is observed in all the cases as supported by HOPM and DSC techniques. The mesophase characteristics such as melting and clearing temperatures and phase stability are discussed. A dramatic increase in nematic phase stability for the synthesised mesogens is noticed in contrast to two phenyl ring based thiophene mesogens reported in literature.
- Reddy, M. Kesava,Reddy, K. Subramanyam,Kumar, B.V.N. Phani,Narasimhaswamy
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- Copper-mediated ortho-nitration of (hetero)arenecarboxylates
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Various (hetero)arenecarboxylic acids were converted to the corresponding Daugulis amides and nitrated selectively in the ortho-position in the presence of [CuNO3(PPh3)2] and AgNO2 at 50 °C. A microwave-assisted saponification allows regenerating the carboxylate group within minutes, which may then be removed tracelessly by protodecarboxylation, or substituted by aryl- or alkoxy-groups via decarboxylative cross-coupling.
- Katayev, Dmitry,Pfister, Kai F.,Wendling, Timo,Goossen, Lukas J.
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supporting information
p. 9902 - 9905
(2014/08/18)
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- New low band gap 2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole and benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole based conjugated polymers for organic photovoltaics
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Two new low band gap D-A structured conjugated polymers, PBDTTBI and PBDTBBT, based on 2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole and benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole acceptor units with benzo[1,2-b;3,4-b′]dithiophene as a donor unit have been designed and synthesized via a Stille coupling reaction. The incorporation of the benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole unit into PBDTBBT has significantly altered the optical and electrochemical properties of the polymer. The optical band gap estimated from the onset absorption edge is ~1.88 eV and ~1.1 eV, respectively for PBDTTBI and PBDTBBT. It is observed that PBDTBBT exhibited a deeper HOMO energy level (-4.06 eV) with strong intramolecular charge transfer interactions. Bulk heterojunction solar cells fabricated with a configuration of ITO/PEDOT:PSS/PBDTBBT:PC71BM/Al exhibited a best power conversion efficiency of 0.67%, with a short circuit current density of 4.9 mA cm-2, an open-circuit voltage of 0.54 V and a fill factor of 25%.
- Murali,Rao, Arun D.,Ramamurthy, Praveen C.
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p. 44902 - 44910
(2014/12/11)
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- Metal-free iodine(III)-promoted synthesis of isoquinolones
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A metal-free oxidative cycloaddition reaction of substituted benzamides and alkynes has been developed for the synthesis of isoquinolones by using bis(trifluoracetoxy)iodobenzene (PIFA) and trifluoroacetic acid (TFA). Under mild conditions, a wide variety of isoquinolones were conveniently prepared via oxidative annulation of simple N-methoxybenzamide and diarylacetylene or aryl/alkyl acetylene derivatives in yields up to 87%.
- Chen, Zhi-Wei,Zhu, Yi-Zhou,Ou, Jin-Wang,Wang, Ya-Ping,Zheng, Jian-Yu
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p. 10988 - 10998
(2015/01/08)
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- Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds
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9-Methylacridine was identified as a generally effective ligand to promote a Pd(II)-catalyzed C(sp3) - H and C(sp2) - H alkylation of simple amides with various alkyl iodides. This alkylation reaction was applied to the preparation of unnatural amino acids and geometrically controlled tri- and tetrasubstituted acrylic acids.
- Zhu, Ru-Yi,He, Jian,Wang, Xiao-Chen,Yu, Jin-Quan
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supporting information
p. 13194 - 13197
(2015/03/30)
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- Copper-catalyzed phosphorylation of sp2 C-H bonds
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The phosphorylation of the ortho C-H bonds in benzamides containing an 8-aminoquinoline moiety as a bidentate directing group with H-phosphonates using copper as a catalyst under mild temperature conditions is described. This method shows high functional group compatibility and selectively gives mono-substituted products. This journal is
- Wang, Shan,Guo, Rui,Wang, Gao,Chen, Shan-Yong,Yu, Xiao-Qi
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supporting information
p. 12718 - 12721
(2015/05/20)
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- Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: Preparation and use of 4-trifluoroboratotetrahydroisoquinolones
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Potassium vinyltrifluoroborate was found to be an efficient partner with benzamide derivatives for Rh(III)-catalyzed annulations. 4- Trifluoroboratotetrahydroisoquinolones were generated under mild conditions, affording a regioisomerically complementary substitution pattern to other alkenes in related reactions. These new boron-containing building blocks were derivatized by N-arylations, retaining the boron substituent for further elaboration.
- Presset, Marc,Oehlrich, Daniel,Rombouts, Frederik,Molander, Gary A.
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supporting information
p. 1528 - 1531
(2013/06/27)
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- Dibenzosuberones as p38 mitogen-activated protein kinase inhibitors with low ATP competitiveness and outstanding whole blood activity
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p38α mitogen-activated protein (MAP) kinase is a main target in drug research concerning inflammatory diseases. Nevertheless, no inhibitor of p38α MAP kinase has been introduced to the market. This might be attributed to the fact that there is no inhibitor which combines outstanding activity in biological systems and selectivity. Herein an approach to the development of such inhibitors on the basis of the highly selective molecular probe Skepinone-L is described. Introduction of a "deep pocket" moiety addressing the DFG motif led to an increased activity of the compounds. Hydrophilic moieties, addressing the solvent-exposed area adjacent to hydrophilic region II, conserved a high activity of the compounds in a whole blood assay. Combined with their outstanding selectivity and low ATP competitiveness, these inhibitors are very interesting candidates for use in biological systems and in therapy.
- Fischer, Stefan,Wentsch, Heike K.,Mayer-Wrangowski, Svenja C.,Zimmermann, Markus,Bauer, Silke M.,Storch, Kirsten,Niess, Raimund,Koeberle, Solveigh C.,Grütter, Christian,Boeckler, Frank M.,Rauh, Daniel,Laufer, Stefan A.
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supporting information
p. 241 - 253
(2013/03/13)
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- NOVEL ARYLALKENE DERIVATIVES AND USE THEREOF AS SELECTIVE ESTROGEN RECEPTOR MODULATORS
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The invention provides novel ethylene derivatives represented by Formula I, which may be used as selective estrogen receptor modulators (SERMs) and useful in the prophylaxis and/or treatment of estrogen-dependent conditions or conditions.
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Paragraph 0126
(2013/07/19)
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