cas 136-64-1, TEREPHTHALIC DIHYDRAZIDE | Articles data

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Design, synthesis and spectroscopic characterization of metal (II) complexes derived from a tetradentate macrocyclic ligand: Study on?antimicrobial and antioxidant capacity of complexes
The paper presents the synthesis of Co(II), Ni(II) and Cu(II) complexes of macrocyclic Schiff base ligand derived from 1, 4-dicarbonyl-phenyl-dihydrazide and ethyl 3-oxobutanoate (2:2). The synthesized ligand and its metal complexes were characterized by elemental analyses, magnetic susceptibility measurements, FTIR, UV–Vis., mass 1H NMR and X-ray diffraction. The Cu(II) complex exhibit distorted octahedral geometry, whereas an octahedral geometry is suggested for other complexes. The synthesized compounds were screened in?vitro for their antimicrobial activities to evaluate their inhibiting potential against bacterial species Pseudomonas aeruginosa, Escherichia coli, Salmonella typhimurium, Staphylococcus aureus and fungal species include Aspergillus flavus, Aspergillus fumingatus, and Candida albicans. The complexation led to a remarkable increase in antimicrobial activity. In addition, the antioxidant activity of the compounds was also investigated through scavenging effect on DPPH radicals. The obtained IC50 value of the DPPH activity for the copper complex was higher than other compounds.
Gull, Parveez,Malik, Manzoor Ahmad,Dar, Ovas Ahmad,Hashmi, Athar Adil
p. 212 - 216
(2017)
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Synthesis and characterization of 1,3,4-oxadiazole derivatives containing alkoxy chains with different lengths
The synthesis, optical properties, electrochemical properties, electronic structures and applications in electroluminescent device of three series of 1,3,4-oxadiazole derivatives, 1,4-bis[(4-methylphenyl)-1,3,4-oxadiazolyl]phenylene (OXD1), 5,5′-di-(4-methyl)-2,2′-p-(2,5-bisalkoxyphenylene)-bis-1,3,4 -oxadiazole (OXD2-n) and 1,4-bis[(4-alkoxyphenyl)-1,3,4-oxadiazolyl]phenylene (OXD3-n) are reported. The molecular structures of the oxadiazole compounds were confirmed by FT-IR, 1H NMR spectroscopy and elemental analysis. The optical and electrochemical properties of the compounds were investigated by UV-vis absorption and photoluminescence spectroscopy as well as cyclic voltammetry. The results show that introduction of two alkoxy groups whose electron-donating ability is stronger than that of methyl groups increases the electron density of the conjugated segment of OXD2-n (with side-on alkoxy substituents) and OXD3-n (with end-on alkoxy substituents), and thus leads to the absorption maximum bathochromic-shift compared to that of OXD1. The HOMO and LUMO energy levels of the compounds studied are in the range of -2.78 to -2.89 and -5.75 to -6.20 eV. Calculations on the representative compounds by the Dmol3 package of MS Modeling 3.0 revealed that the increase of energy levels in both OXD2-n and OXD3-n was due to the change of the frontier molecular orbital distribution in the central benzene ring. The light-emitting devices have been fabricated using blends of MEH-PPV and these compounds as emissive layers, among which, maximum brightness up to 11810 cd m-2 (8.5 V) has been observed, which is 40 times brighter than that with MEH-PPV. The result of the devices suggested that oxadiazole derivatives studied function well as electron-transporting materials and can be used in LEDs, and thus to enhance the efficiency of LEDs.
Zhang, Xiao-bing,Tang, Ben-chen,Zhang, Peng,Li, Min,Tian, Wen-jing
p. 55 - 64
(2007)
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Biological activity studies on metal complexes of macrocyclic Schiff base ligand: Synthesis and spectroscopic characterization
In this study, we prepared the macrocyclic Schiff base ligand (L) derived from 1,4-dicarbonylphenyl-dihydrazide and pentane-2,4-dione (2:2) and its CoII, CuII and NiII complexes. The compounds were characterized by the analytical and spectroscopic methods like elemental analysis, molar conductance measurements, mass spectrometry,1 H nuclear magnetic resonance (NMR), and Fourier transform infrared (FTIR) spectroscopy. The ligand behaves as a tetradentate ligand and coordinates to the metal ions via the nitrogen atoms and the complexes have the mononuclear structures. The analytical and spectroscopic results indicated that the complexes are non-electrolytes in nature and may be formulated as [M(C26H28 N8 O4)X2], where M = CoII, CuII and NiII and X = Cl-. The antimicrobial activities of the ligand and its complexes, as growth inhibiting agents, have been screened in vitro against different species of bacteria and fungi and the results concluded that the metal complexes are effective drugs against the tested strains as compared to the macrocyclic ligand.
Gull, Parveez,Hashmi, Athar Adil
p. 1331 - 1337
(2015)
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Schiff base compound as a corrosion inhibitor for mild steel in 1 M HCl
A new Schiff base compound named 4-(4′-benzoylhydrazine)-pyridinecarboxaldehyde hydrazone (BPBH) was synthesized and investigated as a corrosion inhibitor for mild steel in 1 M HCl using weight loss measurements, electrochemical techniques, and adsorption studies. The structure of BPBH was characterized by elemental analysis, infrared spectroscopy (IR), and 1H nuclear magnetic resonance (NMR). The results clearly suggest that the compound acts as a mixed-type inhibitor of acid corrosion of mild steel. The adsorption of BPBH on the metal surface in 1 M HCl was found to agree with the Langmuir isotherm with a standard free energy of adsorption (Δ G ads 0) of -31.60 kJ/mol. Scanning electron microscopy images indicate that BPBH exhibits good corrosion inhibition performance for mild steel in 1 M HCl. Quantum chemical calculations were also carried out to verify the inhibition efficiencies obtained from all the experiments.
Liu, Hong,Zhu, Lin,Zhao, Qilong
p. 4943 - 4960
(2015)
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Mechanosynthesis of imine, β-ketoenamine, and hydrogen-bonded imine-linked covalent organic frameworks using liquid-assisted grinding
A variety of aromatic amines/hydrazides and aldehydes have been utilized for the construction of crystalline COFs at a faster rate and in high yield, irrespective of their reactivity and solubility using the Liquid-Assisted Grinding (LAG) method.
Das, Gobinda,Balaji Shinde, Digambar,Kandambeth, Sharath,Biswal, Bishnu P.,Banerjee, Rahul
p. 12615 - 12618
(2014)
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Synthesis, characterization, in vitro and in silico studies of bis-hydrazone complexes derived from terephthalic dihydrazide
Bis-hydrazone of terephthalic dihydrazide was designed and synthesized using terephthalic dihydrazide and picolinaldehyde. Various bioactive benzoic acids such as benzoic acid, aspirin and salicylic acid were selected as a counter ion moiety for preparing bis-hydrazone complexes (BHCs). The prepared BHCs were well characterized using spectroscopic techniques like 1H NMR, 13C NMR and FT-IR. The BHCs showed very good in vitro antidiabetic activity in the α-amylase enzyme inhibitory method and moderate activity in the α-glucosidase inhibitory method. The molecular docking interactions of BHCs were performed against the human pancreatic α-amylase enzyme (1HNY.pdb) and homology model of α-glucosidase (3A4A.pdb) to prove the enzyme inhibitory activity. The BHCs showed very good binding energy, the complex BHB showed 5 numbers of hydrogen bonding interactions with amino acid residues of 1HNY.pdb and BHS showed 5 numbers of hydrogen bonding interactions with 3A4A.pdb. Further, the molecular orbital studies were performed using density functional theory calculations in order to support the docking study.
Meethale?Pallolathil, Ramya Rajan,Nithyabalaji, Rajendran,Rathikha, Ramaswamy,Sribalan, Rajendran
(2021)
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Synthesis of Schiff base 24-membered trivalent transition metal derivatives with their anti-inflammation and antimicrobial evaluation
The paper presents the synthesis of macrocyclic complexes [{M(C52H36N12O4)X}X2] of Cr(III), Mn(III) and Fe(III) with Schiff base ligand (C52H36N12O4) obtained through the condensation of 1,4-dicarbonyl phenyl dihydrazide with 1,2-di(1H-indol-1-yl)ethane-1,2-dione. The newly formed Schiff base and its complexes have been characterized with the help of elemental analysis, condensation measurements, magnetic measurements and their structure configuration have been determined by various spectroscopic (electronic, IR, 1H NMR, 13C NMR, GCMS) techniques. The electronic spectra of the complexes indicate a five coordinate square pyramidal geometry of the center metal ion. These metal complexes and ligand were tested for their anti-inflammation and antimicrobial inhibiting potential and compared with standard drugs Phenyl butazone (anti-inflammation), Imipenem (antibacterial) and Miconazole (antifungal).
Kumar, Gajendra,Devi, Shoma,Kumar, Dharmendra
p. 680 - 688
(2016)
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Design, synthesis and characterization of macrocyclic ligand based transition metal complexes of Ni(II), Cu(II) and Co(II) with their antimicrobial and antioxidant evaluation
Three new complexes Ni(II), Cu(II) and Co(II) were synthesized of macrocyclic ligand derived from 1, 4-dicarbonyl-phenyl-dihydrazide and O-phthalaldehyde in the ratio of 2:2. The synthesized compounds were characterized by elemental analyses, molar conductance, magnetic susceptibility measurements, FTIR, UV–Vis., Mass and 1H NMR spectral studies. The electronic spectra of the metal complexes indicate a six coordinate octahedral geometry of the central metal ion. These metal complexes and the ligand were evaluated for antimicrobial activity against bacteria (E.?coli, B.?subtilis, S.?aureus) and fungi (A.?niger, A.?flavus, C.?albicans) and compared against standard drugs chloramphenicol and nystatin respectively. In addition, the antioxidant activity of the compounds was also investigated through scavenging effect on DPPH radicals.
Gull, Parveez,Malik, Manzoor Ahmad,Dar, Ovas Ahmad,Hashmi, Athar Adil
p. 734 - 741
(2017)
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Preparation, regulation and biological application of a Schiff base fluorescence probe
A facile fluorescence switch with Schiff base units was designed and achieved by nucleophilic addition and dehydration reaction. The fluorescence of the probe can be regulated by metal ions (Al3 + and Cu2 +). The whole process shows that the weak fluorescence of the probe enhances with the addition of Al3 +, and then the strong fluorescence of the probe/Al3 + ensemble reduces by introducing Cu2 +. Meanwhile, the solution color changes of the probe with metal ions can be observed under 365 nm UV-vis light from weak light, pale green, green, pale green to weak light. Noticeably, the photo regulation processes of the probe by metal ions can be realized in the biological system and applied in cells imaging. The work provides a new strategy for designing facile regulation probe and develops a new application for Schiff base derivatives.
Yin, Ninghua,Diao, Haipeng,Liu, Wen,Wang, Jingru,Feng, Liheng
p. 1 - 5
(2016)
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Photophysical, thermal properties, solvatochromism and DFT/TDDFT studies on novel conjugated D-A-π-A-D form of small molecules comprising thiophene substituted 1,3,4-oxadiazole
In this paper, we report the design and synthesis of a series of novel conjugated thiophene substituted 1,3,4-oxadiazole derivatives BSTO-4(a-f) of Donor-Acceptor-π-Acceptor-Donor form by utilizing palladium catalyzed Suzuki cross coupling reaction. Structures were characterized by using spectroscopic techniques namely FT-IR, 1H NMR, 13C NMR and Mass spectra. Their thermal, photophysical and solvatochromic properties were studied in detail. Also, the PL investigations in the solid state were carried out. Furthermore, theoretical calculations such as density functional theory (DFT) were performed to get a better understanding of the intramolecular charge transfer property and electronic structures of the compounds. Experimentally measured optical bandgap values are in the range 3.02 to 3.54 eV. All compounds exhibit Stokes shifts in the range of 2776–3964 cm?1 and fluorescence quantum yields (Φf) in the range of 0.06–0.70 in chloroform. These derivatives exhibit high thermal stability that is the 5% weight loss temperature of derivatives are in the range 178–356 °C and the compounds BSTO-4(b, e and f) had the glass transition temperatures (Tg) at 107 °C, 147 °C and 68 °C, respectively. These results demonstrate that the novel thiophene substituted 1,3,4-oxadiazole compounds are promising candidates for potential applications in development of OLEDs, organic electronic devices/optoelectronic devices.
Najare, Mahesh S.,Patil, Mallikarjun K.,Nadaf, AfraQuasar A.,Mantur, Shivaraj,Garbhagudi, Manjunatha,Gaonkar, Supreet,Inamdar, Sanjeev R.,Khazi, Imtiyaz Ahmed M.
(2020)
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Synthesis, spectral characterization and antimicrobial evaluation of Schiff base Cr (III), Mn (III) and Fe (III) macrocyclic complexes
A Schiff base ligand was synthesized by reacting 1,4-dicarbonyl-phenyl- dihydrazide and chromene-2,3-dione (2:2) and a series of metal complexes with this new ligand were synthesized by reaction with Cr (III), Mn (III), and Fe (III) metal salt in methanolic medium. The Schiff base ligand and its metal complexes have been characterized with the help of elemental analysis, conductance measurements, magnetic measurements and their structure configuration has been determined by various spectroscopic (electronic, IR, 1H NMR, 13C NMR, GCMS) techniques. Electronic spectra of the complexes indicate that the geometry of the metal center was five coordinate square pyramidal. These metal complexes were also tested for their antimicrobial activities to assess their inhibiting potential.
Kumar, Gajendra,Devi, Shoma,Johari, Rajeev,Kumar, Dharmendra
p. 269 - 274
(2012)
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Synthesis, spectral characterization, in-vitro microbiological evaluation and cytotoxic activities of novel macrocyclic bis hydrazone
A macrocyclic hydrazone Schiff base was synthesized by reacting 1,4-dicarbonyl phenyl dihydrazide with 2,6-diformyl-4-methyl phenol and a series of metal complexes with this new Schiff base were synthesized by reaction with Co(II), Ni(II) and Cu(II) metal salts. The Schiff base and its complexes have been characterized by elemental analyses, IR, 1H NMR, UV-vis, FAB mass, ESR spectra, fluorescence, thermal, magnetic and molar conductance data. The analytical data reveal that the Co(II), Ni(II) and Cu(II) complexes possess 2:1 metal-ligand ratios. All the complexes are non-electrolytes in DMF and DMSO due to their low molar conductance values. Infrared spectral data suggest that the hydrazone Schiff base behaves as a hexadentate ligand with NON NON donor sequence towards the metal ions. The ESR spectral data shows that the metal-ligand bond has considerable covalent character. The electrochemical behavior of the copper(II) complex was investigated by cyclic voltammetry. The Schiff base and its complexes have also been screened for their antibacterial (Escherichia coli, Staphylococcus aureus, Shigella dysentery, Micrococcus, Bacillus subtilis, Bacillus cereus and Pseudomonas aeruginosa) and antifungal activities (Aspergillus niger, Penicillium and Candida albicans) by MIC method. The brine shrimp bioassay was also carried out to study their in-vitro cytotoxic properties.
Avaji, Prakash Gouda,Vinod Kumar,Patil, Sangamesh A.,Shivananda,Nagaraju
p. 3552 - 3559
(2009)
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FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES
The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.
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(2021/06/22)

Synthesis and molecular docking of some new bis-thiadiazoles as anti-hypertensive α-blocking agents
Twelve bis-thiadiazole derivatives were synthesized in high yield via the reaction of 2,2′-terephthaloyl bis(N-phenylhydrazine carbothioamide) with a variety of hydrazonoyl chlorides in ethanol containing catalytic amounts of TEA. All the newly synthesized compounds were characterized by physical and chemical tools (FT-IR, 1H NMR, 13C NMR, and Mass spectrometry). Moreover, all the novel synthesized derivatives were screened for their antihypertensive α-blocking efficacy against to assess their pharmaceutical significance. The encouraging promising results obtained from antihypertensive α-blocking activity studies on the newly synthesized derivatives make the synthesis of a new series of these compounds and studying of their pharmaceutical importance an active area for more and more investigations. The molecular docking of the most active derivative 15 b against the human dopamine D3 receptor was performed by the Molecular Operating Environment (MOE 2014. 0901) program.
El-Enany, Waleed A. M. A.,Gomha, Sobhi M.,El-Ziaty, Ahmed K,Hussein, Wesam,Abdulla, Mohamed M.,Hassan, Shaimaa A.,Sallam, Hanan A.,Ali, Rania S.
p. 85 - 96
(2019/11/28)

Linkage Engineering by Harnessing Supramolecular Interactions to Fabricate 2D Hydrazone-Linked Covalent Organic Framework Platforms toward Advanced Catalysis
Covalent organic frameworks (COFs) are an emerging class of crystalline porous polymers with tailor-made structures and functionalities. To facilitate their utilization for advanced applications, it is crucial to develop a systematic approach to control the properties of COFs, including the crystallinity, stability, and functionalities. However, such an integrated design is challenging to achieve. Herein, we report supramolecular strategy-based linkage engineering to fabricate a versatile 2D hydrazone-linked COF platform for the coordination of different transition metal ions. Intra- and intermolecular hydrogen bonding as well as electrostatic interactions in the antiparallel stacking mode were first utilized to obtain two isoreticular COFs, namely COF-DB and COF-DT. On account of suitable nitrogen sites in COF-DB, the further metalation of COF-DB was accomplished upon the complexation with seven divalent transition metal ions M(II) (M = Mn, Co, Ni, Cu, Zn, Pd, and Cd) under mild conditions. The resultant M/COF-DB exhibited extended π-conjugation, improved crystallinity, enhanced stability, and additional functionalities as compared to the parent COF-DB. Furthermore, the dynamic nature of the coordination bonding in M/COF-DB allows for the easy replacement of metal ions through a postsynthetic exchange. In particular, the coordination mode in Pd/COF-DB endows it with excellent catalytic activity and cyclic stability as a heterogeneous catalyst for the Suzuki-Miyaura cross-coupling reaction, outperforming its amorphous counterparts and Pd/COF-DT. This strategy provides an opportunity for the construction of 2D COFs with designable functions and opens an avenue to create COFs as multifunctional systems.
Qian, Cheng,Zhou, Weiqiang,Qiao, Jingsi,Wang, Dongdong,Li, Xing,Teo, Wei Liang,Shi, Xiangyan,Wu, Hongwei,Di, Jun,Wang, Hou,Liu, Guofeng,Gu, Long,Liu, Jiawei,Feng, Lili,Liu, Yuchuan,Quek, Su Ying,Loh, Kian Ping,Zhao, Yanli
supporting information
p. 18138 - 18149
(2020/11/02)

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides
The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.
Wu, Dehua,Song, Jintong,Qu, Lang,Zhou, Weilan,Wang, Lei,Zhou, Xiangge,Xiang, Haifeng
supporting information
p. 3370 - 3378
(2020/10/02)

Synthesis, characterization and bioactivity of three carboxylic arylhydrazone compounds
Three novel carboxylic arylhydrazone compounds named 2- oxo propionic acid terephthalal acyl dihydrazone (1), 2-ketoglutaric acid terephthalal acyl dihydrazone (2) and 2-ketoglutaric acid salicyl- hydrazone (3) were prepared and characterized by elemental analysis, IR and 1H NMR. The antibacterial activities of 1 and 2 against wheat rust and coliform were investigated. The results showed that 1 had more excellent antibacterial properties than 2 against both wheat rust and coliform. In addition, the title compounds interaction with calf-thymus DNA (CT-DNA) were measured by fluorescence spectra method which indicating that they combined with CT-DNA by groove binding through hydrogen bonds.
Chen, Fengying,Wu, Wangting,Jin, Zhenguo,He, Shuiyang,Qiao, Chengfang,Yuan, Fei
p. 149 - 154
(2020/02/13)

Pd loaded and covalent-organic framework involved chitosan aerogels and their application for continuous flow-through aqueous CB decontamination
We herein report a series of COF-based poroplastic chitosan aerogels via a facile templated freeze-drying approach. The obtained composite aerogels are hydrophilic, robust, uniform and processable, however, with COF crystallinity and functionalities. Specifically, by introducing Pd@COF species (up to 50 wt%), we fabricated Pd@COF@chitosan aerogels which can be used to build highly efficient continuous flow-through microreactors for chlorobenzene (CB) dechlorination in water at room temperature. Given the versatile structural, shaping, and functional features, this approach could hopefully bring COFs into practical applications, especially concerning the growing global environmental issues.
Li, Fei,Ding, Luo-Gang,Yao, Bing-Jian,Huang, Ning,Li, Jiang-Tao,Fu, Qi-Juan,Dong, Yu-Bin
supporting information
p. 11140 - 11146
(2018/06/26)

Terephthalic acid derived ligand-stabilized palladium nanocomposite catalyst for Heck coupling reaction: without surface-modified heterogeneous catalyst
A new protocol is reported for the synthesis of a heterogeneous palladium nanocomposite stabilized with a terephthalic acid-derived ligand (N,N-bis(4-hydroxy-3-methoxybenzylidene)terephthalohydrazide). This is a highly insoluble ligand in common organic solvents, except dimethylformamide and dimethylsulfoxide. The resulting palladium nanocomposite acts as an efficient catalyst precursor for Mizoroki–Heck coupling reactions conducted under various reaction conditions. The spectral data suggest that the rate, yield and recycling of the catalyst are more effective for C–C coupling reactions. Copyright
Jithendra kumara,Krishnamurthy,Kumara swamy,Shashi kumar,Naik, Satish,Krishna,Naik, Nagaraj
(2016/12/26)

TARGETED CONTRAST AGENTS COMPRISING A HYDRAZIDE FUNCTIONAL GROUP
Described herein is a contrast agent for administration to a subject. The contrast agent includes a targeting portion that includes a hydrazide functional group; a metal ion bound to a metal-complexable portion; and a linker joining the targeting portion and the metal- complexable portion of the contrast agent. The portion that is not bound to a metal ion localizes the contrast agent to necrotic tissue in the subject.
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(2016/11/07)

Solvent dependent colorimetric, ratiometric dual sensor for copper and fluoride ions: Real sample analysis, cytotoxicity and computational studies
A novel colorimetric chemosensor based on terephthalic acid and pyridine aldehyde moiety was designed to detect Cu2+/F- ions in aqueous and DMSO solutions at physiological pH conditions with the detection limit of 0.25 μM and 3 μM for Cu2+/F- ions respectively. The probe was found to be highly selective to sense F- ion rather than CH3COO- and H2PO4- ions. Interestingly, the probe behaved as a promising receptor by detecting F- ions even in ordinary tap water through distinct colour change. Moreover, the chemosensor showed lower cytotoxicity against AGS cancer cells and thus found to be biologically friendly. The reversibility of probe-F- binding was investigated using HCl in UV-vis experiment. The binding mechanism of chemosensor to Cu2+/F- ions was elucidated based on the UV-vis spectroscopy, NMR, ESI-Mass spectroscopy and cyclic voltammogram techniques. Furthermore, theoretical investigation was carried out using Gaussian 09 program.
Senthil Murugan, Arumugam,Abel Noelson, Enose Rajan,Annaraj, Jamespandi
p. 131 - 139
(2016/06/09)

PREPARING METHOD OF HYDRIZIDE COMPOUNDS
The present invention relates to a method for preparing hydrazide and, more specifically, to a method for preparing a hydrazide derivative compound by reacting a hydrazine-carbon dioxide coupled compound with an organic acid or sulfonic acid compound.COPYRIGHT KIPO 2015
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(2017/01/02)

Optically active poly (hydrazide-imide)-MWCNT nanocomposites through ultrasound assisted preparation
An optically active poly(hydrazide-imide) (PHI) containing L-lysine was prepared by interfacial polycondensation. The corresponding polymeric nanocomposites have been prepared using multi-walled carbon nanotube (MWCNT) through sonication. Crystallization was studied by DSC (Differential scanning calorimetry) technique. Incorporation of nanotubes into the polymeric matrix improved the mechanical properties of the PHIMWCNT nanocomposites. Electrical percolation was observed at more than 0.5 wt% of MWCNT in the PHI matrix. All studies revealed that ultrasound assisted method causes effective dispersion of MWCNTs in the PHI matrix. The polymeric nanocompo-sites were characterized by FT-IR, XRD, TEM, DSC, mechanical tests, and the DC electrical conductivity measurements.
Zahmatkesh, Saeed
p. 663 - 667
(2015/11/09)

New crystal compound containing the compound and an organic semiconductor element
Disclosed is a visible light-transmissive liquid-crystalline compound having good hole and electron-transport characteristics and useful as an organic semiconductor material. The compound is represented by a formula (1): wherein R independently represents hydrogen, or alkyl having from 1 to 24 carbon atoms, and any -CH2- in the alkyl may be replaced by -O-, -S-, -CO- or -SiH2-, any -(CH2)2- may be replaced by -CH=CH- or -C=C-, and any hydrogen may be replaced by halogen; Ar represents naphthylene, anthrylene, phenanthrylene, or phenylene; and every hydrogen in phenylene is replaced by halogen, and any hydrogen in naphthylene, anthrylene and phenanthrylene may be replaced by halogen.
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(2016/11/09)

Efficient routes for the synthesis of novel bis(s-triazolo[3,4-b][1,3,4] thiadiazines)
Bis(triazolo[3,4-b]thiadiazine) 4 in which the fused system is linked directly to the benzene core can be synthesized in 75% yield by, firstly, preparation of bis(s-triazole) 2 followed by reaction with phenacyl bromide 3 in refluxing EtOH/DMF mixture containing piperidine. Bis(s-triazolo[3,4-b][1,3,4] thiadiazines) 8 and 11 in which the triazolothiadiazines are linked to benzene core via alkyl or ether linkage were synthesized in 70 and 72% yields, respectively, starting from dicarboxylic acids 5 and 9 upon treatment with two moles of thiocarbohydrazide 6 to give the corresponding bis(4-amino-5-mercapto- s-triazolo-3-y1) derivatives 7 and 10 and subsequent reaction with two equivalents of phenacyl bromide. Bis(6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazines) 15a, 15b, 15c, 15d, 15e, 15f, which are linked to arene cores via sulfanylmethylene spacers, were prepared by the reaction of 4-amino-4H-1,2,4- triazole-3,5-dithiol 12 with the appropriate bis(bromomethyl)benzenes 13a, 13b, 13c, 13d, 13e, 13f to give bis(4-amino-5-mercapto-4H-3-sulfanylmethyl)arenes 14a, 14b, 14c, 14d, 14e, 14f and subsequent reaction with phenacyl bromide. Compounds 15a, 15b, 15c, 15d, 15e, 15f were alternatively obtained in 60-70% yields by twofold substitution of 13a, 13b, 13c, 13d, 13e, 13f with two equivalents of 6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-3-thiol 16 in refluxing EtOH/DMF mixture containing KOH. Bis(triazolothiadiazine) 22 attached to the benzene core through the thiadiazine ring via an amine linkage was prepared in 70% yield starting from p-phenylenediamine 19 by, firstly, acylation with chloroacetyl chloride 18 followed by bis-alkylation with 1,2,4-triazole 20 and subsequent intramolecular ring closure upon treatment with phosphorus oxychloride.
Sarhan, Radwan M.,Badawy, Mohamed A.,Elwahy, Ahmed H. M.
p. E176-E182
(2014/11/07)

Dinuclear vanadium, copper, manganese and titanium complexes containing O,O,N-dichelating ligands: Synthesis, crystal structure and catalytic activity
O,O,N-or O,N-dichelating ligands, H4L1, H 4L2, derived from new bis(hydroxybenzylidene)-substituted terephthalo and oxalo hydrazides were prepared and characterized by FT-IR and NMR spectroscopy (H4-L1 = dicondensation of salicylaldehyde and terephthalic acid dihydrazide, H4L2 = dicondensation of sali-cylaldehyde and oxalic acid dihydrazide). [{VO 2}2(H2L1)] (1), [{Cu(CH 3OH)}2(L1)] (2), [{Mn(CH3OH)} 2(L1)] (3) and [TiO(H3L1) 2] (4) complexes of the potentially hexadentate 2[ONO] donor hydrazone ligand [L1]4 were synthesized by reaction of the appropriate metal salts with H4L1. The complexes [{VO(CH3O)(CH3OH)}2(L2)] (5), [{Cu(CH3OH)}2(L2)] (6), [{Mn(H 2O)2(CH3OH)}2(L2)] (7) and [{TiO(CH3OH)}2(L2)]·2H2O (8) were synthesized by the reaction of corresponding metal salts with H 4L2. All complexes were characterized by microanalyses, FT-IR, UV-Vis and NMR spectroscopic methods. The crystal structures of 1 and 5 were established by X-ray analyses. Compound 1 is a one-dimensional coordination polymer. The catalytic potential of the complexes was evaluated for oxidation of hydrocarbons including cycloalkenes, cyclic alkanes and benzylalcohol using H2O2 as terminal oxidant. Of the studied aroylhydrazone complexes, 4 showed the best selectivity and activity as catalyst.
Hosseini-Monfared, Hassan,Asghari-Lalami, Nasim,Pazio, Aleksandra,Wozniak, Krzysztof,Janiak, Christoph
p. 241 - 250
(2013/10/22)

Synthesis of some novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives from terephthaloyl and isophthaloyl chlorides
An efficient synthesis of novel bis-1,2,4-triazole and bis-1,3,4- thiadiazole derivatives starting from terephthaloyl and isophthaloyl chlorides is described. Terephthaloyl or isophthaloyl chloride was allowed to react with hydrazine hydrate in refluxing ethanol to give a corresponding bis-hydrazide derivative. Further reaction of these compounds with isothiocyanates gave bis-thiosemicarbazide derivatives, which then underwent cyclization to bis-1,3,4-thiadiazoles in the presence of sulfuric acid. The cyclization of these compounds in the presence of sodium hydroxide resulted in the formation of bis-1,2,4-triazole-3-thioles. The structure of these compounds was characterized by IR, NMR, and elemental analysis.
Mobinikhaledi, Akbar,Foroughifar, Naser,Rafiee, Abdolhossein
p. 265 - 269
(2013/09/02)

Synthesis and characterization of schiff base metal complexes and reactivity studies with malemide epoxy resin
A novel malemide epoxy containing Co(II), Ni(II) and Cu(II) ions have been synthesized by curing malemide epoxy resin (MIEB-13) and Co(II), Ni(II) and Cu(II) complexes of macrocyclic bis-hydrazone Schiff base. The Schiff base was synthesized by reacting 1,4-dicarbnyl phenyl dihydrazide with 2,6-diformyl-4-methyl phenol. The Schiff base and its Co(II), Ni(II) and Cu(II) complexes have been characterized by elemental analyses, spectral (IR, 1H NMR, UV-vis., FAB mass, ESR), thermal and magnetic data. The curing reaction of maleimide epoxy compound with metal complexes was studied as curing agents. The stability of cured samples was studied by thermo-gravimetric analyses and which have excellent chemical (acid/alkali/solvent) and water absorption resistance. Further, the scanning electron microscopy (SEM) and definitional scanning colorimetric (DSC) techniques were confirmed the phase homogeneity of the cured systems.
Lakshmi,Shivananda,Prakash, Gouda Avaji,Isloor, Arun M,Mahendra
experimental part
p. 473 - 482
(2012/05/04)

Synthesis and antibacterial activity of some 5,5'-(1,4-phenylene)-bis-1,3, 4-oxadiazole and bis-1,2,4-triazole derivatives as precursors of new S-nucleosides
Five compounds, namely 5,5'-benzene-1,4-diylbis(1,3,4-oxadiazole-2-thiol)6 and 5,5'-benzene-1,4-diylbis(1H-1,2,4-triazole-3-thiol) 7a and its derivatives 7b-d were synthesized. Two related S-nucleosides 9 and 10 have been prepared from 6 and 7a. Some of these synthesized compounds were tested in vitro by spotting on Mueller Hinton Agar medium against some Gram-positive bacteria, Staphylococcus aureus and Enterococcus faecalis and three Gram-negative bacteria Escherichia coli, Pseudomonasaeruginosa, Pseudomonas fluorescens and compared with the known antibiotics cephalosporin (cefotaxim) and gentamycin. Compound 6 showed significant inhibitory activity against Gram-positive E. faecalis and Gram-negative E. coli bacteria while the others have shown variable inhibition activity.
Datoussaid, Yazid,Othman, Adil A.,Kirsch, Gilbert
experimental part
p. 30 - 35
(2012/06/04)

Synthesis and anticancer activities of 1,4-bis(6-aryl-1,2,4-triazolo[3,4-b] -[1,3,4]thiadiazole-3-yl)benzene derivatives
1,4-Bis(6-aryl-1,2,4-triazolo[3,4-b]-[1,3,4]thiadiazol-3-yl)-benzenes (3) were synthesized in high yields by reaction of bis(4-amino-5-mercapto-1,2,4- triazol-3-yl)benzene (1) with carboxylic acids 2 in the presence of POCl 3 and tetrabutylammonium iodide as catalyst. The MTT assay indicated that compounds 3a-i possess inhibitory activity against the proliferation of HepG-2 (liver cancer), A549-1 (lung cancer) and 231-2 (breast cancer). Copyright by Walter de Gruyter Berlin Boston.
Ding, Hao-Yu,Li, De-Jiang
experimental part
p. 69 - 71
(2011/10/02)

Synthesis and antibacterial activities of bis-1,3, 4-oxadiazoline derivatives
Dimethyl terephthalate (1) was reacted with 80% hydrazine hydrate in refluxing methanol for 12 h to afford terephthalate dihydrazide (2). Condensation of 2 with aromatic aldehydes afforded corresponding hydrazones 3a-3j. Cyclization of 3a-3j with acetic anhydride in refluxing for 4-5 h afforded bis-1,3,4-oxadiazoline derivatives(4a-4j). The structures of 4a-4j were characterized by elementary analyses, IR, 1H NMR, and MS spectroscopy. The preliminary antibacterial tests showed that most of them were effective against S.aureus.
Li, De-Jiang,Dan, Fei-Jun,Fu, He-Qing
scheme or table
p. 465 - 468
(2010/03/04)

Synthesis, characterization and antimicrobial study of substituted bis-[1,3,4]-oxadiazole, bis-[1,3,4]-thiadiazole and bis-[1,2,4]-triazole derivatives
Series of compounds 1,4-bis-(2-aryl/alkyl-amino-[1,3,4]-oxadiazol-5-yl)- benzenes, 1,4-bis-(2-aryl/alkyl-amino-[1,3,4]-thiadiazol-5-yl)-benzenes and 1,4-bis-(3-mercapto-4-aryl/alkyl-[1,2,4]-triazol-5-yl)-benzenes have been synthesized by the oxidative cyclization of di-(N-aryl/alkyl thiocarbamido) terephthalamides using alkaline ethanolic solution of iodine containing potassium iodide, ortho-phosphoric acid and aqueous potassium hydroxide solution respectively. These compounds on acetylation afforded bis-acetyl derivatives, on benzoylation afforded bis-benzoyl derivatives and on reaction with ethyl iodide afforded bis-ethylmercapto derivatives respectively. These compounds have been assayed for their antimicrobial activity against gram-positive as well as gram-negative microorganisms.
Deohate, Pradip P.,Berad
experimental part
p. 1153 - 1158
(2009/12/24)

Synthesis, characterization and antimicrobial study of substituted bis-[1,2,4,5]-dithiadiazine and bis-[1,3,4]-thiadiazolidine derivatives
Series of compounds [4-(3-phenylimino-6-aryl/alkylimino-[1,2,4,5]- dithiadiazinane-4-carbonyl)-phenyl]-(3-phenylimino-6-aryl/alkylimino-[1,2,4,5] -thiadiazinan-4-yl)-methanones and [4-(2-phenylimino-5-aryl/alkylimino-[1,3,4]- thiadiazolidine-3-carbonyl)-phenyl]-(2-phenylimino-5-aryl/alkylimino-[1,3,4] -thiadiazolidin-3-yl)-methanones have been synthesized by the interaction of di-(N-aryl/alkyl thiocarbamido)terephthalamides with N-phenyl-S-chloro isothiocarbamoyl chloride and N-phenyl isocyanodichloride respectively. These compounds on acetylation afforded bis-acetyl derivatives. These compounds have been assayed for their antimicrobial activity against gram-positive as well as gram-negative microorganisms.
Deohate, Pradip P.,Berad
experimental part
p. 1050 - 1054
(2010/01/16)

Controlled release of volatile aldehydes and ketones from dynamic mixtures generated by reversible hydrazone formation
Delivery systems generated by reversible hydrazone formation from hydrazine derivatives (see Fig. 1) and carbonyl compounds in H2O efficiently increase the long-lastingness of volatile aldehydes and ketones (R 1R2C=O) in various perfumery applications. The hydrazones are usually obtained in an (E) configuration at the imine double bond (NHN=C) and, in the case of aliphatic acylhydrazones R′CO-NH-N=CR 1R2 (R′ = alkyl), as syn and anti conformers with respect to the amide bond (CO-NHN). An average free-energy barrier of ca. 78kJ/mol was determined for the amide-bond rotation by variable-temperature 1H-NMR measurements (Fig. 2). In the presence of H2O, the hydrazone formation is entirely reversible, reaching an equilibrium composed of the hydrazine derivative, the carbonyl compound, and the corresponding hydrazone. Kinetic measurements carried out by UV/VIS spectroscopy showed that the same equilibrium was reached for the formation and hydrolysis of the hydrazone. Rate constants are strongly pH-dependent and increase with decreasing pH (Table 1). The influence of the hydrazine structure on the rate constants is less pronounced than the pH effect, and the presence of surfactants reduces the rate of equilibration (Tables 1 and 3). The full reversibility of the hydrazone formation allows to prepare dynamic mixtures by simple addition of a hydrazine derivative to several carbonyl compounds. Dynamic headspace analysis on dry cotton showed that the presence of a hydrazine derivative significantly increased the headspace concentrations of the different carbonyl compounds as compared to the reference sample without hydrazine (Table 4). The release of the volatiles was found to be efficient for fragrances with high vapor pressures and low H2O solubility. Furthermore, a special long-lasting effect was obtained for the release of ketones. The simplicity of generating dynamic mixtures combined with the high efficiency for the release of volatiles makes these systems particularly interesting for practical applications and will certainly influence the development of delivery systems in other areas such as the pharmaceutical or agrochemical industry.
Levrand, Barbara,Fieber, Wolfgang,Lehn, Jean-Marie,Herrmann, Andreas
p. 2281 - 2314
(2008/03/29)

New series of blue-emitting and electron-transporting copolymers based on fluorene
A novel series of conjugated copolymers having oxadiazole, quinoline, quinoxaline, and phenylenecyanovinylene moieties in the main chain based on fluorene were synthesized in good yields by palladium-catalyzed Suzuki coupling reaction, a new approach different from the traditional polyhydrazide precursor route (oxadiazole-containing polymers), acid-catalyzed Friedlaender condensation reaction (polyquinolines), and Knoevenagel condensation polymerization (poly(phenylenecyanovinylene)). The thermal, electrochemical, and optical properties of these copolymers were examined. All these polymers possess excellent thermal stability with glass transition temperatures of 114-208 °C and onset decomposition temperatures of 387-415 °C. Cyclic voltammetry studies reveal that these copolymers possess low-lying LUMO energy levels ranging from -3.01 to -3.37 eV and low-lying HOMO energy levels ranging from -6.13 to -6.38 eV and may be promising candidates for electron-transporting or hole-blocking materials in light-emitting diodes. The polymers in thin films emit strong blue luminance around 414-476 nm with narrow bandwidth upon photoexcitation. Photoluminescence spectra of the polymers in the films are only red-shifted by 7-11 nm compared to those in the solution, indicating that the aggregation and the excimer fluorescence are suppressed.
Zhan, Xiaowei,Liu, Yunqi,Wu, Xia,Wang, Shuai,Zhu, Daoben
p. 2529 - 2537
(2007/10/03)

Synthesis and antiviral activity of new bisacridinylhydrazides of aryloxyacetic acids
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Lyakhov,Lyakhova,Panchenko,Litvinova,Andronati
p. 653 - 656
(2007/10/03)

Isolation of Anhydrous Hydrazine as Stable Inclusion Complexes with Hydroquinone and p-Methoxyphenol, and their Solid State Reaction with Esters which gives Pure Hydrazides
Anhydrous hydrazine is isolated in a pure state as a stable inclusion complex crystal with hydroquinone or p-methoxyphenol, the X-ray structure of which have been analysed; the solid-state reaction of the hydrazine inclusion complex and esters gives hydrazides which are virtually uncontaminated with acid hydrazine salt byproducts.
Toda, Fumio,Hyoda, Shunji,Okada, Kengo,Hirotsu, Ken
p. 1531 - 1532
(2007/10/02)

A SPECTRAL STUDY OF URANYL(VI) COMPLEXES OF HYDRAZIDES AND HYDRAZONES
Metal complexes of uranyl(VI) with nitrogen and oxygen containing bidentate and tridentate ligands, carbohydrazide (CHZ), 1,5-diphenylcarbazide (DPC), terephthalic acid hydrazide (TDH) and bis-benzaldehyde terephthalic hydrazone (BBTH) have been studied. The complexes of carbohydrazide and 1,5-diphenylcarbazide in 1:2 metal to ligand molar ratio, whereas TDH and BBTH complexes in 1:1 molar ratio have been synthesized. All the complexes have been characterized as seven-coorinated UO2(VI) systems, in which these ligands coordinate through carbonyl and terminal amino groups. All the complexes show bands in the region 830-840 and 910-920 cm-1, which are assigned to νsym. and νasym. UO2 vibrations.
Chandra, Ramesh,Kapoor, Ramesh N.
p. 1125 - 1132
(2007/10/03)