- Synthesis and crystal structure of 1,4-bis{[(2'-Thenylaminoformyl)phenoxyl] methyl}benzene
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A novel salicylamide derivative i.e., 1,4-bis{[(2'-thenylaminoformyl) phenoxyl]methyl}benzene with the m.f. C32H28N 2O4S2 has been synthesized and the crystal structure was determined by single crystal X-ray diffraction. There are strong intramolecular hydrogen bonding between the amide nitrogen atoms and the ethereal oxygen atoms which stabilized the structure to form a trans configuration. Furthermore the title compound are linked by intermolecular C9-H9O1 hydrogen bonds into an infinite 1D chain parallel to the bc plane.
- Wang, Li,Wang, Xiao-Run,Cheng, Guo-Quan,Peng, Yun-Qiao,Song, Xue-Qin
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Read Online
- Synthesis of 2,24-Diene-12,13,15,16,34,35,37,38-octaphenyl[44]triphenylparacyclophane
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A new octaphenyl[4.4]triphenylparacyclophanediene was readily synthesized in six steps from p -xylene via the installment of bromine atoms, replacement with a vinyl group, carbonylative coupling, intermolecular followed by intramolecular double Grubbs olefin metathesis, Knoevenagel condensation, and Diels-Alder cycloaddition. The belt-shaped structure and trans -stereochemistry of the alkene moieties of the octaphenyl[4.4]triphenylparacyclophane and a synthetic intermediate, 2,21-dioxo-11,30-diene[3.4.3.4]paracyclophane, were determined by X-ray crystallography. The synthetic methodology leading to octaphenyl[4.4]triphenylparacyclophane is applicable for the synthesis of substituted triphenylparacyclophanes and possibly their corresponding bis-hexabenzocoronenylparacyclophanes via a Scholl-Mullen oxidative aryl-aryl coupling reaction.
- Wiredu, Bernard,Thapa, Mahendra,Hua, Sheen Y.,Desper, John,Hua, Duy H.
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Read Online
- Chiral Fluorescent Metal-Organic Framework with a Pentanuclear Copper Cluster as an Efficient Luminescent Probe for Dy3+Ion and Cyano Compounds
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Luminescent probes have been used for the detection of various heavy metals and toxic compounds. A novel sensor with excellent sensitivity and selectivity is in high demand. Herein, we designed and synthesized a three-dimensional copper-organic framework of pcu α-Po primitive cubic topology with a Schl?fli symbol of {4.4.4.4.4.4.4.4.4.4.4.4.*.*.*}. By taking advantage of metal clusters and a triazole ligand as the metal-organic framework (MOF) components, the newly obtained MOF is stable in various environments and can be potentially used as the sensor. Remarkably, this MOF-based sensor shows high sensitivity and selectivity toward a dysprosium ion (Dy3+) in a multiple-lanthanide mixed solution. Besides, it exhibits luminescent quenching toward various cyano compounds. This chiral cluster-based network provides a potential luminescent probe for various inorganic and organic compounds with high sensitivity and selectivity.
- Wang, Ying,Zhou, Yan Ni,Liang, Yu,Cheng, Lin,Fang, Yu
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supporting information
p. 15085 - 15090
(2021/10/20)
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- Synthesis and photophysics of new pyridyl end-capped 3D-dithia[3.3]paracyclophane-based Janus tectons: Surface-confined self-assembly of their model pedestal on HOPG
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Surface-confined supramolecular self-assembly is currently a promising strategy to create well-organised 2D-networks on conducting surfaces. However, using such substrates tends to quench any electronic properties of the adsorbed molecules. In this context, new pyridyl end-capped 3D-dithia[3.3]paracyclophane-based molecules were designed, along with their model compound (pedestal), with the objective of self-assembling these tectons on any substrate. The synthesis of these new molecules was not straightforward and is consequently described in detail. Once the materials were successfully isolated, their optoelectronic properties were investigated to study potential non-covalent interactions: through pH-dependent absorption and emission measurements, and infra-red spectrometry. We evidenced that both ionic bonding and coordination bonding are compatible with the molecules design. Finally, preliminary scanning tunneling microscopy (STM) studies were performed to study the supramolecular self-assembly properties of the model lower-deck (pedestal) on highly oriented pyrolytic graphite (HOPG): we observed a quasi-square lattice of self-assembled 2D-networks that appear to form independently of the underlying HOPG lattice.
- Attias, A.-J.,Auffray, M.,Charra, F.,Kreher, D.,Mathevet, F.,Sosa Vargas, L.
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p. 7665 - 7674
(2020/06/10)
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- PROCESS FOR PREPARING CYCLOHEXANEDIMETHANOLS AND REACTION PRECURSORS THEREOF
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The present disclosure relates to processes for preparing cyclohexanedimethanol and reaction precursors thereof. The processes include reacting a compound of formula (II)with water in the presence of an organic solvent to form a compound of formula (III):The compound of formula (III) can be further used in the preparation of cyclohexanedimethanol.
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Page/Page column 11; 14
(2019/01/29)
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- SYSTEM AND METHOD FOR PREPARING AROMATIC DERIVATIVE
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A system for preparing an aromatic derivative is provided, including: a photo-bromination reaction section for performing a photocatalytic reaction of an aromatic hydrocarbon and a brominating agent to form an aromatic hydrocarbon bromide; a substitution reaction section for performing a substitution reaction of the an aromatic hydrocarbon bromide from the photo-bromination reaction section with an alkali base compound or an alkali carboxylate compound to form an aromatic derivative; and a regeneration unit for reacting an alkali metal bromide formed by the substitution reaction section with an acid to form a hydrobromic acid. The regeneration unit is in fluid communication with the photo-bromination reaction section, such that the hydrobromic acid is recycled to the photo-bromination reaction section. A method for preparing the aromatic derivative is also provided.
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Paragraph 0077-0078
(2018/03/25)
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- New cyanopyridine based conjugative polymers as blue emitters: Synthesis, photophysical, theoretical and electroluminescence studies
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Herein, we report the design of three new blue light emitting conjugated polymers (Th-Py-1, Th-Py-2 and Th-Py-3), carrying cyanopyridine ring as a strong electron accepting unit and thiophene as well as phenylene vinylene scaffolds with different substituents, as electron donating moieties. The newly designed monomers/polymers were synthesized using well-known synthetic protocols such as cyclocondensation, O-alkylation, Suzuki cross coupling, Wittig and Knoevenagel reactions. They were well-characterized by spectral, thermal, photophysical, electrochemical and gel permeation chromatography (GPC) techniques. Further, they were subjected to theoretical studies using DFT simulations, performed at B3LYP/TZVP level using Turbomole 7.2 V software package. The new polymers were tested in PLED devices (ITO/PEDOT: PSS/Polymer/Al) as emissive materials. Optical studies revealed that, all the polymers displayed light absorption in the range of 377–397 nm and blue light emission in the order of 432–482 nm, respectively. Further, their band-gaps were calculated to be in the order of 2.55–2.64 eV using both optical and electrochemical data. Furthermore, the TGA study indicated that, they possess good thermal stability with onset decomposition temperature, greater than 300 ?C under nitrogen atmosphere. Interestingly, use of these polymers in new PLEDs as emissive layers, has shown improved performance when compared to previously reported polymers in similar type of devices. They show blue light emission with a low threshold voltage of 3.5–3.9 V, affirming an efficient electron injection in the diodes.
- Pilicode, Naveenchandra,K M, Nimith,M N, Satyanarayan,Adhikari, Airody Vasudeva
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- Method for preparing cyclohexanedimethanol and reaction precursor thereof
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The invention discloses a method for preparing cyclohexanedimethanol and a reaction precursor thereof. The method comprises the steps that bis(bromomethyl)benzene is used as a raw material to react with water to prepare xylylene glycol as a reaction precursor and further hydrogenation is performed to prepare the cyclohexanedimethanol. The preparation method of the invention mainly comprises solid-liquid reaction and is better in safety, simple reactants and agents are used to prepare the xylylene glycol, the process is simple, complicated residues can be avoided, and the agent recovery process is relatively simple, and the effects of being more environmentally friendly and more economic are realized.
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Paragraph 0136-0138
(2017/11/29)
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- A sPP for bridged binuclear metallocene compound and its preparation method and application
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The invention provides a bridged dinuclear metallocene compound for sPP as well as a preparation method and application thereof. The structure of the metallocene compound is as shown in the formula I, wherein R1 is selected from hydrogen, methyl, methylene, ethyl and phenyl; R2 is selected from hydrogen, tert-butyl, bromine and chlorine. The preparation method of the compound comprises the following steps: carrying out a reaction on p-xylene, N-bromosuccinimide and benzoyl peroxide to obtain p-cyclite; carrying out a reaction on an alkene-enriched compound and a fluorene lithium compound to obtain bridged lithium fluorene metallocene salt; carrying out a reaction on p-cyclite and the bridged lithium fluorene metallocene salt to obtain a ligand; carrying out a reaction on the ligand and n-butyl lithium, and carrying out a reaction with zirconium tetrachloride to obtain the bridged dinuclear metallocene compound for sPP. The invention further provides the application for using the metallocene compound as a catalyst to catalyze a propylene polymerization reaction.
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Paragraph 0054; 0056; 0057; 0058
(2017/08/26)
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- Bridged asymmetric dinuclear metallocene compounds, and preparation and application thereof
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The invention provides bridged asymmetric dinuclear metallocene compounds, and preparation and application thereof. The compounds have the structure disclosed as Formula I, wherein R1s and R2s are selected from C1-C5 alkyl or phenyl, and are different; optionally, the two R1s or two R2s can independently form a naphthene base with the carbon atom connected with the R1 or R2; and R3 and R4 are selected from hydrogen, C1-C8 alkyl, bromine or chlorine. The bridged asymmetric dinuclear metallocene compounds for sPP have the advantages of simple synthesis route, high product yield and easy separation and purification; and when being used for catalyzing propylene polymerization, the bridged asymmetric dinuclear metallocene compounds have the advantages of low cocatalyst consumption, high catalytic activity and high polymer syndiotacticity.
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Paragraph 0108
(2017/07/22)
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- Pinpoint-fluorinated polycyclic aromatic hydrocarbons (F-PAHs): Syntheses of difluorinated subfamily and their properties
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Difluorinated polycyclic aromatic hydrocarbons (PAHs) containing three to five benzene rings were systematically synthesized by the Pd(II)-catalyzed Friedel–Crafts-type cyclization of 1,1,2-trifluoro- and 1,1-difluoro-1-alkenes and the In(III)-catalyzed tandem cyclization of bis(1,1-difluoroallene)s. Using an array of the difluorinated PAHs that were obtained and previously reported monofluorinated PAHs, the physical properties of the pinpoint-fluorinated PAHs were investigated. (i) The 19F NMR signals of the bay-region fluorine atoms were shifted downfield by ca. 8–14 ppm for vic-difluorinated PAHs and ca. 11–19 ppm for non-vic-difluorinated and monofluorinated PAHs. (ii) The introduction of fluorine into PAH molecules increased their solubilities in organic solvents, which was best exemplified by the high solubilities of 6,7-difluoropicene (5.4 wt%) and 6-fluoropicene (5.3 wt%) in THF. (iii) The HOMO–LUMO energy gaps of the pinpoint-fluorinated PAHs were smaller than that of the corresponding fluorine-free PAH (i.e., picene) by 0.02–0.26 eV, and the HOMO and LUMO energy levels were lowered by 0.10–0.22 eV and 0.12–0.41 eV, respectively.
- Fuchibe, Kohei,Shigeno, Kento,Zhao, Nan,Aihara, Hiromichi,Akisaka, Rikuo,Morikawa, Toshiyuki,Fujita, Takeshi,Yamakawa, Kie,Shimada, Toshihiro,Ichikawa, Junji
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p. 173 - 184
(2017/10/23)
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- Three nuclear hyamines template synthesis and molecular sieve solid acid preparation and application
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The invention relates to a synthesis method of a novel trinuclear aromatic ring quaternary ammonium salt template agent SDAIII, a preparation method of a novel HZSM-5 molecular sieve, and an application of the molecular sieve to study of the catalytic performance in the condensation reaction between ethylene glycol and cyclohexanone after the molecular sieve is modified by chlorosulfonic acid. The novel molecular sieve has the main characteristics of high catalytic activity, good stability, large number of reuse, convenience in catalyst separation, simplicity in after-treatment and little pollution, is efficient environment-friendly solid acid, and is expected to be developed into a green catalyst commonly used in laboratories and industrial production.
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Paragraph 0027-0030
(2017/05/03)
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- Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds
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Detection of cerebral β-amyloid (Aβ) by targeted contrast agents is of great interest for in vivo diagnosis of Alzheimer's disease (AD). Partly because of their planar structure several bis-styrylbenzenes have been previously reported as potential Aβ imaging agents. However, these compounds are relatively hydrophobic, which likely limits their in vivo potential. Based on their structures, we hypothesized that less hydrophobic bis-pyridylethenylbenzenes may also label amyloid. We synthesized several bis-pyridylethenylbenzenes and tested whether these compounds indeed display improved solubility and lower Log?P values, and studied their fluorescent properties and Aβ binding characteristics. Bis-pyridylethenylbenzenes showed a clear affinity for Aβ plaques on both human and murine AD brain sections. Competitive binding experiments suggested a different binding site than Chrysamine G, a well-known stain for amyloid. With a Log?P value between 3 and 5, most bis-pyridylethenylbenzenes were able to enter the brain and label murine amyloid in vivo with the bis(4-pyridylethenyl)benzenes showing the most favorable characteristics. In conclusion, the presented results suggest that bis-pyridylethenylbenzene may serve as a novel backbone for amyloid imaging agents.
- Nabuurs, Rob J.A.,Kapoerchan, Varsha V.,Metaxas, Athanasios,Hafith, Sarah,de Backer, Maaike,Welling, Mick M.,Jiskoot, Wim,van den Nieuwendijk, Adrianus M.C.H.,Windhorst, Albert D.,Overkleeft, Herman S.,van Buchem, Mark A.,Overhand, Mark,van der Weerd, Louise
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p. 6139 - 6148
(2016/11/30)
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- 1,4-double (2-methyl styryl) benzenetrisamide preparation method
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The invention relates to a method for preparing 1,4-bis(2- methyl styryl) benzene (referred to as bis-MSB). The method comprises the following steps: with paraxylene and o-tolualdehyde as raw materials, carrying out bromination and wittig reactions, and preparing the 1,4-bis(2- methyl styryl) benzene by using a one-pot method without separating or purifying the intermediate product. The product is purified by alkylbenzene to obtain a 1,4-bis(2- methyl styryl) benzene product for flickering, the yield is 85.6-86.2%, and the product purity is higher than 99.5%. The 1,4-bis(2- methyl styryl) benzene is prepared by the one-pot method to reduce the reaction steps, simplify the operation process and improve the production efficiency, the production method is simple and effective, and industrial production has been realized.
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Paragraph 0021; 0022; 0024; 0025
(2019/02/04)
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- Improved Halogenation of Methyl Aromatics and Methyl Heteroaromatics: Unexpected Reactivity of Tetrahalogeno-diphenylglycolurils
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1,3,4,6-Tetrachloro (TCDGU) and 1,3,4,6-tetrabromo-3α,6α-diphenylglycolurils smooth halogen oxidizers have been exploited in a new direction as reagents for free radical substitution toward some N-halosuccinimide nonreactive bis-heterocycles. An unexpected selectivity and reactivity were observed with methyl benzenes, methyl heterocycles, and methyl-bis-heterocycles of interest. A chemometric study has been performed to optimize five independent factors of the chlorination reaction with TCDGU. The predictive model was established either for the halogenation conversion and the ratio of monochlorination.
- Moretti, Florian,Poisson, Guillaume,Marsura, Alain
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p. 173 - 183
(2016/05/19)
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- The radical reaction from a fluorine-containing compound
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PROBLEM TO BE SOLVED: To provide a radical reaction substitute solvent for carbon tetrachloride which has been used heretofore as a radical reaction solvent. SOLUTION: A chain fluorine-containing hydrocarbon represented by formula (1): CmH2m+2-nFn(wherein m is an integer of 3-10 and n is an integer of 1 to 2m+1) or a cyclic fluorine-containing hydrocarbon represented by formula (2): CpH2p-qFq(wherein p is an integer of 3-10 and q is an integer of 1 to 2p-1) is used as a solvent for various radical reactions. COPYRIGHT: (C)2011,JPO&INPIT
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Paragraph 0036-0037
(2017/01/05)
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- Synthesis and thermal stability of new polynitrostilbenes
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New polynitrostilbenes were directly synthesised by the Knoevenagel condensation of aromatic aldehydes with nitrotoluenes. The differential scanning calorimetry results demonstrated that the introduction of an amino group and C≤C double bonds could improve the thermal stability.
- Wei, Jianping,Li, Fangmei,Xu, Junhui,Peng, Xinhua
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p. 919 - 925
(2015/06/25)
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- Self-assembly behaviors of the cholesteryl trimeric-phenylene vinylene derivative in the H2O/THF system
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Cholesteryl trimeric phenylene vinylene (Chol-TPV) has been synthesized and characterized. The self-assembly behaviors of Chol-TPV in THF/H2O system at different water content (water content: 40% and 80%) and different solute concentration (solute concentration: 1.0 × 10-5 mol/L and saturated concentration) were studied using UV-vis spectrophotometry, photoluminescence spectrophotometry, and circular dichroism spectroscopy. Based on an analysis of the UV-vis and photoluminescence spectra, Chol-TPV shows the typical H-type aggregation at saturated concentration in 80% aqueous THF. However, Chol-TPV shows the non-typical H-type aggregation under other conditions. The circular dichroism signal suggests that the Chol-TPV exists in the right handed helical architectures with high water content at a concentration of 1.0 × 10-5 mol/L, and a helix inversion was found at saturated concentration.
- Zhao, Yu-Zhen,Zhang, Zhen-Lin,Li, Ying,Liu, Xue-Qiang,Liu, Shi-Min,Yu, Jin-Ku,Zhang, Hai-Quan
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- Co-crystal formation between 2-amino-4,6-dimethylpyrimidine and new p-xylylene-bis(thioacetic) acid
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Novel p-xylylene-bis(thioacetic) acid (p-XBTA) and its co-crystals with 2-amino-4,6-dimethylpyrimidine (DMP) have been synthesized and characterized by single-crystal X-ray diffraction, infrared spectroscopy and thermal analysis methods (TG/DSC). Depending on the crystallization conditions, three different multicomponent crystal forms have been isolated with various chemical compositions and stoichiometries of the co-formers. The ATR-FTIR spectra of the co-crystals display the stretching vibration bands for the co-formers with associated shifts confirming the formation of new phases. DSC and TG were used to reveal the relative stabilities of new solids compared to those of the co-formers.
- Ostasz,Lyszczek,Mazur,Tarasiuk
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p. 10262 - 10272
(2015/02/19)
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- IMAGING LIGANDS
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Compound or a salt or solvate thereof for use as an imaging ligand for the detection of aggregated amyloid-β or for use as a medicament according to the formula (I): wherein R1 and R3 may be the same or different optionally substituted pyridinyl group and wherein R2 is hydrogen or a substituent group comprising at least an oxygen atom or a fluor atom.
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Page/Page column 7
(2013/05/22)
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- Effects of molecular configuration of a chiral trimeric phenylene vinylene on its liquid crystalline properties
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Based on an analysis of the 1H NMR, FT-IR, UV-vis spectra, a chiral trimeric phenylene vinylene derivative (ChTPV) synthesized by a Wittig reaction was determined to have a trans-cis configuration, and it could be isomerized to the trans-trans isomer when treated with iodine. The melting point of ChTPV with a trans-trans configuration increased by 162.1 °C compared to the trans-cis isomer, and the ChTPV with trans-trans configuration exhibited the typical liquid-crystalline texture of the smectic A in the heating process. The results indicated that the molecular configuration can influence the formation of the liquid crystalline phase of ChTPV.
- Yu, Ping,Zhang, Zhen-Lin,Wang, Lei,Liu, Chun-Luan,Liu, Shi-Min,Zhang, Hai-Quan
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p. 397 - 400
(2013/06/27)
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- Direct oxidative conversion of methylarenes into aromatic nitriles
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A variety of methylarenes were successfully converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with NBS or DBDMH in the presence of a catalytic amount of AIBN or BPO, followed by the reaction with molecular iodine in aq NH3 in a one-pot procedure. The present reaction is a useful and practical transition-metal-free method for the preparation of aromatic nitriles from methylarenes.
- Tsuchiya, Daisuke,Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
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supporting information
p. 4194 - 4197
(2013/09/12)
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- New soluble multi-site phase transfer catalysts and their catalysis for dichlorocarbene addition to citronellal assisted by ultrasound - A kinetic study
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Two new soluble multi-site phase transfer catalysts (MPTCs), viz., 1,4-bis-(triethylmethylene ammonium chloride)-2,5-dimethyl benzene (BTMACD) containing di-site and 1,4-bis((3,5-bis(triethylmethyleneammonium chloride)phenoxy)methyl)benzene (TEMACPB) containing tetra-site were prepared and proved by FT-IR, 1H NMR, 13C NMR, mass and elemental analysis. The enhancement of CN peak intensity at 1179 cm-1 noticed in FT-IR, the agreement of m/z values, viz., 405 and 888 for di-site and tetra-site respectively with their theoretical values and the percentage of C, H, N elements noticed in elemental analysis has strongly supported the presence of di-site and tetra-site in the BTMACD and TEMACPB catalysts. Further, the presence of number of active-sites in each catalyst was again confirmed by determining their pseudo-first order rate constant for dichlorocarbene addition to citronellal in the presence of ultrasonic irradiation/mechanical stirring. The comparative study reveals that the kobs determined with the combination of ultrasound and mechanical stirring has shown more activity (3 fold) than with their individual effect. Further, the detailed kinetic study performed with superior tetra-site MPTC (TEMACPB) reveals that the k obs are dependent with the stirring speed, [substrate], [catalyst], [NaOH] and temperature. Based on the kinetic results, thermodynamic parameters are evaluated and an interfacial mechanism is proposed.
- Murugan, Eagambaram,Tamizharasu, Gurusamy
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p. 81 - 89,9
(2020/07/31)
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- Synthesis, structural, and biological evaluation of the arene-linked pyrazolyl methane ligands and their d9/d10 metal complexes
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A series of the p-bis[(1-pyrazolyl)methyl] benzene ligands (L 1-L6) in the DMSO system were synthesized. In the mean time, by using the ligands as a linker, a new family of transition metal coordination polymers, namely, [Cu2(L1)2Cl 4] (1), [Cu2(L2)2Cl4] (2), [Ag(L2)(NO3)] (3), [Zn2(L 2)2(SCN)4] (4) and [Cd2(L 2)(SCN)4] (5) [L1 = 1,4-bis((1H-pyrazol-1-yl) methyl)benzene; L2 = 1,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)methyl) benzene] have been constructed by the reaction of the p-bis[(1-pyrazolyl)methyl] benzene and corresponding to the transition metal compounds in a mixed solution of CH3OH/C2H5OH at mild temperature condition. All the coordination polymers and p-bis[(1-pyrazolyl)methyl]benzene ligands were characterized by elemental analysis, IR spectroscopy, 1H NMR and 13C NMR, and some of them were characterized by UV spectroscopy, thermogravimetric analysis, X-ray powder and X-ray single-crystal diffraction. Structural analyses reveal that the ligands L3-L5 (L 3 = 1,4-bis((4-iodo-1H-pyrazol-1-yl)methyl)benzene, L4 = 1,4-bis((4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene, L5 = 1,4-bis((4-nitro-1H-pyrazol-1-yl)methyl)benzene,L6 = 1,4-bis((4-nitro-3,5-dimethyl-1H-pyrazol-1-yl) methyl) benzene) are discrete organic compound molecules and the complexes 1-5 are 1D M-L-M coordination polymers, which are further interlinked via hydrogen bonds resulting in 2D or even 3D supermolecular networks. The luminescent properties of the coordination polymers 3, 4 and 5 were examined by luminescence spectra. The analytic results indicate that different metal complexes with the same ligand have different influence on the characteristic photoluminescence. Furthermore, the cytotoxicity of the ligands L1-L6 and complexes 1-5 were evaluated against hepG2 cells. For the ligands of L1-L6, the different substituents of the pyrazole ring slightly influenced the cytotoxicity of the cell. It is found that nitro-compounds have shown the highest cytotoxicity under the same concentration condition. The cytotoxic activity of the complexes 1-5 are strongly increased by the introduction of the transition metals.
- Wang, Xin-Yu,Liu, Shu-Qing,Zhang, Chun-Yan,Song, Ge,Bai, Feng-Ying,Xing, Yong-Heng,Shi, Zhan
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p. 151 - 164
(2013/01/15)
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- Fluorescent sensor based on a novel conjugated polyfluorene derivative
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A novel water-soluble polyfluorene derivative, poly[(9,9-bis(3′-((N, N-dimethylamino)N-ethylammonium)propyl)-2,7-fluorene)-alt-2,7-(9, 9-p-divinylbenzene)]dibromide (P-2) was synthesized by the palladium-catalyzed Suzuki coupling reaction and it's quaternized ammonium polyelectrolyte derivatives was obtained through a postpolymerization treatment on the terminal amino groups. The electrochemical and optical properties of the copolymers was fully investigated. The results showed that the new polyfluorene derivative had high electronic conductivity and strong fluorescence, therefore it had good potential to be used in chemical and biological sensors, as shown in optical sensing of bovine albumin (BSA) in this study.
- Gao, Weiqiang,Yan, Mei,Ge, Shenguang,Liu, Xiaoxia,Yu, Jinghua
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experimental part
p. 218 - 223
(2012/08/08)
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- Generation of (nonafluoro-tert-butoxy)methyl ponytails for enhanced fluorous partition of aromatics and heterocycles
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The reaction of sodium perfluoro-tert-butoxide with benzylic carbon-bromide bond(s) leads to the formation of (nonafluoro-tert-butoxy)methyl ponytail(s), which can enhance the fluorous solubility and partition of aromatics and heterocycles.
- Zhao, Xi,Ng, Wing Yan,Lau, Kai-Chung,Collis, Alana E. C.,Horvath, Istvan T.
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experimental part
p. 3909 - 3914
(2012/06/30)
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- Gold(I) styrylbenzene, distyrylbenzene, and distyrylnaphthalene complexes: High emission quantum yields at room temperature
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One gold(I)-substituted styrylbenzene, six digold(I) distyrylbenzenes, one tetragold distyrylbenzene, and four digold distyrylnaphthalene complexes were synthesized using base-promoted auration, alkynylation, triazolate formation, and Horner-Wadsworth-Emmons reactions. The gold(I) fragments are either σ-bonded to the aromatic system, or they are attached through an alkynyl or triazolate spacer. Product formation was monitored using 31P{ 1H} NMR spectroscopy. Systems in which gold(I) binds to the central benzene ring or the terminal phenyl rings were designed. All of these complexes have strong ultraviolet absorptions and emit blue light. The position of the gold(I) attachment influences the luminescence efficiency. Complexes with two gold(I) fragments attached to the ends of the conjugated system have fluorescence quantum yields up to 0.94, when using 7-diethylamino-4- methylcoumarin as the emission standard. Density-functional theory calculations on three high-yielding emitters suggest that luminescence originates from the distyrylbenzene or -naphthalene bridge. Copyright
- Gao, Lei,Niedzwiecki, Daniel S.,Deligonul, Nihal,Zeller, Matthias,Hunter, Allen D.,Gray, Thomas G.
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scheme or table
p. 6316 - 6327
(2012/06/30)
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- Environmentally benign electrophilic and radical bromination 'on water': H2O2-HBr system versus N-bromosuccinimide
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A H2O2-HBr system and N-bromosuccinimide in an aqueous medium were used as a 'green' approach to electrophilic and radical bromination. Several activated and less activated aromatic molecules, phenylsubstituted ketones and styrene were efficiently brominated 'on water' using both systems at ambient temperature and without an added metal or acid catalyst, whereas various non-activated toluenes were functionalized at the benzyl position in the presence of visible light as a radical activator. A comparison of reactivity and selectivity of both brominating systems reveals the H2O2-HBr system to be more reactive than NBS for benzyl bromination and for the bromination of ketones, while for electrophilic aromatic substitution of methoxy-substituted tetralone it was higher for NBS. Also, higher yields of brominated aromatics were observed when using H2O2-HBr 'on water'. Bromination of styrene reveals that not just the structure of the brominating reagent but the reaction conditions: amount of water, organic solvent, stirring rate and interface structure, play a key role in defining the outcome of bromination (dibromination vs bromohydroxylation). In addition, mild reaction conditions, a straightforward isolation procedure, inexpensive reagents and a lower environment impact make aqueous brominating methods a possible alternative to other reported brominating protocols.
- Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej
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experimental part
p. 4429 - 4439
(2009/10/09)
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- Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions
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The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.
- Jereb, Marjan,Zupan, Marko,Stavber, Stojan
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experimental part
p. 555 - 566
(2009/09/06)
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- Electrochemical method for the preparation of dibromomethyl, bis(bromomethyl), and bis(dibromomethyl) arenes
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Electrochemical bromination of alkyl aromatic compounds by two-phase electrolysis yields the corresponding α,α-dibrominated products. The reaction has been carried out in a single-compartment electrochemical cell using aqueous sodium bromide (40-50%), containing a catalytic amount of HBr as electrolyte, and chloroform, containing an alkyl aromatic compound, as the organic phase with a Pt plate as anode at 10-15C. Two-phase electrolysis results in high yields (70-90%) of dibromomethyl, bis(bromomethyl), and bis(dibromomethyl) arenes, depending upon the charge passed.
- Kulangiappar,Karthik,Kulandainathan, M. Anbu
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experimental part
p. 2304 - 2309
(2009/12/06)
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- Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) as powerful reagents for benzylic bromination
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N,N,N′,N′-Tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS], and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) [PBPS] can be used for bromination of benzylic positions in solvent.
- Ghorbani-Vaghei, Ramin,Chegini, Mohammad,Veisi, Hojat,Karimi-Tabar, Mehdi
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scheme or table
p. 1861 - 1865
(2009/07/19)
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- Synthesis of novel amide-crownophanes and Schiff base-crownophanes based on p-phenylene, 2,6-naphthalene, and 9,10-anthracene
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(Chemical Equation Presented) The novel macrocyclic diamides 11-13, 16-18 are obtained in 45-66% yields by the reaction of dipotassium salts 10a-c and 15 with each of 1,4-di(bromomethyl)benzene 4, 2,6-di(bromomethyl)naphthalene 6 and 9,10-di(bromomethyl)anthracene 8, repectively, in boiling DMF. On the other hand, the new macrocyclic Schiff bases 28 and 29 are obtained in 44% and 42% yields by heating the appropriate bis-amines 25b, 26b with the corresponding bis-aldehydes 21, 22, respectively, in refluxing acetic acid under high-dilution conditions.
- Muathen, Hussni A.,Aloweiny, Nour A. M.,Elwahy, Ahmed H. M.
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scheme or table
p. 656 - 663
(2009/12/01)
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- Derivatives of 1,4-bis(3-hydroxycarbonyl-4-hydroxyl)styrylbenzene as PTP1B inhibitors with hypoglycemic activity
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Disalicylic acid derivatives with stilbene and bis-styrylbenzene skeleton were synthesized as PTP1B inhibitors. The most potent in this series exhibited a submicromolar IC50 value. One of the compounds 7b was tested in an animal model for its efficacy as an anti-diabetic or an anti-obesity agent. In feeding compound 7b to diet-induced obese mice, no significant differences in weight gain and food consumption were observed between the drug-treated and the obese control mice. However, 7b significantly lowered the fasting glucose level and improved the glucose tolerance in the obesity-induced diabetic mice.
- Shrestha, Suja,Bhattarai, Bharat Raj,Kafle, Bhooshan,Lee, Keun-Hyeung,Cho, Hyeongjin
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p. 8643 - 8652
(2008/12/23)
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- Luminescent amphiphilic dendrimers with oligo(p-phenylene vinylene) core branches and oligo(ethylene oxide) terminal chains: Syntheses and stimuli-responsive properties
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A class of new dendrimers consisting of hydrophobic oligo(p-phenylene vinylene) core branches and hydrophilic oligo(ethylene oxide) terminal chains was synthesized. These amphiphilic dendritic molecules are highly luminescent and exhibit critical micellization behaviors. They also show a lower critical solution temperature (LCST) in an aqueous medium. Both the critical micelle concentration (CMC) and LCST increased with increasing branch number and the ratio of the hydrophilic oligo(ethylene oxide) to hydrophobic oligo(p-phenylene vinylene) moieties. Besides, a temperature-dependent phase transition from a clear to cloudy aqueous solution was observed. The temperature-induced phase transition was also reflected by fluorescence quenching, 1H NMR resonance peak broadening, and UV-vis absorption shift arising from the hydrophobic conjugated core. These changes in the phase structure and photophysical properties were demonstrated to be highly reversible, indicating some interesting stimuli-responsive behaviors. The Royal Society of Chemistry.
- Chang, Dong Wook,Dai, Liming
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p. 364 - 371
(2008/02/03)
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- Secondary interactions in bromomethyl-substituted benzenes: Crystal structures of three α,α′-bis-bromoxylenes, 1,2,3,5-tetrakis(bromomethyl)benzene, and 1,2,4,5-tetrakis(bromomethyl)benzene
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X-Ray structure determinations of all three isomers of bis(bromomethyl) benzene and of two isomeric tetrakis(bromomethyl)benzenes show that the packing of the molecules is determined principally by interactions of the bromomethyl groups (C-H ? Br and Br ? Br), except for ortho-bis (bromomethyl)benzene, in which C-H ? π interactions play a major role.
- Jones, Peter G.,Ku?, Piotr
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p. 725 - 731
(2008/10/09)
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- Visible light induced 'on water' benzylic bromination with N-bromosuccinimide
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Benzylic bromination of various 4-substituted toluenes (Me, tert-Bu, COOEt and COMe) was effectively conducted with NBS in pure water and with a 40 W incandescent light-bulb as an initiator of the radical chain process, while electron donating groups (OMe and NHAc) directed the reaction to electrophilic aromatic substitution.
- Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej
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p. 1097 - 1099
(2007/10/03)
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- Free radical bromination by the H2O2-HBr system on water
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An aqueous solution of hydrogen peroxide and hydrogen bromide illuminated by a 40 W incandescent light bulb serves as a source of bromine radicals. Various substituted toluenes (H, Me, tBu, Br, COOEt, COPh, NO2) were brominated at the benzyl position. This haloperoxidase-like system for benzylic bromination does not require the presence of metal ions or an organic solvent for efficient conversion of methyl-arenes to benzyl bromides.
- Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej
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p. 7245 - 7247
(2007/10/03)
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- Association of fluorous "phase-vanishing" method with visible-light activation in benzylic bromination by bromine
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In this study the "phase-vanishing" method for diffusion-controlled addition of a reagent (Br2) to a reaction phase via a fluorous membrane (C8F18) is combined with an additional mode of activation (visible-light) to achieve the benzyl bromination of various alkyl-substituted aromatic compounds in a concentrated solution. Benzyl bromination of p-tert-butyl-toluene proceeded in various solvents including hexane and methanol, while the reaction of the neat substrate showed a similar selectivity as in carbon tetrachloride. The effect of the substituent on the para position of toluene on the course of bromination revealed three processes: benzyl bromination with H, Me, tBu and CO2Et substituents, aromatic bromination with OMe and NHAc substituents and the reaction of the 4-acetyl derivative at the substituent to form an α-bromo ketone. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Podgorsek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej
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p. 483 - 488
(2007/10/03)
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- Silicaphosphine (Silphos): A filterable reagent for the conversion of alcohols and thiols to alkyl bromides and iodides
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Silicaphosphine (Silphos), [P(Cl)3-n(SiO2) n], as a new heterogeneous reagent is introduced. This reagent converts alcohols and thiols to their corresponding bromides and iodides in the presence of X2 (X=Br, I) in refluxing CH3CN in high to quantitative yields. Use of Silphos provides a highly practical method for the easy separation of the Silphos oxide byproduct by a simple filtration.
- Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu,Kazemi, Foad
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p. 5699 - 5704
(2007/10/03)
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- A simple and regioselective α-bromination of alkyl aromatic compounds by two-phase electrolysis
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Electrochemical bromination of toluene and substituted toluenes by two-phase electrolysis yields the corresponding α-brominated products. The reaction has been carried out in a single compartment cell with platinum electrodes at 0°C in chloroform using an aqueous sodium bromide solution (60%) containing a catalytic amount of HBr. Two-phase electrolysis results in high yields (60-95%) of monobromo compounds with very high regioselectivity (>95%).
- Raju,Kulangiappar,Anbu Kulandainathan,Muthukumaran
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p. 7047 - 7050
(2007/10/03)
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- Side chain bromination of mono and dimethyl heteroaromatic and aromatic compounds by solid phase N-bromosuccinimide reaction without radical initiator under microwave
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A series of side chain mono and dibromo derivatives of mono and dimethyl heteroaromatic and aromatic compounds (1-17) were synthesized by one step solid phase N-bromosuccinimide (NBS) reaction without radical initiator by microwave irradiation. The benzylic mono and dibromo products were exclusively preferred except in the case of 6-methylpyridine amides (8 and 9) where nuclear and also side chain bromination resulted. Naphthyridine systems resulted improved yields. By this method, we also report the synthesis of 2-pivaloylaminopterin-6- carbaldehyde.
- Goswami, Shyamaprosad,Dey, Swapan,Jana, Subrata,Adak, Avijit Kumar
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p. 916 - 917
(2007/10/03)
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- Novel electroluminescent polymers with fluoro groups in vinylene units
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New electroluminescent polymers with fluoro groups in vinylene units, poly(p-phenylen-edifluorovinylene) (PPDFV) and poly(2-dimethyloctylsilyl-p-phenylenedifluorovinylene) (DMOS-PPDFV), have been synthesized by GILCH polymerization. These polymers have been used as the electroluminescent (EL) layers in double-layer light-emitting diodes (LEDs) (ITO/PEDOT/polymer/Al). PPDFV shows photoluminescence around λ max = 580 nm (exciting wavelength, 410 nm) and yellow electroluminescence around λmax = 565 nm. DMOS-PPDFV shows PL around λmax = 495 nm and green EL around λ max = 540 nm. The current-voltage-luminance (I-V-L) characteristics of the polymers show turn-on voltages of 3.0 V approximately. Two fluoro groups were introduced on every vinylene units of poly(p-phenylenevinylene) (PPV) and poly(2-dimethyloctylsilyl-1,4-phenylenevinylene) (DMOS-PPV) to give PPDFV and DMOS-PPDFV in an attempt to increase the electron affinity of the parent polymer. It was found that the efficiency of PLED of DMOS-PPDFV was about 7 times higher than that of DMOS-PPV.
- Jin, Youngeup,Kim, Jinwoo,Lee, Sungeun,Kim, Jin Young,Park, Sung Heum,Lee, Kwanghee,Suh, Hongauk
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p. 6711 - 6715
(2007/10/03)
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- Rational Design and Synthesis of Novel Dimeric Diketoacid-Containing Inhibitors of HIV-1 Integrase: Implication for Binding to Two Metal Ions on the Active Site of Integrase
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Discovery of diketoacid-containing compounds as HIV-1 integrase (IN) inhibitors played a major role in validating this enzyme as an important target for the development of therapeutics against HIV infection. In fact, S-1360, the first clinically used IN inhibitor containing a triazole ring as a bioisostere of a carboxylic acid moiety belongs to this class of compounds. To understand the role of divalent metal-chelating in the inhibition of IN (J. Med. Chem. 2002, 45, 5661-5670), we designed and synthesized a series of novel dimeric diketo-containing compounds with the notion that such dimeric compounds may simultaneously bind to two divalent metal ions on the active site of IN. We rationalized that the two diketo subunits separated by uniquely designed linkers can potentially chelate two metal ions that are either provided from one IN active site or two active sites juxtaposed together in a higher order tetramer. Herein, we show that all the new compounds are highly potent against purified IN with varied selectivity for strand transfer, and that some of the analogues exert potent inhibition of the cytopathic effect of HIV-1 in infected CEM cells. This study represents the first attempt to rationally target two divalent metal ions on the active site of IN and may have potential implications for the design of second generation diketoacid-containing class of inhibitors.
- Long, Ya-Qiu,Jiang, Xiao-Hua,Dayam, Raveendra,Sanchez, Tino,Shoemaker, Robert,Sei, Shizuko,Neamati, Nouri
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p. 2561 - 2573
(2007/10/03)
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- Reductive bromination of aromatic aldehydes using alkylboron dibromides
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The reductive bromination of aromatic aldehydes with isopinocampheyl boron dibromide in hexane at room temperature produces the corresponding benzyl bromides in excellent yields. (C) 2000 Elsevier Science Ltd.
- Kabalka, George W.,Wu, Zhongzhi,Ju, Yuhong
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p. 5161 - 5164
(2007/10/03)
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- Fluorescent bispyrroles. New building blocks for novel π-conjugated polymers
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Several bispyrroles which are bridged through conjugated aromatic moieties were synthesized by the Wittig-Horner-Emmons reaction. Photophysical and electrochemical data of these highly fluorescent monomers reveal that they are useful building blocks for the design of a wide variety of novel π-conjugated polymers, which may find application as potential optoelectronic materials. (C) 2000 Elsevier Science Ltd.
- Eldo,Arunkumar,Ajayaghosh
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p. 6241 - 6244
(2007/10/03)
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- Crystal structure of a new quasi-two-dimensional compound containing 1,4-bis(imidazol-1-ylmethyl)-benzene (bix) and MnII ions
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A novel MnII complex Mn(bix)3(NO2)2 · 4H2O [bix=1, 4-bis(imidazol-1-ylmethyl) benzene] has been synthesized and characterized by X-ray single crystal structure analysis. The complex crystallizes in the PI space group, with lattice parameters a=9.037(2), b=11.498(2), c=12.404(2) A, α=110.09(3), β= 109.62(3), γ=93.05(3)°, V=1119(1)A3, Dc=1.385 Mgm-3, Z=1, R1=0.072, wR2=0.0725. The X-ray analysis shows that it is a quasi-two-dimensional network containing hydrogen bonds, terminal and bridging bix ligands concurrently.
- Shen, Hao-Yu,Liao, Dai-Zheng,Jiang, Zong-Hui,Yan, Shi-Ping,Wang, Geng-Lin,Yao, Xin-Kan,Wang, Hong-Gen
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p. 387 - 390
(2007/10/03)
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- A new synthesis and application of N, N'-dibromo-N, N'-1,2-ethylene bis(2,5-dimethyl benzene sulfonamide); as a novel selective bromination agent for aromatic compounds
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Reaction Between Novel Compound; N, N' dibromo-N, N'-1,2- ethylene bis(2,5- dimethyl benzene sulfonamide) and aromatic compounds in the carbontetrachloride produces bromo aromatic compounds. In the case of benzene rings that contain mono activated substituted, only para - bromo isomer was formed. At the presence of benzoyl peroxide in the reaction mixture α - Hydrogen from alkyl side chain was substituted with bromine.
- Ardeshir, Khazaei,Abbas, Shirdarreh
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p. 4079 - 4085
(2007/10/03)
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