Anthracene In Solution Research Articles

Solute − solvent repulsion effects on the absorption spectra of anthracene in n-hexane investigated under high pressure

The band positions in the UV–VIS absorption spectra of compressed solution of anthracene in n-hexane significantly depend not only on the dispersive but also on the repulsive solute–solvent interactions, what has so far been omitted. Their strength is determined not only by the solvent polarity but also by Onsager cavity radius changing with pressure. The results obtained for anthracene show that repulsive interactions should be included in the interpretation of barochromic and solvatochromic results of aromatic compounds. We show that the barochromic studies in the liquid solvent can be an alternative to solvatochromic studies, e.g. to determine the polarizability of organic molecules in the electronic excited state. The pressure-induced polarity change in n-hexane exceeds that induced by the exchange of n-alkane solvents between n-pentane and n-hexadecane.

Monitoring microplastic-contaminant sorption processes in real-time using membrane introduction mass spectrometry.

Microplastics are environmentally ubiquitous and their role in the fate and distribution of trace contaminants is of emerging concern. We report the first use of membrane introduction mass spectrometry to directly monitor the rate and extent of microplastic-contaminant sorption. Target contaminant (naphthalene, anthracene, pyrene, and nonylphenol) sorption behaviours were examined at nanomolar concentrations with four plastic types: low density polyethylene (LDPE), high density polyethylene (HDPE), polypropylene (PP), and polystyrene (PS). Under the conditions employed here, short-term sorption kinetics were assessed using on-line mass spectrometry for up to one hour. Subsequent sorption was followed by periodically measuring contaminant concentrations for up to three weeks. Short-term sorption followed first order kinetics with rate constants that scaled with hydrophobicity for the homologous series of polycyclic aromatic hydrocarbons (PAHs). Sorption rate constants on LDPE for equimolar solutions of naphthalene, anthracene, and pyrene were 0.5, 2.0, and 2.2 h-1, respectively, while nonylphenol did not sorb to pristine plastics over this time period. Similar trends among contaminants were observed for other pristine plastics with 4- to 10-fold faster sorption rates associated with LDPE when compared to PS and PP. Sorption was largely complete after three weeks, with the percent analyte sorbed ranging from 40-100% across various microplastic-contaminant combinations. Photo-oxidative ageing of LDPE had little effect on PAH sorption. However, a marked increase in nonylphenol sorption was consistent with increased hydrogen-bonding interactions. This work provides kinetic insights into surface interactions and describes a powerful experimental platform to directly observe contaminant sorption behaviours in complex samples under a variety of environmentally relevant conditions.

Effects of 7,12-Dimethylbenz(a)anthracene on Apoptosis of Breast Cancer Cells through Regulating Expressions of Fas Ligand and B-Cell Lymphoma 2

To provide reference basis for the apoptosis of breast cancer cells and the carcinogenesis of breast cancer, the effects of 7,12-dimethylbenz(a)anthracene on apoptosis regulators Fas ligand and B-cell lymphoma-2 were investigated. In this study, 62 female C57BL/6 mice aged from 4 w to 6 w were randomly divided into control group and test group, with 31 mice in each group. The test group was given 7,12-dimethylbenz(a) anthracene solution by gavage at a dose of 50 mg/kg and the control group was given normal saline of equal volume. On the 2nd d after the experiment, all the mice were killed by cervical dislocation. The results showed that after hematoxylin-eosin staining, the tumor cells in the test group were stacked up to form a substantial structure. The expression level of Fas ligand protein in the control group was greatly lower than that in the test group and the positive rate was 20.25 %, which was greatly lower than that of 89.65 % in the test group (p<0.01). The expression level of B-cell lymphoma-2 protein in the mammary gland tissues of mice in the test group was greatly higher than that of the control group and its positive rate was 87.96 %, which was greatly higher than that of 31.48 % in the control group (p<0.01). The expression levels of Fas ligand messenger ribonucleic acid in the mammary gland tissues of mice in the test group and control group were 5.82±4.37 and 1.27±0.12, respectively and there was a statistically obvious difference (p<0.05). The messenger ribonucleic acid expression levels of B-cell lymphoma-2 in the test group and the control group were 18.97±2.65 and 2.02±0.54, respectively, and there was an extremely obvious difference (p<0.01). The apoptosis rate of mammary gland cells in the test group was (19.79±3.53) % and that in the control group was (2.93±0.28) % and there was an extremely obvious difference (p<0.01). It indicated that 7,12-dimethylbenz(a)anthracene inhibited the apoptosis of breast cancer cells by regulating the upregulation of Fas ligand and B-cell lymphoma-2 expression.

Discontinuous solid solutions of anthracene–phenanthrene: Thermodynamics and crystallization kinetics

We explored such issues as the formation mechanism, structure and propriety of the solid solutions of anthracene (ANT)–phenanthrene (PHE). Solution crystallization and solid-state grinding were employed to prepare solid solutions under different conditions. The thermal behavior and PXRD scanning results revealed the formation of discontinuous solid solutions, whose melting points and crystal lattices varied linearly with mixed ratio. Combing with Materials Studio, the formation possibility of solid solutions were investigated by evaluating the change of the energy. The crystal morphology of the solid solutions have a positive correlation with the change of the major part. Finally, the solution crystallization process of solid solution were studied using the population balance model.

Binary solid solutions of anthracene and carbazole: Thermal properties, structure and crystallization kinetics

Abstract The present work explored the thermal properties, structure and crystallization kinetics of the anthracene (ANT)-carbazole (CAR) discontinuous binary solid solutions. The solid solutions with different stoichiometric ratios were synthesized by solid-state grinding or solution crystallization and characterized by differential scanning calorimetry and powder X-ray diffraction to explore their structure, morphology, and co-melting behavior. The molecular simulations results of the lattice energy of the constructed supercells also revealed the formation of ANT-CAR discontinuous solid solutions. The crystallization kinetics of the solid solutions were investigated, and the growth rate of the mixed crystals was determined using the population balance model.

Photocatalytic degradation of anthracene in aqueous dispersion of metal oxides nanoparticles: Effect of different parameters

Contamination with anthracene, as one of polycyclic aromatic hydrocarbons (PAHs), was considered as an important health issue due to its carcinogenic and mutagenic activity. In this paper, we focused on the photocatalytic degradation of anthracene in different media and in presence of various photocatalysts. Zinc oxide nanoparticles (ZnO NPs) and nickel oxide nanoparticles (NiO NPs) were prepared and utilized as efficient photocatalysts to convert anthracene into safer compounds. The as-prepared photocatalysts were characterized by x-ray diffraction (XRD), transmission electron microscopy (TEM) and UV-VIS spectroscopy. The factors affecting the efficiency of photocatalytic degradation, including irradiation time, loading catalyst doses, pH value and H2O2 as an oxidizing agent, were investigated. The optimum photocatalytic degradation of 23 mg/L anthracene in different media was carried out at pH 7.2 with loading catalyst dose of 55.6 mg/L. In case of anthracene emulsion solution, a faster photochemical kinetic was observed in presence of ZnO NPs and more than 90% of photocatalytic degradation percentage was reached in 230 min. However, in case of anthracene aqueous solution and in presence of ZnO NPs/H2O2, a degradation efficiency of 84% was obtained within 50 min. The byproducts of 4- formyl-benzoic acid ethyl ester (98.23%) and 1,2-Benzenedicarboxylic acid, isopropyl methyl ester (0.85%)) were detected by gas chromatography-mass spectrometry (GC–MS). The kinetic studies were achieved and revealed that the photocatalytic degradation process obeyed a Langmuir–Hinshelwood model and followed a pseudo-first order rate expression.

Controlling donor crystallinity and phase separation in bulk heterojunction solar cells by the introduction of orthogonal solvent additives

ABSTRACTThe bulk heterojunction morphology of organic solar cells widely controls their device efficiency and stability. Structural order and domain size of the donor phase strongly impact the charge separation efficiency, recombination rates, and the hole percolation through the bulk to the electrode. Herewith, we report a comprehensive study on the control of polymeric order already initiated in solution by the introduction of orthogonal solvent additives to the common solution of anthracene containing poly(p-phenylene-ethynylene)-alt-poly(p-phenylene-vinylene) (PPE-PPV) copolymer, bearing statistically substituted linear octyloxy and 2-ethylhexyloxy side-chains in 1:1 ratio along the backbone (AnE-PVstat), and fullerene derivative phenyl-C61-butyric acid methyl ester (PCBM). The first solvent, a 1:1 blend of chlorobenzene and chloroform, had been discovered to promote phase separation in solution and deposited films. This effect could be further enhanced and was precisely controlled by addition of methanol to the common solution in various volume fractions. Thus the ability to transfer the polymer aggregates from the solution into films was applied to solar cells and is investigated in detail.

Measuring the Solubility of Anthracene and Chrysene in Supercritical Fluid Carbon Dioxide Using Static Solubility Apparatus Directly Interfaced Online to Supercritical Fluid Chromatography

A continuously stirred high pressure solubility vessel has been directly interfaced online to a supercritical fluid chromatography (SFC) system using a single valve recirculation interface. The recirculation pump built into the interface maintains a constant flow of fresh supercritical fluid carbon dioxide solution from the solubility vessel through the interface sample injection valve in a return flow circuit. A series of progressively more concentrated anthracene and chrysene solutions were separately prepared by incrementing the pressure within the solubility vessel in controlled steps. Prior to performing online SFC solubility measurements for each polyaromatic hydrocarbon, in situ checks were made to establish that fully saturated solutions were formed at each different pressure step. The method also involves the utilization of a self-validation experimental procedure to check the accuracy of solubility measurements. For anthracene, solubility data was obtained at 313, 323, 333, and 343 K through the...

Determination of crystalline thermodynamics and behavior of anthracene in different solvents

To screen suitable solvents for anthracene crystallization, the solubilities of anthracene and metastable zone width were determined in four different solvents, N,N‐dimethyl formamide (DMF), xylene, tetrachloroethylene, and diethylene glycol dimethyl ether from 30 to 80 °C at atmospheric pressure using a self‐made crystallizer. The cooling modes, solvents, and the effects of carbazole on the solvent crystallization process of anthracene were also investigated. The composition of mother liquors and solid products were measured by gas chromatography; the solids were analyzed by scanning electron microscope, X‐ray diffractometer, differential scanning calorimetry, granulometer, and fluorescence spectrometer. The results showed that a uniform anthracene crystal was obtained when using DMF under the forced circulation cooling mode. Solid solution of anthracene and carbazole was initially detected in solvent crystallization. The existence of carbazole in solution has an obvious effect on the crystal morphology of anthracene, to some extent, is beneficial to the crystal growth of anthracene. © 2018 American Institute of Chemical Engineers AIChE J, 64: 2160–2167, 2018

Feasibility of the simultaneous determination of polycyclic aromatic hydrocarbons based on two-dimensional fluorescence correlation spectroscopy

A new approach for quantitative determination of polycyclic aromatic hydrocarbons (PAHs) in environment was proposed based on two-dimensional (2D) fluorescence correlation spectroscopy in conjunction with multivariate method. 40 mixture solutions of anthracene and pyrene were prepared in the laboratory. Excitation-emission matrix (EEM) fluorescence spectra of all samples were collected. And 2D fluorescence correlation spectra were calculated under the excitation perturbation. The N-way partial least squares (N-PLS) models were developed based on 2D fluorescence correlation spectra, showing a root mean square error of calibration (RMSEC) of 3.50μgL−1 and root mean square error of prediction (RMSEP) of 4.42μgL−1 for anthracene and of 3.61μgL−1 and 4.29μgL−1 for pyrene, respectively. Also, the N-PLS models were developed for quantitative analysis of anthracene and pyrene using EEM fluorescence spectra. The RMSEC and RMSEP were 3.97μgL−1 and 4.63μgL−1 for anthracene, 4.46μgL−1 and 4.52μgL−1 for pyrene, respectively. It was found that the N-PLS model using 2D fluorescence correlation spectra could provide better results comparing with EEM fluorescence spectra because of its low RMSEC and RMSEP. The methodology proposed has the potential to be an alternative method for detection of PAHs in environment.

A Tris(diisocyanide)chromium(0) Complex Is a Luminescent Analog of Fe(2,2'-Bipyridine)32.

A meta-terphenyl unit was substituted with an isocyanide group on each of its two terminal aryls to afford a bidentate chelating ligand (CNtBuAr3NC) that is able to stabilize chromium in its zerovalent oxidation state. The homoleptic Cr(CNtBuAr3NC)3 complex luminesces in solution at room temperature, and its excited-state lifetime (2.2 ns in deaerated THF at 20 °C) is nearly 2 orders of magnitude longer than the current record lifetime for isoelectronic Fe(II) complexes, which are of significant interest as earth-abundant sensitizers in dye-sensitized solar cells. Due to its chelating ligands, Cr(CNtBuAr3NC)3 is more robust than Cr(0) complexes with carbonyl or monodentate isocyanides, manifesting in comparatively slow photodegradation. In the presence of excess anthracene in solution, efficient energy transfer and subsequent triplet-triplet annihilation upconversion is observed. With an excited-state oxidation potential of -2.43 V vs Fc+/Fc, the Cr(0) complex is a very strong photoreductant. The findings presented herein are relevant for replacement of precious metals in dye-sensitized solar cells and in luminescent devices by earth-abundant elements.

Some thermodynamic processes of anthracite–carbon dioxide mixture in supercritical fluid state

In the context of the development of the catalyst regeneration procedure via supercritical fluid CO2 extraction, some thermodynamic properties of the anthracene–carbon dioxide mixture in supercritical fluid state have been studied. Data on anthracene solubility in pure and modified (dimethyl sulfoxide, 5 wt %) supercritical carbon dioxide (SC–CO2), the heat capacity of anthracene and its mixtures with carbon dioxide, and the heat of solution of anthracene in SC–CO2 are presented. Anthracene solubility in SC–CO2 is described satisfactorily using the Peng–Robinson equation of state.

A Shape-Persistent Cryptand for Capturing Polycyclic Aromatic Hydrocarbons.

A shape-persistent cryptand 1, containing two face-to-face oriented electron-deficient 2,4,6-triphenyl-1,3,5-triazine units separated by approximately 7 Å, and bridged by two rigid 1,8-naphthyridine linkers and a pentaethylene oxide loop, is created for capturing polycyclic aromatic hydrocarbons. Cryptand 1 formed 1:1 complexes with PAH guest molecules, such as phenanthrene (6), anthracene (7), pyrene (8), triphenylene (9), and tetraphene (10). The single-crystal structure of complex 6⊂1 revealed that 6 was included in the cavity of 1 via face-to-face π···π stacking interactions. Soaking crystalline 1 in a toluene solution of anthracene resulted in anthracene from the toluene solution being picked up by the crystalline solid of 1.

Selective Two-Photon-Absorption-Induced Reactions of Anthracene-2-Carboxylic Acid on Tunable Plasmonic Substrate with Incoherent Light Source.

In this research, we report the development, characterization and application of various plasmonic substrates (with localized surface plasmon resonance wavelength tunable by gold nanoparticle size) for two-photon absorption (TPA)-induced photodimerization of an anthracene derivative, anthracene carboxylic acid, in both surface and solution phase under incoherent visible light irradiation. Despite the efficient photoreaction property of anthracene derivatives and the huge number of publications about them, there has never been a report of a multiphoton photoreaction involving an anthracene derivative with the exception of a reverse photoconversion of anthracene photodimer to monomer with three-photon absorption. We examined the progress of the TPA-induced photoreaction by means of surface-enhanced Raman scattering, taking advantage of the ability of our plasmonic substrate to enhance and localize both incident light for photoreaction and Raman scattering signal for analysis of photoreaction products. The TPA-induced photoreaction in the case of anthracene carboxylic acid coated 2D array of gold nanoparticles gave different results according to the properties of the plasmonic substrate, such as the size of the gold nanoparticle and also its resultant optical properties. In particular, a stringent requirement to achieve TPA-induced photodimerization was found to be the matching between irradiation wavelength, localized surface plasmon resonance of the 2D array, and twice the wavelength of the molecular excitation of the target material (in this case, anthracene carboxylic acid). These results will be useful for the future development of efficient plasmonic substrates for TPA-induced photoreactions with various materials.

Photochemical upconversion in metal-based octaethyl porphyrin–diphenylanthracene systems

This paper studies photochemical upconversion in solutions of octaethyl porphyrin (OEP) and diphenyl anthracene (DPA).

On dimers and complexes of tetracene and the Kasha's molecular excitonic model

Aggregation processes that occur in a solution of 3.4 × 10−5 M tetracene in decalin at 213 K and in a 1.3 × 10−4 M solution of anthracene in methylcyclohexane at 135 K show that they are second‐order kinetic processes responsible for generating the corresponding dimeric structures of these acenes. The UV–Vis absorption spectra of these dimeric structures show the presence of isosbestic points. We also show that the rate constants of these processes appear to depend on the viscosity of the solvent employed. Excitonic interactions involved in these dimers are described in the light of Kasha's model.We also show that a solution of 6.7 × 10−5 of tetracene in toluene at 173 K exhibits aggregation but following a first order kinetics and that the corresponding absorption spectra describing the process at 173 K show no isosbestic points. Consequently, it is concluded that in this solvent, the tetracene does not dimerize, but it forms a complex with toluene. The strong similarity between the first band of the tetracene dimer and the tetracene/toluene complex may give rise to a strong controversy over the excitonic model to be considered. Copyright © 2014 John Wiley &amp; Sons, Ltd.

Effect of the Intermolecular Hydrogen Bond between Carbazole and N,N-Dimethylformamide/Isopropanolamine on the Solubility of Carbazole

The influence of hydrogen bonding on the solubility of carbazole and anthracene in N,N-dimethylformamide (DMF) and isopropanolamine (IPA) is investigated accordingly by 1H nuclear magnetic resonance (NMR) analysis. The chemical shift for the free and hydrogen-bonding proton of the anthracene and carbazole solution in DMF, IPA, and the mixture of the two was collected by a 600 MHz 1H NMR spectrometer. It is proposed that DMF, IPA, and a mixture of the two would be able to efficiently refine carbazole from crude anthracene oil. This phenomenon is shown to be the result of the intermolecular hydrogen bond of N–H···O and N–H···N formed between carbazole and the DMF/IPA mixture solvent, which greatly enhanced the solubility of carbazole in DMF and IPA. The arising steric hindrance effects derived from the intermolecular hydrogen bonding between DMF and IPA result in the significant solubility decline of anthracene and carbazole in the DMF and IPA mixture.

ZnO/anthracene based inorganic/organic nanowire heterostructure: Photoresponse and photoluminescence studies

The effects of surface modification of vertically aligned ZnO nanowires (NWs) with anthracene for the improved photocurrent, photoresponse, and UV photoluminescence have been investigated in this work. The formation of ZnO/anthracene based inorganic/organic NWs heterostructure by surface capping with anthracene solution was confirmed from the high resolution transmission electron microscopy and Fourier transport infrared spectroscopy analyses. After the anthracene capping of ZnO NWs, despite an increase in dark current, we obtained a significant improvement in the photocurrent and photoresponsivity. A sixfold improvement in the UV photocurrent-to-dark current ratio is obtained with capping. Compared to the uncapped NWs, the photoresponse is significantly faster for the ZnO/anthracene system with response and reset times of 1.5 and 1.6 s, respectively. The room temperature photoluminescence spectra show threefold enhanced UV emission with large enhancement in the ratio of UV to green emission intensities. The faster photoresponse and enhanced photocurrent from the ZnO/anthracene heterostructure are explained on the basis of modification of surface defects and interfacial charge transfer process.

ChemInform Abstract: Electron Acceptors of the Fluorene Series. Part 10. Novel Acceptors Containing Butylsulfanyl, Butylsulfinyl, and Butylsulfonyl Substituents: Synthesis, Cyclic Voltammetry, Charge-Transfer Complexation with Anthracene in Solution, and

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Synthesis and properties of blue-light-emitting anthracene derivative with diphenylamino-fluorene

9,10-Bis-(9′,9′-diethyl-7′-diphenylamino-fluoren-2-yl)-anthracene was synthesized from 9.10-anthracene diboronic acid and (7-bromo-9,9-diethyl-fluoren-2-yl)-diphenyl-amine in a Suzuki coupling reaction. A theoretical calculation of the three-dimensional structure suggests that it has a non-coplanar structure and inhibited intermolecular interactions. Upon excitation, the photoluminescence maximum of 9,10-bis-(9′,9′-diethyl-7′-diphenylamino-fluoren-2-yl)-anthracene in solution and film were at 454 nm (solution) and 462 nm (film). The full width at half maximum of 9,10-bis-(9′,9′-diethyl-7′-diphenylamino-fluoren-2-yl)-anthracene is 54 nm regardless of whether it is in a solution or a solid state. A multi-layered device using 9,10-bis-(9′,9′-diethyl-7′-diphenylamino-fluoren-2-yl)-anthracene as emitting material exhibits maximum quantum efficiency of 3.3% (power efficiency of 2.1 lm/W, current efficiency of 4.17 cd/A) and a blue Commission Internationale de l'Eclairage chromaticity coordinates ( x = 0.14, y = 0.17).