Journal of Molecular Structure最新文献

{"title":"New benzothiazole-indole-1,2,3-triazole-N-phenylacetamide derivatives as cytotoxic agents: Design, synthesis, and in vitro cytotoxic evaluations","authors":"Amir Mohammad Taherkhani ,&nbsp;Mohammad Hosein Sayahi ,&nbsp;Bahareh Hassani ,&nbsp;Navid Dastyafteh ,&nbsp;Maryam Mohammadi-Khanaposhtani ,&nbsp;Elahe Rafiei ,&nbsp;Maryam Meshkani ,&nbsp;Sajedeh Safapoor ,&nbsp;Mohammadreza Mohajeri Tehrani ,&nbsp;Bagher Larijani ,&nbsp;Mohammad Mahdavi ,&nbsp;Omidreza Firuzi","doi":"10.1016/j.molstruc.2025.142089","DOIUrl":"10.1016/j.molstruc.2025.142089","url":null,"abstract":"<div><div>A new series of benzothiazole-indole-1,2,3-triazole-N-phenylacetamide derivatives <strong>9a-m</strong> was designed through hybridization of potent cytotoxic pharmacophores. The title derivatives were synthesized by simple and efficient reactions, and their anticancer effects were evaluated by 3-(4,5-Dimethylthiazol- 2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against three cancer cell lines SUIT-2, MCF-7, and U87-MG from pancreas, breast, and brain tumors, respectively. Most of the newly synthesized compounds demonstrated cytotoxic effects against the studied cell lines, and among these derivatives, compound <strong>9j</strong> bearing the dichlorophenyl moiety was the most active one against all the studied cancer cells. In this regard, compound <strong>9j</strong> was more potent than the positive control <strong>(</strong>cisplatin) against MCF-7 and U87-MG cells. Moreover, compounds <strong>9m</strong> and <strong>9k</strong> were more potent than cisplatin against U87-MG. In addition, alterations in the cell cycle and the induction of apoptosis by the most potent compounds were also evaluated in MCF-7 cells. These assays demonstrated that our new compounds increase the percentage of cells in the G0/G1 phase of the cell cycle and also induce apoptosis in cancer cells. Docking studies showed that compound <strong>9j</strong> may have notable interactions with the topoisomerase II alpha enzyme. The findings of this study showed that benzothiazole-indole-1,2,3-triazole-N-phenylacetamide derivatives exhibit promising anticancer activity.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142089"},"PeriodicalIF":4.0,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143705148","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Construction of flower-like BiOI/Bi2O2CO3 p-n heterojunction for photocatalytic degradation of Congo Red dye","authors":"Xiuping Zhang ,&nbsp;Yuanyuan Zhong ,&nbsp;Tian Xiao ,&nbsp;Xiaodong Zhu ,&nbsp;Yu Jiao ,&nbsp;Qiang Yu ,&nbsp;Zhiyong Qi","doi":"10.1016/j.molstruc.2025.142076","DOIUrl":"10.1016/j.molstruc.2025.142076","url":null,"abstract":"<div><div>In this study, Bi₂O₂CO₃ photocatalysts were first synthesized under different hydrothermal temperatures (180 °C, 190 °C, and 200 °C). Congo Red (CR) dye was used as an anionic pollutant model for photocatalytic degradation experiments. The results showed that the photocatalytic performance was optimal at a hydrothermal temperature of 190 °C. Based on this temperature, the modification of Bi₂O₂CO₃ photocatalytic material was studied to solve the problems of easy recombination of photogenerated charge and insufficient quantum utilization. BiOI was coupled with Bi₂O₂CO₃, which has matched band structures, to construct a BiOI/Bi₂O₂CO₃ (BiOI/BOC) p-n heterojunction composite photocatalysts. Photocatalytic degradation experiments indicated that the BiOI/BOC composite with a molar ratio of 0.5 exhibited the highest photocatalytic activity. After 60 min of light irradiation, the degradation degree reached 78.7 %, and the first-order reaction rate constant was 0.0207 min⁻¹, which is 2.5 times that of pure BOC (0.0083 min^–1) and 3.1 times that of BiOI (0.0067 min^–1). The enhanced photocatalytic activity of the BiOI/Bi₂O₂CO₃ composites are attributed to the formation of p-n heterojunction at the contact interface between BiOI and Bi₂O₂CO₃. In the p-n heterojunction, the significant difference in Fermi energy levels between the two results in a strong built-in electric field. Driven by the built-in electric field, e⁻ in the CB of BiOI migrates to CB of Bi₂O₂CO₃, and h⁺ in the VB of Bi₂O₂CO₃ migrates to VB of BiOI, effectively promoting the separation of photogenerated carriers and thus enhancing photocatalytic activity. The photocatalytic degradation mechanism of the BiOI/BOC p-n heterojunction was proposed based on electrochemical tests and active species experiments.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142076"},"PeriodicalIF":4.0,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143685085","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Water-soluble dinuclear zinc(II) complexes bridged by auxiliary para-substituted benzoate ligands: Synthesis, structure, spectroscopic characterization and protein binding affinity","authors":"Tapan Sarkar ,&nbsp;Sujan Sk ,&nbsp;Ranjay K. Tiwari ,&nbsp;Subir Maji ,&nbsp;J.N. Behera ,&nbsp;Manindranath Bera","doi":"10.1016/j.molstruc.2025.142073","DOIUrl":"10.1016/j.molstruc.2025.142073","url":null,"abstract":"<div><div>This work describes the synthesis, structure, spectroscopy and evaluation of protein binding affinity with bovine serum albumin (BSA) of a new series of water-soluble dizinc(II) complexes of molecular formula Na₂[Zn₂(cpdp)(<em>μ-p</em>-O₂CC₆H₄(Cl))](2Br) (<strong>1</strong>), [Zn₂(cpdp)(<em>μ</em>-<em>p</em>-O₂CC₆H₄(CH₃))]<strong>·</strong>5H₂O (<strong>2</strong>) and [Zn₂(cpdp)(<em>μ</em>-<em>p</em>-O₂CC₆H₄(NO₂))] (<strong>3</strong>) (H₃cpdp = N,<em>N</em>'-bis[2-carboxybenzomethyl]-N,<em>N</em>'-bis[2-pyridylmethyl]-1,3-diaminopropan-2-ol; <em>p</em>-C₆H₄(Cl)(CO₂H) = <em>para</em>-chlorobenzoic acid; <em>p</em>-C₆H₄(CH₃)(CO₂H) = <em>para</em>-methylbenzoic acid; <em>p</em>-C₆H₄(NO₂)(CO₂H) = <em>para</em>-nitrobenzoic acid). All three complexes were characterized by multiple analytical techniques, including single crystal X-ray crystallography. Crystal structure analysis disclosed that the zinc centers in <strong>1–3</strong> are assembled <em>via</em> one endogenous bridging alkoxide group of cpdp³⁻ ligand, and one exogenous bridging <em>para</em>-chlorobenzoate/<em>para</em>-methylbenzoate/<em>para</em>-nitrobenzoate, with a self-aggregated closely packed arrangement having an average internuclear Zn<strong>∙∙∙</strong>Zn separation of 3.530 Å. UV–Vis absorption and fluorescence emission spectroscopy, and DFT computation were employed to investigate their binding interactions with BSA protein. Synchronous fluorescence spectra clearly suggest that <strong>1–3</strong> bind to the active sites of BSA, showing that the binding response is more or less equally prominent towards both tryptophan and tyrosine. Fukui functions at the zinc sites, including HOMOs and LUMOs in <strong>1–3</strong> were calculated by DFT computation to predict the probable zinc centers anticipated in the binding phenomena.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142073"},"PeriodicalIF":4.0,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143704721","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Structural resolution of the new polyoxometalate hybrid (C2N4H7O)4(NH4)[HMo7O24]·4H2O: Textile dye decolorization and BSA binding properties","authors":"Thamer Bouallegui ,&nbsp;Rim Zarroug ,&nbsp;Beñat Artetxe ,&nbsp;Brahim Ayed","doi":"10.1016/j.molstruc.2025.142069","DOIUrl":"10.1016/j.molstruc.2025.142069","url":null,"abstract":"<div><div>The hybrid organic-inorganic compound based on polyoxometalates, specifically (C₂N₄H₇O)₄(NH₄)[HMo₇O₂₄]·4H₂O (<strong>1</strong>) was synthesized under reflux conditions. The FT-IR spectroscopy, UV-Vis spectroscopy, and TGA-DTA analysis were utilized to investigate the physico-chemical properties of <strong>1</strong>. Moreover, single crystal X-ray diffraction analyses revealed that the compound crystallizes in a monoclinic system with a <em>C</em>2/<em>c</em> space group. The lattice parameters are as follows: a = 43.1211(7) Å, b = 10.8198(2) Å, c = 17.1667(3) Å, β = 93.146(2)°. The crystal structure of <strong>1</strong> comprises a protonated heptamolybdate anion, protonated dicyandiamide (HPDCD) organic cations resulting from hydrolysis, one ammonium cation, and four lattice water molecules. Hydrogen bonding is instrumental in stabilizing the crystal network. The [HMo₇O₂₄]^5- anions, in conjunction with water molecules, form one-dimensional inorganic chains. The further assembly of these chains results in the formation of two-dimensional inorganic layers. Within these layers, both HPDCD cations and ammonium cations are incorporated. The overall three-dimensional structure of <strong>1</strong> constituted by alternating organic and inorganic layers. Hydrogen bonds were identified as predominant type of intermolecular interaction in the analysis of Hirshfeld surfaces fingerprint graphics. The newly developed hybrid material was employed to decolorize Novacron Blue EC-R textile dye. Optimal conditions for the decolorization process were established. The interaction between bovine serum albumin (BSA) and <strong>1</strong> was evaluated using steady-state fluorescence spectroscopy.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142069"},"PeriodicalIF":4.0,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143685956","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Sustainable catalysts: Advances in geopolymer-catalyzed reactions and their applications","authors":"Fernando Gomes S． Jr. ,&nbsp;Shekhar Bhansali ,&nbsp;Viviane Valladão ,&nbsp;Fabíola Maranhão ,&nbsp;Daniele Brandão ,&nbsp;Carolina Delfino ,&nbsp;Nidhi Asthana","doi":"10.1016/j.molstruc.2025.142017","DOIUrl":"10.1016/j.molstruc.2025.142017","url":null,"abstract":"<div><div>This study investigated using geopolymers as sustainable catalysts, utilizing both computational and experimental methods to improve the synthesis process. We used tools like Latent Dirichlet Allocation (LDA) and hierarchical clustering algorithms to find patterns, gaps, and new topics. We also experimented to see how structural and chemical factors affect the catalyst's performance. Adding industrial waste like blast furnace slag and fly ash made catalysts that worked very well and had properties that worked well in both chemical and environmental settings. It was easier for reagents to move through and get to active sites because of the pores and the addition of nanoparticles like TiO₂ and copper ferrites. This made the catalyst work better. Geopolymer catalysts were more than 90 % effective at breaking down pollutants like Rhodamine B and methylene blue, and they stayed stable after being used more than once. Studies also showed that these materials can be used to make biodiesel, with high yields in optimized transesterification made easier by machine learning. Notably, the resulting glycerol byproduct can serve as a precursor for biopolyesters, further enhancing the economic and ecological benefits of this approach. The results consolidate geopolymers as viable and multifunctional alternatives, promoting sustainability and technological innovation. Their versatility meets industrial and environmental demands, positioning them as promising solutions for global challenges, such as pollutant mitigation and energy transition. To make sure that geopolymers can meet the growing need for clean and long-lasting technologies, future research should focus on making them more industrially scalable, stable over time, and able to use a broader range of precursors.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142017"},"PeriodicalIF":4.0,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143705151","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"An electrochemical detection method for polyvinyl chloride microplastics in water bodies","authors":"Ozge Surucu","doi":"10.1016/j.molstruc.2025.142086","DOIUrl":"10.1016/j.molstruc.2025.142086","url":null,"abstract":"<div><div>Polyvinyl chloride (PVC) microplastics are rapidly increasing contaminants effecting aquatic environments. Therefore, there is an urgent need to develop new strategies for routine analysis of microplastics. In this study, a mixed silver nanoparticles (AgNPs), graphene oxide (GO) and multi wall carbon nanotube (MWCNT) suspension was synthesized for the detection of PVC microplastics. To support the microstructure of nanoparticles, scanning electron microscope-energy dispersive X-ray spectroscopy (SEM-EDX) was used. PVC microplastics were determined in real sea and soft water bodies according to their electrochemical responses using AgNP/GO/MWCNT modified gold (Au) electrode at –0.30 V vs. Ag/AgCl with a wide linear range of (1.00 – 5.00) mg mL^-1 and LOD of 0.79 mg mL^-1. At the same time, other contaminants apart from PVC were tested using inductively coupled plasma-mass spectrometry (ICP-MS) studies and heavy metal content of all water bodies was examined. Thus, long-term source of PVC was detected in sea water bodies with this promising new approach.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142086"},"PeriodicalIF":4.0,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143654867","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Carbazole-based donor with different π-spacer of non-linear optical properties: Synthesis, photophysical properties, viscosity, acidochromism, and DFT studies","authors":"Puja O. Gupta ,&nbsp;Zeba khan ,&nbsp;Zahir Ali Siddqui ,&nbsp;Suryapratap J. Sharma ,&nbsp;Sandeep More ,&nbsp;Nagaiyan Sekar","doi":"10.1016/j.molstruc.2025.142006","DOIUrl":"10.1016/j.molstruc.2025.142006","url":null,"abstract":"<div><div>Dye with carbazole-based donors, such as furan, thiophene, and phenyl-spacer with ethyl cyanoacrylate acceptor, was designed and synthesized to investigate the effects of donor and π-spacer on both linear and non-linear optical (NLO) properties. This study employed density functional theory (DFT), solvent polarity maps, and time-dependent DFT. For furan, phenyl, and thiophene-based carbazole dyes, the maximum absorption and emission were seen in the range of 475–477, 429–437, and 476–484, and in the range of 552–615, 524–610, and 553–619 nm, respectively. Thiophene and phenyl spacer dye displayed the greatest red-shifted and blue-shifted absorption and emission properties, respectively. Significant viscosity sensitivity was demonstrated by all dyes in both non-polar (paraffin: toluene) and polar (PEG: methanol) mediums. Furthermore, above 350 °C, the title dyes demonstrated good thermal stability. Furthermore, the theoretical research showed that dyes with thiophene-spacer had better CT (as measured by FMO, MEP, BLA, BOA, and QC calculations), which results in superior linear and NLO properties in solvent phases.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142006"},"PeriodicalIF":4.0,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143685039","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Exploring antitubercular activity of new coumarin derivatives targeting enoyl acyl carrier protein reductase (InhA): Synthesis, biological evaluation and computational studies","authors":"Manal S Ebaid ,&nbsp;Małgorzata Korycka-Machala ,&nbsp;Moataz A. Shaldam ,&nbsp;Mohamed G. Thabit ,&nbsp;Malwina Kawka ,&nbsp;Bożena Dziadek ,&nbsp;Magdalena Kuzioła ,&nbsp;Hoda Atef Abdelsattar Ibrahim ,&nbsp;Xinsheng Lei ,&nbsp;Abdelsamed I. Elshamy ,&nbsp;Jarosław Dziadek ,&nbsp;Ahmed Sabt","doi":"10.1016/j.molstruc.2025.142074","DOIUrl":"10.1016/j.molstruc.2025.142074","url":null,"abstract":"<div><div>Tuberculosis poses a significant global health challenge, resulting in substantial health, economic, and social issues worldwide. The development of new antitubercular agents is critically important and can be enhanced by targeting various druggable sites for inhibition. The enoyl acyl carrier protein reductase (InhA) enzyme plays a vital role in the survival of Mycobacterium tuberculosis. In this research, a variety of coumarin-derived thiazolidinone and thiazole derivatives were synthesized using a molecular hybridization approach, and their efficacy was subsequently assessed against the wild-type strain Mycobacterium tuberculosis H37Rv. Among the synthesized compounds, compound <strong>5</strong> exhibited the highest potency against wild-type M. tuberculosis, with a minimum inhibitory concentration (MIC) of 20 μg/mL, while demonstrating low cytotoxicity towards mouse fibroblasts at concentrations twice that of the MIC. Furthermore, compound <strong>5</strong> significantly inhibited mycobacterial biofilm formation. This promising compound was also evaluated for its inhibitory effect on InhA, revealing potent activity with an IC₅₀ value of 0.191 µg, surpassing that of the reference drug triclosan. Molecular docking and dynamics simulations indicated that compound <strong>5</strong> exhibited strong <em>in-silico</em> binding, occupying the active site of InhA and interacting with the NAD⁺ molecule, while also demonstrating stable dynamics in relation to InhA.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142074"},"PeriodicalIF":4.0,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143685595","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Fabricating efficient SnO2/hydrochar heterojunction visible light photocatalyst for Cr(VI) reduction","authors":"Fen Zhang ,&nbsp;Chang Liu ,&nbsp;Siyi Wang ,&nbsp;Yongcai Zhang","doi":"10.1016/j.molstruc.2025.142084","DOIUrl":"10.1016/j.molstruc.2025.142084","url":null,"abstract":"<div><div>Despite its low cost, environmental friendliness and excellent stability, SnO₂ exhibits no visible light photocatalytic activity due to its wide bandgap. This study aims to develop an efficient visible light photocatalyst by combining SnO₂ with hydrochar (HC). A series of SnO₂/HC nanocomposites were synthesized using a green one-pot hydrothermal method, by changing the amount of glucose. SnO₂/HC-3 exhibited the maximal photocatalytic Cr(VI) reduction rate (0.030 min⁻¹), which is 30 times higher than SnO₂ and 5 times higher than HC under visible light (λ &gt; 420 nm) irradiation. Moreover, when the photocatalytic experiment conditions were optimized, SnO₂/HC-3 showcased the further improved photocatalytic performance for Cr(VI) reduction. SnO₂/HC-3 also remained good photocatalysis capability for Cr(VI) reduction after four cycles, and demonstrated remarkable photochemical stability. The mechanism for the superior visible light photocatalysis of SnO₂/HC-3 was explored and proposed. Furthermore, SnO₂/HC-3 showcased a high efficiency toward photocatalytic removal of Cr(VI) in the diluted passivation solution of copper alloys under visible light, indicating that SnO₂/HC-3 has an application prospect in practical Cr(VI)-containing wastewater treatment.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142084"},"PeriodicalIF":4.0,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143705260","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Physicochemical properties of (Z)-3-(4-((Hydroxymethyl)(methyl)amino)phenyl)-2-(4-halophenyl) acrylonitriles: A comprehensive experimental and theoretical study","authors":"Venkatesan Perumal ,&nbsp;Enrique Pérez-Gutiérrez ,&nbsp;Margarita Cerón ,&nbsp;Miriam F. Beristain ,&nbsp;Paulina Ceballos ,&nbsp;Thamotharan Subbiah ,&nbsp;M. Judith Percino","doi":"10.1016/j.molstruc.2025.142043","DOIUrl":"10.1016/j.molstruc.2025.142043","url":null,"abstract":"<div><div>In this study, halogen-substituted (-F, -Cl, and -Br) and unsubstituted (Z)-3-(4-((hydroxymethyl)(methyl)amino)phenyl)-2-(4-halophenyl)acrylonitriles (<strong>1–4</strong>) were synthesised to investigate the effect of halogen atoms and N-2-hydroxyethyl group on their physicochemical properties. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations were employed to investigate their frontier molecular orbitals, global reactivity descriptors, optical properties, and internal reorganization energies in comparison to their precursors (<strong>A–D</strong>). The N-2-hydroxyethyl group significantly altered the optical and electronic properties, leading to fluorescence quenching in compounds <strong>1–4</strong>. Crystal structure analysis of compounds <strong>1</strong> and <strong>4</strong>, using CLP-PIXEL, Hirshfeld surface (HS) analysis, and Bader's quantum theory of atoms in molecules (QTAIM), revealed lattice energies 5–6 kcal mol^-1 higher than those of their precursors (<strong>A</strong> and <strong>D</strong>), attributed to O<strong>–</strong>H···O/N interactions facilitated by the N-2-hydroxyethyl group. A slight red shift in λ_max values followed the trend <strong>1</strong> &lt;<strong>2</strong> &lt;<strong>3</strong> &lt;<strong>4</strong>, indicating halogen substitution effects. In contrast a significant shift between compounds <strong>1–4</strong> and their precursors (<strong>A–D</strong>) demonstrated the influence of the N-2-hydroxyethyl group. Experimental band gap values from electrochemical and UV–Vis measurements aligned well with TD-DFT calculations, further supporting the theoretical findings.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1336 ","pages":"Article 142043"},"PeriodicalIF":4.0,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143686082","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}