Applied Organometallic Chemistry最新文献

{"title":"One-Pot Multicomponent Synthesis of Substituted 1,6-Naphthyridine Derivatives Employing 4-Aminocumarin","authors":"Elham Ezzatzadeh,&nbsp;Mahsa Hojjati,&nbsp;Azadeh Parhami,&nbsp;Zinatossadat Hossaini","doi":"10.1002/aoc.7718","DOIUrl":"https://doi.org/10.1002/aoc.7718","url":null,"abstract":"<div>\u0000 \u0000 <p>This study synthesized 1,6-naphthyridine as a novel class of fused heterocyclic compounds with high efficiency using a multicomponent reaction. The reaction involved benzaldehyde or its derivatives, 2 mol of malononitrile, and 4-aminocumarin in an aqueous solution at room temperature in the presence of SiO₂/Fe₃O₄@MWCNTs as a recyclable catalyst. This study examines the antioxidant properties of 1,6-naphthyridine in addition to the other research undertaken in this work. The production process of 1,6-naphthyridine demonstrated several advantageous features, including rapid reactions, high yields of the final product, and straightforward separation of the catalyst and product from the reaction mixture.</p>\u0000 </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"38 12","pages":""},"PeriodicalIF":3.7,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142596185","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":"The Role of L-Ligands in Silica-Supported Ti Oxo/Imido Heterometathesis Catalysts","authors":"Nikolai S. Bushkov,&nbsp;Andrey V. Rumyantsev,&nbsp;Andrey V. Pichugov,&nbsp;Anton A. Zhizhin,&nbsp;Dmitry Yu. Aleshin,&nbsp;Evgenii I. Gutsul,&nbsp;Rina U. Takazova,&nbsp;Dinara Kh. Kitaeva,&nbsp;Fedor M. Dolgushin,&nbsp;Roman A. Novikov,&nbsp;Pavel A. Zhizhko,&nbsp;Dmitry N. Zarubin","doi":"10.1002/aoc.7746","DOIUrl":"https://doi.org/10.1002/aoc.7746","url":null,"abstract":"<div>\u0000 \u0000 <p>We report here the preparation and characterization of new well-defined silica-supported Ti imido complexes that present an L-ligand variation in a structure of currently the most active oxo/imido heterometathesis catalyst (≡SiO)Ti(=N<i>t</i>Bu)(Me₂Pyr)(py)₂ (<b>1s</b>), where py is replaced with stronger electron-donating 4-(<i>N,N-</i>dimethylamino)pyridine (<b>2s</b>) or bidentate 2,2′-bipyridine (<b>3s</b>). The materials were characterized with elemental and mass balance analyses and IR and solid-state NMR that confirmed the selective formation of surface Ti species with terminal imido ligand. Evaluation of the catalytic oxo/imido heterometathesis activity of the obtained materials demonstrated that L-ligands have a pronounced influence on the catalytic performance. In particular, the replacement of pyridine with stronger donating ligands resulted in a significant drop of activity. The catalytic results are discussed in view of the reaction mechanism and implications for further catalyst development.</p>\u0000 </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"38 12","pages":""},"PeriodicalIF":3.7,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142596220","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":"Schiff Base of 3-Aminopropylalkoxysilanes and 3-Aminopropylsilatranes: Importance of Investigations and the Potential Applications","authors":"Nadezhda V. Vchislo,&nbsp;Sergey N. Adamovich,&nbsp;Victoria G. Fedoseeva,&nbsp;Elizaveta N. Oborina,&nbsp;Igor B. Rozentsveig,&nbsp;Francis Verpoort","doi":"10.1002/aoc.7714","DOIUrl":"https://doi.org/10.1002/aoc.7714","url":null,"abstract":"<div>\u0000 \u0000 <p>The escalating fascination with Schiff bases stems from their versatile applications in medicine, pharmacology, biology, fine organic synthesis, and industrial processes. This minireview seeks to provide an in-depth exploration of the synthesis of Schiff bases, specifically focusing on their derivation from 3-aminopropylalkoxysilanes or 3-aminopropylsilatranes. Additionally, the review delves into the utilization of Schiff bases in crafting metal complexes, unraveling their practical significance in various domains. Spanning from 1995 to 2024, this review is aimed at encapsulating the evolution of knowledge and advancements in the chemistry of Schiff bases during this period.</p>\u0000 </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"38 12","pages":""},"PeriodicalIF":3.7,"publicationDate":"2024-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142595681","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":"Novel Ferrocene-Containing Pyrazole Analogs of Curcumin: Synthesis, Characterization, Antioxidant Activity, Cyclic Voltammetry, and In Vitro Biological Evaluation","authors":"Veronika Kovač, Tea Lukačević, Dijana Jadreško, Jasna Mrvčić, Damir Stanzer, Karla Hanousek-Čiča, Teuta Murati, Marina Miletić, Ivana Kmetič","doi":"10.1002/aoc.7753","DOIUrl":"https://doi.org/10.1002/aoc.7753","url":null,"abstract":"Structural modification is an advanced strategy to improve the biological activity of selected compounds and is effectively used to overcome the adverse properties of phytochemicals (e.g., curcumin), such as poor bioavailability and solubility, which limit their clinical use. Considering the fact that ferrocene is a very good candidate for organometallic derivatization of natural products, we have synthesized six new ferrocenylpyrazole analogs of curcumin <b>8–13</b>. The new compounds were characterized by FT-IR, ¹H, and ¹³C NMR spectroscopy and mass spectrometry (ESI-MS, HRMS), and their antioxidant and electrochemical properties as well as their biological activity were investigated. The best antioxidant activity evaluated with the DPPH assay was shown by compound <b>13</b>, but it was lower than the activity achieved by curcumin. The prepared compounds showed no activity against the Gram-positive and Gram-negative bacteria tested, but the pyrazoles <b>8</b>, <b>10</b>, and <b>11</b> and the β-diketone precursors <b>5</b>, <b>6</b>, and <b>7</b> caused weaker inhibition of the growth of the yeast <i>Candida utilis</i> compared to nystatin. The higher antiproliferative activity in tumorous Hepa 1–6, HeLa, and MCF-7 cells compared to normal HaCaT and CHO-K1 cells was achieved by <b>10</b>, <b>12</b>, and <b>13</b>. Compound <b>12</b> showed the strongest inhibitory effect in HeLa cells with an IC₅₀ value of 25.20 μM, while the proliferation of normal cells was significantly less affected. In view of the higher selectivity index, compounds <b>10</b> and <b>12</b> could be considered for further research in the sense of therapeutic use in neoplasms of reproductive tissue.","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":3.9,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142258741","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":"Unraveling the Potential of Mononuclear Zn(II) and Cu(II) Schiff Base Metal Complexes: Microwave-Aided Synthesis, Theoretical Analysis and Application in Biomimetic Catalysis, CT-DNA Interaction, and In Vitro Biological Assays","authors":"Sneha Paul,&nbsp;Thangjam Sanjurani,&nbsp;Jyotirmoy Talukdar,&nbsp;Pranjit Barman,&nbsp;Ankita Das,&nbsp;Piyush Pandey","doi":"10.1002/aoc.7749","DOIUrl":"https://doi.org/10.1002/aoc.7749","url":null,"abstract":"<div>\u0000 \u0000 <p>Given the widespread and diverse effects of transition metal ions such as copper and zinc in multiple biological processes, this research endeavor addresses herein the microwave-aided synthesis of two novel tetradentate ONNO (<b>L1</b>) and tridentate NNO (<b>L2</b>) donor Schiff base ligands derived from 4,5-dimethyl-1,2-phenylenediamine and 4-bromo-2-hydroxybenzaldehyde in a 1:2 ratio and from 4,5-dimethyl-1,2-phenylenediamine and 5-methoxy-2-hydroxybenzaldehyde in a 1:1 ratio, with their respective zinc, <b>ZnL1(1)</b> and <b>ZnL2(3)</b>, and copper, <b>CuL1(2)</b> and <b>CuL2(4)</b>, Schiff base metal complexes, which are comprehensively characterized utilizing physiochemical and analytical techniques, along with geometry optimization using the DFT approach. Spectrophotometric analyses have been used to assess the biomimetic activity in the conversion of 3,5-DTBC to 3,5-DTBQ with turnover numbers 53.4 and 78 h⁻¹ in methanol for <b>2</b> and <b>4</b>, whereas the zinc complexes are found to be ineffective. With CT-DNA, possible modes of interaction with the synthesized complexes have been explored using absorption spectroscopy, where the associated binding constants ranged between 1.541 × 10⁵ and 2.186 × 10⁵ M⁻¹. EtBr-bound DNA was used in the fluorescence quenching experiments with Stern–Volmer constant (<i>K</i>_sv) values in the range 4.084 × 10⁴ and 3.402 × 10⁴ M⁻¹, showing a stronger association with CT-DNA. The compounds' ability to inhibit bacterial strains was also examined in vitro, as well as their ability to reduce inflammation, through the protein denaturation method and the DPPH assay for antioxidant activity have been performed. Furthermore, molecular docking simulations have been carried out to obtain a deeper comprehension of the molecular-level interactions with CT-DNA and cyclooxygenase-2 (COX-2).</p>\u0000 </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"38 12","pages":""},"PeriodicalIF":3.7,"publicationDate":"2024-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142596370","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":"N‐Heterocyclic Carbene–Based Catalysts for Glycerol Valorisation: Current State and Perspectives","authors":"Alexander Cárdenas‐Acero, Carolina Blanco, Edwin A. Baquero","doi":"10.1002/aoc.7760","DOIUrl":"https://doi.org/10.1002/aoc.7760","url":null,"abstract":"<jats:italic>N</jats:italic>‐Heterocyclic carbenes (NHCs) are molecules with exceptional catalytic properties in a wide range of reactions. Recently, there has been a growing interest in using them as catalysts for biomass conversion. In this review, we examine the current state of glycerol valorisation (GV) using several catalytic systems, including metallic complexes bearing NHCs as ligands, polymeric building blocks and organocatalysts. The study covers literature published in the last 15 years, detailing the catalyst scope, reaction conditions and products of GV. This analysis emphasises the importance of varying the steric and electronic properties of NHCs within the reviewed catalytic systems. Furthermore, a critical evaluation of the proposed mechanistic pathways complements these results. A comprehensive understanding of the challenges of using such catalytic systems will emerge by compiling literature on the use of NHCs for the studied reactions. Additionally, this will promote new opportunities for further research in both academic and industrial fields.","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"32 1","pages":""},"PeriodicalIF":3.9,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142258738","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 Innovative Water Splitting Process for a Sustainable In Situ Hydrogen Generation–Reduction of Nitrobenzenes Catalyzed by a New Bimetallic Nanocatalyst","authors":"Hamed Zarei,&nbsp;Sara Sobhani,&nbsp;José Miguel Sansano","doi":"10.1002/aoc.7740","DOIUrl":"10.1002/aoc.7740","url":null,"abstract":"<div>\u0000 \u0000 <p>In this research, bimetallic CdNi nanoparticles encapsulated in a magnetic spent coffee ground (Fe₃O₄@COFF/CdNi) was synthesized as a new nanocatalyst. The structural and chemical characteristics of Fe₃O₄@COFF/CdNi were comprehensively investigated using various techniques, including FT-IR, XRD, XPS, TEM, VSM, EDS, TGA, BET, and ICP. Through XRD, XPS analysis, TEM images, and EDS mapping, the presence of CdNi nanoalloys was conclusively established. Fe₃O₄@COFF/CdNi exhibited remarkable catalytic activity for the hydrogen generation from water using <i>iso</i>-propanol as a clean sacrificial agent. The high catalytic performance of Fe₃O₄@COFF/CdNi was attributed to the synergistic cooperative effect of Cd and Ni within CdNi nanoalloys. Interestingly, this process was performed for the in situ generated hydrogen from water to reduce a range of nitrobenzenes simultaneously into the corresponding anilines in high yields (93%–98%). The magnetic and hydrophilic characteristics of Fe₃O₄@COFF/CdNi facilitated its reusability over five runs. Using water as the most abundant hydrogen source, for the first time for in situ hydrogen generation–reduction of nitrobenzenes without demanding on external light sources or power supplies can be mentioned as a significant milestone of this field of study.</p>\u0000 </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"38 12","pages":""},"PeriodicalIF":3.7,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269349","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":"Copper(I) Complexes With Phenanthroline‐Functionalized NHC Ligands Achieve Effective Anticancer Activity via Mitochondrial and Endoplasmic Reticulum Stress","authors":"Chao Chen, Yilun Zheng, Hong Rao, Fan Huang, Chao Shen, Chunxin Lu","doi":"10.1002/aoc.7756","DOIUrl":"https://doi.org/10.1002/aoc.7756","url":null,"abstract":"Copper complexes exhibit promising anticancer properties, which can be further promoted by suitable ligands. In this study, we synthesized and investigated the anticancer effects of three copper(I) complexes with N‐heterocyclic carbene (NHC) ligands derived from phenanthroline‐functionalized imidazole salts. The synthesis of these NHC‐copper(I) complexes (Cu1‐Cu3) was meticulously characterized using NMR and elemental analysis; their crystal structures were further delineated by X‐ray diffraction. Our findings illustrate the unique geometric configurations of these complexes: Cu1 features a dinuclear arrangement with off‐linear geometry; Cu2 and Cu3 are characterized by a bi‐copper core stabilized by two phenanthroline‐modified carbene ligands. Crucially, in vitro cytotoxic evaluations revealed that these complexes possess suitability anticancer activity. Among them, Cu2 exhibited enhanced cytotoxicity activity, achieving a half‐maximal inhibitory concentration (IC<jats:sub>50</jats:sub>) of 4.36 ± 0.25 μM in colon cancer cell line HCT‐116, markedly surpassing the efficacy of cisplatin. Subsequent investigations elucidated that Cu2 notably increases intracellular reactive oxygen species (ROS) levels and induces mitochondrial membrane depolarization and endoplasmic reticulum stress, leading to oxidative stress‐mediated apoptosis of colon cancer cells.","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"64 1","pages":""},"PeriodicalIF":3.9,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269350","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":"Novel Cu(II) and Zn(II) Nanocomplexes Based on 5,6-Diphenyl-1,2,4-Triazine: Preparation, Spectroscopic, TD-DFT Calculations, Molecular Docking and Solvatochromic Studies","authors":"Mona Boshra,&nbsp;Omima M. I. Adly,&nbsp;Ebtesam M. Abdelrhman,&nbsp;Mohamed F. Eid,&nbsp;Fatma Samy","doi":"10.1002/aoc.7752","DOIUrl":"10.1002/aoc.7752","url":null,"abstract":"<div>\u0000 \u0000 <p>The reaction between 2-hydroxy-1-naphthaldehyde and 3-hydrazino-5,6-diphenyl-1,2,4-triazine produced a novel hydrazone ligand (DTHMN), which reacted with Cu(II) and Zn(II) metal ion in molar ratio 1:1, giving octahedral Cu(II)-DTHMN and tetrahedral Zn(II)-DTHMN nanosized complexes. The structural geometries have been elucidated on the basis of elemental analysis, nuclear magnetic resonance, infrared, electronic, and electron spin resonance spectra, and magnetic and molar conductance measurements as well as x-ray diffraction and thermal analysis. TEM analysis showed that Zn(II)-DTHMN complex has nano-rode morphology shape. On the other hand, Cu(II)-DTHMN has sphere shape within nanodomain. The DTHMN ligand exhibits ONN chelating sites through N-triazine ring, azomethine nitrogen, and deprotonated OH group, forming the mononuclear metal complexes. The synthesized compounds showed a distinct solvatochromic behavior in different polar solvents. A bathochromic alteration is observed when moving from less to high polar solvents, indicating strong solute–solvent interactions accompanied by intramolecular charge transfer (ICT). The ground and excited state dipole moments of these compounds were determined experimentally by solvatochromic shift method using Bilot–Kawski, Lippert–Mataga, Bakhshiev, and Kawski–Chamma–Viallet functions and a microscopic Reichardt's solvent polarity parameter (E_T^N). The dipole moment is increased significantly upon excitation referring to stabilizing the excited species includes n–π* transition by polarity of solvent. The experimental results are generally consistent with those values obtained by B3LYP/GENECP method at 6-311G(d,p) basis set for C, H, N, and O atoms and SDD (Stuttgart/Dresden) basis set for the metal atoms. The compounds were tested for antimicrobial efficiency against Gram-positive bacteria, Gram-negative bacteria, and fungus strain. Finally, molecular docking was used to study the interactions between donors (the current compounds) and receptors FabH–CoA complex (PDB code: 1HNJ).</p>\u0000 </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"38 12","pages":""},"PeriodicalIF":3.7,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142258795","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 Insight Into Experimental and Theoretical Investigation of Structure, Photophysical Property by ESIPT Processes and Biological Activities of Schiff Base Copper Complex","authors":"Iravatham Rama,&nbsp;Singaravel Nathiya,&nbsp;Murugesan Panneerselvam,&nbsp;Annamalai Subashini,&nbsp;Luciano T. Costa,&nbsp;Gothandam Jeeva,&nbsp;Shanmugam Achiraman,&nbsp;Kumar Dhinesh","doi":"10.1002/aoc.7737","DOIUrl":"10.1002/aoc.7737","url":null,"abstract":"<div>\u0000 \u0000 <p>A novel Schiff base (BSSMO) and its copper complex have been synthesized, and their structure was delineated using single crystal XRD studies. Computational techniques were used to design and evaluate BSSMO-based luminophores, revealing a significant intramolecular hydrogen bond within the molecule. Understanding ESIPT is crucial for optimizing photophysical and luminophore properties of organic molecules, especially for advancing optoelectronic devices. The study also explored the mechanisms of GSIPT and ESIPT for these BSSMO-based luminophores using transition state theory, charge distribution, molecular orbital analysis, and quantum theory of atoms in molecules. Results advocated that BSSMO-L2 exhibits higher absorption compared with BSSMO-L1 and the same trend is observed in emission spectral studies. However, the intensity of enol emissions in BSSMO-L2 is lower than that of keto (BSSMO-L3) emissions and the S1 (Keto form) emission of BSSMO-L3 shows significantly larger values, making it attractive for optoelectronic devices. The findings offer valuable insights for the development of ESIPT emitters with distinct photophysical properties. The in silico antidiabetic study of BSSMO-L2 explores the interaction with PPAR-γ protein, revealing a moderate affinity and stable complex, enhancing its bio-potential for future applications. The in vitro anticancer study of Cu-BSSMO-L2 complex shows a potential anticancer effect through mitochondrial and extrinsic death receptor mediated pathways. These insights contribute to the design of novel benzenesulfonamide-based bioactive molecules.</p>\u0000 </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"38 12","pages":""},"PeriodicalIF":3.7,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269305","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}