Pyrazole is among many synthetic compounds’ most privileged five-membered nitrogenous structural nuclei. Among a diverse range of heterocyclic analogs, pyrazole derivatives presented remarkable therapeutic significances, including antibacterial, antifungal, antimalarial, antitubercular anti-leishmanial, antidiabetic, antihypertensive and anticancer effects, etc. Pyrazole motif is also available as a structural part of many marketed drugs and clinical trial candidates bearing therapeutic importance. In traditional synthetic methodologies, synthesizing pyrazole derivatives requires several harsh reaction environments, such as introducing organic solvent, longer duration of time, elevated temperature, and energy consumption. By considering the pyrazoles’ utility and several drawbacks associated with their traditional synthetic approach, researchers have developed more economical reaction conditions to obtain them. In this regard, microwave irradiation, reaction at room temperature, and solvent and catalyst-free circumstances are ecologically favorable and cost-effective. Microwave-assisted organic synthesis (MAOS) of pyrazole derivatives has exhibited environment-friendly reaction conditions with the minor consumption of hazardous chemicals/solvents and significantly reduced reaction duration. Therefore, this review highlights the microwave-associated synthesis of pyrazole derivatives, likely an excellent alternative to eco-friendly synthetic methodologies.
{"title":"Recent Advancements in Microwave Assisted Synthesis of Pyrazole Analogues: An Ecological Synthetic Approach","authors":"Bhupender Nehra , Viney Chawla , Pooja A. Chawla , Manoj Kumar","doi":"10.1080/10406638.2024.2413427","DOIUrl":"10.1080/10406638.2024.2413427","url":null,"abstract":"<div><div>Pyrazole is among many synthetic compounds’ most privileged five-membered nitrogenous structural nuclei. Among a diverse range of heterocyclic analogs, pyrazole derivatives presented remarkable therapeutic significances, including antibacterial, antifungal, antimalarial, antitubercular anti-leishmanial, antidiabetic, antihypertensive and anticancer effects, etc. Pyrazole motif is also available as a structural part of many marketed drugs and clinical trial candidates bearing therapeutic importance. In traditional synthetic methodologies, synthesizing pyrazole derivatives requires several harsh reaction environments, such as introducing organic solvent, longer duration of time, elevated temperature, and energy consumption. By considering the pyrazoles’ utility and several drawbacks associated with their traditional synthetic approach, researchers have developed more economical reaction conditions to obtain them. In this regard, microwave irradiation, reaction at room temperature, and solvent and catalyst-free circumstances are ecologically favorable and cost-effective. Microwave-assisted organic synthesis (MAOS) of pyrazole derivatives has exhibited environment-friendly reaction conditions with the minor consumption of hazardous chemicals/solvents and significantly reduced reaction duration. Therefore, this review highlights the microwave-associated synthesis of pyrazole derivatives, likely an excellent alternative to eco-friendly synthetic methodologies.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 4","pages":"Pages 723-769"},"PeriodicalIF":2.4,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510862","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-21Epub Date: 2024-10-25DOI: 10.1080/10406638.2024.2416597
Qiaojing Zhao , Zhi Yu , Shenjun Qin , Bangjun Liu , Wenchao Shen , Yuzhuang Sun , Yanli Yang , Yongjie Niu , Xin Li , Minmin Zhang , Maxim G. Blokhin
Different coal seams go through distinct biological, physical, and chemical processes. Polycyclic aromatic compounds (PACs) in coal may retain information about these processes, especially in low-rank bituminous coals. Three coal seams with different sulfur contents from the Ningwu Coalfield were studied to understand the relation of different sulfur contents with PAC formation in low-rank bituminous coals. Coal samples were extracted by solvent and separated using liquid chromatography. The collected aromatic hydrocarbon fractions were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 27 sulfur-containing PACs (SPACs) were identified in the high-sulfur samples, whereas only 8 SPACs were found in the low-sulfur coal and middle-sulfur coal. The total SPACs to total PACs ratios (T-SPACs/T-PACs) are 1.15%, 2.17%, and 10.65% in the low-sulfur, middle-sulfur, and high-sulfur coal, respectively. The variations of SPAC species and their content ratios indicate that SPAC formation is controlled by the sulfur contents in the low-rank bituminous coals. A total of 18 oxygen-containing PACs (OPACs) were identified in the low-sulfur coal and middle-sulfur coal, whereas only 11 OPACs were found in the high-sulfur samples. The average ratios of OPACs to the identified aromatic compounds (T-OPACs/T-PACs) are 9.81%, 9.62%, and 6.91% in the low-, middle-, and high-sulfur coals, exhibiting a negative correlation with sulfur contents and indicating that OPACs were also influenced by sulfur contents in low-rank bituminous coals. The ratios of total contents of polycyclic aromatic hydrocarbons (PAHs) to total PACs (T-PAHs/T-PACs) are 89.1%, 88.2%, and 82.0% in the low-, middle-, and high-sulfur coals, respectively, indicating a decreasing trend from low- and middle-sulfur coal to high-sulfur coal. This variation could be caused by the reaction of PAHs and sulfur to form SPACs.
{"title":"Effect of Sulfur Contents on Polycyclic Aromatic Compounds in Low-Rank Bituminous Coals","authors":"Qiaojing Zhao , Zhi Yu , Shenjun Qin , Bangjun Liu , Wenchao Shen , Yuzhuang Sun , Yanli Yang , Yongjie Niu , Xin Li , Minmin Zhang , Maxim G. Blokhin","doi":"10.1080/10406638.2024.2416597","DOIUrl":"10.1080/10406638.2024.2416597","url":null,"abstract":"<div><div>Different coal seams go through distinct biological, physical, and chemical processes. Polycyclic aromatic compounds (PACs) in coal may retain information about these processes, especially in low-rank bituminous coals. Three coal seams with different sulfur contents from the Ningwu Coalfield were studied to understand the relation of different sulfur contents with PAC formation in low-rank bituminous coals. Coal samples were extracted by solvent and separated using liquid chromatography. The collected aromatic hydrocarbon fractions were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 27 sulfur-containing PACs (SPACs) were identified in the high-sulfur samples, whereas only 8 SPACs were found in the low-sulfur coal and middle-sulfur coal. The total SPACs to total PACs ratios (T-SPACs/T-PACs) are 1.15%, 2.17%, and 10.65% in the low-sulfur, middle-sulfur, and high-sulfur coal, respectively. The variations of SPAC species and their content ratios indicate that SPAC formation is controlled by the sulfur contents in the low-rank bituminous coals. A total of 18 oxygen-containing PACs (OPACs) were identified in the low-sulfur coal and middle-sulfur coal, whereas only 11 OPACs were found in the high-sulfur samples. The average ratios of OPACs to the identified aromatic compounds (T-OPACs/T-PACs) are 9.81%, 9.62%, and 6.91% in the low-, middle-, and high-sulfur coals, exhibiting a negative correlation with sulfur contents and indicating that OPACs were also influenced by sulfur contents in low-rank bituminous coals. The ratios of total contents of polycyclic aromatic hydrocarbons (PAHs) to total PACs (T-PAHs/T-PACs) are 89.1%, 88.2%, and 82.0% in the low-, middle-, and high-sulfur coals, respectively, indicating a decreasing trend from low- and middle-sulfur coal to high-sulfur coal. This variation could be caused by the reaction of PAHs and sulfur to form SPACs.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 4","pages":"Pages 697-722"},"PeriodicalIF":2.4,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144510858","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-16Epub Date: 2024-10-07DOI: 10.1080/10406638.2024.2411332
Srood Omer Rashid
Naphthalene and its derivatives are often determined as markers of environmental pollution, although they are also recognized as crucial building blocks in many beneficial compounds. In the course of this study, a range of 1,2-disubstituted naphthalenes bearing nitro, amine, sulfonate, chlorine, and hydroxyl substituents were synthesized and characterized using several spectroscopic techniques, including FT-IR,1H NMR,13C NMR, DEPT-90, DEPT-135, DEPTq, elemental analysis, and high-resolution mass (HRMs). The NMR analysis of the aromatic hydrocarbon moiety in these compounds emphasized the impact of substituent variations on the appearance of 1H and 13C NMR signals. To resolve the issue of overlapping one-dimensional (1D) 1H NMR signals and determine the connectivity of hydrogen and carbon atoms from the aromatic naphtayl ring, we employed a “two-dimensional” experiment, using homonuclear correlation spectroscopy (2D 1H-1H COSY) and heteronuclear single quantum correlation (2D 1H - 13C HSQC) and heteronuclear multiple‐bond correlation spectroscopy (2D 1H - 13C HMBC). This work also investigated the correlation between 1H NMR signals and thin-layer chromatography (TLC) data. X-ray crystallography data validates that the presence of a specific group, not aligned coplanarly with the naphthyl ring, exerts a spatial influence on the manifestation of 1H NMR signals, alongside other electronic effects. This study will offer NMR data, providing insights into the potential applications and analyses of naphthalene derivatives across various theoretical and practical domains.
{"title":"Spectrochemical Insights into Aromatic Hydrocarbons in 1,2-Disubstituted Naphthalenes: Investigations Using 1D and 2D NMR Spectroscopy and X-Ray Crystallography Analysis","authors":"Srood Omer Rashid","doi":"10.1080/10406638.2024.2411332","DOIUrl":"10.1080/10406638.2024.2411332","url":null,"abstract":"<div><div>Naphthalene and its derivatives are often determined as markers of environmental pollution, although they are also recognized as crucial building blocks in many beneficial compounds. In the course of this study, a range of 1,2-disubstituted naphthalenes bearing nitro, amine, sulfonate, chlorine, and hydroxyl substituents were synthesized and characterized using several spectroscopic techniques, including FT-IR,<sup>1</sup>H NMR,<sup>13</sup>C NMR, DEPT-90, DEPT-135, DEPTq, elemental analysis, and high-resolution mass (HRMs). The NMR analysis of the aromatic hydrocarbon moiety in these compounds emphasized the impact of substituent variations on the appearance of <sup>1</sup>H and <sup>13</sup>C NMR signals. To resolve the issue of overlapping one-dimensional (1D) <sup>1</sup>H NMR signals and determine the connectivity of hydrogen and carbon atoms from the aromatic naphtayl ring, we employed a “two-dimensional” experiment, using homonuclear correlation spectroscopy (2D <sup>1</sup>H-<sup>1</sup>H COSY) and heteronuclear single quantum correlation (2D <sup>1</sup>H - <sup>13</sup>C HSQC) and heteronuclear multiple‐bond correlation spectroscopy (2D <sup>1</sup>H - <sup>13</sup>C HMBC). This work also investigated the correlation between <sup>1</sup>H NMR signals and thin-layer chromatography (TLC) data. X-ray crystallography data validates that the presence of a specific group, not aligned coplanarly with the naphthyl ring, exerts a spatial influence on the manifestation of <sup>1</sup>H NMR signals, alongside other electronic effects. This study will offer NMR data, providing insights into the potential applications and analyses of naphthalene derivatives across various theoretical and practical domains.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 3","pages":"Pages 524-539"},"PeriodicalIF":2.4,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143901905","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-16Epub Date: 2024-10-04DOI: 10.1080/10406638.2024.2407964
Sukanya R. , Jini Pramila M. , Arul Dhas D.
The main objective of the study is to analyze the structural behavior and NLO activity of 4-cumyl phenol by experimental and theoretical spectroscopic techniques. Its computational result is compared with the cumene compound. The optimized structural parameters of the title compound were computationally obtained at the B3LYP/6-31G (d, p) basis set. The fundamental modes of vibration were examined by experimental FT-IR, and FT-Raman techniques. The distribution of the vibrational bands was carried out with the help of normal coordinate analysis (NCA). The resulting harmonic wavenumbers were scaled by using NCA method. Topological analysis, such as Electron localization function (ELF), natural bond orbital analysis (NBO), reduced density gradient (RDG) and atoms in molecule (AIM) analysis, molecular electrostatic potential (MEP) have been used to evaluate the intermolecular interaction, especially the hydrogen bonds. UV-visible spectrum of the compound was recorded in the region 200–900 nm and the electronic properties and HOMO-LUMO energies were calculated by time dependent density functional theory approach.
{"title":"Crystal Growth, Structural Elucidation, Chemical Reactivity, Topology Exploration (ELF, LOL, AIM, RDG) and NLO Activity of 4-Cumyl Phenol Crystal Using Quantum Chemical Calculation","authors":"Sukanya R. , Jini Pramila M. , Arul Dhas D.","doi":"10.1080/10406638.2024.2407964","DOIUrl":"10.1080/10406638.2024.2407964","url":null,"abstract":"<div><div>The main objective of the study is to analyze the structural behavior and NLO activity of 4-cumyl phenol by experimental and theoretical spectroscopic techniques. Its computational result is compared with the cumene compound. The optimized structural parameters of the title compound were computationally obtained at the B3LYP/6-31G (d, p) basis set. The fundamental modes of vibration were examined by experimental FT-IR, and FT-Raman techniques. The distribution of the vibrational bands was carried out with the help of normal coordinate analysis (NCA). The resulting harmonic wavenumbers were scaled by using NCA method. Topological analysis, such as Electron localization function (ELF), natural bond orbital analysis (NBO), reduced density gradient (RDG) and atoms in molecule (AIM) analysis, molecular electrostatic potential (MEP) have been used to evaluate the intermolecular interaction, especially the hydrogen bonds. UV-visible spectrum of the compound was recorded in the region 200–900 nm and the electronic properties and HOMO-LUMO energies were calculated by time dependent density functional theory approach.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 3","pages":"Pages 390-405"},"PeriodicalIF":2.4,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143902522","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-16Epub Date: 2024-10-17DOI: 10.1080/10406638.2024.2411322
Mhaske A. K. , Vikhe D. V. , Gadhave A. G. , Uphade B. K.
A nickel ferrite nanocatalyst was synthesized in the presence of simple and cost-effective polysorbates assisted sol gel method as an effective catalyst has been successfully used for one pot multicomponent Hantzsch condensation reaction of different aromatic aldehydes, dimedone and ammonium acetate under solvent-free condition at 110 °C-120 °C. The highlights feature for the synthesis of acridinediones are the recyclability of catalyst, solvent-free reaction condition, use of inexpensive catalyst, highly efficient, facile product isolation, clean reaction, nontoxic substances and great yields in short reaction time. The recovered catalyst can run four times without loss its activity.
{"title":"NiFe2O4 Nanoparticles: An Efficient Catalyst for One-Pot Three Component Synthesis of Acridinediones Derivatives","authors":"Mhaske A. K. , Vikhe D. V. , Gadhave A. G. , Uphade B. K.","doi":"10.1080/10406638.2024.2411322","DOIUrl":"10.1080/10406638.2024.2411322","url":null,"abstract":"<div><div>A nickel ferrite nanocatalyst was synthesized in the presence of simple and cost-effective polysorbates assisted sol gel method as an effective catalyst has been successfully used for one pot multicomponent Hantzsch condensation reaction of different aromatic aldehydes, dimedone and ammonium acetate under solvent-free condition at 110 °C-120 °C. The highlights feature for the synthesis of acridinediones are the recyclability of catalyst, solvent-free reaction condition, use of inexpensive catalyst, highly efficient, facile product isolation, clean reaction, nontoxic substances and great yields in short reaction time. The recovered catalyst can run four times without loss its activity.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 3","pages":"Pages 490-506"},"PeriodicalIF":2.4,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143901904","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-16Epub Date: 2024-10-11DOI: 10.1080/10406638.2024.2409842
Ömer Dilek , Tolga Acar Yeşil , Tahir Tilki
In recent years, the inadequacy and high costs of current cancer treatment drugs have led to an increase in research focused on the design and synthesis of new compounds with potential applications in this field and the evaluation of their anticancer properties using in silico methods. For this purpose, four novel heterocyclic compounds (6–9) were synthesized and characterized using spectroscopic techniques. The DFT approach and B3LYP/6-311G(d,p) basis set were used to compare theoretical data with experimental ones and to obtain optimized geometries. It was observed that experimental and theoretical data were in harmony. In silico techniques were used to investigate the potential of synthesized compounds as drug candidates. ADMEt results have shown that all synthesized compounds have Lipinski’s rule of five which has searched criteria in drug candidates. Molecular docking studies were also performed against cancer-related proteins. The highest docking score between 2XIR protein and compound 8 was found to be −11.7 kcal/mol, while the lowest was −8.2 kcal/mol between 1MP8 protein and compound 9. To do meaningful comparisons standard drugs were also used in Molecular Docking studies. It was observed that all synthesized molecules had higher docking scores than standard drugs except ifebemtinib. It can be suggested that based on ADMET and molecular docking studies compound 8 has the potential to be a drug candidate after further investigations such as in vitro, in silico, etc., have been performed in this area.
{"title":"Promising Novel Heterocyclic Drug Candidates: Synthesis, Characterization, DFT Calculations and In Silico Investigations of Anticancer Behaviors","authors":"Ömer Dilek , Tolga Acar Yeşil , Tahir Tilki","doi":"10.1080/10406638.2024.2409842","DOIUrl":"10.1080/10406638.2024.2409842","url":null,"abstract":"<div><div>In recent years, the inadequacy and high costs of current cancer treatment drugs have led to an increase in research focused on the design and synthesis of new compounds with potential applications in this field and the evaluation of their anticancer properties using <em>in silico</em> methods. For this purpose, four novel heterocyclic compounds (6–9) were synthesized and characterized using spectroscopic techniques. The DFT approach and B3LYP/6-311G(d,p) basis set were used to compare theoretical data with experimental ones and to obtain optimized geometries. It was observed that experimental and theoretical data were in harmony. <em>In silico</em> techniques were used to investigate the potential of synthesized compounds as drug candidates. ADMEt results have shown that all synthesized compounds have Lipinski’s rule of five which has searched criteria in drug candidates. Molecular docking studies were also performed against cancer-related proteins. The highest docking score between 2XIR protein and compound 8 was found to be −11.7 kcal/mol, while the lowest was −8.2 kcal/mol between 1MP8 protein and compound 9. To do meaningful comparisons standard drugs were also used in Molecular Docking studies. It was observed that all synthesized molecules had higher docking scores than standard drugs except ifebemtinib. It can be suggested that based on ADMET and molecular docking studies compound 8 has the potential to be a drug candidate after further investigations such as <em>in vitro</em>, <em>in silico</em>, etc., have been performed in this area.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 3","pages":"Pages 469-489"},"PeriodicalIF":2.4,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143902521","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-16Epub Date: 2024-09-28DOI: 10.1080/10406638.2024.2408462
Zobia Rabbani , Muhammad Usman Khan , Abida Anwar , Ghulam Mustafa , Abrar Ul Hassan , Saad M. Alshehri
Dye-sensitized solar cells (DSSCs) have garnered significant attention due to their exceptional ability to convert solar energy into electricity at a relatively low cost. Novel organic photosensitizers (FZB1-FZB9) from the pyrazine-based aromatic dye (E)-3-(5-(2,3-bis(40-(diphenylamino)-[1,10-biphenyl]-4-yl)-7 (trifluoromethyl)quinoxalin-5-yl)thiophen-2-yl)-2-cyanoacrylic acid (TPPF) have been quantum chemically modeled for their application in dye-sensitized nanocrystalline TiO2 solar cells (DSSCs). The electrochemical and photovoltaic features of modeled dyes are investigated by performing DFT insights, i.e. FMOs, absorption maxima, DOS, TDM, NBO, exciton and binding energy, radiative lifetime analysis (ꚍ), electron-injection (Δ and regeneration analysis ()@TiO2. FMO analysis confirmed the better electron injection as HOMO of designed dyes was found to be more positive than redox potential I/I3 (-4.8 eV), and the LUMO appeared more negative than the conduction band of TiO2 (-4.0 eV). The modeled photosensitizers exhibited red shift λmax from 338-494 nm with a lower energy gap from 5.62 eV in FZB (R) to 5.17 eV in FZB9. Bridging modification reduces the exciton and binding energy for designed dye FZB9 and FZB7 compared to reference FZB. The designed dyes appeared with a lower radiative lifetime of up to 1.32 than the reference dye of 1.63, better light harvesting efficiency (LHE), and the highest NBO charge on bridges of designed photosensitizers for enhanced light emitting efficiency. The investigated dyes exhibited more negative values for electron injection, i.e. −0.003 and the highest values of dye regeneration up to 11.717, which unveils innovative and effective injection of electrons toward semiconductor TiO2. Among all dyes, FZB8 proved best with the novel bridging modification that enables quick charge transfer as exhibited the lowest gap (5.17 eV), lowest excitation energy, better LHE, highest charge on LUMO and more negative electron injection (Δ The outcomes of this computational study confirmed that this research established a new benchmark for achieving novel and efficient photosensitizers, thus recommending them for future DSSC applications.
{"title":"Pyrazine-Based Aromatic Dyes as Novel Photosensitizers with Improved Conduction Band and Photovoltaic Features: DFT Insights for Efficient Dye-Sensitized Solar Cells","authors":"Zobia Rabbani , Muhammad Usman Khan , Abida Anwar , Ghulam Mustafa , Abrar Ul Hassan , Saad M. Alshehri","doi":"10.1080/10406638.2024.2408462","DOIUrl":"10.1080/10406638.2024.2408462","url":null,"abstract":"<div><div>Dye-sensitized solar cells (DSSCs) have garnered significant attention due to their exceptional ability to convert solar energy into electricity at a relatively low cost. Novel organic photosensitizers (FZB1-FZB9) from the pyrazine-based aromatic dye (E)-3-(5-(2,3-bis(40-(diphenylamino)-[1,10-biphenyl]-4-yl)-7 (trifluoromethyl)quinoxalin-5-yl)thiophen-2-yl)-2-cyanoacrylic acid (TPPF) have been quantum chemically modeled for their application in dye-sensitized nanocrystalline TiO<sub>2</sub> solar cells (DSSCs). The electrochemical and photovoltaic features of modeled dyes are investigated by performing DFT insights, i.e. FMOs, absorption maxima, DOS, TDM, NBO, exciton and binding energy, radiative lifetime analysis (ꚍ), electron-injection (Δ<span><math><mrow><msup><mrow><mi>G</mi></mrow><mrow><mtext>inject</mtext></mrow></msup></mrow><mo>)</mo></math></span> and regeneration analysis (<span><math><mrow><msubsup><mrow><mo>Δ</mo><mi>G</mi></mrow><mrow><mtext>dye</mtext></mrow><mrow><mtext>regen</mtext></mrow></msubsup></mrow></math></span>)@TiO<sub>2</sub>. FMO analysis confirmed the better electron injection as HOMO of designed dyes was found to be more positive than redox potential I/I<sub>3</sub> (-4.8 eV), and the LUMO appeared more negative than the conduction band of TiO<sub>2</sub> (-4.0 eV). The modeled photosensitizers exhibited red shift λ<sub>max</sub> from 338-494 nm with a lower energy gap from 5.62 eV in FZB (R) to 5.17 eV in FZB9. Bridging modification reduces the exciton and binding energy for designed dye FZB9 and FZB7 compared to reference FZB. The designed dyes appeared with a lower radiative lifetime of up to 1.32 than the reference dye of 1.63, better light harvesting efficiency (LHE), and the highest NBO charge on bridges of designed photosensitizers for enhanced light emitting efficiency. The investigated dyes exhibited more negative values for electron injection, i.e. −0.003 and the highest values of dye regeneration <span><math><mrow><msubsup><mrow><mo>(</mo><mo>Δ</mo><mi>G</mi></mrow><mrow><mtext>regedye</mtext></mrow><mrow><mtext>regen</mtext></mrow></msubsup></mrow><mo>)</mo></math></span> up to 11.717, which unveils innovative and effective injection of electrons toward semiconductor TiO<sub>2</sub>. Among all dyes, FZB8 proved best with the novel bridging modification that enables quick charge transfer as exhibited the lowest gap (5.17 eV), lowest excitation energy, better LHE, highest charge on LUMO and more negative electron injection (Δ<span><math><mrow><msup><mrow><mi>G</mi></mrow><mrow><mtext>inject</mtext></mrow></msup></mrow><mo>)</mo><mo>.</mo></math></span> The outcomes of this computational study confirmed that this research established a new benchmark for achieving novel and efficient photosensitizers, thus recommending them for future DSSC applications.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 3","pages":"Pages 442-468"},"PeriodicalIF":2.4,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143901902","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-03-16Epub Date: 2024-09-26DOI: 10.1080/10406638.2024.2406931
Mallika S , Thirughanasambantham N , Revathi B , Balachandran V , Natarajan Elangovan , Natarajan Arumugam
This article describes a comprehensive study of the structure and spectroscopy of 2-hydroxy-2-phenylacetophenone (benzoin) using density functional theory (DFT) with Gaussian 09 software. Geometrical parameters were calculated at the B3LYP/6-31G (d, p) and 6-311++G (d, p) levels and compared to the literature values. An FTIR and FT-Raman spectroscopy was employed to identify vibrational modes and functional groups. Spectra were obtained in the range of 4000–400 cm−1 (FTIR) and 4000–50 cm−1 (Raman) and compared with theoretical predictions. The optical properties of FMOs are intrinsically linked to their respective energy levels. Consequently, the ΔE Homo-Lumo (ΔE) values were analyzed after the FMO orbitals were meticulously mapped out, and molecular electrostatic potential surfaces indicated regions prone to electrophilic attack, notably O13 and O16. UV spectra were simulated using TD-DFT and CPCM models in various solvents. NBO analysis revealed a stabilization energy of 37.67 kcal/mol, mainly attributed to the donor BD (1) C12-C14 to acceptor BD*(1) (C12-O13) contacts, with an occupancy of 1.93337. Topological indicators (ELF, LOL, RDG, IRI, and DORI) revealed intramolecular and intermolecular connections. The molecule shows potential pharmacological properties, adhering to Lipinski's rule of five, with the lowest binding energy of −6.91 kcal/mol for the 4PES protein. The stability of the target protein was confirmed by the Ramachandran plot.
{"title":"Structural, Spectral, Pharmacokinetics Analysis (in-Silico), Drug-Likeness, NCI Analysis (ELF, LOL, IRI & DORI) & Molecular Docking Computations of 2-Hydroxy 2-Phenyl Acetophenone a DFT Approaches","authors":"Mallika S , Thirughanasambantham N , Revathi B , Balachandran V , Natarajan Elangovan , Natarajan Arumugam","doi":"10.1080/10406638.2024.2406931","DOIUrl":"10.1080/10406638.2024.2406931","url":null,"abstract":"<div><div>This article describes a comprehensive study of the structure and spectroscopy of 2-hydroxy-2-phenylacetophenone (benzoin) using density functional theory (DFT) with Gaussian 09 software. Geometrical parameters were calculated at the B3LYP/6-31G (d, p) and 6-311++G (d, p) levels and compared to the literature values. An FTIR and FT-Raman spectroscopy was employed to identify vibrational modes and functional groups. Spectra were obtained in the range of 4000–400 cm<sup>−1</sup> (FTIR) and 4000–50 cm<sup>−1</sup> (Raman) and compared with theoretical predictions. The optical properties of FMOs are intrinsically linked to their respective energy levels. Consequently, the ΔE Homo-Lumo (ΔE) values were analyzed after the FMO orbitals were meticulously mapped out, and molecular electrostatic potential surfaces indicated regions prone to electrophilic attack, notably O13 and O16. UV spectra were simulated using TD-DFT and CPCM models in various solvents. NBO analysis revealed a stabilization energy of 37.67 kcal/mol, mainly attributed to the donor BD (1) C12-C14 to acceptor BD*(1) (C12-O13) contacts, with an occupancy of 1.93337. Topological indicators (ELF, LOL, RDG, IRI, and DORI) revealed intramolecular and intermolecular connections. The molecule shows potential pharmacological properties, adhering to Lipinski&#39;s rule of five, with the lowest binding energy of −6.91 kcal/mol for the 4PES protein. The stability of the target protein was confirmed by the Ramachandran plot.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 3","pages":"Pages 343-375"},"PeriodicalIF":2.4,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143902520","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tuberculosis (TB), caused by Mycobacterium tuberculosis (Mtb) infection, stands as a global infectious disease presenting substantial public health challenges due to its high incidence and mortality rates. The prolonged use of conventional anti-TB therapies has led to the emergence of severe drug resistance in Mtb, resulting in extended treatment durations, increased costs, poor patient compliance, and reduced cure rates. This phenomenon has posed a significant burden on global TB prevention and control efforts, necessitating a shift in research focus toward the exploration of novel anti-TB drugs. In this context, utilizing QSAR modeling methods, our study systematically investigated the relationship between the chemical structures of 36 aryl fluorosulfate derivatives and their inhibitory activity against Mtb. Robust and predictive Topomer CoMFA and HQSAR models were developed, featuring Topomer CoMFA model parameters: q2 = 0.659, r2 = 0.969, F = 102.877, N = 6, SEE = 0.138; HQSAR model parameters: q2 = 0.705, r2 = 0.873, SEE = 0.264, HL = 199, N = 4. Leveraging these models, structural modifications were applied to the compounds using the ZINC15 database, leading to the successful design and screening of three novel compounds with desirable inhibitory activity. Molecular docking and ADMET performance prediction results indicated that these three new compounds exhibit strong binding capabilities and promising pharmaceutical potential. This study provides valuable insights and research directions for the development of aryl fluorosulfate derivatives as potential agents for tuberculosis treatment and as novel drugs.
由结核分枝杆菌（Mtb）感染引起的结核病是一种全球性传染病，由于其发病率和死亡率高，对公共卫生构成重大挑战。长期使用常规抗结核疗法导致结核分枝杆菌出现严重耐药性，导致治疗时间延长、费用增加、患者依从性差和治愈率降低。这一现象对全球结核病预防和控制工作造成了重大负担，需要将研究重点转向探索新的抗结核药物。在此背景下，我们利用QSAR建模方法，系统地研究了36种氟硫酸芳基衍生物的化学结构与其对结核分枝杆菌的抑制活性之间的关系。Topomer CoMFA和HQSAR模型具有鲁棒性和预测性，Topomer CoMFA模型参数：q2 = 0.659, r2 = 0.969, F = 102.877, N = 6, SEE = 0.138；HQSAR模型参数：q2 = 0.705, r2 = 0.873, SEE = 0.264, HL = 199, N = 4。利用这些模型，利用ZINC15数据库对化合物进行结构修饰，从而成功设计和筛选了三种具有理想抑制活性的新化合物。分子对接和ADMET性能预测结果表明，这三种新化合物具有较强的结合能力和良好的药物潜力。本研究为开发氟硫酸芳基衍生物作为潜在的结核病治疗药物和新药提供了有价值的见解和研究方向。
{"title":"QSAR Modeling, Molecular Docking and ADMET Study of Aryl Fluorosulfate Derivatives as Potential Anti-TB Agents","authors":"Ya-Kun Zhang , Jian-Bo Tong , Jia-Le Guo , Zhi-Peng Qing","doi":"10.1080/10406638.2024.2408461","DOIUrl":"10.1080/10406638.2024.2408461","url":null,"abstract":"<div><div>Tuberculosis (TB), caused by <em>Mycobacterium tuberculosis</em> (Mtb) infection, stands as a global infectious disease presenting substantial public health challenges due to its high incidence and mortality rates. The prolonged use of conventional anti-TB therapies has led to the emergence of severe drug resistance in Mtb, resulting in extended treatment durations, increased costs, poor patient compliance, and reduced cure rates. This phenomenon has posed a significant burden on global TB prevention and control efforts, necessitating a shift in research focus toward the exploration of novel anti-TB drugs. In this context, utilizing QSAR modeling methods, our study systematically investigated the relationship between the chemical structures of 36 aryl fluorosulfate derivatives and their inhibitory activity against Mtb. Robust and predictive Topomer CoMFA and HQSAR models were developed, featuring Topomer CoMFA model parameters: <em>q</em><sup>2</sup> = 0.659, <em>r</em><sup>2</sup> = 0.969, <em>F</em> = 102.877, <em>N</em> = 6, <em>SEE</em> = 0.138; HQSAR model parameters: <em>q</em><sup>2</sup> = 0.705, <em>r</em><sup>2</sup> = 0.873, <em>SEE</em> = 0.264, <em>HL</em> = 199, <em>N</em> = 4. Leveraging these models, structural modifications were applied to the compounds using the ZINC15 database, leading to the successful design and screening of three novel compounds with desirable inhibitory activity. Molecular docking and ADMET performance prediction results indicated that these three new compounds exhibit strong binding capabilities and promising pharmaceutical potential. This study provides valuable insights and research directions for the development of aryl fluorosulfate derivatives as potential agents for tuberculosis treatment and as novel drugs.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 3","pages":"Pages 423-441"},"PeriodicalIF":2.4,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143901947","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A multicomponent technique was utilized to synthesize pyrroloimidazoles, a novel class of compounds, with exceptional efficiency. The reaction involved the combination of oxoindolinylidene malononitrile, ethyl 2-arylamino-4-dioxo-4-arylbutanoates, hydrazonoyl chlorides, ammonium acetate, and ethyl bromopyruvate in an aqueous solution at room temperature. The presence of Ag/Fe3O4@MWCNTs MNCs intensified the reaction. This study examines the antioxidant properties of pyrroloimidazoles, in addition to other investigations undertaken within the same study. The manufacture of pyrroloimidazole exhibited several advantageous characteristics, such as rapid reactions, elevated yields of the end product, and straightforward separation of the catalyst and product from the reaction mixture.
{"title":"A New Technique Using Multicomponent Reactions of Isatins to Synthesize Pyrroloimidazole Derivatives","authors":"Khatereh Khandan Barani , Majid Moradian , Nasrin Karami Hezarcheshmeh , Farideh Godarzbod","doi":"10.1080/10406638.2024.2411324","DOIUrl":"10.1080/10406638.2024.2411324","url":null,"abstract":"<div><div>A multicomponent technique was utilized to synthesize pyrroloimidazoles, a novel class of compounds, with exceptional efficiency. The reaction involved the combination of oxoindolinylidene malononitrile, ethyl 2-arylamino-4-dioxo-4-arylbutanoates, hydrazonoyl chlorides, ammonium acetate, and ethyl bromopyruvate in an aqueous solution at room temperature. The presence of Ag/Fe<sub>3</sub>O<sub>4</sub>@MWCNTs MNCs intensified the reaction. This study examines the antioxidant properties of pyrroloimidazoles, in addition to other investigations undertaken within the same study. The manufacture of pyrroloimidazole exhibited several advantageous characteristics, such as rapid reactions, elevated yields of the end product, and straightforward separation of the catalyst and product from the reaction mixture.</div></div>","PeriodicalId":20303,"journal":{"name":"Polycyclic Aromatic Compounds","volume":"45 3","pages":"Pages 507-523"},"PeriodicalIF":2.4,"publicationDate":"2025-03-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143901903","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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