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 Journal of the Iranian Chemical SocietyJournal Prestige (SJR): 0.31 Citation Impact (citeScore): 1Number of Followers: 0      Hybrid journal (It can contain Open Access articles) ISSN (Print) 1735-207X - ISSN (Online) 1735-2428 Published by Springer-Verlag  [2351 journals]
• Fabrication of a new peroxyoxalate chemiluminescence system containing the
Cy3 fluorophore and its application to carvedilol detection
• Abstract: Abstract Cy3 is a dye that has been widely applied in fluorescence microscopy and single molecule detection due to its low hydrophobicity and intense fluorescence emission. As a new application, this study proposes using Cy3 as the fluorophore of a peroxyoxalate chemiluminescence system. The system relies on the oxidative reaction of bis-(2,4,6-trichlorophenyl) oxalate (TCPO) with H2O2 in the presence of imidazole, as the catalyst, to produce dioxetane via a chemically initiated electron exchange luminescence (CIEEL) process, excite Cy3 by the excess energy of the dioxetane and permit Cy3 to emit yellow light. The chemiluminescence behavior of the system is investigated using different concentrations of TCPO, imidazole, the oxidant and Cy3 and by considering non-linear least squares curve fitting of the obtained intensity–time profiles into the pooled intermediate model. The evaluated kinetic parameters include experimental and theoretical maximum intensity, the rise and fall rate constants of the chemiluminescence process, experimental and theoretical time required to reach the maximum intensity and total emission yield. Finally, the developed system is adopted to detect a drug, i.e., carvedilol, in different pharmaceuticals. Under the optimal conditions, the system can provide a linear response for determination of 3 × 10− 7 to 3 × 10− 5 M carvedilol (r > 0.9869, n = 6) and a detection limit of 1.21 × 10− 7 M. The relative standard deviation of the detection results for six repetitive determinations is below 3.47% and the obtained recoveries are 99.6% and 101.9%.
PubDate: 2019-04-01

• Improved and scalable methods for the synthesis of midazolam drug and its
analogues using isocyanide reagents
• Abstract: In this research, two improved and scalable methods for the synthesis of midazolam and its analogues have been described. Midazolam has been synthesized using isocyanide reagents in satisfactory yield. In this methodology, imidazobenzodiazepine intermediates can be easily prepared via an improved process. One-pot condensation of benzodiazepines with mono-anion of tosylmethyl isocyanide or ethyl isocyanoacetate under mild condition led to formation of imidazobenzodiazepine. In the first method, tosylmethyl isocyanide (Tos-MIC) is used and the number of synthetic steps are decreased in comparison to previous report. In the second method, ethyl isocyanoacetate which is commonly used for the synthesis of some imidazobenzodiazepines, is consumed to generate midazolam. The latter, a relatively different method for the synthesis of midazolam analogues has been reported. Graphical abstract
PubDate: 2019-04-01

• Fast dispersive liquid–liquid microextraction based on magnetic
retrieval of in situ formed an ionic liquid for the preconcentration and
determination of benzophenone-type UV filters from environmental water
samples
• Abstract: Abstract This work concerns the development of a novel and rapid in situ dispersive liquid–liquid microextraction method for magnetic retrieval of ionic liquid as a new approach for the separation of benzophenone type (BP-type) UV filters via quantification using UPLC with PDA detection. The analytes determined in this study were a group of three benzophenones: 2,4-dihydroxybenzophenone (BP1), 2,2′,4,4′-tetrahydroxybenzophenone (BP2) and 2-hydroxy-4-metoxybenzophenone (BP3). The hydrophilic ionic liquid found suitable for use as an extraction solvent of the targeted analytes was didecyldimethylammonium chlorate (DDAC). An anion exchanger, NaClO4 was added to promote a metathesis reaction and in situ formed the IL, [DDA][ClO4]. The experimental parameters such as the concentration of IL, the molar ratio of DDAC to NaClO4, amount of iron oxide added and volume of water sample were investigated and optimised using a step-by-step optimisation process. The optimum experimental parameters were as follows: 30 mL of sample volume, 1% concentration of DDAC, the molar ratio of DDAC to NaClO4—1:2, and 5 mg of Fe3O4 magnetic nanoparticles. The proposed extraction method is simple and requires no more than 5 min. The detection limit (LOD) obtained for target analytes ranged from 12.320.0 ng L−1, while the correlation coefficient (r2) was from 0.9995 to 0.9999. Finally, the developed method was successfully applied to the determination of BP-type UV filters in environmental water samples, and satisfactory results were obtained.
PubDate: 2019-04-01

• A facile synthesis of highly fluorescent pyrido[2,3- d ]pyrimidines and
1,8-naphthyridines via oxazine transformation and enaminic addition
reactions
• Abstract: The synthesis and fluorescence properties of highly substituted bicyclic pryridine derivatives are described. 2-Substituted-4-oxo-pyrido[2,3-d]pyrimidines 2–8 resulted from the acylation reaction of α-aminonicotinonitrile 1 with aroyl chlorides, diethyl malonate, morpholine-4-carboxylate, acetic anhydride or formic acid under solvent-free conditions. [4 + 2] Cyclocondensation and cycloaddition reactions of compound type 1 with formamide and ammonium thiocyanate tolerated the fused pyrimidines 9 and 11, respectively. Finally, the Friedländer-like reaction was applied for the synthesis of 1,8-naphthyridines 12–15 via reaction of compound 1 with cyclohexanone, dimedone, acetyl acetone and benzyl methyl ketone, respectively, under AlCl3 catalysis. The fluorescence spectroscopic data of compounds 1–4, 6–8, 11, 12, 14 and 15 measured and significant results were observed. Graphical abstract
PubDate: 2019-04-01

• Hydrothermal synthesis and characterization of visible light-driven
I-doped Bi 2 MoO 6 photocatalyst
• Abstract: Abstract 0–3% I-doped Bi2MoO6 samples as visible light-driven-photocatalysts were successfully synthesized by a hydrothermal method. Structure, morphology, composition and optical properties of as-synthesized samples were investigated by X-ray diffraction, Fourier transform infrared spectroscopy, transmission electron microscopy, BET surface area analysis, X-ray photoelectron spectroscopy, UV–visible absorption and photoluminescence spectroscopy. The photocatalytic activities of Bi2MoO6 and I-doped Bi2MoO6 samples were investigated through degradation of rhodamine B as a pollutant model induced by visible radiation. The experimental results show that Bi2MoO6 exhibits enhanced photocatalytic activity by doping with iodine. In addition, the mechanism for photocatalytic degradation of organic molecules by I-doped Bi2MoO6 was discussed.
PubDate: 2019-04-01

• A new effective nano-adsorbent and antibacterial material of
hydroxyapatite
• Abstract: Abstract In the present work, nano-particles of potassium-substituted hydroxyapatite with formula of (Ca2.94K2.06)(PO4)0.94(CO3)2.06(OH) (KHA) are reported showing effective adsorption of Congo red dye in the room temperature. Synthesized sol–gel-derived KHA was identified by XRD, FTIR, TGA/DTA, and EDXA analyses. Moreover, the size of nano-particles and micro-strain of the synthesized KHA were measured using Williamson–Hall (W–H) plots and TEM in amount of 65–70 nm. The capacity of equilibrium adsorption (qm) for 100 ppm of Congo red was evaluated as high as 505.19 mg g−1 under optimum conditions. The adsorption charts and kinetic results obtained at ambient conditions well fitted with the Langmuir equation and the pseudo–first–order model with correlation coefficients of 0.9939 and 0.9867, respectively. The obtained results obviously show that the new synthesized KHA can be used for industrial wastewater purification in a good manner. The title nano-material also shows excellent antibacterial activity as highly prevention of bacteria strain growth with the lowest concentration of 125 µg/mL.
PubDate: 2019-04-01

• Utility of 3-benzylidenefuran-2(3H)-one and
3-benzylideneisobenzofuran-1(3H)-one as precursors of biologically active
novel heterocycles
• Abstract: Abstract In the present work, 3-benzylidenefuran 2 and 3-benzylideneisobenzofuran 3 derivatives were investigated in a comparative study in which they were utilized as building blocks to construct different heterocyclic compounds. Therefore, they were allowed to react with different nitrogen and oxygen nucleophiles under the same conditions to afford some novel compounds 4–16. All the structures of the synthesized compounds 2–16 were elucidated based on their elemental analyses and spectral measurements. The bioactivities of the synthesized compounds were evaluated, where some of tested compounds exhibited promising antimicrobial, antitumor, and antioxidant activities.
PubDate: 2019-04-01

• Visible-light-responsive bismuth oxybromide/graphite-like C 3 N 4 hybrid
material and its application in photocatalysis via internal electric field

• Abstract: Abstract In this work, we propose a facile route to obtain BiOBr/ graphite-like C3N4 hybrid material, which was constructed by in situ depositing BiOBr onto the surface of g-C3N4 as a template via self-assembly procedure at room temperature. This method describes the use of g-C3N4/BiOBr nanocomposite for the superior photocatalytic performances under visible light excitation (λ > 420 nm). The crystalline phase, morphology, textile structure and components of the samples were studied by several tools such as X-ray diffraction, transmission electron microscopy, N2 adsorption–desorption, energy dispersive X-ray spectrum, Fourier transform infrared spectroscopy and Raman spectroscopy. The optical, photoelectrochemical properties and band structure were measured by ultraviolet–visible diffuse reflectance spectroscopy, steady-state photoluminescence spectra, photocurrent response analysis, electrochemical impedance spectra and valence-band X-ray photoelectron spectroscopy techniques, respectively. In addition, the catalytic activities of the hetero-structural material were broadly investigated and compared with single BiOBr or g-C3N4 alone in the same reaction. The as-obtained BiOBr/g-C3N4 composite showed distinctive advantages over BiOBr alone and universality for various substrate, i.e., dichloronaphthol degradation and reduction efficiency of Cr (VI) over BiOBr/g-C3N4 was increased by up to 3 and 2.5 times, respectively. The enhanced photocatalytic activity of the as-prepared BiOBr/g-C3N4 complex was mainly contributed to the effective charge transfer, which can further cause the establishment of the internal electric field in the interface between BiOBr and g-C3N4 to boost the space charge separation. This work gives a new route for designing high efficient semiconductor hybrid photocatalyst with broad absorption region as well as quick charge separation.
PubDate: 2019-04-01

• A theoretical study on the dynamics of gas-phase reaction of methyl cation
with atomic oxygen
• Abstract: Abstract The dynamics and kinetics of the reaction of CH3+ cation with atomic oxygen in its lowest triplet and singlet states in the presence of N2 molecules as the bath gas is theoretically investigated. The potential energies over both surfaces at the CCSD(T)/aug-cc-pVTZ level of theory are explored. Both singlet and triplet surfaces characterize by barrierless initiation step. The entrance channel to form the energized adducts are governed by the capture probability once the centrifugal barrier is surmounted. Multiwell-multichannel mechanisms are found for both singlet and triplet potential energy surfaces. One-dimensional chemical master equation is solved to explore the dynamics and kinetics of the title reaction. The fractional populations of the stationary points as function of time are analyzed to determine the role of the energized intermediates on the dynamics of the title reaction. No significant temperature or pressure dependence for the title reaction was observed over a wide range of temperature (300–3000 K) and pressure (0.1–4.5 atm). The results indicate cis and trans-HCOH+, CH2O+, and H atom are the major products for both surfaces. CVT method was used to explore the importance of tunneling in hydrogen transfer isomerization reactions of CH2O+ to trans-HCOH+ and HOC+ to HCO+ using small-curvature approximation.
PubDate: 2019-04-01

• A study on the supercapacitive behavior of zinc substituted manganese
ferrite nanoparticles
• Abstract: Abstract Synthesis and applications of novel nanomaterials in energy storage are of great importance. In this study, nanoparticles of zinc substituted manganese ferrite (Zn0.5Mn0.5Fe2O4) were synthesized by a simple coprecipitation method. The synthesized nanoparticles were then characterized by field emission scanning electron microscopy, FTIR spectroscopy, atomic force microscopy and X-ray diffraction. The nanoparticles had a spherical morphology with a diameter of ~ 30 nm. The nanoparticles were electrochemically evaluated as a supercapacitor electrode material by cyclic voltammetry, electrochemical impedance spectroscopy and charge/discharge cycling. The nanoparticles represented both double layer and pseudocapacitive behaviors with a specific capacitance of 77.9 F g− 1 at a charge/discharge current of 1.0 A g− 1. The specific energy and power of the nanoparticles were 13.2 Wh g− 1 and 563 W g− 1, respectively. The nanoparticles retained more than 87% of the initial capacitance after 1000 charge/discharge cycles.
PubDate: 2019-04-01

• Verjuice as a green and bio-degradable solvent/catalyst for facile and
eco-friendly synthesis of 5-arylmethylenepyrimidine-2,4,6-trione,

• Abstract: Abstract Verjuice (unripe grape juice), a natural mixture of organic acids, which is identified by pH-metric and TGA analysis, is efficiently used for the promotion of the synthesis of 5-arylmethylenepyrimidine-2,4,6-triones, via Knovenagel condensation reaction between barbituric or thiobarbituric acid and aldehydes. Verjuice is also employed for the effective synthesis of pyrano[2,3-d]pyrimidinone derivatives via a three-component reaction of barbituric acid or its thio analogue, aldehydes and malononitrile. In the same way, pyrimido[4,5-d]pyrimidinone derivatives are simply produced via the reaction of barbituric acid, aldehydes and urea or thiourea in the presence of verjuice. This green methodology rewards notable advantages including simple procedures, acceptable reaction times, easy work-up, high yields, circumventing the use of any expensive starting materials, volatile and hazardous organic solvents during the reaction and work-up process, and use of a natural, low-cost, reusable, and bio-degradable catalyst.
PubDate: 2019-04-01

• Irreversible solid-state metal ion exchange in cobalt(II) metal–organic
nanocapsules synthesized by green mechanochemical process
• Abstract: Irreversible solid-state conversion of Co(II) metal–organic nanocapsule [Co2(bda)2(bpy)2] (1), [bda2− = 2,2′-biphenyl dicarboxylate and bpy = 2,2′-bipyridine], prepared by mechanochemical procedure with empty pore and lozenge-shaped microcube morphology similar to [Cu2(bda)2(bpy)2]∙4H2O (2) analogue with agglomerated nanostructure morphology was studied. The structure of 1 is exactly the same as 2 and the metal ion has distorted octahedral coordination in both of them. In addition to the same structures of 1 and 2, the similar crystal data of them also approved that this reaction can occur in solid state by cation exchange process. Solid-state cation exchange processes of these metal–organic nanocapsules were studied by IR spectroscopy, X-ray powder diffraction (XRD) and scanning electron microscopy (SEM). Graphical abstract
PubDate: 2019-04-01

• Synthesis of novel amidoalkyl naphthol-based azo dyes and evaluation of
their antimicrobial activities
• Abstract: Abstract Several new azo-substituted amidoalkyl naphthol derivatives were synthesized by coupling of octahydro-1H-xanthen and phenol nucleus with diazotized 4-amino benzamide and conversion of the coupling product to amidoalkyl naphthols. This is the first report on the synthesis of amidoalkyl naphthol compounds using benzamide with large azo substituents. Furthermore, antimicrobial activities of all new compounds were studied by in vitro experiment. Some synthesized compounds exhibited potential antimicrobial activities which may guarantee their future application in moderate chemotherapy.
PubDate: 2019-04-01

• Synthesis, characterization and cytotoxicity of new nicotinonitriles and
their furo[2,3- b ]pyridine derivatives
• Abstract: The present research work describes the synthesis of new series of nicotinonitrile (2) and furo[2,3-b]pyridine (3) heterocycles bearing thiophene substituent. The nicotinonitrile derivatives were prepared from the corresponding 3-cyano-(2H)-pyridones (1a–f) in excellent yields. The ring cyclization of the nicotinonitrile derivatives (2a–f) in the presence of sodium methoxide provided the furo[2,3-b]pyridines (3a–f) in moderate to good yields. All the newly synthesized compounds were characterized by extensive NMR analysis data, including 1D-NMR experiments (1H and 13C) and 2D-NMR experiments (COSY, HMBC, HSQC), as well as HRESIMS data. All the final products were subjected for cytotoxic activity against five different tumour cell lines including HeLa (cervical), DU145 (prostate), HepG2 (liver), MDA-MB-231 (breast-ER negative) and MCF7 (breast-ER positive), in addition to HSF1184 (normal human fibroblast) using the MTT assay. Compounds 2d and 3e were found to exhibit promising cytotoxicity with IC50 of < 20 µM against all different tested tumour cell lines. In addition, these compounds showed high selectivity (40–287 folds) for tumour cells over normal cells. Graphical abstract
PubDate: 2019-04-01

• Molecularly imprinted based solid phase microextraction method for
monitoring valproic acid in human serum and pharmaceutical formulations
• Abstract: Abstract In this paper, a straightforward method is presented to detect valproic acid after its microextraction. Molecularly imprinted polymer fiber was used in conjunction with chromatography-flame ionization to achieve this goal. A narrow bore silica capillary was adopted as a mold, via the copolymerization of meth acrylic acid–ethylene glycol dimethacrylate imprinted with VPA, to synthesize the fiber. Extraction temperature, extraction time, salt addition, pH, stirring rate, and desorption temperature—all of which are factors that can influence the extraction process—were measured, and adjusted accordingly. Linearity, precision, and detection limits, as analytical elements, were also evaluated under optimum conditions. Readings showed a linear range of 0.03–100 µg L− 1 (r2 = 0.998), and the limit of detection was measured as 0.01 µg L− 1. The established method was then applied in selective detection of valproic acid in tablet, syrup and human serum samples successfully.
PubDate: 2019-04-01

• A water stable metal–organic framework with 1D nanotube pores for
5-fluorouracil delivery and anti-brain tumor activity
• Abstract: Abstract The employment of porous carriers for anticancer drug delivery has gained much attention in recent years for their excellent drug-loading capacity and controlled release performance. In this work, by utilizing a rigid organic aromatic carboxylic acid ligand, a new Zn(II)–organic framework {[Zn2(bptc)(H2O)]·(DMAc)3(H2O)4}n (1, DMAc is in short of N,N-dimethylacetamide, H4bptc is in short of biphenyl-3,3′,5,5′-tetracarboxylic acid ligand), with considerable water stability has been prepared using the solvothermal technology. The structural analysis result reveals that complex 1 is constructed from fourfold helical metal chains whose net could be simplified into a (6,8)-connected topology. Moreover, complex 1 shows 1D nanotube channels with a window size of 10.7 × 10.7 Å2 along the [001] direction and reveals a large accessible voids of 51.7%. The desolvated 1 (1a) was used to study the loading and releasing of the 5-fluorouracil (5-Fu), which reveals that 1a could uptake around 51.2 wt% of 5-Fu and nearly 85.6% of the absorbed 5-Fu could be released in PBS (7.4 for the pH value) in 100 h at 37 °C. In connection to these, in vitro cytotoxicity of compound 1 together with the anticancer performance of 5-Fu-loaded 1a was evaluated against human oral epidermal cells and human brain tumor cells SF17 via MTT assays.
PubDate: 2019-04-01

• A green ultrasonic-assisted liquid–liquid microextraction technique
based on deep eutectic solvents for flame atomic absorption spectrometer
determination of trace level of lead in tobacco and food samples
• Abstract: Abstract A novel and green ultrasonic-assisted liquid phase microextraction method (LPME) based on deep eutectic solvents (DESs) has been developed for the pre-concentration and extraction of lead from cigarette tobacco and food samples prior to flame atomic absorption spectrometer (FAAS) determination. Multivariate Plackett–Burman design has been employed which make the proposed method more easy and fast as compare to routine practices and eliminated the step by step optimization process. Further, accuracy of the developed UA-DES-LPME has been checked with analysis of certified reference material and addition-recovery experiments for tobacco and food samples. The developed method showed a 4.4 µg L− 1 of limit of detection (LOD) and 14.6 µg L− 1 of limit of quantification (LOQ) with the 4.0% of relative standard deviation (RSD). Moreover, the developed method is more user-friendly, faster, and easier as compared to reported methods.
PubDate: 2019-04-01

• Synthesis, characterization, Hirshfeld surface analysis and theoretical
calculation of new organic–inorganic hybrid material: (C 4 H 7 N 2 ) 6
[As 2 W 18 O 62 ]·4H 2 O
• Abstract: Abstract New hybrid arsenotungstates based on Dawson polyanions [C4H7N2]6[As2W18O62]·4H2O (1) have been isolated by conventional solution method and characterized by single-crystal X-ray diffraction, infrared spectrum and UV–visible spectroscopies and thermogravimetric analysis. Hirshfeld surface analysis was performed to study the intermolecular interactions. Compound 1 crystallizes in hexagonal system, in a P-3 space group, with cell parameters a = 20.2904(2) Å, b = 20.2904(2) Å, c = 16.8246(2) Å, and a V = 5998.38(11) Å3. Compound 1 exhibits a three-dimensional chain constructed from Well–Dawson anions linked together with (C4H7N2)+ cations and water molecules.
PubDate: 2019-04-01

• Natural pigments in dye-sensitized solar cell (DSSC): a DFT-TDDFT study
• Abstract: Abstract The molecular structures and photophysical properties of twelve types of the dyes from natural pigments of chlorophyll, flavonoid, carotenoid and anthocyanin were calculated with density functional theory (DFT) and time-dependent DFT (TD-DFT). Based on the comparison and better agreement between experimental wavelengths of maximum absorption and their calculated values with functionals of B3LYP, CAM-B3LYP and BHand-H, the B3LYP/6-31G** level was chosen for the process of our studies. The dyes’ properties in solvent environment were carried out using conductor-like polarizable continuum model methods (CPCM-DFT and TD-CPCM-DFT). The results show that pigment type affects the photophysical properties, and the dyes of a specific pigment type have nearly the same properties. Anthocyanins have the highest values of ionization potential (IP), electron affinity (EA), electronic chemical potential (µ) (their absolute values), chemical hardness (η), electrophilicity index (ω), electroaccepting power (ω+) and electrodonating power (ω−), which can lead to high efficiency of these dyes type for dye-sensitized solar cells (DSSCs). Energy gap of ELUMO and EHOMO of the dyes respectively with the conduction band edge of TiO2 (ECB) and Eredox of $$\left(\tt {I^ - }/I_{3}^{ - }\right)$$ couple (ΔEL and ΔEH), the free energy difference for electron injection (ΔGinject) and the driving force for dye regeneration (ΔGreg), the maximum absorption wavelengths of peaks (λmax) and oscillator strength values (f) for all the dyes in gas, acetonitrile and water phases were calculated and explained. These parameters show that carotenoids, chlorophylls and anthocyanins are more appropriate pigments than flavonoid pigment and the estimated open-circuit photo-voltage values (eVoc) showed that flavonoids are the desirable pigment. We expect these results could be helpful for DSSC producers to choose highly efficient natural dyes according to their optical and electronic properties.
PubDate: 2019-04-01

• Synthesis and characterization of molybdenum complex supported on magnetic
and non-magnetic supports: comparing their catalytic activity,
selectivity, and reusability
• Abstract: Abstract A molybdenum complex was immobilized on Schiff-base-modified magnetic and non-magnetic particles by covalent linkage. The characterizations of the obtained materials were carried out by means of TG–DTG, SEM, TEM, VSM, XPS, IR, and Raman microprobe techniques. All of them exhibited efficient activities in the oxidation of sulfides to sulfoxides by urea hydrogen peroxide oxidant. The advantages and disadvantages of these catalysts are discussed in detail. Molybdenum complex immobilized on silica bead can be recycled and recovered by simple filtration, but it demonstrated low activity in catalytic oxidation reaction. Immobilization on nano-SiO2 leads to the formation of nanocatalyst having high catalytic activity but inefficient reusability. The best results were obtained with nano-Fe3O4 magnetic support. The immobilized molybdenum complex on silica-coated magnetic nanoparticles can easily be recovered from the reaction system using an external magnet and reused several times with high yields.
PubDate: 2019-04-01

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