Biphenyldisulfonic Acid Research Articles

Surface‐modified NiFe2O4 nanoparticles for the production of biodiesel from fatty acids and microalgae lipids Dunaliella salina

Development of a new and sustainable catalyst is necessary to the society for providing economical technology. Surface modification of nanometal oxides is one of the rapidly growing methods for developing a sustainable catalyst with attractive properties than their parent oxide. In this work, surface‐modified nickel ferrites have been carried out using 4,4′‐biphenyldisulfonic acid (BPDSA) as the linker. Thus, obtained modified material has been characterized using different techniques such as DLS, FT‐IR, TGA, XRD, VSM, and XPS. This well‐characterized, stable, robust, recyclable material offers a good conversion in the fatty acid, that is, oleic acid esterification in the presence of methanol in a short period of time (3.0 h). Based on the kinetic study in the oleic acid esterification, it fits in the pseudo first‐order kinetics, and activation energy was found to be 60.0 kJ/mol. Further, the potentiality of our catalyst was also tested in the transesterification of various raw materials like mustard oil, olive oil, almond oil, and neem oil. In addition, it provides an excellent conversion with microalgae lipid extraction for the production of biodiesel. The kinematic viscosity of the methyl oleate (biodiesel) has been found to be 5.0426 mm2/s at 25°C whereas the dynamic viscosity is 6.0511 mPa, which is nearly the same as biodiesel obtained from Dunaliella salina, microalgae lipid.

Chiral ionic organic single-crystal and its exfoliated two-dimensional nanosheets with enhanced enantioseparation.

A chiral ionic organic single-crystal (CIOC) was prepared for the first time through ionic self-assembly using bipyridium chiral ionic liquid (CIL) and 4,4'-biphenyldisulfonic acid (BDA). The CIOC can be ultrasonically exfoliated to produce two-dimensional nanosheets (2D-NSs). The 2D-NSs presented enhanced enantioseparation compared to the CIOC and CIL when used as gas chromatography stationary phase, which may be due to the exfoliated 2D-NSs exhibiting greater exposure of functional groups. Additionally, better resolution of other organic compounds such as positional isomers, n-alkanes and n-alkanols, Grob mixture, phenols and anilines was obtained in 2D-NSs than CIOC and CIL. This work not only provides a reference for the preparation of chiral ionic organic single-crystals and two-dimensional nanosheets for chiral separation, but also stimulates the preparation of such new ionic organic single-crystals via self-assembly for other potential applications.

4,4′-Biphenyldisulfonic acid induced coordination polymers of symmetrical tetramethyl cucurbit[6]uril with alkaline-earth metals for detection of antibiotics

Three new 3D TMeQ[6]-based coordination polymers of alkali-earth metal ions (Ca2+, Sr2+ and Ba2+) were characterized, and one can highly selectively detect NFX (norfloxacin) molecules via a fluorescence quenching effect.

Hybrid interaction network of guanidinium–biphenyldisulfonic acid for the structure determination of liquid molecules

Guanidinium–biphenyldisulfonic acid (GBPS) was used as a coformer for the co-crystallization of liquid compounds 1–8, and their structures were determined by single crystal X-ray diffraction.

2D Porous Organic Templates via Cocrystallization of Melamine with Disulfonic Acids: Adsorption of Various Alcohols in SCSC Mode

Cocrystallization of melamine with organic sulfonic acids (1,5-naphthalenedisulfonic acid and 4,4′-biphenyldisulfonic acid) gives rise to 2D porous organic frameworks. Each 2D framework has a different channel size according to the length of the organic sulfonic acids. The adsorption of various liquid alcohols (1-butanol, 1-hexanol, 1-octanol, 1-decanol, 1-dodecanol, tert-butanol, and 2-ethyl-1-hexanol) into the channels in the single-crystal to single-crystal (SCSC) mode was effective for each channel. The tailor-made metal-free organic pores presented herein can be useful components of a practical template for a 3D structure determination of various liquid alcohols.

Nanocomposite Supercapacitor Electrode from Sulfonated Graphene Oxide and Poly(pyrrole-(biphenyldisulfonic acid)-pyrrole)

A well-ordered polymer nanocomposite was prepared as a supercapacitor electrode based on sulfonated graphene oxide (SGO) and a two-monomer-connected precursor (TMCP). Biphenyldisulfonic acid (BPDSA...

Growth of close-packed crystalline polypyrrole on graphene oxide via in situ polymerization of two-monomer-connected precursors.

Synthesis of a two-dimensional (2D) highly crystalline composite, P(Py:BPDSA:Py)-GO, from the growth of a close-packed polymer crystal, P(Py:BPDSA:Py), on graphene oxide (GO) sheets via in situ polymerization of two-monomer-connected precursors (TMCPs, Py:BPDSA:Py), in which two pyrrole (Py) molecules are linked through a connector (4,4'-biphenyldisulfonic acid) (BPDSA), is reported. When the TMCP is polymerized on GO, it leads to an exceptionally ordered structure determined by X-ray diffraction (XRD) and high-resolution transmission electron microscopy (HRTEM) studies. X-ray crystallography of the composite shows crystalline peaks with d spacings in the [100] direction. Transmission electron microscopy (TEM) analysis indicates that the composite has a face-centered cubic (FCC) crystal structure. Raman spectroscopy, Fourier transform infrared spectroscopy (FT-IR), and X-ray photoelectron spectroscopy (XPS) show that this composite with a well-defined nanostructure was successfully synthesized. Nitrogen adsorption-desorption isotherms show that this composite, P(Py:BPDSA:Py)-GO, has an improved specific surface area (71 m2 g-1) compared to that of P(Py:BPDSA:Py) (3.1 m2 g-1). The electrochemical properties of the composite studied by cyclic voltammetry indicates a specific capacitance of 480 F g-1 without an additional conducting material such as carbon black, suggesting its use as a pseudocapacitor.

Greatly Improved Conductivity of Double-Chain Polymer Network Binder for High Sulfur Loading Lithium-Sulfur Batteries with a Low Electrolyte/Sulfur Ratio.

Binders have been considered to play a key role in realizing high-energy-density lithium-sulfur batteries. However, the accompanying problems of limited conductivity and inferior affinity of soluble polysulfide intermediates bring down their comprehensive performance for practical applications. Herein, the synthesis of a novel double-chain polymer network (DCP) binder by polymerizing 4,4'-biphenyldisulfonic acid connected pyrrole monomer onto viscous sodium carboxymethyl cellulose matrix, yielding a primary crystal structure is reported. Consequently, the resulted binder enables superior rate performance from 0.2 C (1326.9 mAh g-1 ) to 4 C (701.4 mAh g-1 ). Moreover, a high sulfur loading of 9.8 mg cm-2 and a low electrolyte/sulfur ratio (5:1, µL mg-1 ) are achieved, exhibiting a high area capacity of 9.2 mAh cm-2 . In situ X-ray diffraction analysis is conducted to monitor the structural modifications of the cathode, confirming the occurrence of sulfur reduction/recrystallization during charge-discharge process. In addition, in situ UV-vis measurements demonstrate that DCP binder impedes the polysulfide migration, thereby giving rise to high capacity retention for 400 cycles.

Synthesis, Crystal Structure, and Properties of a New Zinc(II) Coordination Polymer With Mixed 4,4′-biphenyldisulfonic Acid and N-Donor Ligands

A new zinc(II) coordination polymer, namely [Zn(bipy)2(H2O)4]n·n(dsba) (1), has been synthesized by the mixed 4,4′-biphenyldisulfonic acid (H2dsba) and 4,4′-bipyridine (bipy) ligands with Zinc(II) salt under the common solution evaporation method. The results of the X-ray crystal diffraction analysis show that complex 1 belongs to the monoclinic system with P21/c space group. The unit cell constants of complex 1 are a = 9.2579 Å, b = 12.2016 Å, c = 14.447 Å, α = γ = 90˚, β = 93.476˚. Complex 1 exhibits a three-dimensional supramolecular network based on the discrete structure by utilizing various H-bonded interactions. In addition, the properties of complex 1, such as the elemental analysis, FT-IR spectroscopy, X-ray powder diffraction, and fluorescence spectroscopy were also characterized and are discussed in detailed.

Molecular Rectangles with Rod‐Shaped Disulfonic Acids

Polysulfonic acids and their compounds have been scarcely investigated, despite the huge knowledge that we have of the respective polycarboxylic acids and polycarboxylates. This is because of the limited availability of polysulfonic acids, for which reliable synthetic protocols are often lacking. Here, we present the first compound of the recently reported disulfonic acid 1,4-bis(4-sulfophenyl)butadiyne (H2DPBDS) prepared in our groups and a new compound of the commercially available 4,4′-biphenyldisulfonic acid (H2BPDS). The zinc sulfonates [Zn2(BPDS)2(NMP)6]·2NMP [I, NMP = N-methylpyrrolidone; triclinic, P, Z = 2, a = 972.8(2), b = 981.5(2), c = 1915.2(2) pm, α = 87.73(3)°, β = 77.68(3)°, γ = 89.36(3)°, V = 1785.0(6) A3] and [Zn2(DPBDS)2(DMA)6]·2DMA [II, DMA = dimethylacetamide; triclinic, P, Z = 2, a = 973.79(2), b = 1347.53(2), c = 1411.08(2) pm, α = 110.531(1)°, β = 92.445(1)°, γ = 101.931(1)° V = 1683.11(5) A3] display rigid molecular rectangles constructed from two zinc atoms and two sulfonate ligands. The rectangles are assembled through weak interactions to form soft host lattices that incorporate the solvent DMA or NMP molecules, partly through Zn2+ coordination. Thermal analysis shows that the solvent molecules can be completely removed without decomposition of the coordination polymers.

Preparation, crystal structure, and solid-state optical property of a disulfonic acid/amine fluorescent complex composed of 4,4′-biphenyldisulfonic acid and 2-naphthylethylamine

Solid-state disulfonic acid/amine fluorescent host complexes including methanol (MeOH) as guests were successfully prepared using 4,4′-biphenyldisulfonic acid and 2-naphthylethylamine as component molecules. Although the crystal structure of the obtained host complex is similar to that of the corresponding dicarboxylic acid/amine host complex, the solid-state photo-luminescence quantum yield of the disulfonic acid/amine fluorescent host complex is increased relative to those of the corresponding dicarboxylic acid/amine host complex.

Effect of Steric Complementarity on Solid-State Optical Properties of Ternary CT Complexes: 4,4′-Biphenyldisulfonic Acid, Aliphatic Amines, and Tetracyanoquinodimethane

Crystalline ternary charge transfer (CT) complexes were constructed for tuning colors by a supramolecular approach. The complexes are composed of 4,4′-biphenyldisulfonic acid (BPDS, donor), tetracyanoquinodimethane (TCNQ, acceptor), and aliphatic amines. Four salts of BPDS with methyl-, ethyl-, isopropyl-, or t-butylamine underwent insertion of TCNQ between biphenyl moieties to yield the CT complexes with different colors in a range of deep red to light orange. Such a color change was interpreted on the basis of crystal structures of the complexes. BPDS salts produce layer structures which provide nanospaces for TCNQ and alkyl groups. Steric complementarity in the nanospaces explains the above-mentioned color change.

Synthesis and characterization of polyimide‐polysiloxane segmented copolymers for fuel cell applications

AbstractSulfonated polyimides exhibit high strength, good film‐forming ability, chemical resistance, and, in their hydrated state, relatively high proton conductivity. Here we report the one‐pot synthesis of sulfonated polyimide‐polysiloxane segmented copolymers through the reaction of a dianhydride with a mixture of three diamines: a nonionic aromatic diamine (4,4′‐oxydianiline), a sulfonated diamine (4,4′‐diamino‐2,2′‐biphenyldisulfonic acid), and a telechelic diamino polysiloxane. Copolymer compositions were evaluated using 1H NMR and size‐exclusion chromatography. The presence of ion‐containing diamines in the reaction mixture inhibited stoichiometric incorporation of hydrophobic siloxane segments. Siloxane segments were found to lower the thermal stability of the polyimide host. Copolymers with and without siloxane segments were cast into free‐standing films. Equilibrium water sorption studies of cast films show that, for the compositions studied here, the presence of siloxane segments does not interfere with water swelling, suggesting that a microphase‐segregated morphology may exist. TEM and SAXS analyses show evidence of phase‐segregation in sulfonated polyimides and reveal that siloxane segments strongly affect ionic clustering. However, proton conductivity only changes slightly when polysiloxane segments are incorporated. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 3747–3758, 2007

Isomerism Effect on Flexibility of Layered Frameworks in Organic Salts of 4,4′-Biphenyldisulfonic Acid with Primary Amines

Abstract Organic salt of 4,4′-biphenyldisulfonic acid with isopropylamine yields a flexible layered framework with guest-responsive channels, while the salt with n-propylamine does a rigid one with fixed channels. The flexibilities of the framework are modulated by an isomerism effect of alkyl groups on the basis of different directions of methyl groups.

3P118 剛直な荷電高分子の水和特性に及ぼすNaCl濃度の影響(水・水和/電解質,ポスター発表,第45回日本生物物理学会年会)

3P118 剛直な荷電高分子の水和特性に及ぼすNaCl濃度の影響(水・水和/電解質,ポスター発表,第45回日本生物物理学会年会)

Synthesis and properties of novel sulfonated polyimides containing 1,5‐naphthylene moieties

AbstractA series of novel sulfonated polyimides (equivalent weight per sulfonic acid = 310–744 g/equiv) containing 10–70 mol % 1,5‐naphthylene moieties were synthesized as potential electrolyte materials for high‐temperature polymer electrolyte fuel cells. The polycondensation of 1,4,5,8‐naphthalene tetracarboxylic dianhydride, 4,4′‐diamino‐2,2′‐biphenyldisulfonic acid, and 1,5‐diaminonaphthalene gave the title polymer electrolytes. The polyimide electrolytes were high‐molecular‐weight (number‐average molecular weight = 36.0–350.7 × 103 and weight‐average molecular weight = 70.4–598.5 × 103) and formed flexible and tough films. The thermal properties (decomposition temperature > 260 °C, no glass‐transition temperature), stability to oxidation, and water absorption were analyzed and compared with those of perfluorosulfonic acid polymers. The polyimide containing 20 mol % 1,5‐naphthylene moieties showed higher proton conductivity (0.3 S cm−1) at 120 °C and 100% relative humidity than perfluorosulfonic acid polymers. The temperature and humidity dependence of the proton conductivity was examined. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 3901–3907, 2003

Synthesis and characterization of metal-containing sulfonated polyimide membranes and their gas separation properties

We studied the synthesis and characterization of a thermally stable metal-containing in sulfonated polyimides (M-SPI) based on benzophenone tetracarboxylic dianhydride (BTDA), 4, 4′-diamino 2, 2′-biphenyl disulfonic acid (BDSA) and meta-phenylenediamine ( mPDA). X-ray photoelectron spectroscopy (XPS) was chosen as a tool for confirmation of metal substitution in sulfonic acid group. Thermogravimetric analysis (TGA) spectrum of the M-SPI showed approximately 5% weight loss in the range of 250–350°C and the final decomposition began at around 500°C. Wide angle X-ray diffraction (WAXD) spectra of M-SPI show no crystalline behavior, indicating an amorphous structure of the polymer. The water sorption of the M-SPI was investigated at 25°C and 60% RH. The diffusion coefficient and water uptake were estimated to be 2.68×10 −7 cm2/s and 2.33 wt% for Na-SPI 1091 and 3.79×10 −7 cm 2/s and 4.03 wt% for Na-SPI 1082.

Potent Inhibition of Herpes Simplex Virus by MDL 101028, a Novel Biphenyl Disulfonic Acid Urea Co-Polymer

A novel low-molecular-weight sulfonic acid polymer, MDL 101028, was investigated for antiviral activity against herpes simplex virus (HSV) type 1 and type 2 in human embryonic diploid fibroblasts (MRC-5) and in a line of monkey kidney cells (Vero). Potent antiviral activities were obtained when treatment was restricted to the adsorption phase of virus propagation as measured by plaque reduction assay, and this was confirmed by experiments at high multiplicity of infection. Inhibition of virus binding to host cells by MDL 101028 was compared to that of heparin, a known antagonist of virus attachment. Both compounds showed dose-dependent inhibition, with IC50 values of 1.1 and 0.43 μg ml−1, respectively. The effect on cell-to-cell fusion was investigated using a syncytial-positive (syn+) phenotypic mutant of HSV-1 (strain 17i). MDL 101028 (3-1 μm) dramatically halted the spread of syncytial lesions; this effect was accompanied by the destruction of the syncytium and regrowth into the lesion by uninfected Vero cells. In contrast, heparin (10 μg ml−1) only partially reduced the spread of syncytia. Protection was also observed with MDL 29797 (100 μg ml−1), an antagonist of glycoprotein maturation. Unexpectedly, only a marginal effect was observed with acyclovir (10 μg ml−1), a potent inhibitor of viral DNA synthesis and HSV growth. As an extension to the current therapy for herpes simplex infection, acyclovir, the potent anti-fusion activity of MDL 101028 may have a clinical use in tissues or organs in which cell-to-cell fusion contributes to the pathology.

Glycosaminoglycans: molecular properties, protein interactions, and role in physiological processes

Article de synthese sur les glycosaminoglycanes chez les mammiferes: proprietes et structure des proteoglycanes et des proteines de liaison des glycosaminoglycanes; roles dans la regulation des processus cellulaires et la regulation de l'expression des genes; interaction avec les facteurs de transcription

Synthesis and investigation of bis-dimethylaminoethylamide of 4,4′-biphenyl disulfonic acid bis-benzosulfomethylate (benzodisuphene)

1. The benzodisuphene, i.e., bis-dimethylaminoethylamide of 4,4′-biphenyl disulfonic acid bis-benzenesulfomethylate was synthesized. 2. Benzodisuphene is a highly active myorelaxant, with a prolonged action, completely free of side effects. The action of the drug is weakened by proserine.