- An azo based colorimetric probe for the detection of cysteine and lysine amino acids and its real application in human blood plasma
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The present work describes the rational design and synthesis of a simple azo based colorimetric chemodosimeter to selectively detect Cys and Lys in the environment of competitive different class of amino acids in HEPES buffer under physiological conditions. The probes 3a and 3b containing aldehyde functionality upon interaction with Cys and Lys afforded stable thiazolidine and aldimine derivatives and displayed a sensitive ratiometric response in the absorption spectra due to a change in the intramolecular charge transfer (ICT) process. The whole recognition process for amino acids gives rise to a rapid significant colorimetric response with readily detectable naked-eye sensitive color changes in the real biological sample. The mechanism of interaction between the probes and amino acids has been confirmed by the optical behavior, FT-IR, NMR and ESI-MS data analysis.
- Razi, Syed S.,Ali, Rashid,Srivastava, Priyanka,Shahid, Mohammad,Misra, Arvind
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- Chitosan containing azo-based Schiff bases: Thermal, antibacterial and birefringence properties for bio-optical devices
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The present investigation describes the preparation of chitosan/2-hydroxy-5-(4-nitrophenylazo)-benzaldehyde (CHNAB) and chitosan/2-hydroxy-5-(4-tolylazo)-benzaldehyde (CHMAB) derivatives (in 4:5 molar ratio) under mild conditions. These derivatives were s
- Nigam, Nidhi,Kumar, Santosh,Dutta,Pei,Ghosh, Tamal
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- Synthesis and antibacterial activities of mixed ligands complexes of Cu(II) and Zn(II) containing tridentate azo anils ligands and bidentate oxalate ion
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Mixed ligands complexes of copper(II) and zinc(II) were synthesized using azo anils ((HNPDBAB = 2-({2-hydroxy-5-[(4- nitrophenyl)diazenyl]benzylidene}amino)benzoic acid, HPIMNDP = 2-{[(2-hydroxyphen yl)imino]methyl}-4-[(4-nitrophenyl)diazenyl] phenol) and oxalate ion as a coordinating ligands. Elemental analysis, atomic absorption spectroscopy, FTIR, NMR, UV-visible. were used for the characterizations of synthesized azo anils ligands and their mixed ligands complexes. Distorted octahedral geometry was tentatively proposed for these new mixed ligands M(II) {Cu(II) and Zn(II)} complexes. Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Enterobacter aerogenes and Escherichia coli) were screen out for antibacterial activities of azo anils ligands, oxalic acid, metal salts and their mixed ligands M(II) complexes. The antibacterial activities were performed to assess the extent of inhibition potential of free ligand and their mixed ligands M(II) complexes. The results revealed that antibacterial activities of azo anils became more pronounced when these were coordinated to central metal atom.
- Ameen, Muhammad,Rubina Gilini, Syeda,Naseer, Amina,Shoukat, Ishrat,Ali, Syed Danish,Sadiqa, Ayesha
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- A novel chemosensor based on rhodamine and azobenzene moieties for selective detection of Al3+ ions
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The high absorption coefficient, fluorescence quantum yield, photo stability and relatively long wavelengths of rhodamine dye have expanded its applicability as a promising fluorescent probe. In the present investigation, two dyes, namely rhodamine and azobenzene, have been conjugated for the detection of Al3+ in aqueous ethanol. The turn on fluorescence response of chemosensor L towards Al3+ is attributed to the inhibited PET (photo-induced electron transfer) and CHEF (chelation enhanced fluorescence) process along with the spirolactam (non-fluorescent) to ring-opened amide (fluorescent) process. The presence of the PET and CHEF process was corroborated by time-resolved photoluminescence study and the spirolactam ring opening was confirmed by 13C NMR and infrared spectroscopy. In the presence of Al3+, the opened spirolactam ring forms a 1:1 binding complex with the metal, which is supported by its high binding constant (Ka = 7.033 × 103 M-1). The limit of detection (LOD) and limit of quantification (LOQ) values are found to be 1.1 × 10-7 M and 3.6 × 10-7 M, respectively. The reversible recognition of Al3+ was also proved in the presence of Na2EDTA by both UV-Vis and fluorometric titration. The sensing behaviour of the chemosensor towards Al3+ was supported by DFT/TDDFT calculations.
- Mabhai, Subhabrata,Dolai, Malay,Dey, Satyajit,Dhara, Anamika,Das, Bhriguram,Jana, Atanu
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- 'Naked-eye' detection of fluoride and acetate anions by using simple and efficient urea and thiourea based colorimetric sensors
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Simple and efficient sensors 1 and 2 possessing azo and nitrophenyl as signaling units and urea and thiourea moieties as binding sites were designed and synthesized. These sensors were characterized by combination of 1H, 13C, APT, CO
- Okudan, Ahmet,Erdemir, Serkan,Kocyigit, Ozcan
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- Preparation, spectral, X-ray powder diffraction and computational studies and genotoxic properties of new azo-azomethine metal chelates
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A new tridentate azo-azomethine ligand, N′-[{2-hydroxy-5-[(4-nitrophenyl)diazenyl]phenyl}methylidene]benzohydrazidemonohydrate, (sbH·H2O) (1), is prepared by condensation of benzohydrazide and 2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzaldehyde (a) with treatment of a solution of diazonium salt of p-nitroaniline and 2-hydroxybenzaldehyde in EtOH. The five coordination compounds, [Co(sb)2]·4H2O (2), [Ni(sb)2]·H2O (3), [Cu(sb)2]·4H2O (4), [Zn(sb)2]·H2O (5) and [Cd(sb)2]·H2O (6) are prepared by reacting the Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) ions with the ligand. The structures of the compounds are elucidated from the elemental analyses data and spectroscopic studies. It is found the ligand acts as a tridentate bending through phenolic and carbonyl oxygens and nitrogen atom of the CN group similar to the most of salicylaldimines. Comparison of the infrared spectra of the ligand and its metal complexes confirm that azo-Schiff base behaves as a monobasic tridentate ligand towards the central metal ion with an ONO donor sequence. Upon complexation with the ligand, the Cd(II), and Zn(II) ions form monoclinic structures, while Co(II), Cu(II) and Ni(II) ions form orthorhombic structures. Quantum chemical calculations are performed on tautomers and its metal chelates by using DFT/B3LYP method. Most stable tautomer is determined as tautomer (1a). The geometrical parameters of its metal chelates are obtained as theoretically. The NLO properties of tautomer (1a) and its metal complexes are investigated. Finally, the ligand and its metal complexes are assessed for their genotoxicity.
- Bitmez, ?irin,Sayin, Koray,Avar, Bari?,K?se, Muhammet,Kayraldiz, Ahmet,Kurto?lu, Mükerrem
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- Colorimetric detection and ratiometric quantification of mercury(ii) using azophenol dye: 'Dip & read' based handheld prototype device development
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The extreme toxicity of mercury and its derivatives results from its high affinity for thiol groups in proteins and enzymes, leading to the dysfunction of cells and consequent health problems. Thus, developing a rapid, cheap and colorimetric sensor for detecting mercury ions at very low levels remains a challenge. Herein, we have developed a new chromogenic azophenol-based probe which allows the colorimetric detection of Hg(ii) metal ions and subsequently, showed suitability as a RGB chemodosimeter for the selective sensing of Hg(ii) in aqueous medium. The UV-vis absorption and colorimetric study showed that the azophenol-based sensor is highly selective towards Hg(ii) detection without the interference of other analytes. The color change from deep red to yellow in the complex solution after treating with mercury metal ions, which is visible by the naked-eye, makes this probe more convenient and simple to use in real sample analysis. Furthermore, for practical application of the sensor system in real time sample analysis, solid state silica based sensor chips have been developed which are impregnated with probe 1 displaying colorimetric changes for different concentrations of Hg2+, where the intensity of the red color decreased gradually towards a yellow color after the addition of Hg2+, apparently, makes them as potential candidate to conveniently monitor the concentration of Hg2+ in aqueous test solutions.
- Singh, Gagandeep,Raj, Pushap,Singh, Harupjit,Singh, Narinder
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- Azo dye-based colorimetric chemodosimeter for the rapid and selective sensing of cyanide in aqueous solvent
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We developed an azo dye-based chemodosimeter possessing oxime functionality as a reaction unit with cyanides in the aqueous environment. The azo oxime chemical probe rapidly reacted with cyanides through the nucleophilic addition and subsequent proton transfer of resonance-assisted hydrogen bonding OH, which displayed a dramatic color change from colorless to dark violet in DMSO/HEPES buffer.
- Na, Sang-Yun,Kim, Hae-Jo
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- Dual detection highly selective colorimetric chemosensors for fluoride and copper(II) ions based on imine-phenol derivative
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A simple dual detection using colorimetric chemosensor, imine-phenol derivative L (bearing a 2-iminephenol group as a binding unit and a-nitrophenylazo group as a signaling unit), were synthesized for a high yield in two simple steps. Complexations of chemosensor L with various anions in acetonitrile solvent and other metal ions in DMSO/H2O solvent were monitored by UV-visible spectroscopy. The results indicated that the chemosensor L showed high selectivity for F? and Cu2+ ions. Furthermore, the complexes for L-F? and L-Cu2+ were evaluated by computational chemistry using a B3LYP/6-31G (d,p) and a B3LYP/6-311G (d,p) level of calculation. The complexes between L with F? and Cu2+ were magenta and yellow colored, respectively. Chemosensor L can be applied for the analysis of F? and Cu2+ ions with naked-eye detection making colour comparisons between the standard and the real sample. Most importantly, semi-qualitative detection of Cu2+ in water solution were successfully carried out with the developed test kit using chemosensor L.
- Nusuwan, Phoomirut,Jittangprasert, Piyada,Kuno, Mayuso,Pumsa-Ard, Kem,Tongraung, Pan
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- Novel C-2 symmetric molecules as α-glucosidase and α-amylase inhibitors: Design, synthesis, kinetic evaluation, molecular docking and pharmacokinetics
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A series of symmetrical salicylaldehyde-bishydrazine azo molecules, 5a–5h, have been synthesized, characterized by 1H-NMR and 13C-NMR, and evaluated for their in vitro α-glucosidase and α-amylase inhibitory activities. All the synthesized compounds efficiently inhibited both enzymes. Compound 5g was the most potent derivative in the series, and powerfully inhibited both α-glucosidase and α-amylase. The IC50 of 5g against α-glucosidase was 0.35917 ± 0.0189 μM (standard acarbose IC50 = 6.109 ± 0.329 μM), and the IC50 value of 5g against α-amylase was 0.4379 ± 0.0423 μM (standard acarbose IC50 = 33.178 ± 2.392 μM). The Lineweaver-Burk plot indicated that compound 5g is a competitive inhibitor of α-glucosidase. The binding interactions of the most active analogues were confirmed through molecular docking studies. Docking studies showed that 5g interacts with the residues Trp690, Asp548, Arg425, and Glu426, which form hydrogen bonds to 5g with distances of 2.05, 2.20, 2.10 and 2.18 ?, respectively. All compounds showed high mutagenic and tumorigenic behaviors, and only 5e showed irritant properties. In addition, all the derivatives showed good antioxidant activities. The pharmacokinetic evaluation also revealed promising results.
- Shahzad, Danish,Saeed, Aamer,Larik, Fayaz Ali,Channar, Pervaiz Ali,Abbas, Qamar,Alajmi, Mohamed F.,Ifzan Arshad,Erben, Mauricio F.,Hassan, Mubashir,Raza, Hussain,Seo, Sung-Yum,El-Seedi, Hesham R.
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- Synthesis, spectroscopic characterization, and genotoxicity of a new group of azo-oxime metal chelates
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A new azo-oxime ligand, 2-[(E)-(hydroxyimino)methyl]-4-[(E)-(4-nitrophenyl) diazenyl]phenol, (pxoxH2) (2), was prepared by condensation of hydroxylamminehydrochloride and 2-hydroxy5-[(4-nitrophenyl)diazenyl]benzaldehyde (1) with treatment of a solution of diazonium salt of p-nitroaniline and 2-hydroxybenzaldehyde in ethanol. The 6 coordination compounds, [Mn(pxoxH) 2 (H2 O)2 ].H2O (3), [Co(pxoxH) 2 (H2 O)2 ].4H2O (4), [Ni(pxoxH)2 (H2 O)2 ].2H2O (5), [Cu(pxoxH)2 ].H2O (6), [Zn(pxoxH)2 ].6H2O (7), and [Cd(pxoxH) 2 (H2 O)2 ].H2O (8), were prepared by reacting Mn(II), Ni(II) Cu(II), Co(II), Zn(II), and Cd(II) ions with the ligand. The structures of the compounds were elucidated from the elemental analysis data and spectroscopic studies. The azo-oxime metal complexes were also characterized by XRD, magnetic moment, molar conductivity, and thermal analyses. Elemental analyses of the chelates suggested that the metal to ligand ratio was 1:2. It was found that the ligand acts as a bidentate bending through the phenolic oxygen and nitrogen atom of the C=N-OH group similar to most oximes. Upon complexation with the ligand, the Cu(II) and Zn(II) ions formed square planar and tetrahedral structures, respectively, and the Mn(II), Ni(II), Co(II), and Cd(II) ions formed octahedral structures with 2 water molecules as axial ligands. Finally, the ligand and its complexes were assessed for their genotoxicity. TUeBITAK.
- Cabir, Beyza,Avar, Baris,Gulcan, Mehmet,Kayraldiz, Ahmet,Kurtoglu, Mukerrem
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- Schiff base derived from salicylaldehyde-based azo dye as chromogenic anionic sensor and specific turn-on emission sensor for cyanide ion
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A novel Schiff base has been derived from condensing 4-aminoantipyrine with diazotized salicylaldehyde. The derived compound acted as a colorimetric sensor for hazardous aqueous anions like CN?, F?, and CH3COO?
- Chakraborty, Nilanjan,Chakraborty, Arijit,Das, Suman
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- A biginelli-azophenol based robust sensor for rapid diagnosis of cyanide in real samples
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The self-aggregation of multifunctional Biginelli-azophenol (Ligand1) in water (ONPs) led to sensitive and selective detection of toxic pollutant cyanide in an aqueous medium and solid matrix. The origin behind the excellent sensing performance of Ligand1
- Kaur, Manpreet,Kaur, Navneet,Singh, Harupjit,Singh, Narinder
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- Synthesis and antiviral evaluation of 5-(arylazo)salicylaldehyde thiosemicarbazone derivatives as potent anti-bovine viral diarrhea virus agents
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Thiosemicarbazones which previously characterized as a new class that inhibit anti-bovine viral diarrhea virus (BVDV) prompted us for synthesizing a series of new thiosemicarbazone derivatives. Thus, in this study, we reported the synthesis and antiviral evaluation of a series of 5-(arylazo)salicylaldehyde thiosemicarbazone derivatives for their expected antiviral activity. The desired products were synthesized from the condensation of 5-(arylazo)salicylaldehyde derivatives with N-(4)-substituted thiosemicarbazide derivatives. Antiviral screening was performed to test the anti-bovine viral diarrhea virus properties. From the obtained results, compounds 5, 23 and 24 showed highly selective activity against BVDV by blocking the viral RNA synthesis in cell culture. The BVDV in antiviral drug studies is valuable surrogate for the hepatitis C virus (HCV); so, the above results provided a novel candidate for the development of anti-HCV agents.
- Basyouni, Wahid M.,Abbas, Samir Y.,El-Bayouki, Khairy A. M.,Daawod, Reham M.,Elawady, Mostafa K.
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p. 2168 - 2174
(2021/06/01)
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- Triazole derived azo-azomethine dye as a new colorimetric anion chemosensor
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In the pursue of developing anion sensors, an efficient triazole derived azo-azomethine dye chemosensor (S) that differentially senses F ̄ and AcO ̄ ions has been reported. The ions recognition ability of S was investigated by colorimetric and UV–visible spectroscopic methods. Interestingly, this chemosensor molecule is virtually inactive in presence of other anions such as Cl ̄, Br ̄ and I ̄ and HSO4 ̄. We have further presented a ratiometric approach to differentiate F ̄ and AcO ̄ ions. The reversibility of F ̄ ion binding with S was established by the addition of Ca(NO3)2 to the fluoride bound S, which led to the regeneration of S. The quantum chemical calculation of energies of unbound and bound S has been employed using Density Functional Theory (DFT) to understand the interaction between chemosensor and anions. Evidence in support of fluoride-induced deprotonation of a O–H bond during the detection of F? ion has been demonstrated by employing 1H NMR titration experiments.
- Chatterjee, Chinmayee,Sethi, Sipun,Mukherjee, Vishwajeet,Sahu, Prabhat Kumar,Behera, Nabakrushna
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- Synthesis and antibacterial evaluation of diaminomaleonitrile-based azo-Schiff bases and 8,9-dihydro-7H-purine-6-carboxamides
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Some new DAMN-based Schiff base 6a–6g were synthesized via a condensation reaction of the corresponding azo dyes with 1-(2-amino-1,2-dicyanovinyl)-3-phenylurea. In continuation, facile synthesis of new 8,9-dihydro-7H-purine-6-carboxamide 7a–7g was reported via an efficient reaction of azo dyes and 1-(2-amino-1,2-dicyanovinyl)-3-phenylurea in the presence of triethylamine as catalyst. All the synthesized compounds were evaluated for their antibacterial activities against both Gram-positive (Micrococcus luteus and Staphylococcus aureus) and Gram-negative (Pseudomonas aeruginosa and Escherichia coli) bacteria.
- Sheykhi-Estalkhjani, Ammar,Mahmoodi, Nosrat O.,Yahyazadeh, Asieh,Pasandideh Nadamani, Meysam
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p. 3835 - 3852
(2020/05/25)
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- Three indole derived azo-azomethine dyes as effective chemosensors for F-ion and trace water detection
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Three new dyes 13 derived from indol-carbohydrazide and azo-azomethine for the optical detection of F- ion have been developed. Dye 1 was found to be an effective colorimetric sensor for F- ion response with over 250 nm red-shift. Moreover, the resultant dye...HF2- complex (dye-F) could be successfully used as a secondary sensor for analyzing trace water in aprotic organic solvents especially in acetonitrile with a low limit of detection. In addition to detection of low-level water content in solution, test paper incorporated with 1-F complex or 2-F complex was well developed for naked-eye detection of water content in four organic solvents as mentioned above. Importantly, the test paper prepared by introducing 1-F complex or 2-F complex could be developed to prepare an ink-free rewritable paper by using water as the sole trigger. Furthermore, the same test paper could still work for many cycles without obvious loss in color quality.
- Yang, Xiaofeng,Zhu, Fengqiao,Li, Yexin,Yan, Mei,Cui, Yu,Sun, Guoxin
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p. 870 - 879
(2020/08/28)
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- Novel edaravone-based azo dyes: Efficient synthesis, characterization, antibacterial activity, DFT calculations and comprehensive investigation of the solvent effect on the absorption spectra
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The present study deals with designing and synthesizing novel dyes using the drug combination of edaravone and azo compounds which can be used as an indicator for anions and cations. The desired product synthesis was accomplished via a two-step process involving diazotizing the aromatic amines followed by the resultant salts coupling with edaravone. The resulting dyes were obtained with high yields under mild conditions. The structures of the dyes were identified with UV-vis, FT-IR, 1H NMR and 13C NMR spectra and CHN analysis. To investigate the solvatochromism effect, the interaction of different solvents with the selected dyes was evaluated using several parameters including the dielectric constant, refractive index, hydrogen bond donating ability, hydrogen bond accepting ability and dipolarity/polarizability scale. To achieve deep understanding about the stability and geometrical characteristics of the azo-hydrazo tautomers of the synthesized dyes and their UV-visible spectra prediction, some DFT calculations were also carried out on the synthesized dyes. The antibacterial activities of some synthesized compounds were also evaluated using the disk diffusion method. The results revealed different activity of the selected synthesized dyes for antibacterial tests against selected Gram positive and Gram negative bacteria.
- Davasaz Rabbani, Mohammad Amin,Khalili, Behzad,Saeidian, Hamid
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p. 35729 - 35739
(2020/10/27)
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- Room Temperature Reversible Z→E Photoisomerization of Azobenzene Appended to Anthraquinone-Benzimidazole Based Photoswitches with Resolved n→π* Absorption Band
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Light-triggered substituted azobenzene-based molecular switches are well known for their potential applications as molecular machines. The Z-isomer stability affected by heteroaromatic groups, extended aromaticity, different substituents, and varying the solvents based on their polarity. In this regards, five different anthraquinone/imidazole-based azobenzene derivatives have been synthesized with different electronic push/pull substituents. The detailed study of photoswitching processes with kinetic data was appraised by using UV/Vis and 1H-NMR spectroscopic techniques. The investigation of light-induced hydroxyl group conversion to quinone-hydrazone tautomerization has been observed during the isomerization. Most importantly, intermolecular hydrogen bonding interaction between tautomeric form and a higher polar solvent (DMSO) block the isomerization, but in a less polar solvent (DCM), light-induced trans ? cis isomerization takes place by tautomerization pathway with well-separated π→π* and n→π* transitions. Further, the detailed mechanistic study of solvent-assisted light-induced tautomerization with the role of hydrogen bonding and the following WRITE-READ-ERASE-READ system have been derived by using molecular logic gates.
- Phapale, Daulat,Kushwaha, Archana,Das, Dipanwita
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p. 5768 - 5776
(2019/08/26)
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- Synthesis of new bis-benzylidene-hydrazides as a sensitive chromogenic sensor for naked-eye detection of CNˉ and AcOˉ ions
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Some new bis-benzylidene-hydrazides were synthesized via a condensation reaction of the corresponding azo dyes with adipic acid dihydrazide. All compounds because of the three possible stereoisomers showed four sets of signals in NMR. The anion recognition studies exhibited that the nitro bis-benzylidene-hydrazide derivative acts as a highly sensitive and selective chromogenic sensor for naked-eye detection of CNˉ and AcOˉ ions, with a distinct color change from yellow to blue and yellow to purple, respectively. The limit of detection (LOD) was found for 1d toward CNˉ to be 1.1 μM. The result of the Job's plot indicated stoichiometry of binding between chemosensor and anions is found to be 1:2.
- Sheykhi-Estalkhjani, Ammar,Mahmoodi, Nosrat O.,Yahyazadeh, Asieh,Nadamani, Meysam Pasandideh
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p. 4868 - 4874
(2018/08/09)
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- Spiropyran-azobenzene-DBU system as solvent indicator
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A dyad bearing azobenzene and spiropyran units was synthesized and its applications in indicating the polarity and protic or aprotic properties of a solvent were explored. The spiropyran-azobenzene derivative (SPAB) can be induced to different forms in different miscellaneous solvents accompanied with different color changes and spectral characteristics at the presence of organic base DBU. In a nonpolar or low-polar solvent, SPAB exists in thermostable spiropyran form with yellow color output. While in an aprotic polar solvent, the spiropyran part isomerized to merocyanine form giving a blue color. When SPAB is subjected to a protic solvent, the alkylation reaction occurs at the oxygen generating the alkylated-SPAB with red color. This solvent-dependent property can be used for discriminating solvent type.
- Xu, Zhiping,Li, Shen,Shen, Yujun,Chen, Meijun,Shao, Xusheng
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p. 3829 - 3832
(2018/10/04)
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- New generation of nitrite functionalized star-like polyvinyl imidazolium compound: Application as a nitrosonium source and three dimensional nanocatalyst for the synthesis of azo dyes
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The compounds with three-dimensional and ionic structures have attracted considerable attentions because of their unique characteristics as a drug carrier and catalyst. Star-like poly ionic compounds are a new generation of three-dimensional structures which have both; the exclusive ionic features and three-dimensional structures. Recently, we reported the synthesis of diazonium salts from aniline derivatives using carboxyl and nitrite functionalized graphene quantum dots. Methods: Nitrite-functionalized star-like polyionic (NFSP) compound was synthesized as a new generation of three-dimensional nanocatalyst. Herein, the use of NFSP as an efficient reagent and nanocatalyst for the diazotization of aniline derivatives and subsequent synthesis of azo dyes via the reaction with active phenolates under solvent-free conditions was reported. Results: In order to demonstrate the positive impact of NFSP efficiency, the reaction times and yields of the products were compared with other methods and catalysts which have been reported previously. The brilliant performance of NFSP can be ascribed to multifunctional reagent and also trapping the ingredient within catalyst cavities. Conclusion: A highly effective and cost-effective method has been developed for the preparation of azo dyes. In reported method, new three-dimensional catalyst with highly ionic characteristic and multifunctional nitrosonium source is available. These special features reduced the required amount of catalyst, reaction time and also increased the efficiency of catalyst.
- Shomali, Ashkan,Valizadeh, Hassan,Noorshargh, Saeideh
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p. 409 - 418
(2017/07/24)
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- Synthesis, characterization and thermal properties of the new azo-containing salicylidenic Schiff bases and their copper (II) complexes
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In this paper, six new azo Schiff base ligands (1-6) were synthesized in excellent yields by the condensation reaction of 5-(4-nitrophenylazo) salicylaldehyde with ethylamine, hexylamine, ethanolamine and benzylamine in the presence glacial acetic acid, respectively. After characterizing the newly synthesized ligands with melting point, TLC, IR, H-NMR, UV-Visible, elemental analyses and mass spectral data, they were reacted with copper acetate in 1:2 molar ratio (metal: ligand) to obtain copper (II) complexes (1a-6f). The structures of copper (II) complexes were characterized by IR spectra and elemental analyses. The thermal stability of the azo Schiff base ligands and related complexes were studied by using differential scanning calorimetry (DSC) and thermogravimetric analyses (TGA).
- Banaei, Alireza,Karimi, Soheyla,Jafari, Mahin
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p. 278 - 284
(2017/05/22)
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- Selective Naked-eye Detection of Acetate by new Azoisonicotinohydrazide Derivatives
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Three new hydrazone, based on azo-isonicotinohydrazide derivatives, have been designed, synthesized and characterized by FT-IR, 1H NMR and 13C NMR spectroscopy. The new compounds were designed to act as selective molecular sensors for naked-eye detection of acetate anion. To study the effect of the substituent at certain position in the main structure on the selectivity of the sensor, the compounds were designed to have -CH3, -H or -NO2 at that position. Solutions of different anions (F-, H2PO4-, NO2-, NO3-, Cl-, HSO4-, HCO3-) and AcO- were used to test the selectivity. The results revealed that the compound with electron withdrawing group (NO2) interacts selectively with acetate producing a significant feasible color change which makes it considered as selective molecular sensor for naked-eye detection of acetate. The dissociation constant for AcO- with the new sensor was also determined.
- Makki, Sajjad Q.,Balakit, Asim A.
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p. 3160 - 3165
(2018/01/17)
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- Synthesis, Characterization, Antibacterial, and Antifungal Activity of Novel 2-(2-hydroxy-5-((aryl)-diazenyl)phenyl)-3-(4-hydroxyphenyl)-thiazolidin-4-one
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A series of novel thiazolidinones, that is, 2-(2-hydroxy-5-((aryl)-diazenyl)phenyl)-3-(4-hydroxyphenyl)-thiazolidin-4-one, have been synthesized by reaction of various Schiff bases 2-(4-hydroxyphenylimino)methyl)-4-(aryl)diazenyl)phenol with ethanolic thioglycolic acid. Schiff bases were obtained by the reactions of 4-amino phenol with 2-hydroxy-5-((aryl)diazenyl)benzaldehyde. The structures of the newly synthesized compounds were confirmed by IR,1H NMR, mass spectra, and C, H, N elemental analysis. The thiazolidinone derivatives were evaluated for their antibacterial and antifungal activity.
- Chopde, Himani N.,Pandhurnekar, Chandrashekhar P.,Meshram, Jyotsna S.,Pagadala, Ramakanth
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p. 758 - 763
(2017/02/03)
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- Sensitivity and Resolution Development of Spiropyran-based Molecular Photoswitches
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The phenylazo moiety and its donor- and acceptor-substituted derivatives are studied as effective auxochromes to improve their sensitivity and resolution for distinguishing between the spiro (SP; OFF) and mero (ON) forms in molecular photoswitching applications. Thus, 13 azospiropyran derivatives were synthesized and their spectroscopic and photokinetic behaviors were studied. The quality of photochromic reactions of the synthesized photochromic compounds were compared using a dose–response model. Interestingly, by replacing the nitro group in 6-nitrospiropyran (ε = 0.42 × 104 M?1 cm?1) with a simple phenylazo moiety, the SP form is still colorless and the color intensity of the merocyanine (MC) form is improved desirably by extending the conjugation length (1a, ε = 1.35 × 104 M?1 cm?1). The presence of a hydrophilic OH group or a CH3 group at the para position of phenylazo moiety revealed more or less the same photochromic properties as 1a. The OCH3 group substituted at position 6 of the phenylazo moiety at the para position of the azobenzene moiety effectively increased the photochromic properties with the maximum k-value for SP to MC switching. Meanwhile, Cl, Br, COOH, and NO2 groups at the para position of the azobenzene moiety revealed the reduction in photochromic properties compared to 1a.
- Heydaripour, Maryam,Nourmohammadian, Farahnaz,Saadatjoo, Naghi
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p. 847 - 858
(2016/10/22)
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- A metal complex azo class chiral, synthesis method and use thereof
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The present invention discloses azo chiral metal coordination compounds, a synthesis method and applications thereof, and relates to a variety of azobenzene group-containing chiral Schiff base metal coordination compounds substituted with different substituents. According to the present invention, the obtained metal coordination compounds have characteristics of reversible photochromism property of the azobenzene function group, light-emitting property of the Schiff base metal coordination compound, and the chiral characteristic of the molecule, and have good application potential in the photochromism field, and the preparation method has characteristics of simple preparation conditions, easy operation, mild reaction conditions and easily available raw materials, and is suitable for popularization and application.
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Paragraph 0077
(2017/02/24)
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- 2-[2-hydroxy-5-(4-nitroazobenzene)styryl]-8-hydroxyquinoline colorimetric reagent, preparation and application
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The invention discloses a 2-[2-hydroxy-5-(4-nitroazobenzene)styryl]-8-hydroxyquinoline colorimetric reagent, as well as a preparation method and application thereof. The colorimetric reagent which can be applied to analytic chemistry for detecting F, AcO, pH and H2O is prepared from a quinoline derivative and a nitroazobenzene derivative which serve as main raw materials. The colorimetric reagent selectively detects F and AcO by controlling different solvents through a ratio absorption method; meanwhile, the colorimetric reagent can be easily and quickly applied to visual detection of F, AcO, pH and H2O. The preparation cost is low, the detection sensitivity is high, the selectivity is high, the operating conditions are easy to control, and the application prospect is good.
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Paragraph 0012; 0090; 0091
(2017/02/02)
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- Carboxyl and nitrite functionalized graphene quantum dots as a highly active reagent and catalyst for rapid diazotization reaction and synthesis of azo-dyes under solvent-free conditions
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Carboxyl and nitrite functionalized graphene quantum dots was prepared from carboxyl and hydroxyl functionalized graphene quantum dots using NaNO2 in the absence of mineral acids. This functional group conversion was confirmed by FT-IR spectroscopy, photoluminescence and X-ray diffraction. The carboxyl and nitrite functionalized graphene quantum dots was used as an effective nitrosonium ion source and reusable catalyst for the efficient diazotization of a variety of arylamines without using any additional acid. Subsequent azo-coupling of these freshly prepared diazonium salts with a range of active aromatic compounds led to the requisite azo-dyes in excellent yields in very short reaction times with a simple experimental procedure.
- Valizadeh, Hassan,Shomali, Ashkan,Nourshargh, Saideh,Mohammad-Rezaei, Rahim
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p. 522 - 528
(2015/03/18)
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- Synthesis, characterization and antibacterial activities of novel mixed ligands (azo anils and oxalate ion) copper(II) complexes
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Three azo anils ligands; 4-[(4-nitrophenyl)diazenyl]-2-[(phenylimino)met-hyl]phenol (L1), 2- {[(2-methylphenyl)-imino]-methyl}-4-[(4-nitrophenyl)diazenyl]phenol (L2) and 2-[(naphthalen-1-ylimino)- methyl]-4-[(4-nitrophenyl)diazenyl]-phenol (L3) were synthesized and characterized using elemental analysis, FT/IR spectroscopy, 13C and 1H NMR spectroscopy and UV-Vis spectroscopy. Similarly three mixed ligand complexes, {(L1)Cu(II)(OX)}, {(L2)Cu(II)(OX)} and {(L3)Cu(II)(OX)} constituting of azo anils and oxalate ion were also synthesized and characterized using elemental analysis, atomic absorption spectroscopy, FT/IR spectroscopy and UV-Vis spectroscopy and square planner geometry was suggested for Cu(II) complexes. Antibacterial activities of free ligands (azo anils and oxalate) and Cu(II) complexes were determined. Gram positive (Bacillus subtilis and Staphylococcus aureus) and Gram negative (Enterobacter aerogenes and Escherichia coli) bacteria were used for antibacterial study. The results have shown that Cu(II) complexes have privileged antibacterial activities compared to free ligands. The enhancement in antibacterial activities of transition metal complexes compared to corresponding free ligands may be attributed to structural symmetry of transition metal. The order of antibacterial activities of transition metal complexes, {(L1)Cu(II)(OX)} > {(L2)Cu(II)(OX)} > {(L3)Cu(II)(OX)}.
- Ameen, Muhammad,Gilani,Naseer, Amina,Shoukat, Ishrat,Ali
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p. 399 - 406
(2015/10/19)
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- Synthesis and identification of some new 2,3-disubstituted 1,3-oxazepine-4,7-dione derivatives containing azo group and 1,3,4-thiadiazole moiety
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Azoaldehyde derivatives (1a-f) were prepared through coupling reactions between diazonium salts of six primary aromatic amines and alkaline solution of 2-hydroxy benzaldehyde. Compounds (1a-f) were then introduced in acid-catalyzed condensation reactions with 2-amino-5-mercapto-1,3,4-thiadiazole to obtain six new azoimines (2a-f). (2+5) Cycloaddition of (2a-f) with each maleic and phthalic anhydrides respectivily gave nine new oxazepines (3a-f) and (4b, 4d, 4e). The synthesized compounds might have some biological activity.
- Abood, Zeid Hassan,Hussein, Murtadha Mohammed,Shaheed, Ihsan Mahdi
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p. 3074 - 3078
(2016/08/24)
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- Synthesis, characterization, and electrochemical study of some novel, azo-containing Schiff bases and their Ni(II) complexes
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Five novel azo-azomethine ligands with NN'OS coordination spheres were prepared by reaction of methyl-2-{N-(2′-aminoethane)}-amino-1- cyclopentenedithiocarboxylate (Hcden) with (E)-2-hydroxy-5-(phenyldiazenyl) benzaldehyde and its substituted derivatives
- Menati, Saeid,Azadbakht, Azadeh,Azadbakht, Reza,Taeb, Abbas,Kakanejadifard, Ali
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p. 499 - 506
(2013/07/27)
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- Synthesis and studies of selective chemosensors for anions and cations by azo-containing salicylaldimine-based receptors
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Three new chromogenic receptors containing electron-withdrawing groups appended to the azophenol moiety were synthesized, characterized, and their chromogenic behavior toward various anions and cations investigated. These chemosensors show visual changes towards biologically relevant anions like F- and OH-, and also towards various cations such as Cu2+, Co2+, Ni2+, Mn2+, and Zn2 +. Yet, other anions such as Cl-, Br-, and NO3- could not cause any color change. The sensing action was further confirmed by UV-Vis titration. 1H-NMR experiments were carried out to explore the nature of interaction between receptors with F- and OH -. The binding constants (Ka) of the host-guest complexes formed were determined.
- Arabahmadi, Raziyeh,Amani, Saeid
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p. 218 - 226
(2013/04/10)
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- Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica for the diazotization of aniline derivatives and subsequent synthesis of azo dyes
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Imidazolium based nitrite ionic liquid containing trimethoxysilyl group was prepared from the reaction of N-methylimidazole and (3-chloropropyl) trimethoxysilane. This ionic liquid was immobilized on silica covalently to give nanoparticles with the imidazolium nitrite moiety remaining intact. The diazotization reaction was performed as a model reaction to examine the activity of these nanoparticles as a nitrosonium source. Excellent performance was exhibited in the diazotization reaction of various aniline derivatives in the presence of HCl under mild heterogeneous conditions (room temperature and short reaction time). In-situ coupling of diazonium salts to a range of tertiary anilines, phenols and naphthols afforded the requisite azo dyes in good yield, using standard experimental procedures.
- Valizadeh, Hassan,Amiri, Mohammad,Hosseinzadeh, Fatemeh
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experimental part
p. 1308 - 1313
(2012/03/27)
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- Theoretical investigation of the conformation and hydrogen bonding ability of 5-arylazosalicylaldoximes
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Conformations of 5-arylazosalicylaldoximes 6-10 have been predicted from spectral and theoretical studies. The orientation of OH bond is predicted to be anti to CN bond from the PES analysis. The presence of intramolecular hydrogen bonding in oximes 6-10 and their parent aldehydes 1-5 is supported by the additional bond and ring critical points from AIM analysis, hyperconjugative interaction energies determined from NBO analysis and selected geometrical parameters derived from optimized structures. Molecular properties such as dipole moment, polarizability and hyperpolarizabilities for oximes 6-10 and their parent aldehydes 1-5 were also determined by computational studies.
- Manimekalai, A.,Balachander, R.
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p. 175 - 185,11
(2020/08/24)
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- Synthesis, characterization, and tautomeric properties of some azo-azomethine compounds
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The primary azo compound 1-(3-formyl-4-hydroxyphenylazo)-4-nitrobenzene reacts with some aliphatic and aromatic diamines and yields the corresponding azo-azomethine compounds. These compounds were characterized by elemental analysis, IR, UV/Vis, and NMR spectroscopy. The primary azo compound exists entirely in the azo form in solution as well as in the solid phase. The tautomeric structure of azo-azomethine compounds heavily depends on the solvent and the substituents. Aliphatic diamine-based compounds favor the enol-imine tautomer while aromatic diamine-based compounds have structures that lie between the two enol-imine and keto-amine tautomers due to a relatively strong intramolecular hydrogen bond. The compounds exhibit positive solvatochromism (bathochromic shift) so that their absorption bands move toward longer wavelengths as the polarity of the solvents increases. In addition, UV/Vis spectrophotometry has shown that the studied compounds have molar extinction coefficients larger than 40000.
- Hamidian, Kourosh,Irandoust, Mohsen,Rafiee, Ezzat,Joshaghani, Mohammad
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scheme or table
p. 159 - 164
(2012/05/20)
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- Synthesis, spectroscopy, thermal analysis, magnetic properties and biological activity studies of Cu(II) and Co(II) complexes with Schiff base dye ligands
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Three azo group-containing Schiff base ligands, namely 1-{3-[(3- hydroxypropylimino) methyl]-4-hydroxyphenylazo}-4-nitrobenzene (2a), 1-{3-[(3-hydroxypropylimino) methyl]-4-hydroxyphenylazo}-2-chloro-4-nitrobenzene (2b) and 1-{3-[(3-hydroxypropylimino) methyl]-4-hydroxyphenylazo}-4-chloro-3- nitrobenzene (2c) were prepared. The ligands were characterized by elemental analysis, FTIR spectroscopy, UV-Vis spectroscopy, 13C- and 1H-NMR spectroscopy and thermogravimetric analysis. Next the corresponding copper(II) and cobalt(II) metal complexes were synthesized and characterized by the physicochemical and spectroscopic methods of elemental analysis, FTIR spectroscopy, UV-Vis spectroscopy, magnetic moment measurements, and thermogravimetric analysis (TGA) and (DSC). The room temperature effective magnetic moments of complexes are 1.45, 1.56, 1.62, 2.16, 2.26 and 2.80 B.M. for complexes 3a, 3b, 3c, 4a 4b, and 4c, respectively, indicating that the complexes are paramagnetic with considerable electronic communication between the two metal centers.
- Ahmadi, Raziyeh Arab,Amani, Saeid
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experimental part
p. 6434 - 6448
(2012/08/28)
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- A new nitrite ionic liquid (IL-ONO) as a nitrosonium source for the efficient diazotization of aniline derivatives and in-situ synthesis of azo dyes
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A new task-specific nitrite containing ionic liquid derived from the O-nitrosation of N-methyl-N-hydroxybutylimidazolinium chloride was synthesized and used as a source of nitrosonium ion to affect the efficient diazotization of arylamines. The diazonium salts thus obtained were coupled, using standard experimental procedures, to a range of tertiary anilines, phenols and naphthols to afford the requisite azo dyes in good yield. The diazotization and subsequent azo-coupling generated the related azo dyes at 0-5 °C in short reaction times with a simple experimental procedure.
- Valizadeh, Hassan,Shomali, Ashkan
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experimental part
p. 1138 - 1143
(2012/03/27)
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- Synthesis and biological activity evaluation of some binuclear metal complexes of Cu(II) and Zn(II) with tridentate schiff base ligands
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A few kinds of new Schiff bases were synthesized by reaction of 2-aminophenol and corresponding synthesized azo compounds 3a-e. Further reaction of these Schiff bases 4a-e with transition metal salts as Cu(II) and Zn(II) gave corresponding binuclear complexes 5a-e and 6a-e. The antibacterial activity of prepared complexes was investigated against Staphylococcus aureus and Escherichia coli bacteria. The results for some compounds revealed a moderate to good inhibition against Staphylococcus aureus compared with penicillin zone of inhibition.
- Mobinikhaledi, Akbar,Zendehdel, Mojgan,Safari, Parvin,Hamta, Ahmad,Shariatzadeh, S. Mehdi
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experimental part
p. 165 - 170
(2012/06/01)
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- New 1,2,4-triazole-based azo-azomethine dyes. Part II: Synthesis, characterization, electrochemical properties and computational studies
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A new series of monoiminated 1,2,4-triazole-based azo-azomethine dyes have been synthesized via condensation reaction of 4-amino-3-methyl-5-mercapto-1,2,4- triazole with various substituted azo-coupled salicylaldehyde. The dyes have been characterized by using FT-IR, UV-Vis and 1H NMR spectroscopic methods as well as elemental analysis. The electrochemical behavior of the dyes has been investigated by cyclic voltammetry in DMSO at five different scan rates. Solvatochromic behavior of the dyes has been also investigated in four organic solvents with different polarities. Furthermore, the 1H chemical shielding of the dyes were studied by the gauge independent atomic orbital (GIAO) method at the level of density functional theory (DFT).
- Khanmohammadi, Hamid,Erfantalab, Malihe,Bayat, Atena,Babaei, Ali,Sohrabi, Masoud
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p. 876 - 884
(2012/11/07)
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- Ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite as a new reagent for the efficient diazotization of aniline derivatives and in situ synthesis of azo dyes
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A new ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of arylamines into their corresponding diazonium salts which were converted into their related azo dyes via the in situ azo-coupling with aniline derivatives or phenolic compounds. The diazotization of anilines in this ionic liquid and subsequent azo-coupling generated the related azo dyes in good to excellent yields at 0-5 °C in short reaction times via a simple experimental procedure.
- Valizadeh,Amiri,Shomali,Hosseinzadeh
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experimental part
p. 495 - 501
(2012/07/13)
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- Optical and photovoltaic properties of salicylaldimine-based azo ligands
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A series of azo dyes containing salicylaldimine-based ligands as side chains were prepared and characterized. Absorption and emission data in five solvents of different polarities were studied. Photoirradiation studies under an oxygen atmosphere in water showed that the Schiff base side chains enhanced the photo-oxidative stability of the azo chromophore. The electrochemical properties of the dyes were investigated by a cyclic voltammetry. The synthesized salicylaldimine-based azo dyes gave two irreversible oxidation potentials. Complexation behavior of synthesized compounds with titanium (IV) ions was illustrated by the change in their absorption spectra. These ligands are appropriate sensitizers for anchoring to the TiO2 surface chemically in dye-sensitized solar cell (DSSC) productions. Electron injection capacities to TiO2 and photovoltaic performance of the synthesized salicylaldimine-based azo dyes were tested with DSSC.
- Din?alp, Haluk,Yavuz, Sinem,Hakli, ?zgül,Zafer, Ceylan,?zsoy, Cihan,Durucasu, Inci,I?li, Siddik
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scheme or table
p. 8 - 16
(2010/10/20)
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- Some polyhydroxy azo-azomethine derivatives of salicylaldehyde: Synthesis, characterization, spectroscopic, molecular structure and antimicrobial activity studies
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Some new substituted polyhydroxy azo-azomethine compounds were prepared by reaction of tris(hydroxymethyl)aminomethane with (E)-2-hydroxy-5-(phenyldiazenyl) benzaldehyde and its substituted derivatives. The structures of azo and azo-azomethine compounds were determined by IR, UV-vis, 1H NMR and 13C NMR spectroscopic techniques, and/or X-ray diffraction studies. According to IR spectra, all azo-azomethine compounds adopt keto form in solid state. UV-vis analysis has shown the presence of keto-enol tautomerism in solution for all azo-azomethine compounds, except that for nitro substituted derivative, enol form is dominantly favored in solution. At the same time, above mentioned derivative compounds were studied in vitro for their antimicrobial properties. Among the phenylazosalicylaldehyde series compound tested, 4-phenylazosalicylaldehyde, 4-(3-chlorophenylazo)salicylaldehyde, 4-(2-chlorophenylazo)salicylaldehyde, 4-(4-fluorophenylazo)salicylaldehyde, 4-(3-chlorophenylazo)salicylaldehyde and 4-(4-ethylphenylazo)salicylaldehyde showed a weak antimicrobial activity only against gram positive bacteria. On the contrary, phenylazosalicylaldehyde series compounds were reacted tris(hydroxmethyl)aminomethane, that exhibited a strong antimicrobial activity against gram positive bacteria, yeast and mould. Moreover, while the 2-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylimino]methyl}phenol did not show an inhibition on tested microorganism, the addition of phenyldiazine groups to 2-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylimino]methyl}phenol resulted in a strong increases in antimicrobial activity.
- Odaba?o?lu, Mustafa,Albayrak, ?i?dem,?zkanca, Re?it,Aykan, Fatma Zehra,Lonecke, Peter
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- Complexes of a Schiff Base Formed by Condensation of S-Benzyldithiocarbazate with 5 salicylaldehyde
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The synthesis and characterization of Co2+, Ni2+, Cu2+, Cd2+, and Hg2+ complexes of S-benzyl-β-N-3-(4-hydroxy-4'-nitroazobenzene)methylene dithiocarbazate are reported. Elemental analysis, magnetic susceptibility and spectral (ir, Uv-vis, and NMR) measurement have been used to characterize the complexes. The spectral data show that the ligand behaves in a bidentate and/or tridentate manner.
- Monshi, M. A. S.
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- Transition Metal Complexes of 5-[4'-(Nitrophenyl)azo]salicylaldehyde-3-thiosemicarbazone
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Metal complexes formed by the interaction of 5-[4'-(nitrophenyl)azo]salicylaldehyde-3-thiosemicarbazone [HAT] with some bivalent metal ion have been prepared. The ligand behaves as neutral bidentate, as mononegative bidentate or tridentate ligand.
- Monshi, Mahmoud A. S.
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p. 158 - 159
(2007/10/03)
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- Thermo- and Photochromic Dyes: Spiro(indolinebenzopyrans) 2. - Detailed Assignment of the 1H NMR Spectra and Structural Aspects of the Closed Form of 1,3,3-Trimethylspiro(indoline-2,2'-benzopyrans)
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The proton NMR assignments for a series of 12 thermo- and photochromic 1,3,3-trimethylspiro(indoline-2,2'-benzopyrans) dyes is reported.All of the protons in the dye molecule were assigned through a combination of homonuclear decoupling experiments and correlation spectroscopy.The relative stereochemistry of the indolino gem-dimethyl groups was assigned so that, for the S-epimer, the pro-R methyl was found to resonate at 1.24 ppm while the pro-S methyl appeared at 1.37 ppm for compound 1. KEY WORDS: Thermo- and photochromic dyes, Spiro(indoline-2,2'-benzopyrans), 1H NMR assignments
- Keum, Sam-Rok,Lee, Ki-Bong,Kazmaier, Peter M.,Manderville, Richard A.,Buncel, Erwin
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p. 1128 - 1131
(2007/10/02)
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