Phenyl Amino Research Articles

Low‐Cost, High‐Efficiency, and Efficiency Predictable Small Molecule Organic Dyes with Bis(4‐styryl)phenyl Amino Donor for Dye‐Sensitized Solar Cells (Solar RRL 6∕2019)

Low‐Cost, High‐Efficiency, and Efficiency Predictable Small Molecule Organic Dyes with Bis(4‐styryl)phenyl Amino Donor for Dye‐Sensitized Solar Cells (Solar RRL 6∕2019)

Synthesis of (Z)-5-(substituted benzylidene)-2-((substituted phenyl) amino)thiazol-4(5H)-one analogues with antitubercular activity

ABSTRACTWe initiated a program to synthesize thiazolidinone derivatives as antitubercular agent by preparing hybrid molecules having the similar features of reported potent antitubercular agents. We desire to state the advancement and execution of a methodology allowing for the synthesis of some new (Z)-5-(substituted benzylidene)-2-((substituted phenyl) amino)thiazol-4(5H)-one analogues with antitubercular activity. A highly efficient protocol was developed for the synthesis with excellent yields as well as evaluated in vitro for their antimycobacterial activity against Mycobacterium tuberculosis MTB H37Ra and M. bovis BCG strains. Among these synthesized compounds 6a, 6c, 6e, 6f and 6i showed marginal antitubercular activity in the series along with no significant cytotoxicity against the MCF-7 and A549 human cancer cell lines.

Organic Light-Emitting Diodes based on Benzo[q]quinoline Derivatives

In this study, we synthesized two emitting materials based on benzo[q]quinoline derivatives. OLED devices using these materials were facricated in the following sequence;ITO(180nm)/4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine(2-TNATA)(30nm)/N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine(NPB)(20nm)/Emitting materials(30nm)/4,7-diphenyl-1,10-phenanthroline (Bphen)(30nm)/Liq(2nm)/Al(100nm). Particularly, a device using 2,4-di(naphtalene-1-yl)benzo[q]quinoline as an emitter exhibited the efficient emission with a luminous efficiency, a power efficiency, and exteranl quantum efficiency of, and the CIE coordinates of 2.91cd/A, 0.99lm/W, 0.90% at 20mA/cm2, and (0.33, 0.55) at 1000cd/m2, respectively. Interestingly, emissions from electromers and electroplexes were shown to be crucial role in electroluminescences from benzo[q]quinoline derivatives

Synthesis and biological assessment of novel cyanopyridine derivatives

New pyridine derivatives bearing p-dimethyl amino phenyl and p-bromophenyl moieties at position-4 and 6 have been prepared. The behavior of pyridone derivative 2 toward ethyl chloroacetate followed by hydrazine hydrate gave pyridinyl acetohydrazide derivative 7, and its behavior toward carbon electrophiles has been investigated by its reaction with aromatic aldehydes, ethyl acetoacetate, acetyl acetone, cyclohexanone, phthalic anhydride, maleic anhydride, and isatin affording the pyridine derivatives 8a–e to 16, respectively. Treatment of compound 2 with acrylonitrile in Et3N, yielded the N- alkylated derivative 17. Some pyrazole derivatives have been synthesized by interaction of the chalcone 1 with hydrazine hydrate afforded pyrazole derivative 18. Treatment of compound 18 with benzoyl chloride and or acetic anhydride resulted in the formation of the acylated compounds 19 and 20. Elemental and spectroscopic pieces of evidence characterized all the newly synthesized compounds. Some of the synthesized compounds were tested for their antibacterial activities against Gram-positive and Gram-negative bacteria.

Determination of protein tyrosine kinase-7 concentration using electrocatalytic reaction and an aptamer-antibody sandwich assay platform

An aptamer-antibody sandwich assay for the voltammetric determination of protein tyrosine kinase-7 (PTK7) concentrations in buffer and human serum solutions was developed. A DNA aptamer specific to PTK7 was covalently immobilized onto gold nanoparticles (AuNPs) modified screen printed carbon electrode (SPCE) surfaces via a self-assembly of mercaptopropionic acid (MPA) followed by a cross linking of the amine modified aptamer. The sequent adsorption of PTK7 and alkaline phosphatase (ALP) conjugated antiPTK7 onto the aptamer surface formed a sandwich complex of PTK7 aptamer/PTK7/antiPTK7-ALP. Following the confirmation of the surface sandwich complex formation with the aptamer, PTK7 and antibody via a series of real-time surface plasmon resonance measurements, the electrocatalytic reaction of surface bound ALP and 4-amino phenyl phosphate (APP) was monitored using cyclic and differential pulse voltammetries. The voltammetric responses linearly increased as a function of the PTK7 concentration ranging from 100 fM to 10 pM with a detectable concentration as low as 100 fM. As a final demonstration, our aptamer-antibody sandwich assay platform was applied to the analysis of PTK7 in biological samples including normal human serum solutions.

Grafting of active carbon nanotubes onto carbon fiber using one-pot aryl diazonium reaction for superior interfacial strength in silicone resin composites

Abstract A novel and effective method was proposed for grafting carbon nanotubes (CNTs) with amino groups onto the surface of carbon fibers (CFs) by using one-pot aryl diazonium reaction in mild, eco-friendly conditions. Based on the diazonium reaction, CNTs were grafted with phenyl amino groups, and then functionalized CNTs (CNT-NH2 ) were modified onto the fiber surface to enhance fiber surface roughness and wettability , which could potentially increase interfacial strength of composites. Homogeneous multi-scale structures with different concentrations of CNTs were achieved. Interfacial properties of hybrid composites were closely dependent on the grafting density. The resulting hierarchical reinforcements improved composites interfacial strength significantly by the enhanced mechanical interlocking and the formed chemical bonding at the interface.

Low‐Cost, High‐Efficiency, and Efficiency Predictable Small Molecule Organic Dyes with Bis(4‐styryl)phenyl Amino Donor for Dye‐Sensitized Solar Cells

Three small molecule organic dyes (SMODs) with bis(4‐styryl)phenyl amino (BSPA) donor FWD4∼FWD6 are synthesized easily and applied as sensitizers for dye‐sensitized solar cells (DSSCs). The dipole moments (µ) of FWD4∼FWD6 are calculated by using density functional theory (DFT) to be 7.49, 9.64, and 9.22 D, respectively. The DSSCs based on FWD4∼FWD6 exhibit high power conversion efficiencies (η) of 5.83%, 7.62%, and 7.39%, respectively. The linear regression equation η = 0.817 µ–0.370 is created with R2 = 0.999 that reveals the equation owned high accuracy. Highly reliable linear equations are also obtained under different fabrication conditions, which indicates that the power conversion efficiency tendency is influenced only by these dyes’ intrinsic property, the dipole moment. The excellent linear correlation between the dipole moment and power conversion efficiency indicates that it is very likely to predict the power conversion efficiency precisely by calculating the dipole moment, which gives a convenient way to connect the experimental results with theoretical calculations for dyes with similar molecular structures.

Highly Efficient Organic Light-Emitting Diodes Based on Naphthoanthracene Derivatives Containing Different Arylamines.

Herein, we designed and synthesized emitting materials based on naphthoanthracene with the different arylamino-substituents. Organic Light Emitting-Diodes (OLEDs) devices using these materials were fabricated in the following sequence; ITO/N,N'-diphenyl-N,N'-(2-napthyl)-(1,1'-phenyl)-4,4'- diamine (NPB) (500 Å)/Emitters (400 Å)/Alumium quinolate (Alq₃) (150 Å)/lithium quinolate (Liq) (20 Å)/Al (1000 Å). All devices showed efficient emissions. In particular, a device using 4-((5,5-dimethyl-9-phenyl-5H-naphtho[3,2,1-de]anthracen-3-yl)(phenyl)amino)benzonitrile as an emitter exhibited the luminous efficiency, power efficiency, and external quantum efficiency of 9.15 cd/A, 6.36 lm/W, 2.72% at 20 mA/cm², respectively, with the Commission Internationale d'Énclairage (CIE) coordinates of (0.30, 0.62) at 6.0 V.

Design, synthesis, antibiofilm, quorum sensing inhibition, anticancer and docking studies of novel 2-(4-acridine-9-ylamino)isoindoline-1,3-dione

Abstract A series of novel 2-(4-(acridin 9yl amino)phenyl)isoindoline-1,3-dione derivatives 6a–6j were synthesized and screened for antibiofilm, antiquorum sensing and in-vitro anticancer activity against MCF-7 cell lines. The obtained result indicates that the potent compounds are promising chemical entities for the new class of potential antibiofilm and anticancer drug-like molecules. Further, molecular docking has shown that compounds have good binding affinities with protein and ligands. Whereas, DNA cleavage by gel electrophoresis method revealed that compounds 6g and 6h cleaved the DNA completely.

Enhanced performance of perovskite solar cells by incorporation of a triphenylamine derivative into hole-transporting poly(3-hexylthiophene) layers

A 4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) was applied as an additive to hole-transporting poly(3-hexylthiophene) [P3HT] layers in perovskite solar cells. The incorporation of 0.5wt% m-MTDATA to the P3HT layer led to an increased power conversion efficiency of 9.53%, due to an enhancement in the short circuit current, open-circuit voltage and fill factor, compared with that (8.76%) of the control cell without the additive. This enhanced performance was attributed to an increase in the hole mobility and a decrease in the charge recombination of the device with the P3HT:m-MTDATA blend film, compared to those of the control device with the pristine P3HT film.

Benzo[q]quinoline derivatives for efficient organic light-emitting diodes

In this research, we designed and synthesized one emitting material based on benzo[q]quinoline derivative via Suzuki cross coupling reaction. Organic Light-Emitting Diodes (OLEDs) device using this material was fabricated in the following sequence; Indium tin oxide (ITO)/4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (2-TANATA) (30 nm)/N,N'-di(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl)4,4'-diamine (NPB) (20 nm)/emitting material (30 nm)/bathophenanthroline (Bphen) (30 nm)/8-Quinolinolato lithium (Liq) (2 nm)/Al (100nm). This device showed the efficient emission, with a luminous efficiency, a power efficiency, and external quantum efficiency of, and the Commission International de L’Eclairage (CIE) coordinates of 3.32 cd/A, 1.06 lm/W, 1.00% at 20 mA/cm2, and (0.33, 0.56) at 1000 cd/m2, respectively.

Chan‐Lam Coupling: Synthesis of N‐alkylated Derivatives of ϵ‐Caprolactams from Bicyclic Amidine DBU

AbstractThe reactivity of bicyclic amidine 1,8‐diazabicyclo[5.4.0]undec‐8‐ene (DBU) with phenyl boronic acid forming N‐alkylated derivatives represents an advanced example to the existing classical Chan‐Lam Cross Coupling of amines. The conversion of DBU to important heterocyclic scaffolds, in which DBU is acting as a nucleophile forming N‐alkylated derivatives of ϵ‐caprolactam is described. This copper‐catalyzed reaction of DBU with phenylboronic acids represents a new paradigm of Chan‐Lam amination. This type of transformation has opened up a new direction for the synthesis of 1‐(3(phenyl amino) propyl)azepan‐2‐ones directly from the diimide, DBU in a single synthetic operation. The reaction was compatible with bicyclic amidines, 1,5‐diazabicyclo‐[4.3.0]non‐5‐ene (DBN) and 1,5,7 triazabicyclo[4.4.0]dec‐5‐ene (TBD), providing a robust system to access valuable bioactive ϵ‐caprolactams.

Electrochemical and theoretical study on enhanced pseudocapacitance performance of poly orthoaminophenol film in the presence of different derivatives of phenylglycine

We have successfully synthesized three derivative of phenylglycine by Schotten-Baumann method denoted as 2-[(4-methylbenzoyl) amino] phenyl acetic acid (B-Me), 2-(benzoyl amino) phenyl acetic acid (B-H) and 2-[(4-chlorobenzoyl) amino] phenyl acetic acid (B-Cl). Afterward, dealing with improving electrochemical properties of the poly ortho aminophenol (POAP), we fabricated POAP/B-Me, POAP/B-H and POAP/B-Cl films through electro-polymerization of POAP by employing of N-benzoyl derivatives of phenylglycine to consider as the active electrode for SCs. Analysis of electronic wave function (DFT-method) results show that the atomic-scale electronic properties are generally depend on the bonding and electronic molecular structures and electron donating group on the N-benzoyl derivatives has main important effect rather than electron withdrawing group. The electrochemical properties of electrodes and the capacitive behavior of the resulting capacitors were systematically studied using cyclic voltammetry (CV), ac impedance and constant current charge–discharge tests. The specific capacitance of POAP/B-Me electrode was exhibited as high as 614.3 F/g, in comparison with a value of 261 F/g for POAP film. These results make POAP/B-Me it a promising candidate for supercapacitor applications.

Molecular forms and fragments of salivary MMP-8 in relation to periodontitis.

To investigate the molecular forms of salivary matrix metalloproteinase (MMP)-8 in relation to periodontitis. Molecular forms, degree of activation and fragmentation of neutrophilic and mesenchymal-type MMP-8 isoforms were analysed from salivary samples of 81 subjects with generalized periodontitis, 63 subjects with localized periodontitis and 79 subjects without pocket teeth, by using western-immunoblots with computer quantitation. In addition, human recombinant proMMP-8 was in vitro activated by Treponema denticola chymotrypsin-like protease (Td-CTLP), sodium hypochlorite (NaOCl, 1mM, oxidant) or amino phenyl mercuric acetate (APMA, 1mM). In saliva of periodontitis-affected individuals, MMP-8 is found in multiple forms, that is, complexes, active and pro-forms of neutrophilic and mesenchymal-type MMP-8, and especially 20-27kDa fragments. The quantity of these fragments was elevated in both localized and generalized forms of periodontitis. Moreover, the tested activators (Td-CTLP, NaOCl and APMA) activated inactive proMMP-8, resulting in fragments of 20-27kDa, in vitro, and salivary concentrations of T.denticola correlated significantly with salivary levels of fragmented MMP-8. The present results indicate that during the development and progression of periodontitis, MMP-8 appears as activated and fragmented, and treponemal proteases most likely play role in this cascade.

The effect of imide substituents on the optical properties of perylene diimide derivatives.

As one of the most important organic semiconductors, perylene diimide derivatives (PDIs) have been widely applied in optoelectronics. Two kinds of soluble PDIs with different imide substituents have been synthesized and their optical properties have been investigated. The photoluminescence (PL) intensity of the PDI with amino phenyl imide substituents (NH2 -PDI) is much lower than that of the PDI with octyl imide substituents (O-PDI). It can be found that the Stokes shift of O-PDI is positive, whereas, the Stokes shift of NH2 -PDI is negative. The emission intensity of the 0-0 electron transition relative to that of the 1-0 electron transition (I0-0 /I1-0 ) in the PL spectrum of O-PDI is decreased, but the value of I0-0 /I1-0 in the PL spectra of NH2 -PDI is increased as the dielectric constant of the solvent increases. The large overlap between the absorption and PL spectra plays an important role to result in the low PL intensity of NH2 -PDI. The PL decay data show that a non-radiative process, photoinduced electron transfer, also contributes to the low PL intensity of NH2 -PDI. The results can help researchers to understand the effect of the imide substituents on the optical properties of PDIs.

Synthesis, Electrochemical Reduction and Radical Anions of 2‐[Bis(4‐amino(nitro)phenyl)aminomethyl]‐9H‐thioxanthene‐9‐one Derivatives

2‐[Bis(4‐amino(nitro)phenyl)aminomethyl]‐9H‐thioxanthene‐9‐ones and their S‐oxide derivatives have been synthesized, and their electrochemical reduction (ECR) in N,N‐dimethylformamide (DMF) and MeCN has been studied by cyclic voltammetry (CV). The thioxanthene‐9‐one group [Th(O)S] and thioxanthene‐9‐one S‐dioxide group [Th(O)SO2] determine the first one‐electron peak potentials of 2‐[bis(4‐aminophenyl)aminomethyl]‐9H‐Th(O)S/Th(O)SO2. The first peak potentials of the corresponding dinitro compounds are determined by the ratio of reduction potentials of bis(4‐nitrophenyl)amino and 9H‐thioxanthene‐9‐ones moieties. Radical anions (RA) of the synthesized compounds have been obtained by ECR in DMF and MeCN and characterized by EPR spectroscopy together with DFT calculations at the (U)B3LYP/6‐31 + G/PCM level of theory. Th(O)S and Th(O)SO2 groups are thermally stable up to 270 °C. The synthesized 2‐[bis(4‐aminophenyl)aminomethyl]‐9H‐Th(O)S/Th(O)SO2 are electrochemically active monomers for subsequent synthesis of the corresponding electroactive polyimides with thioxanthene‐9‐one based pendant groups for their applications in the design of nonvolatile memory storage devices. The pendant groups are characterized by low redox potentials and reversibility towards electron transfer.

Fully Organic Photocontrolled Deformable Mirror

AbstractA light‐driven deformable mirror based on an organic photoconductive layer is designed and realized. The requirements for the photoconductive organic material are reported showing their effect on the mirror performances. The production and characterization of the photoconductive thick layer consisting in a polystyrene matrix doped with P3HT:PCBM and an arylamine (4,4′,4″‐tris[phenyl(m‐tolyl)amino]triphenylamine) are reported. A prototype of the mirror with a clear aperture of 12 mm is built and its performance measured in terms of reflective surface displacement. Moreover, a light valve device based on this mirror is built and characterized.

Triazine-based conjugated microporous polymers constructing triphenylamine and its derivatives with nitrogen as core for iodine adsorption and fluorescence sensing I2

Abstract Three new triazine-based conjugated microporous polymers with nitrogen as cores containing triphenylamine (TPA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA) and 4,4′,4″-tri[phenyl(m-tonyl)amino]triphenylamine moieties (TMDATA) (TTPA, TTDATA and TTMDATA) were constructed via Friedel-Crafts reaction catalysed by methanesulfonic acid. The resulting CMPs possess high BET surface area of over 308, 491 and 456 m2 g−1, large pore volumes, good stability, and display efficient and reversible guest uptake of 4.92, 4.72 and 4.49 g g−1 in iodine vapour which are higher than that of the CMPs with benzene as core. Two ways to release the adsorbed iodine were explored: either slow release into ethanol or quickly release upon heating (with a high degree of control). Spectral studies make us known that the strong affinity for I2 is mainly due to large porosity, a conjugated π-electron aromatic system, C N bonds, and propeller-like twisted structures. Furthermore, luminescent study indicated that TTPA exhibits high sensitivity to electron-deficient I2 via fluorescence quenching. TTPA shows the largest amount of iodine adsorption and was the first CMP used fluorescence sensing iodine.

The synthesis and dielectric characterization of liquid crystalline hydrogen bonded complex of 3-(4-(dimethyl amino) phenyl)-1-(4-hydroxyphenyl) prop-2-en-1-one with 8-(4-cyanobiphenyl-4′-oxy) octan-1-ol

A new chalcone based nematic schlieren texture liquid crystalline material was prepared from 3-(4-(dimethyl amino) phenyl)-1-(4-hydroxyphenyl) prop-2-en-1-one (DMAC) and 8-(4-cyanobiphenyl-4′-oxy) octan-1-ol (LC8) by molecular self-assembly processes via hydrogen bond formation between tertiary amine group of DMAC and hydroxyl group of the LC8. Hydrogen bond formation was observed by FTIR spectroscopy. Dielectric properties of DMAC has been studied by impedance spectroscopy. The Cole-Cole analysis was used to determine the Resistance-Capacitance (RC) components equivalent circuit situation of doped LC8 on the DMAC. Dependent angular frequency variation of dielectric parameters and ac conductivity properties are non-Debye type relaxation mechanism of interfacial dopant in the liquid crystal molecular structure of the reorientation polarization effects.

“Synthesis and study of novel biological active chalconyl-ester based bent-core LCs: Effect of tail/lateral group”

A newly designed homologues series: 4-bromo-2-(3-(4-dimethyl amino) phenyl) acryloyl)-6-nitrophenyl-3-(4-n-alkoxy phenyl) acrylate has been synthesized and studied through chalconyl vinyl ester linking group at (ortho) position. Novel series consisted thirteen compounds, in which C1 to C5 homologue are nonliquid crystal, while C6 to C18 exhibits SmC and nematic phase at enantiotropically manner. Thus, present novel series is predominantly nematogenic and partly smectogenic mesophase. Mesophase image of present compounds are schlieren like, broken fan and threaded type textures measured by POM equipped with heating stage. All this compounds were characterized by FT-IR and 1H NMR analysis. The mesomorphism is measured by POM, DSC and molecular packing is confirmed by XRD technique. Chalconyl ester based compounds C4 to C12 shows antibacterial as well as antifungal activity compared with corresponding standard drugs. Analytical and spectral data confirmed the molecular structures of the present V-shaped bent core homologous series.