Synthesis Of Tetra Research Articles

Sulfonic Acid-Functionalized Solid Polymer Catalyst from Crude Cashew Nut Shell Liquid: Synthesis of Tetra(indolyl)methanes and Bis(indolyl)methanes from Xylochemicals

Sulfonic Acid-Functionalized Solid Polymer Catalyst from Crude Cashew Nut Shell Liquid: Synthesis of Tetra(indolyl)methanes and Bis(indolyl)methanes from Xylochemicals

Synthesis of tetra(epoxy)-terminated open-cage POSS and its particle thermo-crosslinking with diphenols for fabricating high performance low-k composites adopted in electronic packaging

Polyhedral oligomeric silsesquioxanes (POSSs) are ideal particles to reduce the dielectric constant (k) and loss (tan δ) values of resin matrixes for electronic packaging, but greatly limited by its finite addition due to phase-separation. Herein, tetra(epoxy)-terminated open-cage TG-POSS was synthesized and utilized as a unique building block to crosslink with bisphenol A or hexafluoro-bisphenol A, respectively, for the preparation of novel high performance low-k composites (POSS/BPA or POSS/FBPA). Results reveal that such rational design endows these two materials with homogeneous hybridization even at high POSS loading (>72.0 wt%), which is the main reason for superior dielectric, thermal and hydrophobic properties as compared with counterparts reported previously. Especially, fluorinated POSS/FBPA shows the lowest k value of 2.38, lowest tan δ value of 0.008, highest initial decomposition temperature of 396.1 °C and largest water contact angle of 117.0°, under the extra-contribution of trifluoromethyl units. In addition, its well-dispersed, moderate-crosslinked and rigid-flexible polymer network also leads to outstanding mechanical properties (elongation at break of 3.50% and modulus of 2.75 GPa) for practical applications. Summarily, this work highlights a useful strategy to fabricate high performance low-k composites with high POSS content, which is not only potential for advanced microelectronic industry but also instructive for academic fields.

Nife2o4@Sio2pra/PC-Ni(II) as a highly efficient catalyst for microwave promoted one pot synthesis of tetra substituted imidazoles

A simple and practical microwave irradiation synthetic strategy for preparation of catalyst nanostructured NiFe2O4@SiO2PrA/PC-Ni(II) was developed. The preparation of imidazole derivatives by using this catalyst in the reaction medium is much easier, faster, higher yields, simple separation of products and pure products. The structure of NiFe2O4@SiO2PrA/PC-Ni(II) was characterized by various analyses such as Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), scanning electron microscopy (SEM), magnetic properties by vibrating sample magnetometer (VSM) and thermogravimetric analysis (TGA). The pure products were identified and characterized by physical and spectroscopic data such as melting point, IR and 1H NMR techniques.

DFT analysis and electronic properties, and synthesis of tetra (9-phenyl-9H-xanthen-9-yl) oxy peripheral-substituted zinc phthalocyanine

The 4-((9-phenyl-9H-xanthene-9-yl) oxy) phthalonitrile compound was synthesized and characterized as starting material. Zinc phthalocyanine was obtained by reaction of 4-((9-phenyl-9H-xanthen-9-yl) oxy) phthalonitrile with Zn(CH3COO)2. Novel compounds were characterized using mass spectra, UV–Vis spectroscopy, 1H-NMR, 13C NMR, and infrared spectroscopy. The fluorescence, emission, excitation, and absorption spectra of the zinc phthalocyanine compound were studied in tetrahydrofuran (THF). The determination of these properties is very useful for photodynamic therapy applications. Also, zinc phthalocyanine (Zn-Pc) was optimized with the basic set of 6-311G and LanL2DZ of the Density functional theory (DFT). The energy band-gap HOMO–LUMO of the molecule was determined. Chemical indices were calculated using HOMO–LUMO energies. The electrophilic region and the nucleophilic region were defined from the molecular electrostatic potential (MESP) maps. Dipole moment components have been calculated and can be considered as potential candidates for the design of non-linear optical materials.

Detection of Nanomolar Concentrations H2O2 Using Cobalt (II) Phthalocyanine Modified GCE with MWCNTs

The synthesis of tetra 4-(3-tert-butyl-4-methoxyphenoxy) benzene cobalt (II) phthalocyanine (CoTTBMPPc) from cobalt (II) tetracarboxylic acid phthalocyanine (CoTCAPc) via Oxygen Bridge. These macromolecules displayed admirable solubility in aprotic organic solvents and were characterized by UV-Vis, FT-IR, 1H NMR, XRD, TGA, mass and elemental analysis. The CoTTBMPPc was found to be electrochemically active and was immobilized on the GCE with composite MWCNTs. The modified electrode was used for the Hydrogen Peroxide (H2O2) detection by cyclic voltammetry, differential pulse voltammetry, and amperometry methods. H2O2 exhibits cathodic peak potential on the GCE/MWCNTs/CoTTBMPPc electrode. The linear response was observed in the concentration range (10 to 100 for CV of, 10-150 for DPV and 10-200 nM in amperometry), detection limit (5.33 in CV, 6 in DPV and of 4 nmol L-1 in amperometry) with limit of quantification (16 for CV, 18 for DPV and up to 12 nmol L-1 in amperometry), respectively on the modified electrode. The modified electrode is stable, sensitive, selective and reproducible for the nanomolar detection of H2O2 in neutral PBS electrolyte solution.

Mechanochemically-generated solid state complex of C60-fullerene with tetra-(5,7-diphenyl)calix[4]azulene, NMR, XRD and DFT studies

The synthesis of tetra-(5,7-diphenyl)calix[4]azulene via the reaction of 5,7-diphenylazulene with formaldehyde is described. Its solid-state supramolecular complexation with C60 produced by a grinding of the two components was evaluated by solid-state 13C-NMR spectroscopy and X-ray powder diffraction. Gas-phase DFT studies of possible structures are reported.

Synthesis of Tetra(3‐thienyl)biphenoquinone and its Charge Transfer Complex with Perylene

AbstractTetra(thienyl)biphenoquinones were designed and synthesized. An oxidative coupling of 2,6‐bis(3‐thienyl)phenol with PbO2 in acetic acid afforded the corresponding biphenoquinone along with 2,6‐bis(3‐thienyl)‐p‐benzoquinone. This biphenoquinone showed properties characteristic of a π‐expanded quinone, that is, positively shifted reduction potential and light absorption in the visible region. In contrast to kinetically protected biphenoquinones with bulky substituents at the ortho‐positions of carbonyls, the title compounds take a planar structure because of the small steric repulsion of the five‐membered thiophene rings. Its charge transfer complex with perylene is characterized by a well‐overlapped mixed stack.

Synthesis of tetra(2,2-hydroxyethylene) terephthalamide from PET waste and its application in synthesis of polyesteramide coating

PurposeThe purpose of this paper is to discuss the synthesis of polyesteramide resin from the monomer obtained from poly (ethylene terephthalate) (PET) waste and study of the structure – property relation for the same in polyesteramide coating. The purpose is also not only to just target the polymeric waste but also to study the effect of the structure of monomer obtained from such waste in final coating.Design/methodology/approachPET waste was depolymerised using diethanolamine to tetra(2,2-hydroxyethylene) terephthalamide (THETA). Four functional hydroxyl terminated monomers were generated having amide linkage as a structural part. THETA was used for the synthesis of polyesteramide resin along with fatty amide of oil, and concentration of the THETA was varied. The synthesised polyesteramide resin was cured with MF resin and tested for physico-chemical, thermal and anticorrosive properties.FindingsPET was successfully depolymerised to monomeric level using diethanolamine as a reactive agent. It is observed that as the concentration of THETA increases, the hardness of the coating increases, as aromatic concentration increases in the coating. The amide linkage helps to improve adhesion as well as hydrophobicity because an aliphatic long chain of fatty amide and aromatic linkage of THETA helps in improving anticorrosive properties of the coating.Practical implicationsThis method is the useful key to solve the polymeric waste problem. PET can be easily depolymerised using diethanolamine and polyesteramide resin synthesised from it. Hence, waste material can be converted into the coating by reacting it with renewable resources.Originality/valueTo the best of the authors’ knowledge, this is the first study which uses THETA as a monomer for the synthesis of polyesteramide resin and study of its various concentrations on coating properties. The coating is obtained from waste material; hence, polymeric waste issue is also solved, and dependency on the petroleum resources to obtain raw materials for coating is also depleted partially. The study also helps to understand the effect of the structure of monomers on the properties of the coating.

Synthesis of tetra- and octa-aurated heteroaryl complexes towards probing aromatic indoliums.

Polymetalated aromatic compounds are particularly challenging synthetic goals because of the limited thermodynamic stability of polyanionic species arising from strong electrostatic repulsion between adjacent carbanionic sites. Here we describe a facile synthesis of two polyaurated complexes including a tetra-aurated indole and an octa-aurated benzodipyrrole. The imido trinuclear gold(I) moiety exhibits nucleophilicity and undergoes an intramolecular attack on a gold(I)-activated ethynyl to generate polyanionic heteroaryl species. Their computed magnetic properties reveal the aromatic character in the five-membered ring. The incorporation of the aurated substituents at the nitrogen atom can convert non-aromaticity in the parent indolium into aromaticity in the aurated one because of hyperconjugation. Thus, the concept of hyperconjugative aromaticity is extended to heterocycles with transition metal substituents. More importantly, further analysis indicates that the aurated substituents can perform better than traditional main-group substituents. This work highlights the difference in aromaticity between polymetalated aryls and their organic prototypes.

ChemInform Abstract: A Novel Synthesis of Tetra and Pentacyclic Quinolinopyran Tethered Pyrazole/Coumarin Scaffolds via a Solid State Melt Reaction.

AbstractTitle structures [e.g. (III), (V), (VII), and (VIII)] are efficiently synthesized via domino Knoevenagel intramolecular hetero‐Diels—Alder strategy in a highly diastereo and regioselective fashion.

Synthesis of tetra- and pentaazaheterocyclic systems and benzimidazo[1,2-c]quinazoline derivatives

Starting with 5-carboxy-4-hydroxy-2-phenylpyrimidine and 4-hydroxy-6-methyl(hydroxy)-2-phenylpyrimidinyl-5-propanoic acids derivatives of two heterocyclic systems, benzimidazopyrido- and pyrimidopyrimidine, were synthesized. Synthesis of new S-substituted benzimidazo[1,2-c]quinazolines was also carried out.

A novel synthesis of tetra and pentacyclic quinolinopyran tethered pyrazole/coumarin scaffolds via a solid state melt reaction

A new protocol has been developed for the efficient synthesis of structurally diverse tetra- and pentacyclic quinolinopyran tethered pyrazole/coumarin architectures via a domino Knoevenagel intramolecular hetero-Diels–Alder (IMHDA) strategy using a solid state melt reaction (SSMR) in a highly diastereo and regioselective fashion. Gratifyingly, these heterocyclic frameworks were synthesized under solvent and catalyst free conditions, without the aid of a work-up and column chromatography purification. The generality and functional tolerance of this convergent and environmentally benign method is very attractive.

2,2,3,3-Tetrafluoropropoxy substituted oxo-titanium phthalocyanines axially ligated with common MALDI matrix materials

The synthesis of tetra and octa 2,2,3,3-tetrafluoropropoxy substituted oxo-titanium phthalocyanines (TiOPc) are reported. Using strongly chelating oxygen donor ligands, the reactions of TiOPc with catecholate (1a, 2a), 4-nitrocatecholate (1b, 2b) and caffeic acid (1c, 2c), ellagic acid (1d, 2d) and chlorogenic acid (1e, 2e) are described. The new compounds were characterized by mass, 1 H NMR, FT-IR, and UV-vis spectroscopic techniques as well as elemental analysis.

Synthesis and characterization of O- and S-bridged perfluoroalkylated metal-free and zinc phthalocyanines

The synthesis of tetra and octa perfluoroalkyl substituted zinc and metal free phthalocyanines ( ZnPc and H 2 Pc ) are reported. The compounds 1–5 have been prepared by nucleophilic substitution of 4-nitrophthalonitrile with 1H,1H,2H,2H-perfluorooctanethiol, 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol, 1H,1H-perfluorotetradecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol, respectively. The compounds 6–8 have been prepared by the reaction of 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol with 4,5-dichlororphthalonitrile, respectively. The compound 9 with thia-bridge has been synthesized from 4,5-dichlororphthalonitrile. Zinc and metal free phthalocyanines were obtained from the corresponding phthalonitrile derivatives. All compounds were characterized by using mass, 1 H , 19 F NMR, UV-vis and FT-IR as well as elemental analysis. Tetra substituted Zn ( II ) phthalocyanines are slightly soluble only in THF (Compound 4a and 7a are insoluble) but metal free phthalocyanines are not soluble. Octa substituted Zn ( II ) and metal free phthalocyanine are soluble in polar solvents such as THF and DMSO.

Synthesis of Tetra(2-hydroxyethoxy)-Substituted Dibenzocyclooctyne Derivatives as Novel, Highly Hydrophilic Tool Compounds for Strain-Promoted Alkyne-Azide Cycloaddition Applications

The synthesis of a novel, hydrophilic dibenzocyclooctyne derivative for strain-promoted alkyne-azide cycloaddition (SPAAC) is described. Starting from 2-(3,4-dimethoxyphenyl)acetaldehyde, the corresponding activated carbonate of 2,3,8,9-tetrakis(2-hydroxyethoxy)-5,6-dihydro-11,12-didehydrodibenzo[<i>a</i>,<i>e</i>][8]annulene, termed THE-DIBO, was prepared in seven steps and 24% overall yield. A water-soluble THE-DIBO analogue showed a <i>k₂ </i> value of (21.9 ± 0.2) × 10^–2 M^–1 s^–1 for SPAAC with 2-azidoethanol in water. The high hydrophilicity and steric bulk of THE-DIBO derivatives should to suppress nonspecific thiol-yne addition of proteins to strained alkynes observed for SPAAC labeling in complex proteomes.

ChemInform Abstract: An Oxidant‐Free Single‐Step Synthesis of Tetra‐ or Disubstituted Symmetrical Pyridine Derivatives by a Hf(OTf)4‐Catalyzed Annulation.

AbstractAn unprecedented annulation of enamines with triethyl orthoformate allows the preparation of tetrasubstituted pyridines.

Room‐Temperature Synthesis of Tetra‐ortho‐Substituted Biaryls by NHC‐Catalyzed Suzuki–Miyaura Couplings

Into the groove: The introduction of a C2-symmetric N-heterocyclic carbene ligand with appropriately substituted naphthyl side chains enables the efficient Suzuki–Miyaura coupling to form bulky tetra-ortho-substituted biaryls from aryl bromides and chlorides at room temperature. DFT calculations uncover the subtle steric phenomena at play that lead to the superior catalytic performance. Cyoct=cyclooctyl. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Synthesis of tetra- and octaphosphoryl-containing phthalocyanines

Phthalonitriles containing diphenylphosphoryl substituents as peripheral fragments were synthesized and characterized for the first time. The method of template assembly on the corresponding metal cation was used to obtain tetra- and octaphosphoryl-containing phthalocyaninates of Mg2+, Cu2+, and Co2+. A description is given of the method of synthesis of tetra(diphenylphosphorylmethoxy)phthalocyanine and octa(diphenylphosphoryl)methylphthalocyanine by demetallization of lithium and magnesium phthalocyaninates. The synthesized compounds were characterized using the methods of UV-, IR-, NMR 1H, NMR 31P spectroscopy and MALDI-TOF mass spectrometry.

Synthesis of Polysubstituted 2-Aminopyrroles via a Multicomponent Reaction

Reported is the synthesis of tetra- and pentasubstituted 2-aminopyrroles 5 and 6 by a one-pot three-component reaction of N-(aryl, heteroaryl or alkylsulfonamido)acetophenones 1, diverse aldehydes 2 and cyanoacetic acid derivatives 3, respectively. Based on a previous report (I. V. Magedov et al. Bioorg. Med. Chem. Lett. 2008, 18, 1392), this reaction leads to multisubstituted cis- and trans-pyrrolines which are oxidized in the presence of DDQ to afford multisubstituted pyrroles. The process works well for the synthesis of 5, incorporating a variety of aliphatic, aromatic (including sterically hindered or heteroaromatic) ­aldehydes and malonitrile, cyanoacetamide or ethylcyanoacetate. Base-promoted dehydro­sulfinylation afforded the NH-pyrroles 6.

Synthesis, characterization, photophysical and photochemical properties of 7-oxy-3-methyl-4-phenylcoumarin-substituted indium phthalocyanines

The synthesis of tetra- and octa-(7-oxy-3-methyl-4-phenylcoumarin)-substituted indium(III) phthalocyanine complexes obtained from 3-nitrophthalonitrile, 4-nitrophthalonitrile and 4,5-dichlorophthalonitrile substituted with 7-oxy-3-methyl-4-phenylcoumarin are described for the first time in this study. The new compounds have been characterized by elemental analysis, IR, 1H NMR, electronic spectroscopy and mass spectra. The photophysical and photochemical properties of the compounds are also studied in dimethylformamide (DMF). The effects of the number of the substitution and the position on the photophysical and photochemical parameters of the substituted indium(III) phthalocyanine complexes are also reported. Photophysical and photochemical properties of phthalocyanine complexes are very useful for photodynamic therapy (PDT) of cancer applications. In particular, high singlet-oxygen quantum yields are very important for Type II mechanisms. These complexes have good singlet-oxygen quantum yields and show potential as Type II photosensitizers.