2-aminothiophenol Research Articles

Poly-(2-aminothiophenol) Functionalized Petroleum Coke for Fast Simultaneous Sequestration of Cd(II) and Pb(II) Ions from Industrial Effluents

Background: Nowadays, the challenge between clean water production and promoting an eco-friendly sorbent for the simultaneous fast and efficient removal of heavy metal ions is a hot topic and has attracted much attention. Objective: The objective of this study was to fabricate a novel material (PATP@PET) by incorporating poly-(2-amino thiophenol; PATP) into the matrix of Saudi Arabian petroleum coke (PET) for simultaneous fast and efficient removal of heavy metal ions. objective: The fabrication of a novel material (PATP@PET) by incorporating poly-(2-amino thiophenol; PATP) into the matrix of Saudi Arabian petroleum coke (PET) for simultaneous fast and efficient removal of heavy metal ions Method: The FTIR, EDX, SEM, and XRD techniques assessed the chemical structure and surface morphology of the thio-functionalized petcoke. The effects of medium pH, mass dosage of sorbent, metal ion concentration, and coexisting ions were investigated and optimized using batch sorption. Result: The excellent sorption capacity of PATP@PET sorbent towards the divalent lead and cadmium ions (98.44% and 312.5 mg.g-1 for Pb(II) and 90.15% and 217.4 mg.g-1 for Cd(II)) was realized by strong complex formation with the sulfur atoms of green petcoke and the thiol groups of poly-2- aminothiophenol moieties. The adsorption equilibrium data was best fitted to the pseudo-secondorder kinetic model and Langmuir adsorption isotherm. The reusability performance was tested for 10 cycles, and the simultaneous removal of Pb(II) and Cd(II) ions from industrial effluents was accomplished in 30 minutes with 100% removal efficiency at pH 6-7. Conclusion: PTAP-PET also demonstrated amazing performance for Cd(II) and Pb(II) removal in industrial wastewater samples. Subsequently, PTAP-PET contributes to developing fast, efficient, low-cost water remediation solutions for heavy metal ions that can potentially be translated into industrial- scale applications.

Sulfone-infused covalent organic polymer derived from poly(2-aminothiophenol) and erythrosine B as an excellent tool for C–H activation

The generation of a low HOMO-LUMO energy gap makes organic polymer-based composites an important class of materials with outstanding catalytic efficiency. The present work describes the simple and direct synthesis of an excellent photocatalyst, PC (C26H16NO7S)n via doping of erythrosine-B dye on sulfone infused poly(2-amino thiophenol) assembly (PA, (C6H4NO2S)n). The O 1 s spectrum displays peaks at 531.8 eV and 533.3 eV, representing the O=C and O–C groups of the in-situ generated fluorescein loaded on PA surface. Through absorption study (Tauc’s plot), the optical band gap (Eg) for polymer PA (2.9 eV) and photocatalyst PC (2.1 eV) has been calculated. Further, due to the efficient absorbance in the range of 400–600 nm with a low optical band gap, the applicability of the catalyst, PC has been checked in photocatalytic C–H activation in thiophene, and the generation of C–C bond with p-nitro aryldiazonium salt.

Potential anti-amoebic effects of synthetic 1,4-benzothiazine derivatives against Acanthamoeba castellanii

A rare but lethal central nervous system disease known as granulomatous amoebic encephalitis (GAE) and potentially blinding Acanthamoeba keratitis are diseases caused by free-living Acanthamoeba. Currently, no therapeutic agent can completely eradicate or prevent GAE. Synthetic compounds are a likely source of bioactive compounds for developing new drugs. This study synthesized seventeen 1,4-benzothiazine derivatives (I –XVII) by a base-catalyzed one-pot reaction of 2-amino thiophenol with substituted bromo acetophenones. Different spectroscopic techniques, such as EI-MS, 1H-, and 13C NMR (only for the new compounds), were used for the structural characterization and conformation of compounds. These compounds were assessed for the first time against Acanthamoeba castellanii. All compounds showed anti-amoebic potential in vitro against A. castellanii, reducing its ability to encyst and excyst at 100 μM. Compounds IX, X, and XVI showed the most potent activities among all derivatives and significantly reduced the viability to 5.3 × 104 (p < 0.0003), 2 × 105 (p < 0.006), and 2.4 × 105 (p < 0.002) cells/mL, respectively. The cytotoxicity profile revealed that these molecules showed lower to moderate cytotoxicity, i.e., 36 %, 2 %, and 21 %, respectively, against human keratinocytes in vitro. These results indicate that 1,4-benzothiazines showed potent in vitro activity against trophozoites and cysts of A. castellanii. Hence, these 1,4-benzothiazine derivatives should be considered to develop new potential therapeutic agents against Acanthamoeba infections.

Multi-functions of amino thiophenol additives for shielding lithium metal anode in advanced Li-S battery

Lithium-sulfur (Li-S) batteries have been considered as a promising candidate for the next generation of battery systems due to their high specific capacity and energy density. However, some barriers impede the application of Li-S batteries, such as the “shuttle effects” of lithium polysulfides (LPS), the poor electrical conductivity of sulfur, and lithium dendrite formation on lithium metal electrodes. Herein, we investigated a series of amino thiophenol as electrolyte additives: 2-amino thiophenol (2-ATP), 3-amino thiophenol (3-ATP), and 4-amino thiophenol (4-ATP); as well as p-phenylenediamine (PPD). These additives react with Li to form a stable and uniform solid electrolyte interphase (SEI) to protect the Li anode and minimize the interaction of Li with soluble LPS. Initial specific capacity at 0.1C and reversible specific capacity after 100 cycles are 1420 and 1043 mAh/g, 1429 and 982 mAh/g, 1148 and 871 mAh/g, 1317 and 791 mAh/g for 4-ATP, 3-ATP, 2-ATP, and PPD, respectively. Long-term cycling testing of Li-S cells was conducted at 0.2C and the cell with 4-ATP additives deliver an initial specific capacity of 1159 mAh/g and capacity retention of 77% after 300 cycles. The morphology and composition of the after-cycled SEI layers were examined by SEM and XPS. The findings suggest amino thiophenols (ATPs) form stable and smooth closed-packed SEI layers, that ameliorate lithium dendrite problems and LPS reactions with Li metal. 4-ATP is found to exhibit the best electrochemical performance followed by 3-ATP, 2-ATP, and PPD, which are in good agreement with the surface morphology. In addition, the amine group can assist the reaction between the thiol group and S8 on the cathode and modify the redox pathway of polysulfide.

Easily Applicable Heterogeneous Catalyst from Sustainable Resources: Anchoring of Pd Nanoparticles onto Chemically Poly(2-amino thiophenol)-Modified Wool Fabrics

For preparing the Pd nanoparticle (PdNP)-decorated heterogeneous catalyst material, wool fabric was utilized as a practical platform after enriching its chemical functionality with two straightforward chemical processes. First, wool keratin was transformed to a reduced structure (WSH) with NaHS by extracting −SH groups and then reconstructed to the S–S linkages by the covalent attachment of 2-amino thiophenol (2-ATP). The graft copolymerization of 2-ATP onto this 2-ATP/WSH surface was ensured to prepare a P2ATP-g-WSH copolymer fabric. As the second process, the polymerization of 2-ATP was also performed on the WSH fabrics to prepare a P2ATP/WSH composite. The PdNP anchoring was subsequently ensured onto these copolymer and composite samples through the in situ reduction of Pd2+ to the PdNPs. The conditions yielding the highest PdNP content were investigated in detail, and the PdNP formation abilities of both fabrics prepared by different routes were compared. It was observed that the contribution of PdNPs through the P2ATP/WSH composite route was relatively high compared to that of the copolymer route. The structural and morphological alterations in the wool nature, the existence, the oxidation state, and the relative abundance (%) of PdNPs with respect to the Pd2+ ions were evidenced by many techniques in detail. After examining the performance of the PdNP composites in the catalytic reduction of two nitroarenes to the aminoarenes, the Pd/P2ATP/WSH demonstrated satisfactorily high performance in terms of reduction yield (%), reduction rate constant (min–1), and reusability, compared to that of Pd/P2ATP-g-WSH.

Multi-Functions of Amino Thiophenol Additives for Shielding Lithium Metal Anode in Advanced Li-S Battery

Multi-Functions of Amino Thiophenol Additives for Shielding Lithium Metal Anode in Advanced Li-S Battery

Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein.

A new class of benzothiazole-appended quinoline derivatives (6–8) was synthesized via one-pot TPGS micellar-mediated acid-catalyzed nucleophilic addition, followed by aerobic oxidative cyclization of 3-formylquinoline-2-one (2), 3-formylquinoline-2-thione (3), and 2-azidoquinoline-3-carbaldehyde (4) individually with 2-amino thiophenol (5). The structures of the prepared compounds were confirmed using suitable spectroscopic methods complemented with single-crystal X-ray diffraction analysis. Time-dependent density functional theory-based optimization of molecular structures, bond lengths, bond angles, HOMO–LUMO energy gaps, and molecular electrostatic potential maps was theoretically computed at the B3LYP/6-311++g(d) level. The molecular docking studies recommended that 6–8 bound to the active site cavity of CD81 effectively with the binding energies of −6.9, −6.3, and −6.5 kcal mol–1, respectively. Further, MD simulation studies of compound 6 suggested that the binding resulted in the stabilization of the CD81 molecule. Thus, all theoretical predictions associated with the experimental verifications motivated to discover novel approaches for cancer therapy.

Unraveling a self-assembling mechanism of isomeric aminothiophenol on Ag dendrite by correlated SERS and matrix-free LDI-MS

Correlated spectroscopic analysis can provide complementary chemical insights that are often unattainable by either approach used in isolation. We distinguished the different self-assembling behavior of isomeric aminothiophenols (ATPs) on Ag dendrite by the correlation of surface-enhanced Raman spectroscopy and laser-induced desorption ionization mass spectrometry, demonstrating that steric effect impinged significantly upon surface molecular density and plasmon-driven catalytic reaction yield, which led to drastic variations in the resulting SERS spectra. The correlative measurement shows that ortho-substitute barely formed a self-assemble monolayer, relative to the para-isomer, which can form a close-packed self-assembled monolayer and perform a decent azo-coupling reaction. Comparison between normal and SERS spectra of ATP isomers supports the fact that additional disulfide- or hydrogen-bonding interactions are established in para-ATP solid crystal, but neither of ortho- nor meta-isomers. This work is expected to create a significant impact on the development of an orthogonally correlated spectroscopic tool in deciphering chemical insights and underlying reaction mechanism. Graphical abstract.

Synthesis of 2-substituted benzothiazoles via the Brønsted acid catalyzed cyclization of 2-amino thiophenols with nitriles

A convenient and efficient method for the synthesis of 2-substituted benzothiazoles from simple and readily available 2-amino thiophenols and nitriles is described. The Brønsted acid-catalyzed cyclization reaction was performed under metal and solvent-free conditions.

Synthesis and Characterization of Pd(II) And Pt(II) Complexes with Bis [Hg (2-Apt)] Compound.

The reaction of one mole of Hg(II) acetate with two mole of 2-amino thiophenol gave one mole of [Hg(2-apt)] compound. While the reaction of one mole of [Hg(2-apt)] with two moles of MCL2 salt. Produced new complexes in general formula [M2{Hg(2-apt)Cl4] where M=Pt(II) or Pd(II).All the prepared complexes were identified using FT-IR, 1H-NMR,13C-NMR,elemental analyses (CHNS) and molar conductivity. The results exhibited that metal bounded to the ligand via S and N in squar planer geometries..

Preparation of tin-modified mono-ammonium phosphate fertilizer and its application as heterogeneous catalyst in the benzimidazoles and benzothiazoles synthesis

This work presents an efficient, easy and green method for the benzimidazoles and benzothiazoles synthesis by a condensation reaction of 1,2-diamino benzene and 2-amino thiophenol with various aromatic aldehydes using SnP2O7 as a new heterogeneous catalyst. This catalyst was prepared by adding MAP to the solution of SnCl2 and characterized by microscopic and spectroscopic methods namely X-ray diffraction, scanning electron microscopy and infrared which proved that the chemical structure of MAP has been modified when SnCl2 was added leading to the formation of SnP2O7. On the other hand, the reaction conditions were optimized namely the nature of the solvent and the mass of the catalyst. The high yields (85–97%) and very short reaction times (5–40 min) obtained for various benzimidazoles and benzothiazoles derivatives synthesis show that the new catalyst is very interesting because of its good catalytic activity and its reusability for at least five cycles without any degradation of its activity.

Embellished hollow spherical catalyst boosting activity and durability for oxygen reduction reaction

Transition metals hybridized to heteroatom doped carbon material can be regarded as the most promising non-noble candidate for boosting the sluggish kinetics of oxygen reduction reaction (ORR). However, it has always been a challenge to vastly boost the activity, and simultaneously retain a favorable structure from the supporting material. Herein, we prepared a high surface area hollow spherical carbon as a supporting material, and employed aminothiophenol (ATI) and poly-aminothiophenol (PATI) as heteroatom precursors to synthesize nitrogen and sulfur co-doped catalysts, i.e. HCS-A and HCS-PA, respectively. The two catalysts possessed chemically similar surface composition, and nearly identical chemical states for each element. However, only HCS-A was able to vastly inherit both morphological advantage and high surface area from the carbon support. In further half-cell electrochemical testing, HCS-A performed better ORR activities and higher selectivity toward 4 electron pathway than HCS-PA in both acidic and alkaline media. Moreover, HCS-A was proven to have excellent durability in half-cell testing, methanol tolerance as well as outstanding peak power density in both fuel cells and zinc-air batteries. This work not only indicates the promising performances of HCS-A, but more importantly offers a new viewpoint on the selection of heteroatom precursor to retain a favorable structure.

Design, synthesis, structural elucidation and antimicrobial screening of novel 1, 5-benzothiazepine derivatives derived from thieno [3, 2-d] pyrimidine nucleus

1, 5-Benzo Thiazepine is the Main Seven membered Heterocyclic ring systems reported for their cardiac and Psychotherapeutic activities.1, 5 Benzo Thiazepines were highlighted as important Biologically active Scaffolds. In This Article New series of benzo [b] [1, 5]-thiazepine derivatives 6 a-j were synthesized by applying the cyclo condensation of (E)-3-(thieno [3, 2-d] pyrimidin-6-yl)-1-p-Substituted prop-2-en-1-one derivatives 4a-j with 2amino thio phenol (5) in DMF. The new intermediate Chalcone derivatives 4a-j were obtained from interaction of various P-substituted Acetophenone & Heterocyclic Acetyl derivatives 3(a-j) and thieno[3, 2-d]pyrimidine-7carbaldehyde. The synthesized 1, 5-benzothiazepines 6a-j have been screened for their antimicrobial activity. From anti-bacterial and anti-fungal activity screening results, it has been observed that compounds 6h, 6e, 6i and 6d possess good activity.

Microwave assisted aqueous phase synthesis of benzothiazoles and benzimidazoles in the presence of Ag2O

A simple and high yielding method for synthesized benzothiazoles and benzimidazole in water under micro wave irradiation by the reaction of 2-amino thiophenol and o-phenylenediamine with various aromatic aldehydes in the presence of Ag2O. Ag2O can be recovered and reused without significant loss of activity.

Molecularly imprinted electrochemical sensor based on bioinspired Au microflowers for ultra-trace cholesterol assay

A novel imprinted sensor for ultra-trace cholesterol (CHO) detection based on electropolymerized aminothiophenol (ATP) molecularly imprinted polymer (MIP) on a glassy carbon electrode (GCE) modified with dopamine@graphene (DGr) and bioinspired Au microflowers has been developed in this work. As the specific recognition element, the bioinspired Au microflowers were formed by Au nanoparticles (AuNPs) and wrapped by bionic polydopamine film (PDA) through electropolymerization method. These excellent biocompatible materials could capture the target CHO effectively. The morphology of the MIP modified electrode was characterized by scanning electron microscopy (SEM) and atomic force microscope (AFM). The hydrogen-bonding interaction between templates and monomers was characterized by ultraviolet spectroscopy. Under the optimal experimental conditions, the sensor's linear response range was between 10−18 and 10−13 M, with a detection limit of 3.3×10−19 M, which was much more sensitive than most available CHO detection methods in previously reports. Moreover, the MIP sensor exhibited high sensitivity for CHO, low interference, and good stability. The human serum samples analysis confirmed the applicability of this MIP sensor to quantitative analysis of ultra-trace CHO.

Quantification of Protein Biomarker Using SERS Nano-Stress Sensing with Peak Intensity Ratiometry

We report a surface enhanced Raman spectroscopy (SERS) ratiometry method based on peak intensity coupled in a nano-stress sensing platform to detect and quantify biological molecules. Herein, we employed an antibody-conjugated [Formula: see text]-aminothiophenol (ATP) functionalized on a bimetallic-film-over-nanosphere (BMFON) substrate as a sensitive SERS platform to detect human haptoglobin (Hp) protein, which is an acute phase protein and a biomarker for various cancers. Correlation between change in the ATP spectral characteristics and concentration of Hp protein was established by examining the peak intensity ratio at 1572[Formula: see text]cm[Formula: see text] and 1592[Formula: see text]cm[Formula: see text] that reflects the degree of stress experienced by the aromatic ring of ATP during Hp protein–antibody interaction. Development of this platform shows the potential in developing a low-cost and sensitive SERS sensor for the pre-screening of various biomarkers.

Microwave Assisted Facile Synthesis and Biological Evaluation of Novel 2-Indolyl -1, 5-Benzothiazepines

Background: The research work reports facile, eco-friendly microwave- assisted solvent free synthesis of coupled heterocyclic system 2-(1H-indol-3-yl)-4-substitued-2, 3-dihydrobenzo [1, 5] thiazepine derivatives obtained by cyclo condensation of 1-substituted-3(1H-indolyl)-2-propen-1-ones with 2-amino thiophenol in presence of eco-friendly catalyst zirconium(IV) oxy chloride, in solvent-free conditions. The reaction was completed in 3-6 minutes and gives better yields than the conventional synthesis which requires 6-8 hrs. Result and Conclusion: The newly synthesized compounds were evaluated for antihypertensive activity in Sprague- Dawley rats by tail- cuff method and compared with diltiazem, the standard antihypertensive drug. The data suggested that some of the compounds of the current series exhibited enhanced antihypertensive activity than the standard. As benzothiazepines are bioisosters of benzodiazepines, the synthesized novel indolyl-benzothiazepine derivatives were also screened for CNS activities such as CNS depressant activity by actophotometer and anticonvulsant activity by MES and PTZ model on mice. The title compounds have exhibited good CNS depression and anticonvulsant activity. The compounds thus have shown dual antihypertensive and CNS depressant, anticonvulsant activity and are biologically potential molecules. The molecular docking was performed for the synthesized compounds to assess their binding affinities to GABA-A receptor in order to rationalize their anticonvulsant activities in a qualitative way.

Shaping Gold Nanostar Electric Fields for Surface-Enhanced Raman Spectroscopy Enhancement via Silica Coating and Selective Etching

The application of gold nanostars in direct and indirect surface-enhanced raman spectroscopy (SERS) sensing has significantly grown in the past few years, mainly because of the particles’ excellent field enhancement properties. However, experimental demonstrations correlating SERS signal enhancements to specific morphology features of the nanostars are still scarce, primarily because of the complexity of the nanostar morphology itself. Herein, we have addressed this fundamental issue by synthesizing surfactant-free gold nanostars, coating them with a uniform silica layer, and then etching the silica away selectively with NaBH4 to expose increasing amounts of the metallic surface. We have then functionalized the nanoparticles with a Raman active molecule, aminothiophenol (ATP), and compared the resulting SERS spectra with those obtained on surfactant-free stars functionalized with ATP. Through comparison of the experimental results with the electric field intensities and distributions calculated via finite...

Cyanine IR-780 for distinguishing 2-amino thiophenols from position isomers

Developing highly selective fluorescent probes for the determination of thiophenol is very significant due to its toxicity influence in biological system. In this work, we firstly found that the commercial available cyanine dye 3H-Indolium, 2-(2-(2-chloro-3-(2-(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indol-2-ylidene)ethylidene)-1-cyclohexen-1-yl)ethenyl)-3,3-dimethyl-1-propyl-, iodide had a remarkable capability of determining the amino-substituted thiophenols. Especially, the 2-amino thiophenol induced a fluorescence change of this cyanine dye with the largest intensity in comparison to the 3- and 4-amino thiophenols, implying Cyanine IR-780 can distinguish 2-amino thiophenols from position isomers. Despite the 2-amino thiophenol quenched the fluorescence of cyanine dye, their complex system further played a role in detecting the glutathione with high selectivity over cysteine and homocysteine. It was worth mentioning that similar selectivity can also be observed in living cells.

Design, synthesis and Anti-depressant activity of some novel derivatives of Benzothiazepine

Antidepressants are the drugs used to treat depression thereby elevates mood and modifies the behavior. The main aims in the development of new antidepressants were greater efficacy, absence of side effects, lack of toxicity in over dose and earlier onset of action. In this study, a series of novel substituted benzothiazepine was synthesized and evaluated for antidepressant-like activity by using or forced swim test (FST). This study was designed to synthesized; identify and antidepressant-like activity of novel derivatives of benzothiazepine. Our synthetic route started from substituted aromatic aldehyde which was reacted with 2-aminothiophenol and ethyl or methyl acetoacetate led to the formation of the title compounds. Total 22 benzothiazepine derivatives were synthesized. All compounds were tested for antidepressant activity by using or forced swim test (FST). All the synthesized compounds were subjected to antidepressant-like activity study on Sprague-Dawley rats by despair swim test. Imipramine was used as standard control. The results showed that all the compounds showed antidepressant activity. Among them two Compounds (A 3 , A 6 ,B 1 B 3 , and B 6 ) showed significant antidepressant-like activity comparing with standard control imipramine. We investigated the importance of functional group substitutions, in the structural framework of the compounds for their antidepressant-like activity. All compounds showed significant antidepressant-like activity at dose (30 mg/kg). Finally, the encouraging result of the antidepressant-like activity displayed by these compounds may be of interest for further structural modifications to the lead compound and next level studies in the hope of finding a new potent antidepressant prescription.