Vinyl Biphenyl Research Articles

Synthesis and Electroluminescence Properties of 3-(Trifluoromethyl)phenyl-Substituted 9,10-Diarylanthracene Derivatives for Blue Organic Light-Emitting Diodes

Diaryl-substituted anthracene derivatives containing 3-(trifluoromethyl)phenyl) groups, 9,10-diphenyl-2-(3-(trifluoromethyl)phenyl)anthracene (1), 9,10-di([1,1′-biphenyl]-4-yl)-2-(3-(trifluoromethyl)phenyl)anthracene (2), and 9,10-di(naphthalen-2-yl)-2-(3-(trifluoromethyl)phenyl)anthracene (3) were synthesized and characterized. The compounds 1–3 possessed high thermal stability and proper frontier-energy levels, which make them suitable as host materials for blue organic light-emitting diodes. The electroluminescent (EL) emission maximum of the three N,N-diphenylamino phenyl vinyl biphenyl (DPAVBi)-doped (8 wt %) devices for compounds 1–3 was exhibited at 488 nm (for 1) and 512 nm (for 2 and 3). Among them, the 1-based device displayed the highest device performances in terms of brightness (Lmax = 2153.5 cd·m−2), current efficiency (2.1 cd·A−1), and external quantum efficiency (0.8%), compared to the 2- and 3-based devices.

Shear behavior at high pressures and viscoelastic properties in water and in brine solutions with high salinities for a tetra-polymer containing poly(ethylene oxide) side chains

A novel tetra-polymer (PASV) was synthesized using acrylamide(AM), vinyl biphenyl (VP), sodium 2-acrylamido-2-methylpropane sulphonate (NaAMPS), and a novel salt-tolerant allyl-capped macromonomer AE.

Viscous and Interfacial Behaviors, and AFM Morphologies of a Tetra-Polymer in Aqueous Solutions for Enhanced Oil Recovery

An acrylamide-based tetra-polymer (PAVO) containing a macro-monomer APEO: allyl-capped octylphenoxy poly(ethylene oxide) and vinyl biphenyl (VP), was measured in 30 g/L NaCl with static light scattering. The result shows that the molecular weight is low and the polymer chains are expanded. The apparent viscosities are much higher in 90 g/L NaCl than in water for PAVO at polymer concentrations higher than 1 g/L, the salt-thickening effects induced by the Na+, Ca2+, and Mg2+ ions are exhibited, and both surface and interfacial tensions are low in water and 90 g/L NaCl. In order to reveal the mechanism giving rise to solution properties for this polymer, the effects of polymer concentration on associating behaviors of the polymer chains in water and in 90 g/L NaCl, were investigated by the ultraviolet spectral analysis using pyrene as a probe. Resistance factor and residual resistance factor are remarkably higher in 120 g/L salt for PAVO than for HPAM. Atomic force microscope (AFM) morphologies of PAVO in water show that the expanded polymer chain bundles are formed at the polymer concentrations of 0.5–1.5 g/L, which demonstrates that the introduction of the APEO macro-monomer together with VP can make the polymer chains expanded.

Solution behavior and associating structures of a salt-tolerant tetra-polymer containing an allyl-capped macromonomer

A novel salt-tolerant macromonomer, allyl-capped octylphenoxy poly(ethylene oxide) (AOP) with the degree of polymerization equal to 20, was synthesized, and then a novel acrylamide(AM)-based tetra-polymer (PSAA) containing sodium 2-acrylamido-2-methylpropane sulphonate (NaAMPS), AOP, and vinyl biphenyl (VP) was synthesized by aqueous free-radical copolymerization. Static light scattering measurement shows that the weight-average molecular weight of PSAA is only 6.75 × 106 g/mol, but the z-average radius of gyration in 30 g/L NaCl is up to 189 nm. The apparent viscosities of aqueous PSAA solutions are very low at all polymer concentrations. However, for PSAA in 70 g/L NaCl, the critical association concentration (C p *) decreases from 0.4 g/L in water to 0.3 g/L, and the apparent viscosity increases sharply with an increase in polymer concentration and is higher surprisingly than that in water above C p *. The influences of NaCl and CaCl2 concentrations on solution viscosities of PSAA were measured, and the brine solutions display the strong salt-thickening effect in a wide range of salt concentration. This is different from hydrophobically associating polymers reported in the literature. Moreover, the thickening mechanisms of PSAA in water and brine solutions were investigated by a fluorescent probe and atomic force microscope (AFM).

Associative behavior in aqueous solutions for a salt-thickening tetra-polymer with allyl-capped macro-monomer

An associative acrylamide-based tetra-polymer (PAVO) with sodium 2-acrylamido-2-methylpropane sulphonate (NaAMPS), vinyl biphenyl (VP) and a novel macromonomer APEO: allyl-capped octylphenoxy poly(ethylene oxide) (degree of polymerization: 14), exhibited low apparent viscosities in water. However, the apparent viscosities were much higher in brine solutions with high salinities, e.g., 100 g/L NaCl. The NaCl or CaCl2 solutions displayed excellent salt-thickening effect induced by metallic uni- or bivalent cations. In order to reveal the correlative relationship between associative structures and solution properties for this polymer, the intermolecular hydrophobic associations in water and in brine solutions, as a function of polymer, NaCl and CaCl2 concentrations, and APEO and VP feed amounts, were investigated by the fluorescence spectroscopy. Moreover, the sizes of polymer chains and aggregates in NaCl solutions were measured with dynamic light scattering (DLS). The results showed that the excellent thickening behavior in NaCl or CaCl2 solutions was owing to the expanded conformation of non-linear polymer chains and the suitably strong intermolecular associations induced by metallic uni- or bivalent cations. Optimum intermolecular associations could be formed by the incorporation of APEO together with VP to PAVO.

Dynamic Light Scattering Characterization of a Water-Soluble Terpolymer with Vinyl Biphenyl in Unsalted and Brine Solutions

The sizes and distributions of polymer chains and associating aggregates, hydrophobic associations, and apparent viscosities were investigated with dynamic light scattering (DLS), fluorescence spectroscopy and viscometry for the hydrophobically associating terpolymer poly[acrylamide(AM)/vinyl biphenyl(VP)/sodium 2-acrylamido-2-methylpropane sulphonate(NaAMPS)] (PAAP) in unsalted and brine solutions. The effects of polymer, NaCl concentration, and temperature on the conformation of polymer chains and the formation of associating structures in aqueous solutions were studied. Intra- and inter-molecular hydrophobic associations were formed and the polymer chains were coiled in unsalted solutions below a critical association concentration (Cp*): 0.05 g·dL−1, and the apparent viscosity was very low and varied slightly with polymer concentration, but a large number of large aggregates were formed because of the presence of dominant intermolecular associations above Cp*, and the apparent viscosity increased abruptly with increasing polymer concentration. The PAAP chains were comparatively expanded (Rh: 21–92 nm) in brine solutions, resulted from the simultaneous incorporation of the bulky pendant side groups, including the biphenyl and 2-acrylamido-2-methylpropane sulphonate groups. With the addition of NaCl, large associative aggregates in unsalted solutions were destroyed to form comparatively expanded mono-macromolecules and smaller aggregates. However, as the NaCl concentration was increased from to 15 to 80 g·L−1, more large aggregates were again formed, leading to the obvious salt-thickening behavior. The variation of Rh with temperature proved that intermolecular hydrophobic association is an endothermic process.

Synthesis of D-(π-A)2 organic chromophores for dye-sensitized solar cells

New bi-anchoring donor-π-acceptor (D-π-A) metal-free organic dyes based on diphenylamine, carbazole as donor, cyano vinyl biphenyl as a π-linker and cyanoacrylic acid, rhodanine-3-acetic acid as acceptor/anchor are synthesized, characterized and used for the dye-sensitized solar cell (DSSC) applications. Among the fabricated DSSCs, device based on the carbazole as donor, cyano vinyl biphenyl as a π-linker and cyanoacrylic acid as acceptor exhibits a high power conversion efficiency of 2.37% with a short-circuit current density of 5.18 mAcm−2, an open-circuit photo voltage of 0.766 V and a fill factor of 50.8% under AM1.5 illumination (85 mWcm−2) compared to other devices.

Synthesis and solution properties of an associative polymer with excellent salt‐thickening

AbstractTo enhance apparent viscosities in brine solutions with high salinities for associative water‐soluble polymers, a novel macromonomer (APEO): allyl‐capped octylphenoxy poly(ethylene oxide) (degree of polymerization: 14) was synthesized, and a novel tetra‐polymer (PAVO) was synthesized by copolymerizing APEO, acrylamide (AM), sodium 2‐acrylamido‐2‐methylpropane sulfonate (NaAMPS), and vinyl biphenyl (VP). The macromonomer and the PAVO polymer were characterized with Fourier transform infrared (FTIR) spectroscopy and proton nuclear magnetic resonance (1H‐NMR). The apparent viscosities of PAVO in pure water were very low over all polymer concentrations, and the critical association concentration (C*p) was 0.15 g dL−1. However, in brine solutions above 40 g L−1 NaCl or 10 g L−1 CaCl2, the intermolecular hydrophobic associations of octylphenyl groups and biphenyl groups were enhanced dramatically, the polymer chains were still comparatively extended due to the incorporation of APEO into the polymer, C*p was reduced to 0.10 g dL−1, and the apparent viscosities were significantly higher than in pure water. The PAVO brine solutions exhibited excellent salt‐thickening induced by metallic univalent or bivalent cations, heat‐thickening effect, shear‐thickening behavior, and thixotropy. Moreover, the brine solution also performed good resistance to ageing because of the simultaneous incorporation of bulky side groups. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012

SEM Morphologies of a Water-Soluble Terpolymer with Vinyl Biphenyl in Aqueous and Brine Solutions

A terpolymer PAAP, synthesized from acrylamide (AM), vinyl biphenyl (VP), and sodium 2-acrylamido-2-methylpropane sulfonate (NaAMPS), exhibits intermolecular hydrophobically associating behavior in water and aqueous brine solutions. A scanning electron microscope (SEM) was used to observe the conformations of polymer chains and morphologies of their associating microstructures in pure water and in brine solutions. This was done to reveal the relevant relationships between solution properties and associated microstructures for the PAAP polymer in pure water and brine solutions, and the mechanisms for the previously reported viscoelastic behavior of PAAP solutions. Continuous supermolecular associating network structures are formed via strong intermolecular hydrophobic association of biphenyl groups in an aqueous 0.1 g⋅dL−1 PAAP solution, which leads to the excellent viscoelastic character of aqueous PAAP solutions. With increasing polymer concentration, the network structures of the polymer become much larger and more compact in aqueous solution, which results in the excellent thickening properties of their solutions. The SEM results reveal that the elongated conformations of molecular chains in aqueous PAAP solutions are favorable for intermolecular hydrophobic association. With the addition of NaCl, the associating network structures of PAAP are destroyed because of electrostatic shielding effects on the –\(\mathrm{SO}_{3}^{-}\) groups, and huge tree-like associated structures are formed. This results in a decrease in the solution viscosity and a loss of viscoelastic properties of PAAP solutions. However, with increasing NaCl concentration, the number and size of the aggregates increase, which results in the salt-thickening behavior of PAAP brine solutions.

Aggregation behavior of a water‐soluble terpolymer with vinyl biphenyl characterized by a fluorescent probe

AbstractA terpolymer (PAAP) of acrylamide, sodium 2‐acrylamido‐2‐methylpropane sulfonate, and vinyl biphenyl as a hydrophobic monomer was synthesized to obtain a polymeric oil‐flooding agent with low molecular weight and application in oil reservoirs with medium to low permeability. The intermolecular self‐assembling mechanisms in the PAAP solutions were investigated with a pyrene fluorescence probe as functions of the polymer concentration, surfactant, and temperature. The hydrophobically associating morphologies of PAAP in an unsalted solution were observed with scanning electron microscopy. The results show that the high solution viscosity of PAAP was due to the strong intermolecular hydrophobic associations of the biphenyl groups, and the critical association concentration was 0.05 g/dL for the unsalted and brine PAAP solutions. The nonpolarity and association degree in the hydrophobic microdomains were greatly influenced by the polymer concentration. With the addition of the optimum sodium dodecyl benzene sulfonate concentration, the interpolymer hydrophobic associations were strengthened remarkably via the connection of the surfactant with biphenyl groups from different polymer chains. The number and sizes of the aggregates increased in the range of 20–50°C. These results demonstrate that the thickening effect of the PAAP polymer in the aqueous solution was due to intermolecular associations of the biphenyl groups. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010

Rheologic Properties of a Water-Soluble Terpolymer with Vinyl Biphenyl

A water-soluble acrylamide-modified terpolymer (PAAP) with sodium 2-acrylamido-2-methylpropane sulfonate and vinyl biphenyl as the hydrophobic monomer was synthesized to obtain a polymeric thickening agent applied in middle- and low-permeability oil reservoirs. The polymer is expected to possess a low molecular weight and high solution viscosity. The steady-state consecutive shear cycles of PAAP in aqueous and brine solutions were measured, and the viscoelastic properties of PAAP solutions were investigated as a function of polymer, NaCl and sodium dodecylbenzene sulfonate (SDBS) concentrations. The aqueous PAAP solutions exhibits pseudoplastic and thixotropic behavior over the range of shear rate and shear thickening behavior at very low shear rate. The steady-state shear results show that some disrupted associating aggregates at high shear rate can be reformed during the shear reversion process and the suitable shear rate is favorable to the formation of hydrophobically associative structures in the brine solutions. Above 0.05 g⋅dL−1 PAAP, aqueous PAAP solutions have predominantly elastic character over the range of angular frequency that is strengthened with increasing polymer concentration. The PAAP brine solutions exhibit predominantly elastic behavior only above 3 rad⋅s−1 and a salt-thickening effect. By addition of an optimum amount of SDBS (0.5–0.8 mmol⋅L−1), the complex viscosities become much higher than the dynamic viscosities, although the loss tangent values increase owing to the formation of loose associative structures.

Electroluminescence from Polyphenylene-Based Materials

Poly(phenylene) and its copolymers are a new family of electroluminescent materials with high thermal stability. Their photoluminescent and physical properties were modified in a controlled fashion by copolymerization of the cyclohexadiene-1,2-diacetate monomer (DAC) with both vinylbiphenyl (VBP) and vinyl-N-carbazole (VCZ). Polyphenylene thin films exhibited green photoluminescence centered around 520 nm. The incorporation of unaromatized comonomers into polyphenylene films blue-shifted wavelengths of maximum photoluminescence centered around 500 nm for the DAC/VBP copolymer (8:2). Similarly, polyphenylene thin films exhibited green electroluminescence centered around 505 nm for a device configuration of Al(-)/polyphenylene/ITO(+). The incorporation of unaromatized comonomers into polyphenylene films blue-shifted wavelengths of maximum electroluminescence centered around 495 nm for a device configuration of Al(-)/DAC-VBP copolymer (8:2)/ITO(+).

Solvent effects on the polymerization of multi‐armed vinyl biphenyl derivatives containing pendant oligo(oxyethylene)cyclotriphosphazenes

AbstractPolymerization of vinyl biphenyl derivatives containing a pendant oligo(oxyethylene)cyclotriphosphazene (VBMEP, (OCH2CH2)nOCH3, n = 1; VBDEP, n = 2; VBTEP, n = 3) was carried out in various solvents. The conversions of these monomers increased with increasing β values, solvent hydrogen bond acceptor abilities, indicating that the hydrogen bond formation is the most important factor in the polymerization. 13CNMR study showed that the reactivity of the monomer is influenced by the hydrogen bond interaction. In ethanol, the kinetic orders of monomer and initiator concentrations for the polymerization of VBDEP were different from those in 1,2‐dichloroethane (DCE), which suggest the predominant occurrence of primary radical termination. The intrinsic viscosity of poly(VBDEP) with M̄n = 22 000 in DCE was two times higher than that in ethanol, and plots of intrinsic viscosity versus conversion of VBDEP gave a straight line. The results suggest that the polymer chains in ethanol are in a coiled conformation, whereas in DCE they are in a relatively extended structure, and that the propagation is affected by the conformational change. These behaviors originated from the hydrogen bond formation between polymers and solvents are discussed. The copolymerization of styrene with multiarmed monomers and the properties of polycascade polymers obtained are also described. © 1993 John Wiley & Sons, Inc.

Facile Synthesis of 4-Bromo-4′-Vinyl Biphenyl and Its Polymerization: A Preliminary Study

Abstract 4-Bromo-4′-vinyl biphenyl, a reactive functional monomer was synthesized in satisfactory yield through a convenient procedure. This monomer readily polymerized offering a powdery polymer which is soluble in a number of organic solvents. The molecular and spectroscopic properties of the polymer were investigated. Preliminary experiments with respect to the reactivity of the bromophenyl residues suggest that they are highly accessible to chemical reagents.