Terphenyl Research Articles

Adherence of p-Terphenyl (PTP) film on the dichroic filter used for the X-ARAPUCA device

The adherence of the p-Terphenyl film to the substrate in the X-ARAPUCA dichroic filter is directly correlated with the long-term efficiency and durability of this device. This study presents the results of different cleaning methods established to analyze their contributions to the film's adherence to the substrate. The samples underwent analysis of their crystalline and morphological structure using XRD and AFM techniques. Three distinct techniques were employed in the adherence tests: ultrasonic bath, scratch test, and cryogenic immersion method with turbulence, as these devices will be submerged in liquid argon in the DUNE experiment.Results suggest that the deposited PTP layer exhibits a monoclinic crystalline structure, with topography revealing percolated planar grains and roughness ranging from 13 nm to 18 nm. The various adherence techniques employed yielded consistent results, highlighting the standard cleaning process involving Soap + H2O + N2 + Kiln as the preferred method.

Improving the Electroluminescence Properties of New Chrysene Derivatives with High Color Purity for Deep-Blue OLEDs.

Two blue-emitting materials, 4-(12-([1,1':3',1″-terphenyl]-5'-yl)chrysen-6-yl)-N,N-diphenylaniline (TPA-C-TP) and 6-([1,1':3',1″-terphenyl]-5'-yl)-12-(4-(1,2,2-triphenylvinyl)phenyl)chrysene (TPE-C-TP), were prepared with the composition of a chrysene core moiety and terphenyl (TP), triphenyl amine (TPA), and tetraphenylethylene (TPE) moieties as side groups. The maximum photoluminescence (PL) emission wavelengths of TPA-C-TP and TPE-C-TP were 435 and 369 nm in the solution state and 444 and 471 nm in the film state. TPA-C-TP effectively prevented intermolecular packing through the introduction of TPA, a bulky aromatic amine group, and it showed an excellent photoluminescence quantum yield (PLQY) of 86% in the film state. TPE-C-TP exhibited aggregation-induced emission; the PLQY increased dramatically from 0.1% to 78% from the solution state to the film state. The two synthesized materials had excellent thermal stability, with a high decomposition temperature exceeding 460 °C. The two compounds were used as emitting layers in a non-doped device. The TPA-C-TP device achieved excellent electroluminescence (EL) performance, with Commission Internationale de L'Eclairage co-ordinates of (0.15, 0.07) and an external quantum efficiency of 4.13%, corresponding to an EL peak wavelength of 439 nm.

Synthesis and Characterization of a Polystyrene-based Scintillator for Gamma Detection

This study aimed to create and examine plastic scintillators made from a polystyrene matrix, which are widely used in radiation detection due to their favorable properties such as rapid decay time, low cost, resistance to moisture, and ease of fabrication. The scintillators were doped with p-terphenyl (PTP) and 1,4-bis[2-(phenyloxazolyl)]-benzene (POPOP) using an injection method with an extruder machine. The materials were then characterized using various techniques. Fourier Transform Infrared Spectroscopy (FTIR) revealed the presence of aromatic chains which are essential for the scintillation process. Differential Scanning Calorimetry (DSC) analysis showed stable thermal properties with a glass transition temperature of approximately 100ºC. Scanning Electron Microscopy (SEM) showed that the surface of the polymer is amorphous with small bumps and protrusions likely caused by the PTP and POPOP dopants. The optical evaluation indicated that the sample could absorb UV photons up to 340 nm and emit photons in the wavelength range of 400-500 nm with a peak at 421 nm. Gamma spectra analysis indicated that the plastic scintillators performed well in gamma detection and could be used in a Radiation Portal Monitor (RPM).

Excited-State Modification of Phenylimidazole-Based Cyclometalated Ir(III) Complexes through Secondary Bulky Aryl Substitution and Inductive Modification Enhances the Blue Emission Efficiency in Phosphorescent OLEDs

To elucidate the key parameters governing the emission properties of phenylimidazole (pim)-based Ir(III) emitters, including their electronic structure and the bulky aryl substitution effect, a series of pim-based iridium(III) complexes (Ir(Rpim-X)3, Rpim-X = 1-R-2-(X-phenyl)-1H-imidazole) bearing secondary pendants of increasing bulkiness [R = methyl (Me), phenyl (Ph), terphenyl (TPh), or 4-isopropyl terphenyl (ITPh)] and three different primary pim ligands (X = F, F2, and CN) were designed and synthesized. Based on photophysical and electrochemical analyses, it was found that the excited state properties are highly dependent on the bulkiness of the secondary substituent and the inductive nature of the primary pim ligand. The incorporation of bulky TPh/ITPh substituents in the second coordination sphere significantly enhanced the emission efficiencies in the solid state (ΦPL = 72.1-84.9%) compared to those of the methyl- or phenyl-substituted Ir(III) complexes (ΦPL = 30.4% for Ir(Mepim)3 and 63.7% for Ir(Phpim)3). Further modification of the secondary aryl substituent (Ir(TPhpim)3 → Ir(ITPhpim)3) through the incorporation of an isopropyl group and F substitution on the primary pim ligand (Ir(TPh/ITPhpim)3 → Ir(TPh/ITPhpim-F/F2)3) resulted in a slight decrease in the LUMO and a significant decrease in the HOMO energy levels, respectively; these energy level adjustments consequently amplified emission blue shifts, thereby enabling efficient blue electroluminescence in phosphorescent organic light-emitting diodes. Theoretical calculations revealed that the excited-state properties of pim-based Ir(III) complexes can be modulated by the nature of the peripheral substituent and the presence of an EWG substituent. Among the fabricated blue-emitting TPh/ITPh-substituted Ir(III) complexes, Ir(ITPhpim-F)3, Ir(TPhpim-F2)3, and Ir(ITPhpim-F2)3 were tested as blue-emitting dopants for blue phosphorescent OLEDs owing to their high solid radiative quantum yields (ΦPL = 75.9-84.9%). The Ir(ITPhpim-F)3-doped multilayer device displayed the best performance with a maximum external quantum efficiency of 21.0%, a maximum current efficiency of 43.6 cd/A, and CIE coordinates of 0.18 and 0.31.

Conjugated microporous polymers for near-infrared photothermal control of shape change

Herein, a facile and highly efficient synthetic method to prepare organic photothermal materials with high photo-stability and outstanding photothermal performance is reported. Through direct polymerization of commercial aromatic monomers in the presence of anhydrous aluminium chloride and dichloromethane, four kinds of conjugated microporous polymers (CMPs) were obtained. Detailed structural analysis confirmed that the resultant CMPs possessed abundant micropores with an extended π-conjugated skeleton. Under near-infrared (NIR) light irradiation (808 nm, 1.0 W cm−2), all the CMPs showed fast heating-up behavior with their maximum temperatures higher than 150°C. Moreover, the efficiency of photothermal conversion ( η ) of the CMPs was found to increase linearly with the increase in the number of conjugated benzene rings within the monomer. Poly-TPE from tetraphenylethylene (TPE) and Poly-TP from o -terphenyl (TP) showed high η values of over 47%. Poly-TPE was additionally used as a photothermal filler to remotely and spatially control the shape recovery of thermal-sensitive shape memory polymers (SMPs), while its introduction (1 wt%) had little influence on the thermal and mechanical properties of the polymer matrixes. Owing to their excellent NIR photothermal performance as well as a one-step synthetic preparation, these CMPs may be promising photothermal materials for practical applications.

Enhanced UV light detection using a p-terphenyl wavelength shifter

UV-glass photomultiplier tubes (PMTs) have poor photon detection efficiency for wavelengths below 300 nm due to the opaqueness of the window material. Costly quartz PMTs could be used to enhance the efficiency below 300 nm. A less expensive solution that dramatically improves this efficiency is the application of a thin film of a p-terphenyl (PT) wavelength shifter on UV-glass PMTs. This improvement was quantified for Photonis XP4500B PMTs for wavelengths between 200 nm and 400 nm. The gain factor ranges up to 5.4±0.5 at a wavelength of 215 nm, with a material load of 110±10μg∕cm2 (894 nm). The wavelength shifter was found to be fully transparent for wavelengths greater than 300 nm. The resulting gain in detection efficiency, when used in a typical C̆erenkov counter, was estimated to be of the order of 40%. Consistent coating quality was assured by a rapid gain testing procedure using narrow-band UV LEDs. Based on these results, 200 Photonis XP4500B PMTs were treated with PT for the upgraded low-threshold C̆erenkov counter (LTCC) to be used in the CEBAF Large Acceptance Spectrometer upgraded detector (CLAS12) at the Thomas Jefferson National Accelerator Facility.

Synthesis and Properties of Phenylene-containing Copolymer via the Catalytic Heck Coupling Reaction of Dipropargyl Group and Terphenyl Group

Synthesis and Properties of Phenylene-containing Copolymer via the Catalytic Heck Coupling Reaction of Dipropargyl Group and Terphenyl Group

Synthesis of symmetrical terphenyl derivatives by PdCl2-catalyzed Suzuki–Miyaura reaction of dibromobenzene using 3-(diphenylphosphino)propanoic acid as a ligand

ABSTRACTA simple and efficient catalytic system for PdCl2 catalyzing the Suzuki–Miyaura reaction of dibromobenzene and arylboronic acid has been developed by using 3-(diphenylphosphino)propanoic acid as a ligand in dimethylsulfoxide at 100 °C. Using this method, a series of symmetrical terphenyl derivatives were obtained with remarkably good yields, up to 93%.

Distribution Coefficient of 1,4-diphenyl-1,3-butadiene in p-terphenyl Single Crystal and Its Influence on Scintillation Crystal Light Output

The method of gas chromatography-mass spectrometry (GC-MS) was used to determine the amount of 1,4-diphenyl-1,3-butadiene(DFB) in p-terphenyl (PTP) crystal. We studied five p-terphenyl single-crystal boules with different initial DFB concentrations. Values of DFB concentration determined in different part of such the boule are presented. These data are used to estimate the values of distribution coefficient. The value of distribution coefficient which calculated experimentally was compared with theoretical calculated value. The effect of 1,4-diphenyl-1,3-butadiene concentration on light output was studied. The dependence of a number of useable fragments of the boule from initial amount of DPB was analyzed.

Synthesis and properties of sulfonated block poly(arylene ether)s containing m-terphenyl groups as proton conductive membranes

We have utilized m-terphenyl (MTP) moiety as a component of hydrophobic blocks for sulfonated multiblock poly(arylene ether) copolymers. For this purpose, bisphenol-type MTP monomer was polymerized with bis(4-fluorophenyl)sulfone to obtain hydroxyl-terminated hydrophobic oligomers, which were copolymerized with sulfonated hydrophilic blocks to obtain the targeted multiblock copolymers. The block copolymers possessed high apparent molecular weight (Mw=74–180kDa) and gave bendable membranes by solution casting. Transmission electron microscopic (TEM) images revealed that the membranes exhibited hydrophilic/hydrophobic phase-separated morphology with distinct interfaces. The domain sizes were dependent on the compositions of the multiblock copolymers, indicating the sequenced structure is responsible for the morphology. The introduction of MTP moieties in the hydrophobic blocks resulted in the membrane with the higher ion exchange capacity (IEC) value (2.13meq/g) and higher proton conductivity (ca. 320mS/cm at 80°C and 90% relative humidity) than that of the previous polymers sharing the same hydrophilic but different hydrophobic (p-biphenyl, BP) moieties (1.69meq/g, ca. 200mS/cm under the same conditions, respectively). In contrast, humidity dependence of dynamic mechanical properties in MTP membranes was similar to BP membranes, suggesting the introduction of MTP moieties in the hydrophobic segments has minor impact on the mechanical stability and its dependence on the humidity.

Phase sensitive pulse shaping for molecule selective three-photon excitation

In this paper we present a method for selective three-photon excitation of the two dyes, p-Terphenyl (PTP) and BM-Terphenyl (BMT), in solution by using shaped pulses. A good agreement between experiment and theoretical simulation is obtained. With this method it is possible to achieve a considerable change of the fluorescence contrast between the two dyes which is relevant for imaging applications of biological molecules.

Сравнение активности катализаторов в реакции дегидрирования пергидрометатерфенила

In order to develop new catalytic composite materials for hydrogen storage based on organic chemical compounds, the comparative tests of the activity of various catalysts (on the basis of Pt, Pd, Cr and Ni) were carried out in the dehydrogenation reaction of perhydro- m -terphenyl. Tests were carried out at temperatures 300–320 °C in the flow reactor (internal diameter of 10 mm). The control of volumes of evolved hydrogen, conversion of perhydro- m -terphenyl to m -terphenyl and selectivity to m -terphenyl was made during the reaction. It is shown that the best indicators are obtained when using the catalyst 3%Pt/C on the basis of carbon sibunit carrier.

Electrochemical polymerization of p‐terphenyl in mixed electrolyte of boron trifluoride diethyl etherate and CH2Cl2

AbstractHigh quality poly(p‐phenylene) (PPP) film with conductivity of 0.015 S cm−1 was synthesized electrochemically by direct anodic oxidation of p‐terphenyl (PP) oligomers in boron trifluoride diethyl etherate (BFEE) containing 37.5% CH2Cl2 (v/v). The oxidation onset potential of PP in this medium was measured to be only 1.23 V vs. saturated calomel electrode (SCE), which was lower than that determined in CH2Cl2 + 0.1 mol L−1 Bu4NBF4 (1.87 V vs. SCE). As‐formed PPP films showed good electrochemical behavior, good electrochromic property and good thermal stability. The structures and morphology of doped and dedoped PPP were investigated by UV‐vis, FTIR, and Scanning electron micrographs. The infrared spectroscopic measurements for the estimation of chain lengths revealed that PPP was composed of about 10 phenyl rings. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010

A new hydrogen storage system based on efficient reversible catalytic hydrogenation/dehydrogenation of terphenyl

Noble metal catalysts on mesoporous SiO 2 and modified carbon supports were found to enhance the activities of terphenyl (TPh) hydrogenation and tercyclohexane (TCH) dehydrogenation without side reactions, such as cracking, hydrogenolysis, ring opening and/or coke formation. The noble metal catalysts could be used for a reversible hydrogen storage system. Five percent Pt/SiO 2 catalyst was highly active in TCH dehydrogenation without stirring, due to an easier diffusion of organic molecules to the small catalyst particles during dehydrogenation. In view of a long-term stability in TPh hydrogenation and TCH dehydrogenation, a catalyst with relatively low Pt content on the oxidized graphite coal (Sibunit-ox) was the most promising for a hydrogen storage system because Pt agglomeration on the support was found to be much less than Pd agglomeration in the Pd/Sibunit-ox catalyst.

Two-Color Two-Photon Excitation Using Femtosecond Laser Pulses

The use of two-color two-photon (2c2p) excitation easily extends the wavelength range of Ti:sapphire lasers to the UV, widening the scope of its applications especially in biological sciences. We report observation of 2c2p excitation fluorescence of p-terphenyl (PTP), 2-methyl-5-t-butyl-p-quaterphenyl (DMQ) and tryptophan upon excitation with 400 and 800 nm wavelengths using the second harmonic and fundamental wavelength of a mode-locked Ti:sapphire femtosecond laser. This excitation is energetically equivalent to a one-photon excitation wavelength at 266 nm. The fluorescence signal is observed only when both wavelengths are spatially and temporally overlapping. Adjustment of the relative delay of the two laser pulses renders a cross correlation curve which is in good agreement with the pulse width of our laser. The fluorescence signal is linearly dependent on the intensity of each of the two colors but quadratically on the total incident illumination power of both colors. In fluorescence microscopy, the use of a combination of intense IR and low-intensity blue light as a substitute for UV light for excitation can have numerous advantages. Additionally, the effect of differently polarized excitation photons relative to each other is demonstrated. This offers information about different transition symmetries and yields deeper insight into the two-photon excitation process.

Natural Terphenyls: Developments since 1877

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Natural Terphenyls: Developments since 1877

Natural Terphenyls: Developments since 1877

Single-Molecule Nanoprobes Explore Defects in Spin-Grown Crystals

Thin, platelike single crystals of p-terphenyl (PT) doped with terrylene impurity molecules can be prepared by spin-coating from solution. Strikingly, individual terrylene molecules can be observed traveling inside the crystal over distances of several micrometers by using single-molecule fluorescence imaging at room temperature. Analysis of the motion by single-particle tracking and correlation methods indicates that the molecules act as nanoprobes by exploring long, thin crack-like defects with correlated orientations, defects that can be difficult to observe by other means. Apparently, the regions accessible to the moving molecules are in the interior of the crystal and hence are partially protected from oxidation. In addition to the traveling molecules, which photobleach in times on the order of 32 s under continuous irradiation at 2 kW/cm2, two other spatially fixed populations are observed: one with transition dipole oriented along the c-axis of the crystal with a characteristic photobleaching time greater than 32 h, and one with a characteristic photobleaching time of 18 min.

Functional Electrolyte: Additives for Improving the Cyclability of Cathode Materials

A novel type of additives for improving cathode cyclability has been developed. Three electrolyte additives, biphenyl (BP), o-terphenyl (OT), and m-terphenyl (MT) have been investigated for improving the cyclability of cathode materials like LiCoO 2 and LiMn 2 O 4 . The effect of these additives is correlated to the properties of the surface film on the cathode electrode, which comes from the decomposition of the additives at high potentials.

Liquid crystalline binary mixtures at the air–water interface

The interaction behaviour of the binary mixtures composed of the liquid crystals 4-octyl-4′-cyanobiphenyl (8CB) and 4-pentyl-4′-cyanoterphenyl (5CT) as well as biphenyl (BP) and terphenyl (TP) at different molar ratios has been studied using Langmuir technique. The surface pressure-mean molecular area isotherms have been recorded. The miscibility of the components in Langmuir films has been determined by using the additivity rule and collapse surface pressure criterion. It has been found, that 8CB is partially miscible with BP and TP. 5CT is miscible with TP, whereas the mixtures of two liquid crystals, 8CB and 5CT reveal the phase separation over a whole range of composition.