Abstract Tris Research Articles

Tris (2,3-Dibromopropyl) Isocyanurate (TDBP-TAZTO or TBC) Shows Different Toxicity Depending on the Degree of Differentiation of the Human Neuroblastoma (SH-SY5Y) Cell Line

Tris (2,3-dibromopropyl) isocyanurate (TDBP-TAZTO or TBC) is a heterocyclic hexabromated flame retardant. It is widely used during the production of many synthetic compounds. High concentrations of TDBP-TAZTO were found in river water, surface sediments, soil, earthworms, and carp tissues. Moreover, it has been shown that this compound can cross the blood–brain barrier and accumulate in the gut and brain of carp. The aryl hydrocarbon receptor (AhR) has been characterized as a multifunctional intracellular sensor and receptor. AhR is an activator of cytochrome P450 1A1 and 1A2, which metabolize various toxic compounds. The aim of the study was to explain how/whether TDBP-TAZTO increases the expression and/or activity of the CYP1A1 enzyme and the AhR and TUBB3 expression during SH-SY5Y cell differentiation. SH-SY5Y cells were differentiated for 7 and 14 days using retinoic acid. Cell viability, ethoxyresorufin-O-deethylase (EROD) activity, and mRNA expression of CYP1A1, AhR, and TUBB3 were assessed. Our experiment showed that, during the differentiation process, the ability of TDBP-TAZTO to induce EROD activity in SH-SY5Y cells subsequently decreased, which may have been an effect of cell differentiation into neurons. Moreover, the results suggest that TDBP-TAZTO can affect the differentiation process. Since no CYP2B6 mRNA expression was detected, the CAR receptor may not be involved in the TDBP-TAZTO mechanism of action. However, more research is needed in this field to elucidate this mechanism precisely.

Validated Gas Chromatography – Mass Spectrometry (GC-MS) Method for Simultaneous Quantitation of Tris(4-Chlorophenyl)Methane and Tris(4-Chlorophenyl)Methanol in Rat Plasma and Fetus

Tris(4-chlorophenyl)methane (TCPMe) is a byproduct of dichlorodiphenyltrichloroethane synthesis. TCPMe and its metabolite tris(4-chlorophenyl)methanol (TCPMOH) are environmentally prevalent and have been detected in wildlife and humans. Due to inadequate data addressing its toxicity, the National Toxicology Program (NTP) is testing TCPMe in Hsd:Sprague Dawley SD (HSD) rats following perinatal exposure. In support of the toxicology studies, a gas chromatography – mass spectrometry (GC-MS) method was validated to simultaneously quantitate TCPMe and TCPMOH in male Sprague Dawley rat plasma (primary matrix) over calibration standard ranges of 2–200 ng/mL and 1–100 ng/mL, respectively. The method was linear (r2 ≥ 0.9975), accurate (relative error (RE) ≤ ±12.8 (TCPMe) and ±14.5% (TCPMOH), and precise (relative standard deviation (RSD) ≤ 7.6 (TCPMe) and 3.8% (TCPMOH)). The limits of quantitation were 2 and 1 ng/mL and the limits of detection were 0.73 and 0.07 ng/mL for TCPMe and TCPMOH, respectively. Samples, as high as 2000 ng/mL for TCPMe (RSD ≤ 3.9, RE ≤ ±1.0) and 1000 ng/mL for TCPMOH (RSD ≤ 1.0, RE ≤ ±2.9), were successfully diluted with plasma into the validated concentration range. The method was selective and both TCPMe and TCPMOH were quantified in all secondary matrices (HSD male and female plasma, gestation day (GD)18 plasma, amniotic fluid, and fetus, postnatal day (PND)4 dam and pup plasma) using a primary matrix curve (RE ≤ ±14.4% and 11.5; RSD ≤ 7.6 and 11.8%, respectively). These results demonstrate that the method is suitable for simultaneous quantitation of TCPMe and TCPMOH in rodent plasma and fetuses for the evaluation of gestational and lactational transfer following perinatal exposure of TCPMe in NTP studies.

Propeller-Shaped Aluminum Complexes with an Azaperylene Core in the Ligands

Tris(8-hydroxyquinoline) aluminum(III) (Alq3) and its derivatives, characterized by a propeller-shaped three-dimensionally π-conjugated structure, have been intensively studied in the few past decades on account of their potential utility in optoelectronic applications. Reported herein are the synthesis and properties of π-extended Alq3 complexes that contain an azaperylene core in each ligand. Intramolecular palladium-catalyzed direct C–H arylations or base-promoted arylations were employed to prepare these large Alq3 analogues. A single-crystal X-ray diffraction analysis of one of the obtained Al complexes revealed a unique three-dimensional packing structure within the crystal, i.e., a honeycomb packing along the ab-plane and columnar π-stacks along the c-axis. An Alq3 analogue with azaperylene-dicarboximide ligands exhibited deep blue color in solution with an intense absorption band that extended to 780 nm (λmax = 634 nm; ε = 58,000 M−1 cm−1).

Synthesis and characterization of some novel Mn(III) glycinato complexes with catalytic applications

Tris(glycinato)Mn(III) and its mixed ligand complexes with azido-, thiocyanato-, chloro- and bromo- groups have been synthesized and characterized by UV–Vis spectrophotometry, IR spectrophotometry, elemental analysis, magnetic susceptibility measurements, thermal analysis, Dart-mass spectrometry, EPR spectral studies, and X-ray powder diffraction studies. The molar extinction coefficient values of the complexes are in the range of spin allowed 5T2g → 5Eg transitions. The magnetic susceptibility measurements of all the complexes confirmed the presence of four unpaired electrons and high spin d4 systems. Room temperature EPR spectrum gives g isotropic value 2.002 indicative of octahedral geometry for the complex. PXRD studies suggest monoclinic system with space group P21/c with a = 9.1382(60) Å, b = 15.5340(11) Å, c = 10.2576(68) Å, and β = 110.598(15)°. The particle size of the complexes lies in the range 26.60–38.79 nm. The tris(glycinato)Mn(III) is an efficient heterogeneous catalyst for decolorization of Xylenol Orange and Methyl Red in the presence of H2O2. It also initiates polymerization of acrylonitrile.

Tris(N-methylferrocenyl-N-(2-phenylethyl)dithiocarbamato-S,S′)cobalt(III) for anion sensing and preparation of cobalt-iron sulfide nanoparticles: A new photocatalyst for the degradation of dyes

Tris(N-(pyrrol-2-ylmethyl)-N-butyldithiocarbamato-S,S′)cobalt(III) (1) and tris(N-methylferrocenyl-N-(2-phenylethyl)dithiocarbamato-S,S′)cobalt(III) (2) have been synthesized and characterized by elemental analysis and spectroscopy (IR, UV-vis and NMR). The elemental analysis and IR, 1H and 13C NMR spectra are consistent with the formation of the cobalt(III) complexes with dithiocarbamate ligands. The anion binding properties of 1 and 2 based on host-guest interaction have been examined with the use of cyclic voltammetry.This study showed that both complexes preferred to bind with I-compared to other halides. 2 has been used as precursors for the preparation of cobalt-iron sulfide nanoparticles. TEM image of cobalt-iron sulfide nanoparticles showed that the particles are spherical. The elemental compositions of the nanoparticles were confirmed by energy dispersive X-ray spectroscopy. IR spectral studies on nanoparticles confirm the presence of capping agent (triethylenetetramine). The nanoparticles were explored as photocatalysts to study the degradation of dyes using methylene blue and rhodamine-B in aqueous solution under UV irradiation. The cobalt-iron sulfide works as an efficient photocatalyst for degradation of rhodamine-B.

Effect of the flame retardant tris (1,3-dichloro-2-propyl) phosphate (TDCPP) on Na+-K+-ATPase and Cl− transport in HeLa cells

Tris (1, 3-dichloro-2-propyl) phosphate (TDCPP) is one of the most diffused phosphorus flame retardants in the environment and is highly persistent and abundant in residential dust samples. To date the cellular targets and mechanisms underlying its toxic effects are not completely understood. The aim of this work was to study the effects of TDCPP on ion transport mechanisms fundamental for the cellular ionic homeostasis, such as Na+-K+-ATPase and Cl− transport. HeLa cells were used as experimental model. TDCPP showed a dose-dependent effect on cell viability in cells exposed for 24 h as assessed by MTT test (IC50 = 52.5 µM). The flame retardant was able to exert a dose and time-dependent inhibition on the Na+-K+-ATPase activity. A short-term exposure (1 h) was able to exert a significant inhibition at 75 and 100 µM TDCPP, suggesting that TDCPP is able to directly interfere with the Na+-K+-ATPase phosphate catalytic activity. The sensitivity of the pump to lower TDCPP concentrations increased with the increase of the time of exposure. Following 24 h exposure a significant inhibition of about 40% was evident already at 10 µM and the IC50 value observed was 12.8 ± 6.0 µM. Moreover, TDCPP was also able to impair the NKCC mediated Cl− transport in HeLa cells, as assessed in YFP-H148Q/I152L-expressing HeLa cells. Following 1 h exposure TDCPP significantly inhibited the transport by about 30%. The kinetic analysis demonstrated a noncompetitive mechanism of inhibition. In conclusion, results demonstrated the impairment of ion transport mechanisms fundamental for ion homeostasis by TDCPP on HeLa cells.

Disposition of tris(4-chlorophenyl)methanol and tris(4-chlorophenyl)methane in male and female Harlan Sprague Dawley rats and B6C3F1/N mice following oral and intravenous administration

Tris(4-chlorophenyl)methane (TCPME) and tris(4-chlorophenyl)methanol (TCPMOH) have been detected in various biota and human tissues.The current studies were undertaken to investigate the disposition and metabolism of TCPME and TCPMOH in rats and mice.[14C]TCPME was well absorbed (≥66%) in male rats and mice following a single oral administration of 1, 10, or 100 mg/kg. The excretion of [14C]TCPME-derived radioactivity in urine (≤2.5%) and feces (≤18%) was low. The administered dose was retained in tissues (≥ 64%) with adipose containing the highest concentrations. The metabolism of TCPME was minimal. The disposition and metabolism of [14C]TCPME in females was similar to males.The time to reach maximum concentration was ≤7 h, the plasma elimination half-life was ≥31 h, and the bioavailability was ≥82% following a 10 mg/kg oral dose of [14C]TCPME in male rats and mice.The disposition of [14C]TCPMOH was similar to that of [14C]TCPME.Following an intravenous administration of [14C]TCPME or [14C]TCPMOH in male rats and mice, the pattern of disposition was similar to that of oral administration.In conclusion, both TCPME and TCPMOH are readily absorbed and highly bioavailable following a single oral administration pointing to importance of assessing the toxicity of these chemicals.

Theoretical studies on the derivatives of tris([1,2,4]triazolo)[4,3-a:4′,3′-c:4′′,3′′-e][1,3,5]triazine as high energetic compounds

Tris([1,2,4]triazolo)[4,3-a:4′,3′-c:4′′,3′′-e][1,3,5]triazine inherited from triazole and triazine is suggested theoretically as a new framework for insensitive and high-energetic materials.

Synthesis by ring closing metathesis and properties of an electroactive calix[6]arene [2]catenane

Tris-(N-phenylureido)-calix[6]arenes are heteroditopic non-symmetric molecular wheels that, in apolar media, bind viologen-based molecular axles in a pseudorotaxane-type fashion. Because of the precise kinetic requirements associated with the threading process, in apolar solvents, the dicationic portion of the axle enters the calixarene annulus exclusively from the upper rim. With the general aim to develop new prototypes of molecular devices and machines whose functions could be governed through a wider set of control elements, we envisaged that the unique properties of these calixarene wheels could be transferred to the synthesis of new catenanes for the construction of unidirectional rotary motors. Herein, we describe the synthesis of a tris(N-phenylureido)calix[6]arene-based catenane by applying the intramolecular ring-closing metathesis reaction for the catenation step on a pre-formed pseudorotaxane.

Laser-induced luminescence in hybrid nanofilms

Tris(8-hydroxyquinoline) boron (Bq3) was synthesized by a high-temperature exchange reaction. Bq3 powders containing various polymorphous modifications were synthesized, and their photoluminescent characteristics were analyzed. Films of Alq3/B2O3/Al hybrid materials (HMs) were deposited on glass substrates by vacuum thermal evaporation. It is shown that local heating by a diode laser (785 nm) with an intensity of 150 W/cm2 for one second causes irreversible transformation in the HM film structure. The chromaticity coordinates of the photoluminescence of laser-irradiated regions considerably differ from those of the initial HM film luminescence.

Fabrication and Characterization of Solution Processed Top-Gate-Type Organic Light-Emitting Transistor

Tris(8-hydroxyquinolinato) aluminium (Alq3 based top-gate-type organic light emitting-transistors (OLETs) have been fabricated by using a simple solution process. The OLET consists of a bulk layer of indium-tin oxide (ITO) and hole injection layer of poly(2,3-dihydrothieno-1,4-dioxin)– poly(styrenesulfonate) (PEDOT:PSS) as an anode (source), organic electroluminescent layer of Alq3 and aluminium (Al) as cathode (drain) and gate. A Current–voltage–luminance (J–V–L) characteristic of the OLETs shows that the current density is depended on polarity of gate bias. Initial internal electric field contributes to the charge diffusion between gate and cathode channel. A vice versa characteristic observed for luminance at cathode–anode and gate–anode channels.

Orthoamide und Iminiumsalze, LXXXIV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: Tris(dichlormethyl)amin / Orthoamides and Iminiumsalts LXXXIV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: Tris(chloromethyl)amine

Tris(chloromethyl)amine (4) can be prepared by chloromethylation of urotropin with paraformaldehyde or 1,3,5-trioxane and ethyl-trichlorosilane in good yields. Photochlorination of tris(chloromethyl)amine affords tris(dichloromethyl)amine (2). Both reactions can be performed on large scale.

Study on Properties and Application of PG/CS Composite PCMs

Tris (hydroxymethyl) ethane (PG) as a phase change material, micro-porous xonotlite (CS) as matrix, PG/CS composite PCMs were prepared by melt-soaking method, and the effect of micro-porous structure of xonotlite on heat absorption capacity, bending strength and insulation performance of composites, and the exudation of PG was studied. Otherwise, for the work environment and characteristics of propulsive device of vehicle, this paper explored the feasibility that phase change materials (PCMs) worked as the insulation material in short-time insulation system of the vehicle. Experimental results show that, when the most probable pore diameters of xonotlite was not less than 63nm, the composites presented better and almost same absorption capacities of matrix (CS) to PCM (PG) in different composites; when up to 85nm, the composite exhibited the lowest leakage rate (less than 5%), the optimal mechanical property and thermal insulation performance. This Study proposed a new idea for the design of the insulation material in the thermal protection system of propulsive device of vehicle.

Synthesis, structure, and DNA-binding properties of manganese(II) and nickel(II) complexes with tris(N-ethylbenzimidazol-2-ylmethyl)amine ligand

Tris(N-ethylbenzimidazol-2-ylmethyl)amine (Etntb), [Mn(Etntb)(DMF)(H2O)](pic)2 (1), and [Ni(Etntb)(DMF)(H2O)](pic)2 (2) (pic = picrate) have been synthesized and characterized by elemental analyses, molar conductivities, UV–Visible spectra, and IR spectra. Single-crystal X-ray diffraction revealed that the complexes have the same arrangement with distorted octahedral coordination geometries. DNA-binding properties of the free ligand, 1, and 2 have been investigated by electronic absorption, fluorescence, and viscosity measurements. The results suggest that the ligand and its complexes bind DNA via intercalation, and their binding affinity for DNA follows the order 2 > 1 > ligand.

Fluorodinitroethyl Ortho-carbonate and -formate as Potential High Energy Dense Oxidizers

Tetrakis(2-fluoro-2,2-dinitroethyl) ortho-carbonate (1) and tris(2-fluoro-2,2-dinitroethyl) orthoformate (2) were synthesized by the reaction of carbon tetrachloride, respectively chloroform, with 2-fluoro-2,2-dinitroethanol and catalytic amounts of anhydrous iron(III) chloride. The compounds were characterized by single-crystal X-ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, and multi-temperature DSC measurements. The suitability of the compounds as potential oxidizers in energetic formulations has been investigated and discussed. The heats of formation of the products were determined experimentally using bomb calorimetric methods. With this value and the experimental (X-ray) density, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code. The sensitivity towards impact, friction and electrostatic discharge was tested using the BAM drop hammer, a friction tester and a small-scale electrostatic discharge device.

New aspects of the chemistry of CS2: synthesis of mercapto-triorganosilyl-thiones by use of tris(trimethylsilyl)methyllithium

Tris(trimethylsilyl)methyllithium (TsiLi) reacts with CS2 via cleavage of the C=S double bond and unexpected rearrangement to give sulfur-containing organosilicon compounds. The intermediate, from the reaction between TsiLi and CS2 is not stable but it has been trapped by various alkyl halides to give mercaptobis-(trimethylsilyl)-thiones. These reactions are quantitative and high yields in short periods of time have been obtained.

Synthesis and coordination properties of new preorganized ligand on the triphenylphosphine oxide platform

Tris(2-cyanomethoxyphenyl)phosphine oxide was synthesized by the reaction of tris-(2-hydroxyphenyl)phosphine oxide with chloroacetonitrile. Its coordination properties were studied for the complexation with neodymium(iii) and copper(ii) nitrates using vibrational spectroscopy, NMR, and quantum chemical calculations.

Synthesis and Characterization of Tris (nonyl) Phenyl Phosphite and Interfacial Study with Karanja Oil in Acetonitrile Solution

Tris (nonyl) phenyl phosphite is a triarylphosphite. It is obtained when nonylphenol reacts with the phosphorus trichloride. The reaction between nonylphenol and phosphorus trichloride is a nonelementary reaction, an intermediate of this reaction is stable and greatly affects the yield of tris (nonyl) phenyl phosphite. Phosphorus trichloride has three chlorine atoms and it replaces one by one with nonylphenol. This reaction mechanism is a series parallel. It is in series with respect to phosphorus trichloride (PCl3) and parallel with respect to nonyl phenol. The reaction between PCl3 and nonylphenolis is highly exothermic reaction. Therefore, to avoid run away conditions and to control the heat of the reaction, PCl3 is required to be added in a controlled manner. The interfacial tension (IFT) of tris (nonyl) phenyl phosphite/Karanja oilin acetonitrile solution was measured by an interfacial tensiometer (Model Kruus K-100). The critical micelle concentration (CMC) and interfacial tension at CMC (γcmc) were calculated.

The double salt tris(diisopropylammonium) tetrachloridoferrate(III) dichloride: Synthesis, crystal structure, and vibrational spectra

Tris(diisopropylammonium)tetrachloridoferrate(III) dichloride crystallizes in the monoclinic space group P21/c (a = 7.6685(2) A, b = 17.6079(3) A, c = 23.3217(4) A, β = 91.396(2)°, V = 3148.1(1) A3, Z = 4, T = 113 K) with three diisopropylammonium cations (dip), one tetrachloridoferrate(III) anion, and two chloride anions in the asymmetric unit. The dip cations and the chloride anions form hydrogen bonded one-dimensional polymers along [010]. The tetrachloridoferrate(III) anion, habituated in between these chains, is not involved in any hydrogen bonding. The structural characterization is supported by infrared and Raman spectroscopic data.

Synthesis and Photoluminescence Property of Tris(8-hydroxyquinoline) Bismuth Rod-Like Structures at Room Temperature

Tris(8-hydroxyquinoline) bismuth complex has been synthesized with a facile method in a mixed solvent system containing bismuth nitrate and 8-hydroxyquinolineat at room temperature. The molecular formula of the products is speculated by the C, H and N element analysis and thermal gravimetric analysis, and FTIR was also utilized to measure the structure, which further confirms the molecular formula of the products. The observation of FESEM and TEM shows that the morphology of tris(8-hydroxyquinoline) bismuth complexes is rod-like structure. The results of photoluminescence emission indicate that inorganic element plays key roles in the luminescence property. According to the results, we found that the photoluminescence of tris-(8-hydroxyquinoline) bismuth is stronger than that of 8-hydroxyquinoline.