Diphenylamine Derivatives Research Articles

Design and evaluation of novel N-substituent diphenylamine derivatives as tubulin colchicine binding site inhibitors

Novel N-substituent diphenylamine derivatives as tubulin inhibitors targeting colchicine-binding site have been designed based on structural simplification and structural fusing strategy. Most designed compounds exhibited the moderate or potent antiproliferative activities against five cancer cell lines. Among them, compound 4k displayed the significant selectivity for osteosarcoma cells MG-63 and U2OS with the IC50 value of 0.08–0.14 μM. Further investigations verified 4k could inhibit tubulin polymerization by targeting colchicine binding site. Meanwhile, compound 4k not only effectively induced tumor cell cycle arrest at the G2/M phase, but also slightly induced cell apoptosis. These results indicated that N-substituent of diphenylamine derivatives are deserved for further development as tubulin colchicine binding site inhibitors.

DESIGN, SYNTHESIS, IN SILICO STUDIES, AND PHARMACOLOGICAL EVALUATION OF 5-ARYL-4-(CHLOROACETYLAMINO)-3-MERCAPTO-1,2,4-TRIAZOLE DERIVATIVES AS ANTICONVULSANT AGENTS

Objective: In this study, we reported the synthesis of a novel series of 5-aryl-4(chloroacetylamino)-3-mercapto-1, 2,4-triazoles. Methods: These compounds were synthesized to screen for anticonvulsant effects in a Maximal Electroshock Seizure (MES) model and a Subcutaneous Pentylenetetrazole (sc‐PTZ) seizure model in rats. Furthermore, molecular docking studies with gamma-aminobutyric acid and in silico ADME prediction were carried out to determine interactions of these compounds with Benzodiazepine (BZD) receptors and their similarity with standard drugs. The rotarod test was used to evaluate neurotoxicity. Results: 08 out of 40 compounds exhibited neurotoxicity at the maximum tested dose. Most of the compounds showed anti‐MES effects without any signs of neurological deficit. All the tested compounds significantly reduced seizures induced by PTZ compared to the control group. Carbamazepine and phenytoin were used as positive controls for anticonvulsant effects. Compounds 3d, 3h (a diphenylamine derivative of 5-aryl-4(chloroacetylamino)-3-mercapto-1,2,4-triazole), and 4a (a piperidinyl derivative of 5-aryl-4(chloroacetylamino)-3-mercapto-1,2,4-triazole) exhibited greater safety than phenytoin and carbamazepine in terms of neurotoxicity. The docking scores for the identified compounds 3d, 3h and 4a was 6.5133; 6.6558 and 5.6524, respectively. Nearly all the compounds (90%) demonstrated decreased locomotor activity. Conclusion: It is gratifying that the compounds with higher hydrophobicity showed better performance in the seizure models. Many triazole derivatives holding a suitable aryl or alkyl group gave a better anticonvulsant activity in their analogs.

Design, synthesis and biological evaluation of novel diphenylamine analogues as NLRP3 inflammasome inhibitors

The aberrant activation of the NLRP3 inflammasome has been implicated in the pathogenesis of numerous inflammation-related diseases. Development of NLRP3 inflammasome inhibitors is expected to provide a new strategy for the treatment of these diseases. Herein, a novel series of diphenylamine derivatives were designed based on the lead compounds H20 and H28, and the preliminary structure–activity relationship was studied. The representative compound 19 displayed significantly higher inhibitory activity against NLRP3 inflammasome compared to lead compounds H20 and H28, with an IC50 of 0.34 μM. Mechanistic studies indicated that compound 19 directly targets the NLRP3 protein (KD: 0.45 μM), blocking the assembly and activation of the NLRP3 inflammasome, leading to anti-inflammatory effects and inhibition of cellular pyroptosis. Our findings indicated that compound 19 is a promising NLRP3 inhibitor and could potentially serve as a lead compound for further optimization.

Rational Design of Coumarin-Based Hybridized Local and Charge-Transfer Blue Emitters for Solution-Processed Organic Light-Emitting Diodes.

Hybridized local and charge-transfer (HLCT) with the utilization of both singlet and triplet excitons through the "hot excitons" channel have great application potential in highly efficient blue organic light-emitting diodes (OLEDs). The proportion of charge-transfer (CT) and locally excited (LE) components in the relevant singlet and triplet states makes a big difference for the high-lying reverse intersystem crossing process. Herein, three novel donor (D)-acceptor (A) type HLCT materials, 7-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-3-phenyl-1H-isochromen-1-one (pPh-7P), 7-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-3-methyl-1H-isochromen-1-one (pPh-7M), and 6-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-3-methyl-1H-isochromen-1-one (pPh-6M), were rationally designed and synthesized with diphenylamine derivative as donor and oxygen heterocyclic coumarin moiety as acceptors. The proportions of CT and LE components were fine controlled by changing the connection site of diphenylamine derivative at C6/C7-position and the substituent at C3-position of coumarin moiety. The HLCT characteristics of pPh-7P, pPh-7M, and pPh-6M were systematically demonstrated through photophysical properties and density functional theory calculations. The solution-processed doped OLEDs based on pPh-6M exhibited deep-blue electroluminescence with the maximum emission wavelength of 446 nm, maximum luminance of 8755 cd m-2, maximum current efficiency of 5.83 cd A-1, and maximum external quantum efficiency of 6.54 %. The results reveal that pPh-6M with dominant 1LE and 3CT components has better OLED performance.

The dopant-free hole transport material based on benzo[1,2-b:4,5-b']dithiophene with high efficiency in inverted perovskite solar cells

In the commercialization process of organic-inorganic hybrid perovskite solar cells (OIH–PSCs), the research of dopant-free hole transport materials (HTMs) with high efficiency is still an urgent problem. In this work, we synthesize two organic small molecule HTMs with well-known benzodithiophene (BDT) as the central unit, abbreviated as BDTO-MTP and BDTT-PMTP. Compared with BDTO-MTP (with oxygen-substituted alkyl chain and diphenylamine derivatives as the terminal group), BDTT-PMTP introduces thiophene to replace oxygen beside the central group, triphenylamine to replace diphenylamine derivatives as the terminal group. Both BDTO-MTP and BDTT-PMTP exhibit high hole mobility without doping. It is worth noting that two new materials are introduced into inverted OIH-PSCs as a doped-free hole transport layer, the champion efficiency of MAPbI3-based devices based on BDTT-PMTP reaches 21.08%, and the highest efficiency of BDTO-MTP-based devices can also reach 19.54%. The results show that the planar building blocks with the similarity of BDT will be an excellent and universal choice for the future design of dopant-free small molecule HTMs with high efficiency.

Structural characterization and transformation of nitrogen compounds in waste tire pyrolysis oils

The waste tire pyrolysis oil (WTPO) has been widely concerned because it's a promising recycling method of waste tires. However, the high content of nitrogen in WTPO is unfavorable to its application. In this work, nitrogen compounds in the full distillation range of a waste tire pyrolysis oil were characterized by gas chromatograph-nitrogen chemiluminescence detector (GC–NCD), gas chromatograph-mass spectrometry (GC–MS) and Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS). In the gasoline fraction of WTPO, the most abundant nitrogen compounds were benzonitrile, aniline and small molecule nitriles. In the diesel fraction of WTPO, the most abundant nitrogen compounds were benzothiazole, quinoline derivatives, p-phthalodinitrile, benzonitrile derivatives, hexadecanenitrile and octadecanenitrile. In the heavy fraction of WTPO, significant amounts of NxOy (x = 2–3 and y = 1–2) species were discovered after the separation of solvent dissolution and solid phase extraction. The molecular structures of these NxOy species were determined as amide derivatives of diphenylamine by tandem mass spectra of FT-ICR MS. Therefore, the origin of nitriles in the light fractions of WTPO was suspected as the pyrolysis of these amides in the heavy fractions. Finally, the nitrogen transformation during the pyrolysis of waste tires was suggested based on the results of quantum chemistry simulations. These results would be helpful for the treatment and removal of these undesirable nitrogen compounds in WTPO.

Effect of Hyper-Cross-Linking on the Electrochromic Device Properties of Cross-Linkable Carbazole–Diphenylamine Derivatives

Triphenylamine derivatives are promising organic electrochromic (EC) materials due to their easy synthesis, low oxidation potentials, high charge-carrier mobilities, electrochemical stability, coloration efficiency, and tunability of EC properties via substitution. Further, the cross-linking strategy provides an added advantage to the small-molecule-based EC devices in terms of better-quality EC films with enhanced EC properties. Herein, we discuss the EC properties of two carbazole–diphenylamine derivatives, C-Sty2 and C-Sty3, with two and three thermally cross-linkable styryl units, respectively, following a donor−π–donor (D−π–D) design, where both the carbazole moiety and cross-linking styrene groups modulate the photophysical and EC properties. Both styryl derivatives formed rigid, uniform, and transparent films with high solvent resistance and exhibited excellent thermal and electrochemical stability upon cross-linking. C-Sty3, with three cross-linkable styryl units, could form more extended cross-links, leading to hyper-cross-linked films with distinct, regular, and porous morphology compared to C-Sty2. Spectroelectrochemical studies of the films showed a color change from a transparent colorless state to an initial light-yellow color and then a final dark-blue color with a color contrast of 65% at 890 nm for C-Sty2 and 78% at 850 nm for C-Sty3. The hyper-cross-linked films of C-Sty3 demonstrated enhanced coloration efficiency (248 cm2/C), optical contrast, and open-circuit memory compared to C-Sty2. Electrochemical impedance spectroscopy analysis showed lower solution and charge-transfer resistances (Rs and Rct, respectively) for hyper-cross-linked films of C-Sty3, indicating higher conductivity and ion diffusion compared to C-Sty2. Thus, a comparison of the EC properties of two polymers with the same electroactive groups reveals the significance of hyper-cross-linking in the EC properties of these cross-linked polymers. Furthermore, the EC properties of the hyper-cross-linked D−π–D derivative, C-Sty3, were compared to those of previously reported molecules, demonstrating the importance of highly branched conducting polymers for EC applications.

Effect of donor/acceptor on the charge transfer and exciton harvest of pyrene-phenanthroimidazole dyads

Designing blue emitters with polyaromatic hydrocarbons such as anthracene and pyrene is more challenging as their derivatives are prone for aggregation caused emission quenching. We report herein three new pyrene-based deep blue emitting materials containing phenanthroimidazole moiety and a diphenylamine donor or cyano acceptor. Though the absorption of the compounds is similar, the emission were altered by the peripheral unit, due to the modulation in the donor-acceptor interaction and the intramolecular charge transfer (CT) in the excited state. The solvatochromic emission data indicated the presence of hybridized local and CT excited state for the parent core and its diphenylamine derivative. However, the cyano derivative inherits more CT characteristics. Additionally, all the dyes were found to exhibit acidochromism due to the facile interaction of phenanthroimidazole moiety with the acid. All the dyes were used for organic light-emitting diodes (OLED) applications with tris(4-carbazoyl-9-ylphenyl)amine (TCTA) host material, which exhibited deep blue or cyan-blue color electroluminescence with high external quantum efficiency. The device consisting of a dye with parent core as a dopant in TCTA host exhibited highest external quantum efficiency (EQE) of 7.5% with current efficiency 3.3 cd/A and luminance 2734 cd/m2 attributable to the effective utilization of excitons harvested through the HLCT channel.

Benzothioxanthene Dicarboximide as a Tuneable Electrogenerated Chemiluminescence Dye

AbstractOverlooked for years, the promising benzothioxanthene dicarboximide (BTXI) structure is nonetheless known to be an excellent fluorophore. As a further step towards the exploration of this rylene structure, the generation of electrochemiluminescence (ECL) in acetonitrile solutions is investigated herein as well as its direct comparison with a diphenylamine (DPA) derivative. Electrochemical characterization shows that the bare BTXI can be reversibly reduced or oxidized, characteristics which suggest the possibility that the electrogenerated reactive species can be exploited in the context of ECL. As a result, the BTXI moiety was found to be ECL‐active in both annihilation and co‐reactant mechanisms. Tri‐n‐propylamine (TPA) and benzoyl peroxide (BPO) were selected as sacrificial co‐reactants for promoting ECL. An ECL efficiency of 13 % (BTXI) and 6 % (BTXI‐DPA) compared to that of Ru(bpy)32+ was found when using TPA in oxidative ECL. Moreover, the ECL efficiency increased to 75 % and 55 % of Ru(bpy)32+ with BPO (i. e. reductive‐oxidation ECL) for BTXI and BTXI‐DPA, respectively. These results can be understood by calculating the free enthalpy of the redox reactions associated with each ECL pathway. Although the BTXI‐DPA red emitter exhibits more suitable thermodynamic properties, the BTXI green emitter is nonetheless more effective in combination with a co‐reactant due to a much larger photoluminescence quantum yield. The ECL spectra of the two molecules are compared to their photoluminescence spectra, revealing the involvement of the same excited states in the two different photoemission processes. In turn, the chemical engineering of BTXI is shown to be an effective platform for achieving tuneable ECL generation.

Design, synthesis, and biological evaluation of novel diphenylamine derivatives as tubulin polymerization inhibitors targeting the colchicine binding site

A novel series of diphenylamine derivatives were designed and synthesized, and their biological activities were evaluated. The anti-proliferative activities of the derivatives were tested against five human cancer cell lines (MCF-7, MDA-MB-231, A549, HeLa and HT29). Among them, compound 5f exhibited the promising anti-proliferative activity against HT29 cell lines with the IC50 value of 23 nM. Further biological studies depicted that compound 5f inhibited cancer cell migration, colony formation and angiogenesis. Besides, dynamics studies and molecular docking studies revealed that compound 5f inhibited tubulin polymerization which may be a result of the compound binding to the colchicine site of tubulin. Furthermore, compound 5f arrested HT29 cell cycle at G2/M phase, and induced HT29 cell apoptosis by upregulating cyclin B1, Bcl-2, Bax, Cleaved-caspase9, Cleaved-caspase3, PARP, Cleaved-PARP proteins, and downregulating p-cdc25c (S216), p-cdc2 (T15) proteins. Mitochondrial membrane potential (MMP) and reactive oxygen species (ROS) were also determined to confirm the cell apoptosis process. Finally, compound 5f greatly inhibited the tumor growth in HT29 xenograft mice by 75.5% at 10 mg/kg. Meanwhile, compound 5f owned the good pharmacokinetic properties. All the results promised that 5f is of potential to act as an antitumor candidate and worthy of further investigation.

Biotransformations of anthranilic acid and phthalimide to potent antihyperlipidemic alkaloids by the marine-derived fungus Scedosporium apiospermum F41-1

A new diphenylamine derivative, scediphenylamine A (1), together with six phthalimide derivatives (2–7) and ten other known compounds (8–17) were obtained from the marine-derived fungus Scedosporium apiospermum F41-1 fed with synthetically prepared anthranilic acid and phthalimide. The structure and absolute configuration of the new compound were determined by HRMS, NMR, and X-ray crystallography. Evaluation of their lipid-lowering effect in 3T3-L1 adipocytes showed that scediphenylamine A (1), N-phthaloyl-tryptophan-methyl ester (4), 5-(1,3-dioxoisoindolin-2-yl) pentanamide (5), perlolyrine (10) and flazine (11) significantly reduced triglyceride level in 3T3-L1 cells by inhibiting adipogenic differentiation and synthesis with the EC50 values of 4.39, 2.79, 3.76, 0.09, and 4.52 μM, respectively. Among them, perlolyrine (10) showed the most potent activity, making it a candidate for further development as a potential agent to treat hyperlipidemia.

High-Performance Simple Nonfused Ring Electron Acceptors with Diphenylamino Flanking Groups.

Four simple nonfused ring electron acceptors (H-2F, CH3-2F, OCH3-2F, and SCH3-2F) were designed and synthesized. The use of diphenylamine derivatives as the flanking group for the construction of nonfused ring electron acceptors can improve solubility, avoid the formation of oversized aggregates, and enhance the intramolecular charge-transfer effect to extend absorption spectra. The substituent group at the diphenylamine unit has a great impact on the absorption and energy level of acceptors, electron mobility and morphology of blend films. Unlike the other three acceptors, CH3-2F can form ordered molecular stacking and a face-on orientation in the donor/acceptor blend film. A single-crystal analysis demonstrates that CH3-2F can form a two-dimensional electron transport network. Among these four acceptors, CH3-2F-based organic solar cells provide the highest PCE of 12.28%. Our work has demonstrated that triarylamine is a helpful construction unit for low-cost and high efficiency nonfused ring electron acceptors.

Spectral-Luminescent and Electroluminescent Properties of Charge-transfer Systems Based On Electron-donating Diphenylamine Derivatives and Acceptors of Dibenzothiophene Sulfone and Phenanthridine.

Spectral characteristics and luminescence under the photo- and electro-excitation of substituted dibenzthiophene sulfone and phenanthridine were studied in this paper. Diphenylamines are substituents introduced in the 2nd and 7th positions (linear configuration) or the 3rd and 6th positions (angular configuration) of dibenzthiophene sulfone or phenanthridine. All molecules show delayed fluorescence, both in solutions and films produced by thermal vacuum deposition. The value of the energy gap between the S1 and T1 states has been estimated and is shown to depend not only on the spatial arrangement of the fragments among themselves (linear or angular), but also on the nature of the substituent in diphenylamine. The highest electroluminescence brightness was found for the molecules, in which triplet levels are involved, both through the process of triplet-triplet annihilation and through thermally activated delayed fluorescence.

Multicomponent synthesis and preliminary anti-inflammatory activity of lipophilic diphenylamines

Non-Steroidal Anti-inflammatory Drugs (NSAIDs) are some of the most prescribed medications for pain but the incidence of adverse effects –especially during chronic treatment– points out the requirement of new analgesics. In this study, we showed an efficient two-steps synthesis of diphenylamine-containing dipeptides consisting of a multicomponent process followed by a Buchwald-Hartwig cross-coupling reaction. We prepared 16 diphenylamine derivatives and evaluated their in vivo anti-inflammatory activity through an ear edema model using 12-O-tetradecanoylpholbol-13-acetate. Furthermore, the toxicity of the more potent compounds in the Artemia salina model and their cell viability using murine RAW 264.7 cells is reported. The fluorinated compound 10k becomes a reliable candidate since it reduced the TPA-induced edema to 92%, lacked cytotoxicity against murine macrophages, and had minimal toxicity in Artemia salina.

Efficient strategies to improve the performance of 6,12-dihydroindeno[1,2-b]fluorine core based hole transport materials

For improving the performance of hole transport materials (HTM) in the utilization of perovskite solar cells (PSCs), the structure-performance relationships of HTM must be revealed. In this work, six HTMs with same 6,12-dihydroindeno[1,2-b]fluorine (IDF) core are studied theoretically to reveal the influences of difference type and number of electron-donating group on the performances of HTMs. Results showed that star-shaped HTMs should have larger open-circuit voltage (VOC), better optical performances than linear-shaped HTMs. Meanwhile, using one thiophene substitute a benzene on the electron-donating group Diphenylamine derivative (DPA) is expected to enhance the VOC of PSCs and Stokes shift of HTM. Both the type and number of electron-donating group have slight effects on hole injection, electron-blocking and molecular stability of HTM. Most importantly, both thiophene substituted DPA (T-DPA) group and linear structure make the molecular stacking more compact, leading the transfer integral in the main hopping pathway improved evidently. Thus, the hole mobilities of HTMs are increased obviously. Furthermore, results also show that two thiophene substituted DPA could lead the molecular stacking more compact, which could be favorable for improving the hole mobility of HTMs. Our investigation proves and provides two efficient strategies to modulate the performances of HTMs and reveals the structure-performance relationships of HTMs.

Electron Push-Pull Effects on Intramolecular Charge Transfer in Perylene-Based Donor-Acceptor Compounds.

A series of asymmetric donor-acceptor (D-A) perylene-based compounds, 3-(N,N-bis(4'-(R)-phenyl)amino)perylene (Peri-DPA(R)), were successfully prepared to explore their intramolecular charge transfer (ICT) properties. To induce ICT between the donor and acceptor, diphenylamine (DPA) derivatives (electron donor units) with the same functional groups (R = CN, F, H, Me, or OMe) at both para positions were linked to the C-3 position of perylene to produce five Peri-DPA derivatives. A steady-state spectroscopy study on Peri-DPA(R)s exhibited a progressively regulated ICT trend consistent with the substituent effect as it progressed from the electron-withdrawing group to the electron-donating group. In particular, a comparative study using a D-A-D (donor-acceptor-donor) system demonstrated that not only the electron push-pull substituent effect but also subunit combinations influence photophysical and electrochemical properties. The different ICT characters observed in Lippert-Mataga plots of D-A(CN) and D-A-D(CN) (CN-substituted D-A and D-A-D) led to the investigation on whether ICT emission of two systems with differences in subunit combinations is of the same type or of a different type. The femtosecond transient absorption (fs-TA) spectroscopic results provided direct evidence of ICT origin and confirmed that D-A(CN) and D-A-D(CN) exhibited the same transition mix of ICT (from donor to acceptor) and reverse ICT (rICT, from arylamine to CN unit). Density functional theory (DFT)/TD-DFT calculations support the presence of ICT for all five compounds, and the experimental observations of rICT presented only for CN-substituted compounds.

Synthesis and Pharmacological Evaluation of 2-(4-(3 (Substituted Phenyl) Acryloyl) Phenoxy)-N, N Diphenylacetamides

Recently a series of Schiff bases of diphenylamine derivatives have been synthesized and evaluated in vitro for their antibacterial activity against pathogenic both Gram-positive bacteria B. subtitles and Gram-negative bacteria E. coli using ciprofloxacin as standard drug at conc. of 50 μg/ml and 100 μg/ml. Literature review revels that chalcones possesses various biological activities like antimicrobial, antiviral, anti-inflammatory, anticancer and sedative etc. Therefore the present study was designed on synthesis and pharmacological evaluation of 2-(4-(3 (Substituted Phenyl) Acryloyl) Phenoxy)-N, N Diphenylacetamides. Target compound was synthesized by reaction of chloroacetylchloride with diphenylamine to afford 2-chloro-N, N-diphenylacetamide which further by reaction with substituted Chalcones and characterized following recrystallization and evaluated for anti-microbial potential through cup-diffusion method. In results, the target compounds were tested for activity against B. Subtilis, E.Coli and C. albicans. The chalcones having the lipophilic 4-chloro group (RKCT2) showed the greatest antimicrobial activity (zone of inhibition 20 & 22 mm against. B. subtilis, E. Coli, C. Albicans respectively. It suggests further researchers to go through anti-microbial evaluations against a more varieties of bacteria and fungi.
 Keywords: Schiff bases of diphenylamine derivatives, antibacterial activity, Gram-positive bacteria, 2-(4-(3 (Substituted Phenyl) Acryloyl) Phenoxy)-N, N Diphenylacetamides

Armed with the Facts: A Method for the Analysis of Smokeless Powders by Ambient Mass Spectrometry.

The work presented here follows several others in investigating what capabilities, if any, ambient mass spectrometry might have toward the analysis of compounds commonly associated with smokeless propellant powders. This family of instrumental techniques has attracted curiosity from the field of forensic science due to its desirable properties such as rapid collection of information-rich data, combined with minimal requirements for sample mass and preparation. Experiments were conducted with a "Direct Sample Analysis" ion source integrated with a time-of-flight mass spectrometer. The ionization behaviors of nitroglycerin, methyl and ethyl centralite, akardite, diphenylamine, nitrosodiphenylamine, and nitrated diphenylamine derivatives were investigated specifically, with accurate-mass data presented for each. Diphenylamine standards were used to demonstrate the performance of this instrument, which exhibited good response linearity across 1 order of magnitude and sub-nanogram detection limits. Thirty smokeless powder extracts, recovered from ammunition potentially in circulation within Australia, were analyzed to determine whether the technique is appropriate for rapid analysis of smokeless powder particles. Results demonstrated that the technique might be applied to compare individual particles with each other or to a database. Such a capability may be of value in the examination of explosive devices containing smokeless powder, postblast residues therefrom, or muzzle discharge from a close-range shooting. However, when efforts were made to detect residues from the hands of a volunteer shooter, only some returned positive results, and a high background signal from the sample collection stub indicates that detection using this instrument is thus far insufficiently reliable.

Synthesis, Toxicity Profile and Pharmacological Evaluation of Some New N,N-Diphenyl Amine Derivatives with Special Reference to Analgesic and Anti-inflammatory Activity

The present work was aimed to synthesize eight new diphenylamine derivatives by the reactions of 2-chloro-N-(4-(diphenyl amino) thiazol-2-yl)acetamide with substituted phenols in the chloroform along with anhydrous potassium carbonate and potassium iodide. The structures of newly synthesized compounds were characterized by IR, NMR, Mass and elemental analysis techniques. Toxicity profile (acute and subacute oral toxicity) and biological activity (analgesic and anti-inflammatory activity) of the synthesized derivatives was performed. Findings of the present work suggested that the synthesized compounds may be one of the excellent potent compounds to treat pain and inflammation. Therefore compounds of this group especially AK-4 (N-(4-(diphenylamino)thiazol-2-yl)-2-(2- nitrophenoxy)acetamide) could be an excellent starting point to build up new lead compounds in the management of pain and inflammation.

High‐Efficiency CsPbI2Br Perovskite Solar Cells with Dopant‐Free Poly(3‐hexylthiophene) Hole Transporting Layers

AbstractCsPbI2Br is emerging as a promising all‐inorganic material for perovskite solar cells (PSCs) due to its more stable lattice structure and moisture resistance compared to CsPbI3, although its device performance is still much behind this counterpart. Herein, a preannealing process is developed and systematically investigated to achieve high‐quality CsPbI2Br films by regulating the nucleation and crystallization of perovskite. The preannealing temperature and time are specifically optimized for a dopant‐free poly(3‐hexylthiophene) (P3HT)‐based device to target dopant‐induced drastic performance degradation for spiro‐OMeTAD‐based devices. The resulting P3HT‐based device exhibits comparable power conversion efficiency (PCE) to spiro‐OMeTAD‐based devices but much enhanced ambient stability with over 95% PCE after 1300 h. A diphenylamine derivative is introduced as a buffer layer to improve the energy‐level mismatch between CsPbI2Br and P3HT. A record‐high PCE of 15.50% for dopant‐free P3HT‐based CsPbI2Br PSCs is achieved by alleviating the open‐circuit voltage loss with the buffer layer. These results demonstrate that the preannealing processing together with a suitable buffer layer are applicable strategies for developing dopant‐free P3HT PSCs with high efficiency and stability.