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Wound infection poses a significant global health threat, as it is a leading cause of morbidity and mortality among surgical patients and individuals with burn injuries, resulting in substantial healthcare burdens and devastating outcomes worldwide. Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli have frequently been implicated as major pathogens causing wound infections. This has eventually and consistently given rise to antimicrobial resistance divulging a need to mitigate infectious outbreaks. Herein, we employed a computational density functional theory (DFT) method at ωB97XD/6-311++g(d, p) level of theory to evaluate the performance of the thiophene derivative 5-(4-bromo-5-(methylthio)thiophen-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol 4, which is experimentally synthesized into five compounds (4a, 4b, 4c, 4d, and 4e). The chemical reactivity, kinetic stability, nature of interactions and functional characteristics of the thiophene derivatives were ascertained. The resistance gene PDB ID: 1K25, 2D45, 4UOT, and 7K2X were employed and docked with thiophene derivatives. Interestingly, molecular docking analysis demonstrated that ligands 4a, 4b, 4c, 4d, and 4e are more effective against proteins 1K25, 4U0T and 7K2X than amoxicillin and methicillin. Upon docking with the 2D45 protein, compounds 4c and 4e (− 5.9 kcal/mol) exhibited potential similar to that of methicillin (− 5.9 kcal/mol), while 4a and 4b showed slightly better affinities (− 6.1 kcal/mol and 6.0 kcal/mol). Using Lipinski's Rule of Five (Ghose filter, Veber rules, Muegge filter, and Egan's rule), 4d and 4e were determined to be the most promising candidates for drug development due to their compliance with all evaluated criteria, indicating favourable properties for oral bioavailability and drug likeness. This research suggested that thiophene derivatives can serve as promising antibacterial agents against wound-infected bacteria. [ABSTRACT FROM AUTHOR]

We report the C–F bond heteroarylation of trifluoromethylarenes with heteroarenes by using Ir(ppy)3 catalyst and Bu3 SnI under visible-light irradiation. Various heteroarenes such as pyrrole, furan, and thiophene derivatives were applied to the present reaction. The present heteroarylation enables the transformation of various functionalized trifluoromethylarenes because of the mild reaction conditions. Notably, the late-stage transformation of a drug molecule, bicalutamide, was demonstrated. Mechanistic studies including a light on–off interval experiment, Stern–Volmer luminescence-quenching measurements, and DFT calculations clarified two critical roles of Bu3 SnI for the successful progress of the heteroarylation. Bu3 SnI functions as a fluoride ion scavenger to suppress the undesired C–F bond re-formation. Bu3 SnI also acts as a single-electron source for the reduction of photoexcited Ir(ppy)3 * to generate Ir(II) species to effectively reduce ArCF3. [ABSTRACT FROM AUTHOR]

Upon reaction with α,β‐unsaturated nitriles (2 a–d) and/or salicylaldehyde, 3‐(naphthalen‐2‐yl)‐3‐oxopropanenitrile (1) yields pyridine derivatives 3 a–d and/or the imino chromene derivative 4. Compound 1 reacted with phenyl isothiocyanate in a basic medium to give the intermediate potassium salt 6. Upon stirring at room temperature, the intermediate 6 with some α‐halogenated compounds yielded the acyclic compounds 7, 9, 11, 13, and 15. On the other hand, refluxing intermediate 6 with the same α‐halogenated compounds in DMF in the presence of TEA afforded the corresponding thiophene derivatives 8, 10, 12, 14, and 16. The reaction of thiol 17 with hydrazine hydrate derivatives 18 a–d yielded the corresponding pyrazole derivatives 21 a–d. Compound 20 reacted with o‐phenylenediamine or o‐aminothiophenol in the presence of DMF/TEA to give the corresponding benzothiazole or benzoimidazole derivatives 27 a and 27 b, respectively. Thirty new synthesized compounds were examined for their antibacterial activity against Gram‐positive bacteria including S. aureus and B. subtilis, Gram‐negative bacteria such as P. aeruginosa and E. coli, and yeast‐like fungi like C. albicans in vitro. Compounds 15, 16, 21 d, 27 a, 27 b, exhibited the highest antibacterial activity against Gram‐positive bacteria. Molecular docking experiments were conducted to explore the binding affinities and interaction modalities of selected derivatives with the target PDB‐3cmt protein. [ABSTRACT FROM AUTHOR]

A series of catalysts, X%PMoV (X=10, 20, 30, 40, 50), were prepared through loading X% (mass fraction of SBA-15) Keggin-type H4PMo11VO40 (PMoV) on mesoporous SBA-15 by incipient-wetness impregnation method, which were utilized as visible-light catalysts for photothermal oxidation desulfurization at room temperature. The catalysts were characterized by brunauer Emmett Trller (BET), fourier transform infrared spectroscopy (FT-IR), powder X-ray diffration (PXRD), transmission electron microscope (TEM), X-ray photoelectron spectroscopy (XPS), and UV-Vis. X%PMoV catalysts showed photothermal conversion ability in acetonitrile solvent, and the photothermal conversion efficiency increased with the increase of PMoV. The oxidation desulfurization experiment of dibenzothiophene (DBT, as an example) was carried out in model oil with oxidant H2O2. The results show that the catalyst has the synergistic oxidative desulfurization ability of photocatalysis and photo-driven thermal catalysis on DBT. Due to the effective load of the active PMoV in the SBA-15 channels, the catalyst has good cyclic stability and substrate oxidation product selectivity when the load is 30%. The photothermal catalytic desulfurization strategy is also applicable for other thiophene derivatives and thioether compounds. This paper provides a new idea for using visible-light absorption active components loaded on zeolite for photocatalytic and thermocatalytic desulfurization applications. [ABSTRACT FROM AUTHOR]

The synthesis of unsymmetrical diorganyl selanes was accomplished under electrochemical conditions in an undivided cell utilizing a magnesium cathode and a carbon anode made out of aryl and alkyl iodides and diselanes. This electrochemical cross-electrophile coupling (eXEC) was accomplished using a simple nickel catalyst formed in situ out of Ni(acac)2 and 2,2′-bipyridine in DMF at ambient temperatures. The reaction showed good functional group compatibility, and heteroaryl iodides, such as thiophene or pyridine derivatives, were well accepted. [ABSTRACT FROM AUTHOR]

We report a bioinspired approach to tune surface nanostructures by soft‐template electropolymerization in micellar conditions. Monomers highly favoring π‐stacking interactions are particularly interesting for favoring the polymer deposition in one direction. Here, original triphenylamine‐based monomers di‐substituted by thiophene and carbazole are investigated. Conjugated building blocks monomers are tested to favor deposition vs polymerization, even if the monomers are not perfectly planar. The carbazole derivatives have a much higher electrodeposition capacity than the thiophene derivatives, which is unexpected if thiophene and carbazole are taken alone. Moreover, in all electrodeposited films, monomer seems to be present as shown by cyclic voltammetry experiments, confirming previous works. The amount of monomer vs oligomers is highly dependent on the investigated monomer. For the resulting surface structures, hollow spheres and nanoribbons are particularly formed with some investigated monomers by cyclic voltammetry while nanotubes are observed at constant potential. The formation of nanotubes indicates a polymer growth more favored in one direction. These surfaces are less hydrophobic (water contact angle up to 111.5°) compared to films with spherical nanoparticles but these results can be explained only by the presence of air inside the surface roughness. [ABSTRACT FROM AUTHOR]

Sn2+ oxidation and halide migration are recognized as the major constraints for high‐performance tin halide perovskite solar cells (TPSCs), as they increase the defect state density and thus decrease the carrier lifetime and diffusion length. In this study, two chloride salts of thiophene derivatives are reported to interact with Sn2+ through ligand bonding and immobilize halide ions through hydrogen bonding. Due to the stronger interactions between 1‐(2‐thiophene)ethylamine hydrochloride (α‐TEACl) and the perovskite components, better defect passivation is realized. In addition, thanks to the coordination ability, the lattice stability of tin perovskite is enhanced, and the photoluminescence carrier lifetime and carrier diffusion length are substantially extended from 4.51 ns and 180.78 nm to 23.17 ns, and 1102.20 nm, respectively, which are both among the highest reported values for tin halide perovskites. Consequently, the target device with α‐TEACl achieved a power conversion efficiency (PCE) of up to 14.02%. At the same time, the α‐TEACl device showed excellent long‐term operational stability, retaining ≈92% of the initial efficiency after 2000 h aging in the N2 atmosphere. This work provides a new perspective for regulating the defect passivation and ion migration in lead‐free tin halide perovskites. [ABSTRACT FROM AUTHOR]

A series of 2,5-diaryl-1,3,4-thiadiazole derivatives have been synthesized from fused benzothio-phene-2-carboxylates and alkyl-substituted 2,2′-bithiophene-5-carboxylate. Photophysical and electrochemical properties of the synthesized compounds have been studied. Extension of the conjugation chain in the donor moiety of substituted 1,3,4-thiadiazoles has been found to narrow the energy band gap due mainly to increase of the HOMO energy. [ABSTRACT FROM AUTHOR]

Abstract Background The glassy clover snail, Monacha obstructa (Pfeiffer), is considered one of the major agricultural pests that ruin many field crops, vegetables, orchards of fruits, plants of ornament as well as many other plantations. Synthesis of the Schiff base ligand, namely bis-[4-benzylidene-thiophene-2′-yl] methane (L), produced from the reaction between thiophene-2-carboxaldehyde and diaminodiphenylmethane (MDA), alongside its copper complex were conducted. The output chemical compounds were evaluated in vitro for their molluscicidal activity against the glassy clover snail, M. obstructa by performing the contact technique. Stock solutions were prepared via using (distilled water + DMF) mixture. Furthermore, the impact of these compounds on some critical biochemical indicators: cholesterol, total protein, and acetylcholinesterase (AChE), was evaluated. Results The outcome results demonstrated the significantly higher molluscicidal activity of the Cu(II) chelate compared to its free ligand (L), which in turn reveals the importance of metal chelation in enhancing toxicity against the target species. Particularly, the LC25 and LC50 values are (27.25, 34.65) and (17.88, 25.31) ppm for the ligand (L) and its copper construction, respectively. Additionally, the data confirmed the significant effectiveness of the tested compounds on the assessed biochemical indicators of treated snails. Total protein and cholesterol levels were elevated after treatment with both the ligand (L) and its copper complex while AChE activity increased after treatment with the ligand (L) and reduced upon the exposure to the Cu(II) chelate. Conclusions The findings established that the copper complex exhibited a markedly higher molluscicidal activity compared to the free ligand (L). Also, the results confirmed the significant effects of the investigated compounds on the assessed biochemical indicators of treated M. obstructa snails.

Thiophene polycyclic derivatives are widely used in organic light‐emitting diodes, photovoltaics, and medicinal chemistry applications. Understanding the electronic and structural factors controlling their intersystem crossing rates is paramount for these applications to be successful. This study investigates the photophysical, electronic structure, and excited state dynamics of 1,2‐benzodiphenylene sulfide, benzo[b]naphtho[1,2‐d]thiophene, and benzo[b]naphtho[2,3‐d]thiophene in polar aprotic and non‐polar solvents. Steady‐state absorption and emission spectroscopy, femtosecond transient absorption spectroscopy, and DFT and TD‐DFT calculations are employed. Low fluorescence quantum yields of 1.2 to 2.7 % are measured in acetonitrile and cyclohexene, evidencing that the primary relaxation pathways in these thiophene derivatives are nonradiative. Linear interpolation of internal coordinates calculations predict that an S−C bond elongation reaction coordinate facilitates the efficient intersystem crossing to the T1 state. Excitation of 1,2‐benzodiphenylene sulfide and benzo[b]naphtho[1,2‐d]thiophene at 350 nm or benzo[b]naphtho[2,3‐d]thiophene at 365 nm, populates the lowest‐energy 1ππ* state, which relaxes to the 1ππ* minimum in tens of picoseconds or intersystem crosses to the triplet manifold in ca. 500 ps to 1.1 ns depending on the position at which the benzene rings are added. Excitation at 266 nm does not affect the intersystem crossing rates. Laser photodegradation experiments demonstrate that the thiophene polycyclic derivatives are highly photostable. [ABSTRACT FROM AUTHOR]

Background: The glassy clover snail, Monacha obstructa (Pfeiffer), is considered one of the major agricultural pests that ruin many field crops, vegetables, orchards of fruits, plants of ornament as well as many other plantations. Synthesis of the Schiff base ligand, namely bis-[4-benzylidene-thiophene-2′-yl] methane (L), produced from the reaction between thiophene-2-carboxaldehyde and diaminodiphenylmethane (MDA), alongside its copper complex were conducted. The output chemical compounds were evaluated in vitro for their molluscicidal activity against the glassy clover snail, M. obstructa by performing the contact technique. Stock solutions were prepared via using (distilled water + DMF) mixture. Furthermore, the impact of these compounds on some critical biochemical indicators: cholesterol, total protein, and acetylcholinesterase (AChE), was evaluated. Results: The outcome results demonstrated the significantly higher molluscicidal activity of the Cu(II) chelate compared to its free ligand (L), which in turn reveals the importance of metal chelation in enhancing toxicity against the target species. Particularly, the LC25 and LC50 values are (27.25, 34.65) and (17.88, 25.31) ppm for the ligand (L) and its copper construction, respectively. Additionally, the data confirmed the significant effectiveness of the tested compounds on the assessed biochemical indicators of treated snails. Total protein and cholesterol levels were elevated after treatment with both the ligand (L) and its copper complex while AChE activity increased after treatment with the ligand (L) and reduced upon the exposure to the Cu(II) chelate. Conclusions: The findings established that the copper complex exhibited a markedly higher molluscicidal activity compared to the free ligand (L). Also, the results confirmed the significant effects of the investigated compounds on the assessed biochemical indicators of treated M. obstructa snails. [ABSTRACT FROM AUTHOR]

Preparing well-ordered nanotubes on material surface is fundamental for a huge number of applications. Natural surfaces and theoretical approaches show that porous structures such as nanotubes are key parameters for both surface hydrophobicity and water adhesion. Here, a very easy soft-template electropolymerization approach is used to form nanotubes. A solvent of low water-solubility (dichloromethane) is mixed to water in the presence of a surfactant electrolyte for stabilizing the micelles formed in solution. The monomers investigated are thiophene and carbazole derivatives, and are all fully conjugated for favoring the deposition versus polymerization. Indeed, in all the electrodeposited films, the monomer is mostly present as confirmed by cyclic voltammetry. The key parameters in the resulting nanotubes is the monomer structure because a preferential growth is necessary and this one is induced here especially by π-stacking interactions in the direction perpendicular to monomer. The surfaces composed of nanoparticles or nanotubes are the most hydrophobic with an apparent contact angle up to 130.9° accompanied with strong water adhesion, as reported on gecko foot or rose petal. [ABSTRACT FROM AUTHOR]

Chiral multi‐resonance thermally activated delayed fluorescence (CP‐MR‐TADF) materials hold promise for circularly polarized organic light‐emitting diodes (CP‐OLEDs) and 3D displays. Herein, we present two pairs of tetraborated intrinsically axial CP‐MR‐TADF materials, R/S‐BDBF‐BOH and R/S‐BDBT‐BOH, with conjugation‐extended bidibenzo[b,d]furan and bidibenzo[b,d]thiophene as chiral sources, which effectively participate in the distribution of the frontier molecular orbitals. Due to the heavy‐atom effect, sulfur atoms are introduced to accelerate the reverse intersystem crossing process and increase the efficiency of molecules. R/S‐BDBF‐BOH and R/S‐BDBT‐BOH manifest ultra‐pure blue emission with a maximum at 458/459 nm with a full width at half maximum of 27 nm, photoluminescence quantum yields of 90 %/91 %, and dissymmetry factors (|gPL|) of 6.8×10−4/8.5×10−4, respectively. Correspondingly, the CP‐OLEDs exhibit good performances with an external quantum efficiency of 30.1 % and |gEL| factors of 1.2×10−3. [ABSTRACT FROM AUTHOR]

BACKGROUND: Hot compressed water (HCW), also known as subcritical water (SCW), refers to high‐temperature compressed water in a special physical and chemical state. It is an emerging technology for natural product extraction. The volatile organic compounds (VOCs) generated from the Maillard reaction between l‐ascorbic acid (ASA) and l‐cysteine (Cys) have attracted significant interest in the flavor and fragrance industry. This study aimed to explore the formation mechanism of VOCs from ASA and Cys and examine the effects of reaction parameters such as temperature, time, and pH in HCW. RESULTS: The identified VOCs were predominantly thiophene derivatives, polysulfides, and pyrazine derivatives in HCW. The findings indicated that thiophene derivatives were formed under various pH conditions, with polysulfide formation favored under acidic conditions and pyrazine derivative formation preferred under weak alkaline conditions, specifically at pH 8.0. CONCLUSION: The Maillard reaction between ASA and Cys mainly produced thiophene derivatives, polysulfides, and pyrazine derivatives in HCW. The generation mechanism was significantly dependent on the surrounding pH conditions. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Thiophene, a heterocyclic compound characterized by a five-membered ring comprising four carbon atoms and one sulfur atom, has garnered significant attention in recent research due to its versatile applications in medicinal and chemosensing fields. Thiophene derivatives formed complexes with various transition metals. These complexes exhibit promising anti-inflammatory, anticancer, antibacterial, antifungal and other biological properties. Certainly, the complexation phenomenon involving thiophene derivatives can be effectively used for the recognition of various cations. Thiophene-based compounds can act as selective ligands, forming stable complexes with specific heavy metal ions. This property has significant implications for environmental monitoring, industrial safety, and public health, as the presence of heavy metal ions beyond permissible levels can lead to detrimental effects. This paper explored the versatile applications of thiophene derivatives, investigating their chemosensing potential for the determination of various metal ions covering the period from 2018 to 2024. Thiophene derivatives serve as versatile ligands for metal ions and exhibit fluorescence and colorimetric changes for selective detection of metal ions. Additionally, this study also explores the anticancer efficacy demonstrated by metal complexes derived from thiophene, with a specific emphasis on those formed with platinum-group metals (Ir(III), Ru(II), Ru(III), Rh, Os(II), Os(IV), Pd(II), Pt(II)). [ABSTRACT FROM AUTHOR]

Photosensitizers that are good producers of singlet oxygen, and the photocatalytic reactions promoted by these photosensitizers, have always been of great interest. In this study, we aimed to develop new photosensitizers based on cyclotriphosphazene and evaluate their performance in photocatalytic reactions. In this context, three new cyclotriphosphazene derivatives, each bearing BODIPY and thiophene units, were synthesized, and their molecular structures were characterized using spectroscopic techniques. Both the BODIPY derivatives and their cyclotriphosphazene derivatives had absorption in the visible region, and also, the resulting cyclotriphosphazene compounds exhibited significantly better molar absorption coefficients compared to the precursor BODIPY units. Incorporation of the halogen atom into the molecules resulted in the redshift of absorption and emission maxima, as well as decrease in the fluorescence characteristics of these molecules. The singlet oxygen-producing abilities of the molecules were evaluated by the chemical trapping method using DPBF as the singlet oxygen scavenger molecule, and the change was monitored by UV-vis absorption spectroscopy. Cyclotriphosphazene compounds 7 and 8 performed significantly better than both methylene blue and their precursor units, with singlet oxygen quantum yield values of 0.85 and 0.91. Finally, the ability of these compounds to convert 1,3-cyclohexadiene into peroxides (2,3-dioxabicyclo[2.2.2]oct-5-ene and 3-hydroperoxycyclohexa-1,4-diene) was evaluated. The compounds displayed notable photocatalytic activity toward the oxidation of 1,3-cyclohexadiene compared to tetraphenyl porphyrin (TPP), a known photocatalyst. [ABSTRACT FROM AUTHOR]

The targeted compounds in this research, resveratrol analogs 1–14, were synthesized as mixtures of isomers by the Wittig reaction using heterocyclic triphenylphosphonium salts and various benzaldehydes. The planned compounds were those possessing the trans-configuration as the biologically active trans-resveratrol. The pure isomers were obtained by repeated column chromatography in various isolated yields depending on the heteroaromatic ring. It was found that butyrylcholinesterase (BChE) was more sensitive to the heteroaromatic resveratrol analogs than acetylcholinesterase (AChE), except for 6, the methylated thiophene derivative with chlorine, which showed equal inhibition toward both enzymes. Compounds 5 and 8 achieved the highest BChE inhibition with IC50 values of 22.9 and 24.8 μM, respectively. The same as with AChE and BChE, methylated thiophene subunits of resveratrol analogs showed better enzyme inhibition than unmethylated ones. Two antioxidant spectrophotometric methods, DPPH and CUPRAC, were applied to determine the antioxidant potential of new heteroaromatic resveratrol analogs. The molecular docking of these compounds was conducted to visualize the ligand-active site complexes' structure and identify the non-covalent interactions responsible for the complex's stability, which influence the inhibitory potential. As ADME properties are crucial in developing drug product formulations, they have also been addressed in this work. The potential genotoxicity is evaluated by in silico studies for all compounds synthesized. [ABSTRACT FROM AUTHOR]

The objective of this study is to synthesize novel heterocyclic scaffolds containing a thiophene moiety using easily accessible acetoacetamide as a key synthon. The reaction of acetoacetamide with diazonium salts resulted in the formation of the corresponding thiophene derivatives 4a–c. Additionally, the reaction of acetoacetamide derivative 3 with malononitrile, ethyl cyanoacetate, or 2‐cyanoacetamide, along with elemental sulfur, under refluxing in dioxane containing triethylamine afforded thiophene‐containing derivatives 5a–c. Furthermore, compound 3 reacted with phenyl isothiocyanate in dry dimethylformamide and K2CO3 to yield compound 7. In situ alkylation of the non‐isolable salt 6 was achieved by the addition of methyl iodide, resulting in the formation of methylthio‐thiophene‐2‐carboxamide 8. Compound 7 was employed with numerous alpha‐halogenated reagents in ethanol, affording thiazole derivative 9 and thiophene derivatives 10a and 10b, respectively. Moreover, compound 8 was reacted with hydrazine to produce the 1H‐pyrazole‐4‐carboxamide derivative 11. Additionally, refluxing acetoacetamide derivative 3 with malononitrile and/or ethyl cyanoacetate in dioxane, in the presence of catalytic amount of triethylamine afforded 4‐imino‐3,7‐dimethyl‐4H‐pyrido[1,2‐a]thieno[3,2‐e]pyrimidin‐9(5H)‐one derivatives 12a and 12b. Furthermore, the reactivity of acetoacetamide derivative 3 with 2‐cyanoacetohydrazide was investigated through refluxing the reactants in dioxane, which subsequently yielded the corresponding cyanoacetamide derivative 13. The chemical identity of the newly synthesized compounds was determined by employing infrared spectroscopy (IR), 1H NMR, and 13C NMR techniques. Newly synthesized heterocycles incorporating thiophenes were evaluated for their antioxidant and antimicrobial potentials. Notably, thiophene scaffolds 5a, 10b, 11, and 13 displayed notable antioxidant and antimicrobial activities. [ABSTRACT FROM AUTHOR]

Based on the tremendous pharmacological activities of compounds containing thiazole and carboxamide moieties, the current study aims to prepare new series of thiazole, pyrazole, pyridine, and thiophene derivatives incorporating thiazole carboxamide moiety. Construction of the target compounds was achieved via different chemical transformations and using easily accessible starting materials. The structures of the synthesized compounds were confirmed by all possible spectral and elemental analyses. Results from the in-silico studies showed different Lipophilicity (log p) and Number of Lipinsk's violations due to the presence of NH2, C≡N, OH, and C=O groups which make more electrostatic hydrogen bond interactions in compounds 17 and 20 which increase their TPSA (Å2). These results were confirmed through docking simulation with PDBID: 5I9I which showed the least binding affinity with different proteins, and optimization of these heterocyclic compounds with computational calculations and identification of their physical descriptors which showed more stabilities and directed us for biological evaluation for further studies. [ABSTRACT FROM AUTHOR]

The diketopyrrolopyrrole (DPP) unit represents one of the building blocks more widely employed in the field of organic electronics; in most of the reported DPP-based small molecules, this unit represents the electron acceptor core symmetrically coupled to donor moieties, and the solubility is guaranteed by functionalizing lactamic nitrogens with long and branched alkyl tails. In this paper, we explored the possibility of modulating the solubility by realizing asymmetric DPP derivatives, where the molecular structure is extended in just one direction. Four novel derivatives have been prepared, characterized by a common dithyenil-DPP fragment and functionalized on one side by a thiophene unit linked to different auxiliary electron acceptor groups. As compared to previously reported symmetric analogs, the novel dyes showed an increased solubility in chloroform and proved to be soluble in THF as well. The novel dyes underwent a thorough optical and electrochemical characterization. Electronic properties were studied at the DFT levels. All the dyes were used as active layers in organic field effect transistors, showing balanced charge transport properties. [ABSTRACT FROM AUTHOR]

We designed and synthesized 1,1′,3,3′-tetraaryl-4,4′-bibenzo[c]thiophene derivatives, 1,1′,3,3′-PhtBu-4,4′-BBT (BBT-PhtBu4), 1,1′,3,3′-PhCN-4,4′-BBT (BBT-PhCN4), and 1,1′-PhtBu-3,3′-PhCN-4,4′-BBT (BBT-PhtBu2PhCN2), which have four electron-donating tert-butylphenyl groups, four electron-withdrawing cyanophenyl groups, and two tert-butylphenyl groups and two cyanophenyl groups, respectively, on each thiophene ring by the Stille coupling reaction using 1,1′-diaryl-3,3′-distannyl-4,4′-BBT or 1,1′,3,3′-tetrastannyl-4,4′-BBT. It was found that the photoabsorption and fluorescence maximum wavelengths (λabsmax and λflmax) of BBT-PhtBu4, BBT-PhCN4, and BBT-PhtBu2PhCN2 appear in a longerwavelength region, in comparison with those of 1,1′-diaryl-4,4′-BBT derivatives BBT-PhtBu2 with a tert-butylphenyl group and BBT-PhCN2 with a cyanophenyl group on each thiophene ring. Moreover, the cyclic voltammetry (CV) curves of the 4,4′-BBT derivatives indicated that the introduction of the electron-donating tert-butylphenyl group and/or the electron-withdrawing cyanophenyl group into the benzo[c]thiophene skeleton leads to the lowering of the oxidation potential. In addition, an electron-donating phenyl substituent is more effective than an electron-withdrawing phenyl substituent in the lowering of the oxidation potential. Density functional theory (DFT) calculations as well as the experimental results revealed that increasing the number of electron-donating and electron-withdrawing phenyl groups on the thiophene ring results in the increase of the HOMO energy level and the lowering of the LUMO energy level, respectively, that leads to a decrease in the HOMO–LUMO band gap, that is, a bathochromic shift of the photoabsorption band. Thus, this work provides not only facile synthetic methods for 1,1′,3,3′-tetraaryl-4,4′-BBT derivatives with the same or different aryl substituents on the thiophene rings but also useful methods to precisely adjust their optical and electrochemical properties. [ABSTRACT FROM AUTHOR]

In this study, E-nose and SPME-GC/MS were applied to compare the odour patterns and volatile compounds of two truffle species harvested in different areas of Campania (Southern Italy). In total, 107 Tuber mesentericum (black truffle) and 60 Tuber borchii (bianchetto truffle) truffles were sampled in areas of Avellino, Salerno, Benevento, and Caserta. The E-nose correctly discriminated between Tuber mesentericum and Tuber borchii truffles. The GC/MS analysis revealed qualitative-quantitative differences between Tuber mesentericum and Tuber borchii, with a prevalence of volatile phenols and aromatic compounds for the black truffle, which are responsible for smoky and floral aromas, and ketones, alcohols, aldehydes, and thiophene derivatives for the bianchetto truffle, mostly responsible for earthy mushroom- and garlic-like aromas. The discriminant analysis performed on the E-nose data pattern provided an average correct classification between 55 and 60% for the same species collected in different sites. Tuber borchii truffles were better discriminated based on the harvesting altitude (hilly and coastal areas). GC/MS revealed quantitative differences in the volatile compounds of truffles of the same species collected in different areas, with variations in abundance based on the harvesting site. The distinctive profile of volatile compounds could represent a useful chemical marker to be investigated to authenticate the truffle harvesting area. [ABSTRACT FROM AUTHOR]

Herein, the constructing synthon 3‐oxobutanamidothiophene derivatives 2 a and 2 b were synthesized and utilized for building a wide variety of pyran, thiazole, pyrazole or pyrimidine ring heterocyclic compounds that can be used as anticancer medications. 3‐Oxobutanamidothiophene derivatives 2 a,b were coupled with 4‐substitutedphenyl diazonium chloride to produce the corresponding hydrazones derivatives 3 a–f. Various thiophene‐pyran derivatives 4 a,b were synthesized through the treatment of thiophene components 2 a,b with different arylidene‐malononitrile. 2‐Aminothiophene derivatives 5 were prepared via Gewald's reaction between 2 a,b, elemental sulfur, and various activated nitrile derivatives. The 3‐oxobutanamidothiophene derivatives 2 a,b were reacted with PhNCS and the potassium salt intermediates 6 a,b with ethyl bromoacetate to pick up the corresponding thiophene‐thiazolidin‐4‐one derivatives 7. Treatment of the conforming thiocarbamoyl compounds 8 a,b, which undergo heating with three types of α‐halogenated reagents to afford the corresponding substitutedthiophene‐3‐carboxamides 9 a,b. Condensation of keteneN,S‐acetals 10 a,b with hydrazines furnished the thiophene‐pyrazole‐4‐carboxamide hybrids 11 a,b, while condensation with urea and/or thiourea afforded the corresponding thiophene‐pyrimidine‐5‐carboxamides 12 a,b. The recently synthesized thiophene compounds were characterized there in vitro anticancer properties against HepG2 (hepatocellular carcinoma) and MDA‐MB‐231 (breast cancer) were evaluated. Molecular docking was also performed to predict the binding modes of synthesized derivatives with the good anticancer results designed as potential inhibitors for a specific target. [ABSTRACT FROM AUTHOR]

Herein, we demonstrated a visible light mediated tandem oxidation–organo catalyzed C−S bond functionalization protocol for the cleavage of aromatic C−S bond. The investigation encompassed the functionalization of C−S bonds within sulfones, sulfoxides, and aliphatic sulfide derivatives. However, the process of functionalizing the C−S bond in aromatic sulfides remains uncertain. The presented protocol demonstrates the C−S bond functionalization on benzo[b]benzo[4,5]thieno[2,3‐d]thiophene derivative and amines including primary and secondary amines as well. A radical mediated mechanism was proposed for the tandem oxidation–organocatalyzed C−S bond functionalization protocol. [ABSTRACT FROM AUTHOR]

Hydroquinones bearing an electron‐withdrawing group at the C2‐position can effectively underwent oxidative coupling with (hetero)arenes (e. g. indoles, electron‐rich benzene derivatives) in the presence of 2,3‐dichloro‐5,6‐dicyano‐p‐benzoquinone (DDQ) and FeCl3 to produce the corresponding biaryl products. In the present reactions, the DDQ‐mediated oxidation of hydroquinone derivatives produce benzoquinone intermediate, which subsequently underwent FeCl3‐catalyzed nucleophilic addition of (hetero)arenes to the α,β‐unsaturated carbonyl moiety to give the biaryl product in a one‐pot manner. Especially, the indole‐based biaryl products were further converted into tetracyclic aromatics through DDQ‐mediated oxidation followed by FeCl3‐catalyzed intramolecular cyclization. Thiophene derivatives were also applicable to give the tetracyclic aromatics. Moreover, the photophysical properties of the indole‐ and thiophene‐based tetracyclic aromatics in the solution and the solid states were investigated. [ABSTRACT FROM AUTHOR]

The novel chalcone‐sulfonate derivatives bearing thiophene motif were synthesized and characterized using 1H NMR, 13C NMR, and HRMS analysis. The evaluation of in vitro and in silico potential pancreatic lipase inhibition activity of the novel chalcone‐sulfonate derivatives bearing thiophene motif was scanned. IC50 values of compounds 5 i (28.76±2.11 μM) and 5 f (30.58±0.45 μM) were determined to be more effective pancreatic lipase inhibitors for in vitro studies. The best potential inhibitor for pancreatic lipase binding affinity was found as compound 5 f (−9.8 kcal mol−1) for in silico studies. Although compounds 5 f and 5 i were identified as the best pancreatic lipase inhibitor candidates in vitro and molecular docking studies, compounds 5 f and 5 i were predicted mutagenic and carcinogenic properties in mice according to ADMET studies. Deeply, compound 5 h was a more effective pancreatic lipase inhibitor according to enzyme inhibition, molecular docking, and ADMET studies. It can be said that compound 5 h may be a more efficient drug candidate than orlistat in the treatment of obesity. [ABSTRACT FROM AUTHOR]

It is known that compounds containing sulfur in their structure have a wide range of biological activities, such as antibacterial, antiallergic, antimicrobial, anticancer, and anticonvulsant. In addition, nitrogen-containing heterocyclic compounds are also found in nature and the structure of drugs. Various compounds, such as piperidine and its derivatives, are also widely used in the synthesis of many drugs. Various Schiff bases have been synthesized in drug development studies, and they have been used in clinical applications as drugs and drug candidates. In this context, the synthesis of new thiophene-based Schiff bases containing piperidine rings is aimed. Green chemistry objectives were adhered to in the syntheses. Thiophene-2-carbaldehyde and piperidine derivatives were used as starting compounds, and new compounds containing thiophene-based piperidine were synthesized without adding any catalyst or solvent to the reaction medium. The desired Schiff base compounds were successfully synthesized in high yield and in a short time. [ABSTRACT FROM AUTHOR]

Seven new thiophene hydrazide derivatives were prepared through the coupling of active methylene of 2-cyano-N'-(thiophen-2-ylmethylene)acetohydrazide with diazonium salts of aromatic amines, and heterocyclic amines at 0–5°C in pyridine. The new hydrazonothiophene derivatives could exist in two possible tautomeric forms, which are the enol and keto tautomer. The optimized molecular structures and calculation of the total energies of both tautomers revealed that the enol tautomer is energetically lower than its corresponding keto form. A prediction study for the biological activities of the newly synthesized thiophene hydrazide derivatives were performed via using PASS online software, which displayed promising activities in the treatment of posttraumatic stress disorder, as phosphodiesterase X inhibitor, and as sarcosine oxidase inhibitor. In addition, DFT calculations showed that the new hydrazonothiophene derivatives containing CH3, OCH3, and COOH groups have chemical activity among all the newly synthesized compounds due to their lower band gaps. [ABSTRACT FROM AUTHOR]

Several studies indicate that breast cancer has been associated with increases in mortality rates worldwide. There are several risk factors to developed breast cancer such as obesity, high fat diet, Lack of physical activity, alcohol, use of oral contraceptives, genetic mutations, and others. In addition, some reports suggesting that breast cancer gene 1 (BRCA1) has been related to breast cancer development. This research aimed to determine the possible interaction of thiophene (1) and their analogs (2 to 25) with BRCA-1 using the 3pxb protein and niraparib drug as controls in a docking model The results showed differences in the interaction of thiophene and its analogs with the surface of the 3pxb protein compared to niraparib drug. Besides, other data indicate that the inhibition constant (Ki) associated with thiophene-derivatives-protein complex formation for 11, 13, 16, 18, and 20 was similar manner to Ki for niraparib. These data suggest that compounds 11, 13, 16, 18, and 20 could inhibit the biological activity of BRCA-1; this phenomenon can be translated as a decrease in breast cancer cell growth. [ABSTRACT FROM AUTHOR]

Rhodium-catalyzed reactions of 3-ethynyl-2-pentamethyldisilanylthiophene derivatives (1a–1c) have been reported. At 110 °C, compounds 1a–1c reacted in the presence of a rhodium complex catalyst, yielding thiophene-fused siloles (2a–2c) through intramolecular trans-bis-silylation. To understand the production of 2a from 1a, the mechanism was investigated using density functional theory (DFT) calculations. [ABSTRACT FROM AUTHOR]

A straightforward approach is employed to synthesize methylene‐bridged poly(hetero aromatic)s based on furan, pyrrole, thiophene, and thiophene derivatives. The process involves an electrophilic aromatic substitution reaction facilitated by a visible light‐initiated system consisting of manganese decacarbonyl and an iodonium salt. The approach mainly relies on the formation of halomethylium cation, the attack of this cation to heteroaromatic, regeneration of methylium cation on the heteroaromatic, and reactivity differences between halomethylium and heteroaromatic methylium cations for successful polymerizations. This innovative synthetic strategy lead to the formation of polymers with relatively high molecular weights as the stoichiometric imbalance between the comonomers increased. Accordingly, these newly obtained polymers exhibit remarkable fluorescence properties, even at excitation wavelengths as low as 330 nm. Moreover, by harnessing the halogens at chain ends of homopolymers, block copolymers are successfully synthesized, offering opportunities for tailored applications in diverse fields. [ABSTRACT FROM AUTHOR]

Functionalization of β‐C−H bonds of thiophenes such as their vinylation is more challenging than for their α‐positions. The use of Pd‐catalysis allowed us to vinylate such thienyl β‐positions. Oxidative addition of 2‐(2‐bromoaryl)thiophenes to palladium followed by a Pd 1,4‐migration activates these thienyl β‐C−H positions, then, classical Pd‐catalyzed Heck reaction gives the β‐vinylated 2‐arylthiophene derivatives. In the course of this coupling reaction, the bromide substituent on the aryl unit acts as a traceless directing group. It should also be mentioned that the created C−C bond results from the functionalization of two C−H bonds. This synthesis scheme tolerates a range of substituents on both the aryl ring and the alkene. In addition, this procedure employs an easily available air‐stable catalyst and an inexpensive base. This reaction allows the programmed Pd‐catalyzed synthesis of 2,3,5‐trisubstituted thiophenes using first Suzuki C2‐coupling, then Pd‐catalyzed direct C5‐arylation and finally Pd 1,4‐migration Heck C3‐vinylation. [ABSTRACT FROM AUTHOR]

In this paper it is experimentally demonstrated that the electron‐spin/molecular‐handedness interaction plays a fundamental role in the chiral recognition process. This conclusion is inferred comparing current versus potential (I–V) curves recorded using chiral electrode surfaces, which are obtained via chemisorption of an enantiopure thiophene derivative: 3,3′‐bibenzothiophene core functionalized with 2,2′‐bithiophene wings (BT2T4). The chiral recognition capability of these chiral‐electrodes is probed via cyclic voltammetry measurements, where, Ag nanoparticles (AgNPs) capped with enantiopure BT2T4 (BT2T4@AgNP) are used as the chiral redox probe. Then, the interface handedness is explored by recording spin‐polarized I–V curves in spin‐dependent electrochemistry (SDE) and magnetic‐conductive atomic force microscopy (mc‐AFM) experiments. The quality of the interfaces is thoroughly cross‐checked using X‐ray photoemission spectroscopy, Raman, electrodesorption measurements, which further substantiate the metal(electrode)‐sulfur(thiophene) central role in the chemisorption process. Spin‐polarization values of about 15% and 30% are obtained in the case of SDE and mc‐AFM experiments, respectively. [ABSTRACT FROM AUTHOR]

In an effort to identify novel anti-cancer agents, we employed a well-established High Throughput Screening (HTS) assay to assess the cytotoxic effect of compounds within the ChemBridge DIVERSet Library on a lymphoma cell line. This screen revealed a novel thiophene, F8 (methyl 5-[(dimethylamino)carbonyl]-4-methyl-2-[(3-phenyl-2-propynoyl) amino]-3-thiophenecarboxylate), that displays anti-cancer activity on lymphoma, leukemia, and other cancer cell lines. Thiophenes and thiophene derivatives have emerged as an important class of heterocyclic compounds that have displayed favorable drug characteristics. They have been previously reported to exhibit a broad spectrum of properties and varied uses in the field of medicine. In addition, they have proven to be effective drugs in various disease scenarios. They contain anti-inflammatory, anti-anxiety, anti-psychotic, anti-microbial, anti-fungal, estrogen receptor modulating, anti-mitotic, kinase inhibiting and anti-cancer activities, rendering compounds with a thiophene a subject of significant interest in the scientific community. Compound F8 consistently induced cell death at a low micromolar range on a small panel of cancer cell lines after a 48 h period. Further investigation revealed that F8 induced phosphatidylserine externalization, reactive oxygen species generation, mitochondrial depolarization, kinase inhibition, and induces apoptosis. These findings demonstrate that F8 has promising anti-cancer activity. [ABSTRACT FROM AUTHOR]

Owing to their simple chemical structures and straightforward synthesis, poly(thiophene vinylene) (PTV) derivatives are promising types of polymer donors for organic solar cells (OSCs). However, the structural rigidity of PTVs results in the formation of films with poor mechanical properties, which limits the application of PTVs in intrinsically stretchable (IS)‐OSCs. Here, new carboxylate‐containing PTVs are developed with tuned molecular weight (MW) (PETTCVT‐X, X = L, M, and H) and realize efficient and mechanically durable IS‐OSCs. The crystallinity of the PTVs increases progressively with increasing MW, leading to enhanced hole mobility and suppressed charge recombination of the OSCs. Moreover, both the mechanical stretchability and electrical properties of the PTVs increase significantly with increasing MW, owing to the formation of tie‐chains that connect the isolated crystalline domains. Consequently, OSCs featuring a PTV with the highest MW (PETTCVT‐H) exhibit the highest power conversion efficiency (PCE, 15.3%) and crack‐onset strain (COS, 7.1%) among the series, compared to lower values for the PETTCVT‐L (PCE = 9.7% and COS = 1.3%) and PETTCVT‐M‐based OSCs (PCE = 12.5% and COS = 3.7%). Therefore, the IS‐OSCs employing PETTCVT‐H present the highest initial PCE (10.1%) and stretchability (strain at PCE80% (retaining 80% of the initial PCE) = 16%). [ABSTRACT FROM AUTHOR]

In this study, a biodegradable and eco-friendly biocatalyst (eggshell/Fe3O4) was synthesized utilizing eggshell impregnated with Fe3O4 nanoparticles. The characterization of prepared catalyst was carried out by Fourier transform infrared radiation (FT-IR), scanning electron microscopy (SEM), X-ray Diffraction (XRD), energy-dispersive X-ray (EDX), thermal gravimetric analysis-differential thermogravimetry (TGA-DTG), vibrating sample magnometer (VSM), and atomic force microscopy (AFM). The eggshell/Fe3O4 biocatalyst was served in multi-component reactions (MCRs) for the synthesis of 2-amino thiophene derivatives from variety aromatic aldehydes, malononitrile, ethyl acetoacetate, and sulfur (S8). To achieve optimal reaction conditions, a thorough examination was conducted on key factors, such as the solvent type, reaction time and temperature, and the ratio of eggshell to Fe3O4. The findings suggest that high yield product can be obtained at microwave temperature (MW) in EtOH solvent within 10 min. Additionally, the eggshell/Fe3O4 biocatalyst exhibited high catalytic activity, which was sustained over the five cycles, without any significant decline in its performance.

Purpose: This paper aims to prepare new modified alkyd resins and use it as an antimicrobial binder for surface coating applications. Design/methodology/approach: Various modified alkyd resins were prepared by partial replacement of 3,6-dichloro benzo[b]thiophene-2-carbonyl bis-(2-hydroxy ethyl)-amide as a source of polyol with glycerol and confirmed by acid value, FT-IR, 1H-NMR. The modified alkyd resins were covering a wide range of oil lengths and hydroxyl content (0%, 10%, 20% and 30% excess-OH). The antimicrobial activity of the prepared alkyds was also investigated. The coatings of 60 ± 5 µm thickness were applied to the surface of glass panels and mild steel strips by means of a brush. Physico-mechanical tests, chemical resistance and antimicrobial activities were investigated. Findings: The obtained results illustrate that the introduction of benzo[b]thiophene derivative as a modifier polyol within the resin structure improved the film performance and enhanced the physico-mechanical characteristics, chemical resistance and the antimicrobial activities. Practical implications: The modified alkyd resins can be employed as antimicrobial binders in paint compositions for a variety of surfaces, particularly those that are susceptible to a high number of bacteria. Originality/value: Modified alkyd resins based on antimicrobial heterocyclic compounds have the potential to be promising in the manufacturing of antimicrobial coatings and development of paints, allowing them to function to prevent the spread of microbial infection, which is exactly what the world requires at this time. Also, they can be applied in different substrates for industrial applications. [ABSTRACT FROM AUTHOR]

This study demonstrated the synthesis of a number of pyrazolo[1,5-a]quinazoline derivatives about 24 products based on the starting material 4-(2-phenylhydrazono)-4H-pyrazol-3-amine derivatives 1a-f. Moreover, other ring systems including thiophene, pyrazole, thiazole and pyran (16 compounds) were prepared based on another starting compounds 2-(furan-2-ylmethylene)cyclohexane-1,3-dione 10 and 5,5-dimethyl-3-phenyl-2-thioxo-2,3,5,6-tetrahydrobenzo[d]thiazol-7(4H)-one 18. The multi-component reaction was used to prepare all the previous compounds. The structures of all the synthesised compounds were confirmed by the analytical and spectral data. Some selected compounds were chosen to test their anticancer activity against six cancer cell lines, namely A549, HT-29, MKN-45, U87MG, SMMC-7721 and, H460 utilizing foretinib as the positive control and the standard MTT assay in vitro. Toward the tested cell lines, nine compounds were the most cytotoxic compounds. The results obtained revealed that the synthesized compounds are good cytotoxic agents and of great impact for future work. [ABSTRACT FROM AUTHOR]

In this study, we synthesized a novel corrosion inhibitor derived from thiophene and conducted a comprehensive evaluation of its inhibitory properties through both experimental and theoretical approaches. Our investigation encompassed experimental assessments employing Mass loss tests and electrochemical techniques. Additionally, we performed computational studies to delve into the electronic structure and bonding characteristics of the inhibitor, aiming to elucidate its inhibitory mechanism. Our findings revealed that the synthesized inhibitor displayed remarkable inhibitory efficiency, demonstrating its effectiveness in preventing the corrosion of mild steel. Specifically, the thiophene derivative exhibited an impressive inhibitory efficiency of 92.8%, underscoring its potential as a robust corrosion inhibitor for mild steel. Furthermore, this study delved into optimizing the conditions for employing the thiophene derivative as a corrosion inhibitor. Our investigation revealed that the most effective inhibition was achieved at a concentration of 0.5 mM and a temperature of 303 K. To elucidate the interaction between the inhibitor and the mild steel surface, we applied the Langmuir adsorption isotherm concept, shedding light on both the physical and chemical adsorption processes of the thiophene derivative on the metal's surface. Our investigations demonstrated that the addition of the inhibitor significantly reduced the corrosion rate of the metal. Our computational results further reinforced these experimental findings, indicating that the inhibitor formed stable adsorption complexes on the metal surface. This dual confirmation from experimental and computational approaches strengthens the confidence in the inhibitor's efficacy in mitigating corrosion. [ABSTRACT FROM AUTHOR]

The synthesis of three conjugated copolymers TPP1–3 was carried out using a palladium-catalyzed [3+2] cycloaddition polymerization of 1,6-dibromopyrene with various dialkynyl thiophene derivatives 3a–c. The target copolymers were obtained in excellent yields and high purity, as confirmed by instrumental analyses. TPP1–3 were found to divulge a conspicuous iodine adsorption capacity up to 3900 mg g−1, whereas the adsorption mechanism studies revealed a pseudo-second-order kinetic model. Furthermore, recyclability tests of TPP3, the copolymer which revealed the maximum iodine uptake, disclosed its efficient regeneration even after numerous adsorption-desorption cycles. Interestingly, the target copolymers proved promising nickel ions capture efficiencies from water with a maximum equilibrium adsorption capacity (qe) of 48.5 mg g−1. [ABSTRACT FROM AUTHOR]

Polyoxovanadates (POVs) have received widespread attention in catalytic applications due to their various structures and remarkable redox properties. By introducing a second transition metal, POV-based inorganic–organic hybrid (POVH) catalysts show increasing stability and more catalytic active sites compared with pure POVs. In this perspective article, POVH materials as oxidative catalysts have been classified into two main categories according to the interactions between transition metal-complex units and POV clusters: (i) hybrids with metal–organic units act as isolated cations and (ii) hybrids with an organic ligand coordinate to the second transition metal, which is further linked to a POV cluster via oxygen bridges directly or indirectly to give zero-, one-, two- or three-dimensional supramolecular structures. The oxidative conversion of organic compounds, including thiophene derivatives, thioethers, alkanes, alcohols, and alkenes, and oxidative detoxification of a sulfur mustard simulant or degradation of lignin, along with the oxidative photo/electrocatalytic transformation of organic compounds catalyzed by POVH materials, are discussed in detail. Furthermore, the challenges and prospects toward the development of POVH catalysts are explored briefly from our perspectives. [ABSTRACT FROM AUTHOR]

Diketopyrrolopyrrole (DPP) derivatives with thiophene capping rings are widely used as semiconductors in organic electronics. Their optoelectronic properties can be adjusted by adding different electroactive groups or by extending the conjugation of the central core, as well as by regulating their self‐assembly through noncovalent interactions. One effective strategy demonstrated to improve the performance and morphology of organic solar cells is incorporating hydrogen‐bonding units into DPPs. While the functionalization of the DPP lactams and the coupling of aromatic units to the thiophene rings are the most common procedures to tune the properties of such derivatives, modifying the thiophene capping units with hydrogen‐bonding groups is a challenging synthetic task. Despite this difficulty, incorporating amide‐containing substituents into the thiophene rings of single core thiophene‐capped DPP derivatives could yield exciting results, as the advantages of having hydrogen‐bonded π‐conjugated systems based on these modified DPPs have not been explored thoroughly. This work reports on an efficient method for synthesizing such derivatives. [ABSTRACT FROM AUTHOR]

This work aimed to produce novel heterocyclic compounds such as chromene, thieno[3,2-f]chromene, chromeno[5,6-d]thiazole and quinoline derivatives. The newly synthesized heterocyclic compounds were evaluated against cancer cell lines aiming to get new anticancer agents. Dimedone underwent different multi-component reactions to produce fused thiophene, thiazole, coumarin, pyran and pyridine derivatives. Some reactions were catalyzed by effective magnetically separable nanocatalyst. The anti-proliferative activity of the newly synthesized compounds toward six cancer cell was studied. In addition, inhibitions of the most active compounds the thieno[3,2-f]chromene derivatives 16a–f toward cancer cell lines classified according to the disease were also studied. Moreover, the newly synthesized compounds were screened for their anticancer potentials against hepatocellular carcinoma HepG2 and cervical carcinoma HeLa cell lines. Anti-proliferative evaluations, inhibitions were performed for all of the synthesized compounds where the varieties of substituent through the aryl ring and the heterocyclic ring afforded compounds with high activities. Inhibitions toward cancer cell lines classified according to the disease together with inhibitions toward HepG2 and cervical carcinoma HeLa cell lines were measured. Molecular docking of compounds 15c and 18c was performed. [ABSTRACT FROM AUTHOR]

In this work, two D-A monomers 2,3-di(5-methylfuran-2-yl)-5,7-di(thiophene-2-yl) thiopheno[3,4-b] pyrazine (MFTTP) and 2,3-di(5-methylfuran-2-yl)-5,7-di(4-methoxythiophen-2-yl) thiopheno [3,4-b] pyrazine (MFMOTTP) were first obtained by Stille Coupling reaction, and then the corresponding composites were obtained by in-situ oxidative polymerization method with supercapacitor carbon. The surface morphology, chemical structure, and the element valence states of two materials were characterized by scanning electron microscopy, infrared and XPS, respectively. The specific surface areas of PMFTTP@SC and PMFMOTTP@SC are measured as 756.5 and 954.9 m2/g, respectively. The CV curves were used to determine the initial oxidative and initial reduction potentials, both polymers have a narrow band gap with E g values below 1.5 eV, electron clouds in the HOMO and LUMO orbits of the polymer are mainly distributed on the aromatic rings of the polymer backbone. Polymer composite materials were used as the anode materials and the lithium sheets were used as counter electrode, and then lithium ion batteries are assembled. The first discharge specific capacities of PMFTTP@SC and PMFMOTTP@SC are 741.9 and 951.3 mAh/g at a current density of 100 mA/g, and as the electrodes are activated in the subsequent cycles, their coulomb efficiencies can reach more than 92% from the third cycle. In contrast, PMFMOTTP with methoxy-thiophene as the donor unit has higher conductivity and lower corresponding impedance due to its stronger electron donating ability and abundant pore structure, which is also more conducive to the lithiation/delithiation redox process. [ABSTRACT FROM AUTHOR]

Metal surfaces can become damaged by corrosion when they interact with their surroundings, leading to huge financial losses. The use of corrosion inhibitors is one of the most crucial ways to combat the risky and hazardous effects of corrosion. In the present research, electrochemical techniques and surface analysis have been used to characterize the inhibition properties of (3-hydroxy-4-((4-nitrophenyl)diazenyl)-5-(phenylamino)thiophen-2-yl)(phenyl)methanone for the corrosion of carbon steel in an aerated 1.0 M HCl solution. Steel's corrosion resistance was discovered to be improved by the presence of the examined inhibitor in 1.0 M HCl medium through the adsorption of the inhibitor species to create a barrier layer. The findings showed that when inhibitor concentrations increased and solution temperatures decreased, the inhibition performance (%IE) of the compound under study enhanced. In the light of inhibitor probe's chemical makeup and theoretical analysis, the mechanism of the inhibition process was addressed. In a 1.0 M HCl solution containing 5 × 10−5 M of the inhibitor, the inhibition performance, at room temperature, was found to be almost 97%. The electrochemical results revealed that the examined compound successfully prevented carbon steel corrosion as a mixed-type inhibitor. The Langmuir and Freundlich isotherms are pursued by the adsorption of the examined inhibitor. Additionally, using Arrhenius and transition state equations, the activation thermodynamic parameters ΔEa, ΔH*, and ΔS* were determined and explained. The adsorption process was illustrated using DFT computation and MC simulations. The experimental findings and theoretical simulations concurred surprisingly well. Finally, the paper presents a discussion of the inhibitory mechanism. [ABSTRACT FROM AUTHOR]

An efficient synthesis of highly fluorescent trisubstituted thiophenes was achieved via iodine-catalyzed, base-promoted annulation employing elemental sulfur as a sulfur source. The compounds exhibit excellent photophysical properties like solid-state fluorescence, high quantum yield and solvatochromism. As these thiophene derivatives have potential application in the development of optoelectronic devices, gram-scale synthesis of the desired heterocycles was demonstrated. [ABSTRACT FROM AUTHOR]

A highly efficient protocol for stereoselective synthesis of novel polycyclic benzo[b]thiophene derivatives was developed. Using quinine-derived bifunctional thiourea (5 mol%) as a catalyst, asymmetric [3+3] annulation of N-(benzo[b]thiophen-2-yl)-sulfonamide with 2-alkynyl cycloenone could provide dihydrobenzo[4,5]thieno[2,3-b]pyridine derivatives in moderate to good yields (up to 93%) with mostly excellent enantioselectivities (up to 97% ee) under mild conditions. In addition, large-scale experiments and derivatizations were explored. In particular, the target product in large-scale experiments could be easily purified by filtration and the filtrated product showed >99% ee. [ABSTRACT FROM AUTHOR]

Polymerized small molecule acceptors have recently greatly facilitated the development of all‐polymer solar cells (All‐PSCs) with respect to the power conversion efficiencies (PCEs). However, high‐performance and low‐cost polymer donors for All‐PSCs are still lacking, limiting further large‐scale manufacturing of All‐PSCs. Herein, this work designs and synthesizes a new thiophene derivative, FETVT, featuring vinyl‐bridged fluorine and ester‐substituted monothiophene. Incorporation of FETVT into a polymer yields a high‐performance polythiophene derivative PFETVT‐T, which exhibits deep‐lying HOMO level, suitable solution pre‐aggregation ability, finely‐tuned polymer crystallinity, and appropriate thermodynamic miscibility with the polymer acceptor L15. As a result, binary based on PFETVT‐T achieves a record PCE of 11.81% with agood stability, representing a breakthrough for polythiophenes and their derivatives‐based All‐PSCs, which is also significantly higher than that (1.92%) of All‐PSCs based on its isomerized analog. Remarkably, PFETVT‐T achieves an impressive PCE exceeding 16% via the implementation of a ternary blend design. These findings offer a hopeful pathway toward attaining high‐performance, stable, and cost‐effective PSCs. [ABSTRACT FROM AUTHOR]

Synthetic methodologies involving direct C−H functionalization are promising to improve sustainability in organic synthesis. However, these newly developed strategies may have a scarce appeal for larger scale applications due to the high catalyst loading, harsh conditions or their typically long reaction times that affect severely the process productivity. Flow chemistry technology is a recognized tool to improve both the efficiency and scalability in organic synthesis that can overcome these issues. In the present paper we studied an "in flow" method for the direct arylation of thiophene derivatives with aromatic bromides to promptly afford heteroaromatic biaryls, which are recurrent motifs both in biologically active molecules and in functional materials. By using a packed‐bed reactor containing potassium carbonate as the solid base and an automated system, we could develop a reliable methodology for thiophene arylation in flow with yields up to 90 % within a residence time of 30–60 minutes. This strategy is suitable for a wide variety of substrates and allowed the reaction to be carried out at gram‐scale reaching a productivity value of 1.1 g h−1. [ABSTRACT FROM AUTHOR]

Synthesis of nitriles, esters, amides of the substituted 2-amino-1-(4,5,6,7-tetra-hydrobenzo[b]thiophen-2-yl)-4-oxo-5-(2-oxo-2-arylethylidene)-4,5-dihydro-1H-pyrrole-3-carboxylic acids bearing the nitrile group at the thiophene ring by the reaction of the substituted 3-(3-cyanothiophen-2-yl)iminofuran-2(3H)-ones with the appropriate cyanoacetic acid derivatives was developed. The synthesized compounds demonstrated pronounced antinociceptive activity and low toxicity (toxicity class V of practically nontoxic substances). [ABSTRACT FROM AUTHOR]