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There is an increasing demand for the development of catalytic reagents that are nontoxic due to the growing environmental concerns in the present organic transformation. Bismuth(III) compounds have significant potential as catalysts for a range of organic synthesis due to their low toxicity, strong Lewis acid catalytic activity, and great flexibility. In this research work, a series of various chemically and pharmacologically important six‐membered fused nitrogen‐/oxygen‐based heterocycle derivatives were efficiently prepared via a one‐pot multicomponent reaction starting from aromatic aldehydes, malononitrile, and barbituric acid in presence of green and reusable Lewis catalyst bismuth(III) triflate, that is, Bi(OTf)3 in EtOH/H2O (1:1) media. Bi(OTf)3 has the additional benefit of being reusable catalyst, ready availability, eco‐friendliness, and easy to handle to obtain corresponding products in excellent yields (83%–94%). Structure of all synthesized products was characterized on the basis of FT‐IR, 1H‐NMR, 13C‐NMR, and ESI–MS analysis. [ABSTRACT FROM AUTHOR]

Objective: To synthesize bis-Schiff bases bearing thiobarbituric acid and to screen their anti-urease inhibitory potential. Methods: In this study, 1,3-dimethylbarbituric acid derivatives were synthesized by a four-step process. Using K2CO3, 2,4-dihydroxy benzaldehyde and chloro ethyl acetate were esterified in DMF in the first step under reflux condition. The reaction was then carried out by combining the esterified aldehyde with 1,3-dimethylbarbituric acid at room temperature for about an 1 h. Hydrazine hydrate was then mixed with compound (II) in ethanol solvent with acetic acid acting as catalyst. Finally, substituted aromatic aldehydes were treated with bis-hydrazide (III) using ethanol and acetic acid as a catalyst. Results: The newly synthesized compounds were screened for their urease inhibition (in vitro). Four analogs, including (IIIj) (IC50 = 15.22 ± 0.49 μM), (IIIg) (IC50 = 16.05 ± 0.16 μM), (IIIa) (IC50 = 16.29 ± 0.73 μM), and (IIIb) (IC50 = 21.17 ± 0.21 μM) were found most powerful inhibitors than standard thiourea (IC50 = 22.80 ± 2.20 μM). The urease inhibition was also seen in compound (IIIi), (IIIc), (IIIh), (IIIe), (IIId), and (IIIf) however it was less from standard. The structure stability and chemical reactivity of the compounds were checked by density functional theory (DFT) method. Furthermore, the molecular docking simulation was performed to check the protein (urease) and ligand interactions and binding affinities by using AutoDock Vina. Conclusions: The synthesized derivatives attributed temendous potential against urease enzyme. Compound (IIIj) was found as the most potent anti-urease agent. Additional research including taxicological and in vivo is necessary to know the safety, effectivness and mechanism of action of these potent molecules. [ABSTRACT FROM AUTHOR]

Barbituric acid is a heterocyclic compound with various pharmacological and biological applications. This review paper provides a comprehensive overview of barbituric acid's synthesis, reactions, and bio-applications, highlighting its multifaceted role in various fields. Many heterocyclic derivatives were formed based on barbituric acid, for instance, pyrano-fused pyrimidine derivatives, spiro-oxindole derivatives, chrome-based barbituric acid derivatives, and many more via the atom economic method, Michael addition reaction, Knoevenagel condensation reaction, etc. In the context of bio-applications, this review examines the production of a wide range of bioactive drugs like anti-histamine, anti-leprotic, sedative–hypnotic, anti-inflammatory, anti-urease, antiviral, anti-AIDS, antimicrobial, antioxidant, anticonvulsant, anesthetic agent, antitumor, and anticancer drugs using efficient multicomponent reactions. By showcasing the versatility and potential of this compound, it aims to inspire further research and innovation in the field, leading to the development of novel barbituric acid derivatives with enhanced properties and diverse applications, with coverage of the literature relevant up to 2024. [ABSTRACT FROM AUTHOR]

Two novel metal complexes, C1 and C2, were synthesized through the reaction of an azo dye ligand, obtained by coupling 4‐chloroaniline with 1,3‐dimethyl barbituric acid. The structure of the ligand was confirmed using Fourier‐transform infrared spectroscopy (FTIR) and Nuclear magnetic resonance (NMR). UV–Vis spectroscopy was employed to assess the ligand's sensing ability toward six different metal ions. Comprehensive characterization of the synthesized metal complexes was conducted using elemental analysis, X‐ray photoelectron spectroscopy (XPS), thermogravimetric analysis–difference thermogravimetry (TGA‐DTG), FTIR, UV–Vis spectroscopy, electron paramagnetic resonance (EPR) spectroscopy, and single‐crystal X‐ray diffraction (SC‐XRD). X‐ray analysis revealed octahedral coordination geometry with a 2:1 ligand‐to‐metal ratio and dimethylformamide (DMF) coordination with the metal atom in both complexes. Hirshfeld analysis and 2D fingerprint plots were employed to investigate supramolecular and intermolecular interactions within the crystal system. Density functional theory (DFT/B3LYP) calculations were utilized to compute energy gaps and other important theoretical features. Sensing experiments with tetrabutylammonium fluoride (TBAF) were conducted at a concentration of 1 × 10−5 M. Furthermore, the bioactivity of the synthesized metal complexes and ligand L was evaluated through molecular docking studies against Protein Data Bank (PDB IDs) 4XUY (Staphylococcus aureus) and 3BQW (Aspergillus niger). Also, antimicrobial activity was assessed using the agar well diffusion technique, revealing that complexes C1 and C2 exhibited enhanced antimicrobial activities against the tested organisms compared to the parent azo dye ligand. The computational and experimental bioactivity data are in good agreement with each other. [ABSTRACT FROM AUTHOR]

An effective protocol for synthesis of some new pyrazolylbarbiturate derivatives is reported through a one-pot, three-component reaction between barbituric/thiobarbituric acid, aroylphenylhydrazones and arylglyoxal derivatives. All reactions were conducted in ethanol as solvent without using any catalyst and products were obtained by simple filtering of the precipitated solids in high yields. All products were characterized by 1H and 13C NMR and IR spectral and elemental analysis data. [ABSTRACT FROM AUTHOR]

A method was proposed for the synthesis of some new molecular hybrids containing quinoline, 1,2,3-triazole and barbituric acid residues via Knoevenagel condensation, O-prorgylation and copper(I)-catalyzed azide alkyne cycloaddition reactions. The fourteen compounds were screened for the anticancer activity against MCF-7, MDA-MB-468 and MDA-MB-231 cell lines using MTT assay. Some compounds were screened for inhibitory activity against tyrosine kinase EGFR. Finally, in silico studies like molecular docking on EGFR and VEGFR-2 and ADMET have supported the in vitro results. [ABSTRACT FROM AUTHOR]

A systematic study has been conducted on barbiturate complexes of all five alkali metals, Li–Cs, prepared from metal carbonates or hydroxides in an aqueous solution without other potential ligands present, varying the stoichiometric ratio of metal ion to barbituric acid (BAH). Eight polymeric coordination compounds (two each for Na, K, and Rb and one each for Li and Cs) have been characterised by single-crystal X-ray diffraction. All contain some combination of barbiturate anion BA− (necessarily in a 1:1 ratio with the metal cation M+), barbituric acid, and water. All organic species and water molecules are coordinated to the metal centres via oxygen atoms as either terminal or bridging ligands. Coordination numbers range from 4 (for the Li complex) to 8 (for the Cs complex). Extensive hydrogen bonding plays a significant role in all the crystal structures, almost all of which include pairs of N–H···O hydrogen bonds linking BA− and/or BAH components into ribbons extending in one dimension. Factors influencing the structure adopted by each compound include cation size and reaction stoichiometry as well as hydrogen bonding. [ABSTRACT FROM AUTHOR]

A series of 2‐ and 3‐methylindole (MI)‐based barbituric acid (BA) and thiobarbituric acid (TBA) derivatives (2MIBA, 2MITBA, 3MIBA and 3MITBA) in Donor (D)‐π‐Acceptor (A) configuration having strong intramolecular charge transfer (ICT) interactions were synthesized by the simple and efficient route. Methyl substituent at the 2‐ and 3‐ position alters the coplanarity of the DA systems leaving 2MI derivatives as nonplanar whilst 3MI derivatives as planar one and the latter forms an intramolecular hydrogen bond between indole N−H and −C=O of BA or TBA, which facilitates the excited state intramolecular proton transfer (ESIPT) emission in 3MIBA and 3MITBA. Comparing the UV‐visible absorption spectra in the solution phase reveals that the ICT band of 2MITBA and 3MITBA are red‐shifted from the 2MIBA and 3MIBA due to the stronger electron‐accepting nature of C=S than the C=O. Since these molecules exert photo‐induced intramolecular charge transfer followed by a rotation around the bridging methylene group, only weak fluorescence is noted. Nevertheless, in an aggregated state, both 3MIBA and 3MITBA exhibit significant aggregation‐induced enhanced emission (AIEE) characteristics in their THF/water mixture, but the effect is not promising for 2MIBA and 2MITBA. Further, melamine‐3MITBA co‐assembly aided through an intermolecular hydrogen bonding network can also be used as a solid‐state emitter. [ABSTRACT FROM AUTHOR]

Hot‐water‐soluble starch (HWSS) was employed as binder for fabrication of a composite from magnetite and Ag nanoparticles (NPs). Electron microscopy images showed a good dispersion of magnetite NPs in the matrix of HWSS. This observation indicates that HWSS tends to coat the maximum surface of magnetite by encapsulation of individual magnetite NPs, leading to disassembly of their aggregates. The HWSS‐coated magnetite NPs were employed as nano‐support for immobilization of fine Ag NPs generated in situ via reduction of Ag+ cations by glucose. Monitoring of the formation and growth of Ag NPs by UV–Vis spectroscopy made it possible to set up an optimal condition for fabrication of the nano‐composite and to verify the supremacy of HWSS‐coated magnetite NPs over bare magnetite NPs as support in this new protocol. Valuable insights into the texture of the nano‐composite were obtained by VSM, FT‐IR and XRD studies. The bio‐derived nano‐composite displayed an interesting magnetic property and an efficient catalytic activity in the three‐component synthesis of pyrano[2,3‐d]pyrimidines. It is a robust heterogeneous catalyst and can be simply retrieved from reaction mixtures by magnetic separation method. [ABSTRACT FROM AUTHOR]

The study focuses on the synthesis of isatin- barbituric acid compounds through a two-step process. In the first step, using mannich reaction, new derivatives of Isatin are synthesized by reacting Isatin with either barbituric acid, along with formaldehyde. This reaction results in the formation of Isatin-barbituric acid derivative. In the second step, these Isatin derivatives are further reacted with various aniline derivatives to generate new compounds containing Isatin. Spectroscopic methods including FTIR, ¹H NMR, and 13C NMR are used to characterize the produced molecules. The study investigates the biological effects of several of the synthetic chemicals on certain bacterial strains, including Klebsiella pneumoniae and Staphylococcus aureus. The potential antibacterial activities of these substances are evaluated. [ABSTRACT FROM AUTHOR]

Insolubility of functional molecules caused by polymorphism sometimes poses limitations for their solution‐based processing. Such a situation can also occur in the preparation processes of supramolecular polymers formed in a solution. An effective strategy to address this issue is to prepare amorphous solid states by introducing a "coformer" molecule capable of inhibiting the formation of an insoluble polymorph through co‐aggregation. Herein, inspired by the coformer approach, we demonstrated a solubility enhancement of a barbiturate π‐conjugated compound that can supramolecularly polymerize through six‐membered hydrogen‐bonded rosettes. Our newly synthesized supramolecular coformer molecule features a sterically demanding methyl group in the π‐conjugated unit of the parent molecule. Although the parent molecule exhibits low solubility in nonpolar solvents due to the formation of a crystalline polymorph comprising a tape‐like hydrogen‐bonded array prior to the supramolecular polymerization, mixing with the coformer compound enhanced the solubility by inhibiting mesoscopic organization of the tapes. The two monomers were then co‐polymerized into desired helicoidal supramolecular polymers through the formation of heteromeric rosettes. [ABSTRACT FROM AUTHOR]

Insolubility of functional molecules caused by polymorphism sometimes poses limitations for their solution‐based processing. Such a situation can also occur in the preparation processes of supramolecular polymers formed in a solution. An effective strategy to address this issue is to prepare amorphous solid states by introducing a "coformer" molecule capable of inhibiting the formation of an insoluble polymorph through co‐aggregation. Herein, inspired by the coformer approach, we demonstrated a solubility enhancement of a barbiturate π‐conjugated compound that can supramolecularly polymerize through six‐membered hydrogen‐bonded rosettes. Our newly synthesized supramolecular coformer molecule features a sterically demanding methyl group in the π‐conjugated unit of the parent molecule. Although the parent molecule exhibits low solubility in nonpolar solvents due to the formation of a crystalline polymorph comprising a tape‐like hydrogen‐bonded array prior to the supramolecular polymerization, mixing with the coformer compound enhanced the solubility by inhibiting mesoscopic organization of the tapes. The two monomers were then co‐polymerized into desired helicoidal supramolecular polymers through the formation of heteromeric rosettes. [ABSTRACT FROM AUTHOR]

In this paper, two polymers (P-AMB and P-DMAB) with aggregate induced emission (AIE) effect were synthesized successfully. Compared with the polymer monomer BNEA, P-AMB and P-DMAB not only have stronger AIE effect, but also have excellent water solubility and better light stability. In addition, the two polymers were tested for their response to different anions in aqueous solution, and both showed high selectivity and sensitivity to S2−. The sensing mechanism of S2− was studied by ultraviolet visible spectrum, infrared spectrum and 1H NMR spectrum studies. These two polymer sensors have strong anti-interference ability and wide pH response range (5.0 ~ 10.0) when detecting S2−, and could be used for qualitative and quantitative detection of S2− in 100% aqueous solution. [ABSTRACT FROM AUTHOR]

The four-component condensation of ethyl acetoacetate, phenylglyoxal hydrate, barbituric acid, and primary amines was used to obtain polysubstituted pyrroles containing a barbituric acid fragment. In some cases, by-products formed by the three-component condensation of phenylglyoxal hydrate, barbituric acid, and amines were isolated. [ABSTRACT FROM AUTHOR]

Fabrication of fluorescent water‐soluble citric acid‐urea based carbon dots have been done using an organic pioneer possessing barbituric acid for the recognition of adenosine triphosphate (ATP). The carbon dots has been characterized through various techniques, such as, powder X‐ray diffraction (PXRD), Fourier‐transform infrared spectroscopy (FTIR), high‐resolution transmission electron microscopy (HRTEM), UV‐visible (UV‐vis), and Fluorescence (FL) spectroscopy. The emissive nature of carbon dots made them worthwhile for the detection of ATP in different plant samples, for instance, curry leaves, coriander, tulsi and jasmine flower leaves. Also, the barbituric acid precursor (1) has been successfully applied for the detection of bisulfate anion in real samples with good recovery. The absorption responses for bisulfate ion permitted it to be used as effective colorimetric sensor in water and the color changes have been scrutinized using smartphone application. [ABSTRACT FROM AUTHOR]

When derivatives of barbituric acid, tetra aromatic aldehyde bearing ether groups and malononitrile or Meldrum acid have one-pot three-component reactions, the analogous new poly pyranopyrimidine derivatives are formed as poly heterocyclic compounds. Deduction of the structures of the products was performed using their IR, 1H-NMR, and 13C-NMR spectroscopy along with CHN analysis. Besides, the synthesized heterocycles were also evaluated concerning their biological activities, including toxicity examination, anti-inflammatory effects, antioxidant activities, and anti-bacterial effects. [ABSTRACT FROM AUTHOR]

New hydrazone derivate, (1Z,2E)-2-(2-(1-(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)ethyl)hydrazineylidene)-2-(p-tolyl)acetaldehyde oxime (H2L) was synthesized by 5-acetyl-1,3-dimethyl-barbituric acid and p-methyl isonitrosophenylhydrazine. Its molecular and crystal structures were determined by single crystal X-ray analysis. It belongs to triclinic system P-1 space group with a = 7.1722 (3) Å, b = 10.5362 (4) Å, c = 11.7675 (5) Å, α = 98.844 (4)°, β = 98.882 (4)°, γ = 104.330 (4)°, Z = 2 and V = 833.95 (6) Å3. In the molecular structure, the intramolecular N–H···O and N–H···N hydrogen bonds enclose S(6) ring motifs. In the crystal structure, the intermolecular C–H···O and O–H···O hydrogen bonds link the molecules into centrosymmetric dimers, enclosing R22(10) and R44(10) ring motifs, in which they may be effective in stabilization of the structure. The Hirshfeld surface analysis of crystal structure indicates that the most important contributions for crystal packing are from H...H (48.5%), H...O/O...H (23.7%) and H...C/C...H (9.7%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in crystal packing. Computational chemistry indicates that in the crystal, O–H···O and C–H···O hydrogen bond energies are 95.9 and 87.5 kJ mol−1. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that stabilization is dominated via the nearly equal strengths of the electrostatic and dispersion energy contributions. [ABSTRACT FROM AUTHOR]

One-pot three-component reactions of tetra aromatic aldehyde, including ether groups, derivatives of barbituric acid with ammonia, and ammonium acetate, result in new poly barbituric moiety and, correspondingly, tetra pyrimidodipyrimidine heterocycles. IR, 1H-NMR, and 13C-NMR spectroscopy along with CHN analyses were used to derive the structures of the products. Moreover, the synthesized compounds were investigated in terms of biological performance, consisting of toxicity examination, along with antioxidant, anti-inflammatory, and antibacterial activities. [ABSTRACT FROM AUTHOR]

Naphthopyranopyrimidine derivatives are an important class of naturally occurring tetraheterocyclic organic compounds that are used as dyes, fluorescent materials for visualization of biomolecules, and in laser technology. Moreover, they are known for biological and pharmaceutical activities. Herein, we briefly reviewed the history of synthesis approaches of naphthopyranopyrimidine and spironaphthopyranopyrimidine derivatives from naphthols, aldehydes/isatins, and barbituric acid/1,3-dimethylbarbituric acid/thiobarbituric acid/1,3-dimethyl-2-thiobarbituric acid/6-amino-1,3-dimethyluracil in the presence of both homogeneous and heterogeneous catalysts reported by research groups. [ABSTRACT FROM AUTHOR]

A simple, practical, and efficient one-pot three-component protocol was employed for the synthesis of functionalized 5-aryl-5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-diones by reacting barbituric acid, aromatic aldehydes, and substituted anilines using p-toluenesulfonic acid as a readily available and very inexpensive catalyst. The synthesized compounds were characterized by 1H and 13C NMR, FT-IR, and mass spectra and elemental analyses and screened for their in vitro antimicrobial potential against bacterial strains Dickeya sp. and fungal strain Fusarium oxysporum. 7-Nitro-5-(4-nitrophenyl)-5,10-dihydropyrimido[4,5-b]-quinoline-2,4(1H,3H)-dione showed better antimicrobial potential (MIC 3000 µg/mL and MFC 5000 µg/mL) as compared to the other screened compounds. [ABSTRACT FROM AUTHOR]

A concept of piezo-responsive hydrogen-bonded π-π-stacked organic frameworks made from Knoevenagel-condensed vanillin–barbiturate conjugates was proposed. Replacement of the substituent at the ether oxygen atom of the vanillin moiety from methyl (compound 3a) to ethyl (compound 3b) changed the appearance of the products from rigid rods to porous structures according to optical microscopy and scanning electron microscopy (SEM), and led to a decrease in the degree of crystallinity of corresponding powders according to X-ray diffractometry (XRD). Quantum chemical calculations of possible dimer models of vanillin–barbiturate conjugates using density functional theory (DFT) revealed that π-π stacking between aryl rings of the vanillin moiety stabilized the dimer to a greater extent than hydrogen bonding between carbonyl oxygen atoms and amide hydrogen atoms. According to piezoresponse force microscopy (PFM), there was a notable decrease in the vertical piezo-coefficient upon transition from rigid rods of compound 3a to irregular-shaped aggregates of compound 3b (average values of d33 coefficient corresponded to 2.74 ± 0.54 pm/V and 0.57 ± 0.11 pm/V), which is comparable to that of lithium niobate (d33 coefficient was 7 pm/V). [ABSTRACT FROM AUTHOR]

A new synthetic procedure for obtaining two previously reported donor-acceptor butadiene dyes, namely 5-(3,3-bis(4-methoxyphenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione and 5-(3,3-bis(4-(dimethylamino)phenyl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, based on the InCl3-catalyzed coupling 1,3-diethyl-2-thiobarbituric acid with 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol and 1,1-bis(4-(dimethylamino)phenyl)prop-2-yn-1-ol, respectively, is presented. The reactions, which cleanly proceed in water under MW irradiation, involve the initial generation of the corresponding enals by Meyer-Schuster rearrangement of the alkynols and their subsequent Knoevenagel condensation with the 2-thiobarbituric acid derivative. By following the same approach, the novel butadiene 5-(3,3-bi([1,1′-biphenyl]-4-yl)allylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, which was characterized by 1H and 13C{1H} NMR, IR, UV-Vis, elemental analysis and HRMS, was synthesized in 79% yield. [ABSTRACT FROM AUTHOR]

• The new aggregation induced emission (AIE) molecule (BNOH) was synthesized. • The relationship between the molecular structure and appearance of AIE was studied. • The effect of BNOH intermolecular hydrogen bond on molecular AIE was studied. • The formation mode of BNOH molecular aggregates was studied and determined. Barbiturates had been widely studied as a molecule with aggregation induced emission (AIE) phenomenon, but barbiturates as a group with multiple hydrogen bond donor and acceptor sites, the relationship between intermolecular hydrogen bond and AIE phenomenon has not been mainly studied. In this paper, a new barbiturate fluorescence molecule BNOH with hydroxyl group was designed and synthesized in order to analyze the relationship between hydrogen bond and molecular AIE phenomenon by increasing the functional group (–OH) that was easy to form hydrogen bond. By spectroscopic analysis, BNOH had structural torsion in aqueous mixed solution, which led to fluorescence decrease, while in aprotic mixed solvent, there was strong AIE phenomenon. DFT and TD-DFT calculations at the B3LYP/6-31G (d) were performed for a deeper understanding of optical transitions. In addition, in order to investigate the difference of its fluorescence phenomenon, two other barbiturate derivatives were synthesized and their spectra were compared with BNOH. The relationship between hydrogen bond and AIE phenomenon of barbiturates was proved, and the fluorescence mechanism of BNOH in organic solvent was proposed and determined. We believe that this study will not only increase the understanding of barbiturate AIE compounds, but also contribute to the study of the important role of hydrogen bonds in the fluorescence phenomenon of barbiturate AIE compounds. A barbituric acid compound (BNOH) with significant AIE effect, which was resulted from the regular aggregation by the intermolecular hydrogen bonds, has been synthesized in this work. [Display omitted] [ABSTRACT FROM AUTHOR]

• The formation of cocrystal between nitrofurantoin and barbituric acid was investigates, and no related research has been reported. • Dynamic information monitoring of cocrystal synthesis process of barbituric acid and nitrofurantoin. • Research on weak intermolecular interaction in eutectic synthesis of barbituric acid and nitrofurantoin. Cocrystal can effectively improve the physical and chemical properties of active pharmaceutical ingredients, which provides the possibility of changing the key medicinal properties of active pharmaceutical ingredients. This capability has garnered increasing attention in pharmaceutical field. In this study, we synthesized a cocrystal of barbituric acid and nitrofurantoin and characterized it using terahertz and Raman spectroscopy. Density functional theory simulation was used to calculate the terahertz and Raman spectra of the barbituric acid and nitrofurantoin cocrystal. The calculated results indicated that the spectra in the C configuration aligned most closely with the measured vibrational spectra, thus providing confirmation of the synthesis of the cocrystal. The study focused on analyzing intermolecular interactions, vibration modes, and molecular structure in the cocrystal. It is found that intermolecular hydrogen bonds play a crucial role in cocrystal synthesis. These results provide a wealth of information and basic bench marks for investigating the structure and intermolecular interactions of barbituric acid and nitrofurantoin cocrystals. It also provides a reference for the simulation of drug cocrystal formation and the intermolecular hydrogen bond interaction between active pharmaceutical ingredients and various cocrystal based on Raman and terahertz vibrational spectroscopy combined with DFT theory. [Display omitted] [ABSTRACT FROM AUTHOR]

The primary aim of this research is to comprehensively assess the applicability of chitosan biopolymer towards water treatment application and to enhance its adsorption capacity towards Remazol brilliant blue R-19 dye. This has been achieved through physical modification to obtain the material in hydrogel form and chemical modification by crosslinking it with barbituric acid. The characterization of the resulting Chitosan-barbituric acid hydrogel (CBH) was carried out using various analytical techniques such as SEM-EDX, FT-IR, TGA-DTA, XRD, and BET. CBH was employed as the adsorbent to eliminate R-19 dye from aqueous media. Utilizing response surface methodology (RSM), the parameters were fine-tuned, leading to the achievement of more than a 95% removal for R-19 dye. The adsorption behavior closely adhered to the Langmuir isotherm and pseudo-second-order kinetics. An interesting observation indicated that the rise in temperature leads to rise in adsorption capacity of CBH. The maximum adsorption capacities evaluated at 301.15 K, 313.15 K, 318.15 K, and 323.15 K were 566.6 mg g−1, 624.7 mg g−1, 671.3 mg g−1, and 713.5 mg g−1 respectively, in accordance with the Langmuir isotherm model. Examining the thermodynamics of the adsorption process revealed its spontaneous nature (ΔG = −21.14 to −27.09 kJ mol−1) across the entire temperature range. Furthermore, the assessment of the isosteric heat of adsorption (ΔH ads) was conducted using the Clausius–Clapeyron equation, with results indicating an increase in ΔH ads from 1.85 to 2.16 kJ mol−1 with temperature rise from 301.15 K to 323.15 K due to augmented surface loading. This suggested the existence of lateral interactions between the adsorbed dye molecules. The potential of adsorbent for regeneration was investigated, demonstrating the ability to reuse the material. Sustainability parameter calculated for synthesis process reflected a notably low E-factor value of 0.32 demonstrated the synthesis is environment friendly. [Display omitted] • Chitosan was crosslinked using barbituric acid to get hydrogel. • It was characterized and subjected to R-19 dye amputation. • The q m value was increased to 713.5 mg g−1at 323.15 K under optimum conditions. • RSM was used to optimize the pH, dose, time and concentration against temperature. • Studies of regeneration demonstrated that the adsorbent CBH is economically viable. [ABSTRACT FROM AUTHOR]

• Synthesis of indoloquinoxaline based D-π-A type conjugated molecules. • Fluorescent probe for hypochlorite detection. • "TURN ON"/"TURN OFF" type of fluorescent probe behaviour. We have successfully synthesized three new donor-π-acceptor (D-π-A) type indoloquinoxaline-based conjugated molecules in which electron rich indoloquinoxaline unit is coupled with different acceptor units such as barbituric acid, thiobarbituric acid and reduced isatin through thiophene spacer. All three molecules are characterized by IR, NMR and mass analysis. The photophysical, electrochemical, thermogravimetric analysis and DFT calculations studies were carried out for the synthesized molecules. The molecules were explored as a chemosensor for the detection of hypochlorite and the sensing mechanisms of these molecules towards hypochlorite were examined by 1H NMR spectra. These molecules exhibit weak fluorescence emission due to a strong intramolecular charge transfer (ICT) effect between indoloquinoxaline moiety and different acceptors. Interestingly, compounds, M1 and M3 showed enhanced fluorescence recognition performance, whereas compound M2 showed quenching fluorescence recognition performance for hypochlorite ion. Our study suggests that altering the D-π-A structure and employing suitable ICT effect can enhance the detection ability of molecules for the target analyte. [Display omitted] [ABSTRACT FROM AUTHOR]

Magnetic nanofiber cellulose (NFC) was selected as a biopolymer surface for the reaction with ferric metformin and a novel nanocatalyst was prepared. This green heterogeneous organometallic catalyst was analyzed by physiochemical techniques. The new metformin drug complex supported on magnetic NFC was used as a powerful and efficient catalyst for the synthesis of functionalized 4H-pyrans derivatives. The antimicrobial activity of the products showed excellent activity against all the bacterial and fungal strains (especially compounds 7q and 6r). [ABSTRACT FROM AUTHOR]

A detailed kinetic study on the tautomerization reactions of barbituric acid (BA) at elevated temperatures from 270 K up to 1000 K was performed in this work. The B3LYP/6-311 + G(3df,2p) density functional theory (DFT) calculations were performed to evaluate the rate constants of transition states (TS) conversions of the tautomerization reactions. The connections from a given TS to the corresponding local minima of the reactant and product sides were confirmed by means of employing the intrinsic reaction coordinate (IRC) method. Moreover, the quantum theory of atoms in molecules (QTAIM) approach was employed to analyze the molecular mechanisms of reactions. The effects of vibrational normal mode frequencies of the reactant and TS were investigated on the curvature of the corresponding Arrhenius plot in the presence and absence of the tunneling effect. For each tautomerization reaction, the investigated reaction was partitioned into three different stages and four zones. The obtained results were plotted along with the corresponding reaction coordinates for each reaction considering and comparing different factors in agreement with already affirmed concepts. As a consequence, details of performed kinetic study on the tautomerization reactions of BA were successfully provided in this work. [ABSTRACT FROM AUTHOR]

Formations of bimolecular barbituric acid (BA) complexes through hydrogen-bonding (HB) interactions were investigated in this work. BA has been known as a starting compound of pharmaceutical compounds developments, in which the molecular and atomic features of parent BA in homo-paring with another BA molecule were investigated here. The models were optimized to reach the stabilized structures and their properties were evaluated at the molecular and atomic scales. Density functional theory (DFT) calculations were performed to provide required information for achieving the goal of this work. Six dimer models were obtained finally according to examining all possible starting dimers configurations for involving in optimization calculations. N-H... O and C-H... O interactions were also involved in dimers formations besides participation of the X-center of parent BA in interaction. Molecular and atomic scales features were evaluated for characterizing the dimers formations. As a consequence, several configurations of BA dimers were obtained showing the importance of performing such structural analyses for developing further compounds from BA. [ABSTRACT FROM AUTHOR]

Synthesis of one‐dimensional nanofibers with distinct topological (higher‐order structural) domains in the same main chain is one of the challenging topics in modern supramolecular polymer chemistry. Non‐uniform structural transformation of supramolecular polymer chains by external stimuli may enable preparation of such nanofibers. To demonstrate feasibility of this post‐polymerization strategy, we prepared a photoresponsive helically folded supramolecular polymers from a barbiturate monomer containing an azobenzene‐embedded rigid π‐conjugated scaffold. In contrast to previous helically folded supramolecular polymers composed of a more flexible azobenzene monomer, UV‐light induced unfolding of the newly prepared helically folded supramolecular polymers occurred nonuniformly, affording topological block copolymers consisting of folded and unfolded domains. The formation of such blocky copolymers indicates that the photoinduced unfolding of the helically folded structures initiates from relatively flexible parts such as termini or defects. Spontaneous refolding of the unfolded domains was observed after visible‐light irradiation followed by aging to restore fully folded structures. [ABSTRACT FROM AUTHOR]

Synthesis of one‐dimensional nanofibers with distinct topological (higher‐order structural) domains in the same main chain is one of the challenging topics in modern supramolecular polymer chemistry. Non‐uniform structural transformation of supramolecular polymer chains by external stimuli may enable preparation of such nanofibers. To demonstrate feasibility of this post‐polymerization strategy, we prepared a photoresponsive helically folded supramolecular polymers from a barbiturate monomer containing an azobenzene‐embedded rigid π‐conjugated scaffold. In contrast to previous helically folded supramolecular polymers composed of a more flexible azobenzene monomer, UV‐light induced unfolding of the newly prepared helically folded supramolecular polymers occurred nonuniformly, affording topological block copolymers consisting of folded and unfolded domains. The formation of such blocky copolymers indicates that the photoinduced unfolding of the helically folded structures initiates from relatively flexible parts such as termini or defects. Spontaneous refolding of the unfolded domains was observed after visible‐light irradiation followed by aging to restore fully folded structures. [ABSTRACT FROM AUTHOR]

Synthesis of one‐dimensional nanofibers with distinct topological (higher‐order structural) domains in the same main chain is one of the challenging topics in modern supramolecular polymer chemistry. Non‐uniform structural transformation of supramolecular polymer chains by external stimuli may enable preparation of such nanofibers. To demonstrate feasibility of this post‐polymerization strategy, we prepared a photoresponsive helically folded supramolecular polymers from a barbiturate monomer containing an azobenzene‐embedded rigid π‐conjugated scaffold. In contrast to previous helically folded supramolecular polymers composed of a more flexible azobenzene monomer, UV‐light induced unfolding of the newly prepared helically folded supramolecular polymers occurred nonuniformly, affording topological block copolymers consisting of folded and unfolded domains. The formation of such blocky copolymers indicates that the photoinduced unfolding of the helically folded structures initiates from relatively flexible parts such as termini or defects. Spontaneous refolding of the unfolded domains was observed after visible‐light irradiation followed by aging to restore fully folded structures. [ABSTRACT FROM AUTHOR]

In this study, the synthesis of pyrido[2,3‐d:5,6‐d′]dipyrimidines using CoFe2O4@SiO2‐PA‐CC‐guanidine‐SA magnetic nanoparticles with excellent yields has been reported. Pyrido[2,3‐d:5,6‐d′]dipyrimidines were synthesized from the four‐component reaction of barbituric acid derivatives, benzaldehyde derivatives and ammonium acetate in water at room temperature. The synthesized catalyst was identified using Fourier‐transform infrared spectroscopy (FT‐IR), scanning electron microscopy (SEM), energy‐dispersive X‐ray spectroscopy (EDX), X‐ray powder diffraction (XRD), thermogravimetric analysis (TGA) and vibrating sample magnetometer (VSM) techniques. [ABSTRACT FROM AUTHOR]

Density functional theory (DFT) calculations were performed to investigate electronic and structural properties of barbituric acid (BA) and sixtheen of its derivatives to show impacts of structural functionalization on the features of parent BA. The models were optimized and the minimum energy structures were confirmed by frequency calculations. Molecular and atomic descriptors were evaluated for the optimized models, in which the results of formation binding strength and molecular orbital features indicated significance of such functionalization processes on the observed properties. The highest occupied and the lowest unoccupied molecular orbitals (HOMO and LUMO) and their related parameters all indicated magnitudes of changes from one molecule to another one. Furthermore, atomic scale quadrupole coupling constants (Cq) were evaluated for the nitrogen and oxygen atoms of BA compounds showing significance of structural functionalization impacts on the atomic properties of parent BA. As a consequence, such structural analyses of BA compounds could show their characteristic features for further developments especially for their efficient pharmaceutical applications. [ABSTRACT FROM AUTHOR]

Mesoporous NiO nanoarchitectures (NAs) with controlled hexagonal platelet‐ and flower‐like morphology were synthesized using facile hydrothermal methods in different reaction conditions. The NiO NAs were characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), N2 adsorption /desorption isotherms, and wide‐angle X‐ray diffraction. It was found that controlled morphology, large surface areas, and high crystallinity of NiO NAs offered high catalytic reactivity toward Knoevenagel condensation reactions. Large reaction yields in an aqueous media and easy separation of the NiO NAs without losing the catalytic activity were observed. Further, the formation mechanism of -C=C- bonds over NiO NAs surface was explored by density functional theory (DFT). These findings open a new avenue for efficient -C=C- bonds formation using reusable NiO NAs catalyst without using any expensive solvents. [ABSTRACT FROM AUTHOR]

An efficient, one-pot, three-component synthesis of some novel heteroaryl aminoindandione derivatives using ninhydrin, various heteroaryl amines, and barbituric/2-thiobarbituric acids catalyzed by p-toluenesulfonic acid as organocatalyst has been achieved within a short period of time. The present methodology offers several advantages including operational simplicity, clean reaction, high yield, short reaction times, high atom economy, easy workup procedure, and simple purification of products by nonchromatographic methods. [ABSTRACT FROM AUTHOR]

A number of new stable methanobenzo[7,8][1,3] dioxocino[4,5‐d]pyrimidine‐1,3(2H)‐dione derivatives (4a‐l) were synthesized using a simple one‐pot procedure with considerable efficiency. Reaction parameters were further optimized in order to achieve a single‐product procedure. Plausible routes for reaction progress were investigated and it was proved that the reaction goes through regioselective condensation yielding an interesting V‐shaped structure. Spectral data of all products under study were used to elucidate the chemical structure and X‐ray structure analysis was performed to unambiguously prove the proposed structure for 4c. [ABSTRACT FROM AUTHOR]

• Newly synthesized oxime barbiturate derivative hydrazone ligand characterized by X-ray crystallography, offering detailed insights into crystal structure, H-atom contacts, and void analysis. • Ligand with -Cl group compared to -CH3 group, revealing higher binding constants and stronger DNA interactions for the -Cl-containing ligand, potentially enhancing biological activity. • Utilizing crystallography, Hirshfeld surface analyses, crystal voids, interaction energy calculations, and energy frameworks, providing a thorough understanding of the ligand's structural and functional properties. • Synthesized compounds exhibit significant inhibitory effects on various cancer cell lines, displaying dose-dependent responses at 24, 48, and 72 h, comparable to etoposide, suggesting their potential as anticancer agents. • Ligands demonstrate promising potential for inducing selective lethality in both cancer and healthy cells, emphasizing their effectiveness as anticancer agents. This study focuses on a newly synthesized compound using 5-acetyl-1,3-dimethyl-barbituric acid and p-chloroisonitrosophenylhydrazine, inspired by a previously synthesized and characterized oxime barbiturate derivative. The compound's biological activity is investigated in comparison to the previously illuminated compound. Additionally, a thorough examination of the The significance of H-atom contacts in determining crystal packing has been validated by Hirshfeld surface representations. Void analysis demonstrates the absence of significant voids, contributing to mechanical stability. Intermolecular interaction energies underscore the dominance of electrostatic and dispersion contributions. Energy frameworks visually convey the magnitude of interaction energies, emphasizing the nearly equal strength of electrostatic and dispersion contributions in crystal stabilization. Furthermore, the study examines the biological activities of the synthesized compounds on various cancer cell lines. Cytotoxicity analyses via MTT assays reveal substantial inhibitory effects of the compounds on cancer cells over 24, 48 and 72 h, displaying dose-dependent responses. Particularly, despite lower cytotoxicity compared to cisplatin, the compounds exhibit comparable activity to etoposide. Cytotoxic selectivity indices (SI) suggest potential selective cytotoxicity against cancer cells. In conclusion, this comprehensive analysis integrates crystallographic insights with biological activity assessments, providing a holistic understanding of the structural and functional properties of the synthesized compounds. The results contribute to advancements in crystal engineering and offer a promising avenue for the development of anticancer agents with selective cytotoxicity. [Display omitted] [ABSTRACT FROM AUTHOR]

[Display omitted] • Chitosan-barbituric acid (CBA) for exclusion of CrVI and CN– from aqueous solution. • Operational parameters were optimized by experiments and RSM. • More than 90% removal of CrVI and CN– ions in single stage. • CBA adsorption capacities were 534.75 mg g−1 and 251.66 mg g−1 respectively. • CBA could be regenerated through a number of cycles. The objective of this study is to transform chitosan biopolymer by crosslinking with barbituric acid into an amine-rich product that could be applied as a water treatment agent. Chitosan-barbituric acid (CBA) was synthesized by lyophilization process and characterized using FT-IR, XRD, TGA-DTA, SEM-EDX, BET surface area and BJH pore size distribution analysis. The pH pzc was found to be 7.7 indicating applicability towards both cations and anion adsorption. The CBA was used for seizure of CrVI and CN– from aqueous solutions in batch adsorption as well as fixed bed column experiments. Response surface methodology (RSM) was used as a statistical tool to optimize the functioning parameters resulting in more than 90 % removal of these ions. As shown by isotherm and kinetics data, Langmuir isotherm and pseudo second order kinetics exhibited a good fit for the adsorption process. The maximum adsorption capacities of CBA towards CrVI and CN– evaluated using Langmuir isotherm fitment were 534.75 mg g−1 and 251.66 mg g−1 at pH 4.0 and 6.0 respectively. Thermodynamic studies indicated spontaneous and enthalpy driven course with large negative enthalpy changes of −56.39 and −31.81 kJ mol−1 respectively. Fixed bed column studies showed that the material could be used for larger sample volume treatment even at 200 mg/L CrVI and 100 mg/L CN−1 concentration. Regeneration studies of adsorbent was conducted over five adsorption–desorption cycles with removal efficiency more than 50 %indicating reusability of the adsorbent. Analysis of adsorbent sustainability revealed that the synthesis was eco-friendly as indicated by low value of E-factor of 0.32. [ABSTRACT FROM AUTHOR]

In order to find new drugs with potent antiproliferative effect, a series of novel barbituric acid derivatives containing azoles at the C-5 position were designed, synthesized, and evaluated for antiproliferative activity against three human cancer cell lines (BEL-7402, MCF-7, and HCT-116) using MTT assay. Several of the synthesized compounds exhibited potent antiproliferative effects. The most promising compound was 5-((1-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl) methylene)pyrimidine-2,4,6(1H,3H,5H)-trione (3s), which showed considerably high antiproliferative activity in the BEL-7402 cell line, with a half-maximal inhibitory concentration of 4.02 µM and 20.45-fold higher selectivity for BEL-7402 cells than for normal L02 cells. The apoptosis experiment showed that compound 3s induced apoptosis and cell necrosis in a concentration-dependent manner and exert its anti-proliferative activity. Therefore, compound 3s exhibited better therapeutic activity and specificity compared with the positive control 5-fluorouracil. [ABSTRACT FROM AUTHOR]

Dihydro [2,3D] pyridine substituted enaminosulfonamide compounds have been synthesized and their effects on carbonic anhydrase II (hCAII) have been evaluated. Pyrido [2,3 d] pyrimidines were synthesized from barbituric acid derivatives, malonanitrile, aldehyde derivatives in basic condition and then hydrolyzed with hydrochloric acid. The targeted compounds were synthesized from amino sulfanilamide, dihydro [2,3D] pyridine compounds, and triethylorthoformate. ¹H NMR, 13C NMR, FT-IR and elemental analysis were used for the structural analysis of the compounds. The half maximal inhibitory concentration (IC50) values of the compounds were determined to be between 27.03 and 104.39 μM for hCA II and 19.85-76.64 μM for Ki. [ABSTRACT FROM AUTHOR]

A novel series of (thio)barbituric-phenoxy-N-phenylacetamide derivatives 7a-l was synthesized and evaluated against Helicobacter pylori urease. The latter assay revealed that all the synthesized compounds 7a-l (IC50 = 0.69 ± 0.33–2.47 ± 0.23 μM) were significantly more potent than two used standard inhibitors, thiourea (IC50 = 23 ± 0.73 μM) and hydroxyurea (IC50 = 100 ± 1.7 μM). Docking study of the synthesized compounds demonstrated that these compounds as well fitted in the urease active site. Moreover, molecular dynamic study of the most potent compound 7d showed that this compound created important interactions with the active site flap residues, Cys592 and His593. Furthermore, in silico pharmacokinetic study predicted that all the synthesized compounds are drug-like. [ABSTRACT FROM AUTHOR]

The well-resolved terahertz (THz) absorption spectrum of barbituric acid has been investigated using terahertz time-domain spectroscopy. Four distinct THz spectral features and two shoulder peaks were observed in the range of 10–124 cm–1. A complete analysis was performed with density functional theory, which provided an excellent agreement between solid-state simulation and experiment. The solid-state analysis indicates that the six experimental spectral features observed at low temperature consist of nine infrared-active vibrational modes. Further simulations based on hydrogen-bond isotopologues were performed to study the involvement of hydrogen bonds in the collective modes. A feature at 118.0 cm–1 mainly stems from the collective vibration of dimer hydrogen bonds (m) while features at 102.0 and 109.6 cm–1 primarily come from the collective vibrations of linear hydrogen bonds (n). The results may be useful for monitoring molecular reaction in industrial production according to the state of hydrogen bonds. [ABSTRACT FROM AUTHOR]

A well‐defined and stable "AB" binary system in the presence of "C" a crystalline synthon ground in a ball mill undergoes selective transformation in the solid state according to the equation AB+C→AC+B. When the amount of C is increased two times then the equation AB+2C→AC+BC is valid. The other variants are more complex. The pathway BC+A is allowed and leads to the AC and B products. The pathway AC+B is not preferred, and no transformation is observed. These non‐obvious correlations were observed for cocrystal of barbituric acid (BA):thiobarbituric acid (TBA) recently reported by Shemchuk et al. (Chem. Commun. 2016, 52, 11815–11818) in the presence of 1‐hydroxy‐4,5‐dimethyl‐imidazole 3‐oxide (HIMO). This synthon shows high affinity for the BA0.5TBA0.5 cocrystal as well for its individual components, BA and TBA. Single‐quantum, double‐quantum (SQ‐DQ) 2D 1H very fast MAS NMR with a spinning rate of 60 kHz was employed as a basic and most diagnostic tool for the study of cocrystals transformations. Analysis of the experimental data was supported by theoretical calculations, including computation of the stabilization energy, Estab, defined as the energy difference between the energy of a co‐crystal and the sum of the energies of particular components in the respective stoichiometric ratios. Two mechanisms of synthon replacement have been proposed. Pathway 1 assumes a concerted mechanism of substitution. In this approach, synthon attack is synchronized in time with the departure of one of the components of the binary system. Pathway 2 implies a non‐concerted process, with an intermediate stage in which three separate components are present. Evidence suggesting a preference for Pathway 2 is shown. [ABSTRACT FROM AUTHOR]

The reaction of symmetrical (thio)barbituric acids with aldehydes in the presence of 4‐methyl morpholine yielded a new form of 4‐methyl morpholinium bis‐(thio)barbiturate containing charge‐separated intermolecular and eight‐membered intramolecular H‐bonds. X‐ray Crystallography, FT‐IR, and 1H and 13C‐NMR spectroscopy techniques were used for structure characterizations. Some of these compounds showed potent anticancer activities. Cytotoxicity of the synthetic compounds against HeLa and MCF‐7 cell lines were performed by MTT assay. In addition, a comparative molecular field analysis was carried out, and the effects of substituents on the biological activities of these compounds were explained. [ABSTRACT FROM AUTHOR]

A turn on fluorescence probe was designed cleverly and synthesized simply through the condensation reaction between coumarin derivative and barbiturate, for sensitively specific recognition of hypochlorite ion (ClO−). This probe displayed a transient monitor process (about 5 min) to ClO− in a wide range of pH values (3‐10), and the monitor limit could be estimated as low as 0.73μM. What's more, this probe could perform fluorescence imaging of ClO− in living cells, and make ClO− in aqueous solution appear on the convenient test strip visually. [ABSTRACT FROM AUTHOR]

A simple and efficient method for the synthesis of novel 4‐hydroxy‐4H‐chromene‐pyrazoles and 4‐hydroxy‐4H‐chromene‐barbiturates was developed from the reaction of 2‐ethoxy‐2H‐chromene chalcones with pyrazolin‐5‐one and barbituric acid catalyzed by l‐proline in water. The developed protocol is applicable for the construction of biologically important 4H‐chromenes from easily accessible chalcones having various substituents. This reaction proceeds through Aldol condensation, Michael addition and hydrolysis reactions followed by the elimination of ethoxy group. This methodology offers cleaner conversion, a shorter reaction time and high yields. For the first time, we report the synthesis of novel 4‐hydroxy‐4H‐chromenes from 2‐ethoxy‐2H‐chromene chalcones and pyrazolin‐5‐one/barbituric acid using l‐proline (72–86 % yield in 6 h). Water was used as the solvent for all the compounds it represents a green synthetic protocol. [ABSTRACT FROM AUTHOR]

A three-component reaction between barbituric/thiobarbituric acid, phosphines, and dialkyl acetylenedicarboxylates in dry acetonitrile led to the formation of barbiturate/thiobarbiturate-functionalized stable zwitterionic salts in a one-pot process. When trialkyl phosphites were used instead of phosphines, barbiturate/thiobarbiturate-functionalized phosphonates were obtained in good yields. [ABSTRACT FROM AUTHOR]

Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned substrates with diethyl malonate, diethyl-2-alkyl malonate, pentane-2,4-dione, or ethyl-3-oxobutanoate yielded corresponding products. Significant advantages of this sonochemical synthetic protocol with regard to the conventional thermal methods include easy reaction setup and work-up steps, reasonably mild conditions, shorter reaction times (∼30 min) and comparably high product yields. The characterization of the synthesized compounds was based on melting points, FT-IR, GC-MS, 1H-NMR techniques, and the obtained data were also checked from the previously published studies. [ABSTRACT FROM AUTHOR]

• Positive impact of self-assembly on the photovoltaic performance is demonstrated. • Study of the donor-π-acceptor oligothiophene comprising barbituric acid. • Note of hydrogen-bonded supramolecular-array of barbiturated-oligothiophene via SEM. • Efficiency enhancement by ~50% due to self-assembly approach. • Device outcome strongly supports the impact of self-assembly in BHJ devices. The positive impact of self-assembly on the photovoltaic properties of a donor-π-acceptor oligothiophene molecule coded as CP3 , which contains a barbituric acid as a terminal acceptor unit and triphenylamine as donor, enabling hydrogen-bonded spherulites to assemble in its films is described. The hydrogen-bonded supramolecular array of barbiturated-oligothiophene molecules were directly visualized by scanning electron microscopy. Bulk-heterojunction solar cells comprising CP3 and the fullerene PC 61 BM show a power conversion efficiency of 6.31%, which is markedly higher than a structural analogue CP4 , which comprises a N -ethylrhodanine terminal acceptor unit incapable of participating in the same degree of self-assembly, supporting the impact of self-assembly in BHJ devices. [ABSTRACT FROM AUTHOR]