The Front Cover illustrates the SN2-like ring-opening reactions of THF derivatives with the chalcogen elements O, S, Se and Te on both Si(001) and Ge(001) surfaces. The periodic table at the back embodies the trends presented in the work. On the left, the deformation density of the first NOCV in the THF precursor structure showcases the charge transfer towards the surface. The across-trench product of the tellurium derivative is shown on the right. The center features the across-trench transition state geometry of THSe with a deformation density indicating an SN2-like reaction. More information can be found in the Research Article by R. Tonner-Zech and co-workers (DOI: 10.1002/ejoc.202400560).
{"title":"Front Cover: Trends in the Reactivity of Pentacyclic Ether Derivatives on Silicon and Germanium Surfaces Revealed by Energy Decomposition Analysis for Extended Systems (Eur. J. Org. Chem. 37/2024)","authors":"Franz Thiemann, Hendrik Weiske, Ralf Tonner-Zech","doi":"10.1002/ejoc.202483701","DOIUrl":"10.1002/ejoc.202483701","url":null,"abstract":"<p><b>The Front Cover</b> illustrates the S<sub>N</sub>2-like ring-opening reactions of THF derivatives with the chalcogen elements O, S, Se and Te on both Si(001) and Ge(001) surfaces. The periodic table at the back embodies the trends presented in the work. On the left, the deformation density of the first NOCV in the THF precursor structure showcases the charge transfer towards the surface. The across-trench product of the tellurium derivative is shown on the right. The center features the across-trench transition state geometry of THSe with a deformation density indicating an S<sub>N</sub>2-like reaction. More information can be found in the Research Article by R. Tonner-Zech and co-workers (DOI: 10.1002/ejoc.202400560).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202483701","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374408","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yingying Zheng, Jie Li, Xiaotian Wu, Shanshan Ma, Xueyan Lv, Lei Feng, Qiang Han, Chen Ma
An efficient I2-promoted Povarov multicomponent reaction for the synthesis of 2,2′-biquinolines or N-heteroaromatic benzothiazole is described. In this case, the methyl group of methyl aza-arenes is involved in the Povarov reaction via an iodination/Kornblum oxidation sequence.
{"title":"I2-Promoted Povarov Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and N-Heteroaromatic Benzothiazoles","authors":"Yingying Zheng, Jie Li, Xiaotian Wu, Shanshan Ma, Xueyan Lv, Lei Feng, Qiang Han, Chen Ma","doi":"10.1002/ejoc.202400714","DOIUrl":"https://doi.org/10.1002/ejoc.202400714","url":null,"abstract":"An efficient I<sub>2</sub>-promoted Povarov multicomponent reaction for the synthesis of 2,2′-biquinolines or <i>N</i>-heteroaromatic benzothiazole is described. In this case, the methyl group of methyl aza-arenes is involved in the Povarov reaction via an iodination/Kornblum oxidation sequence.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142369577","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}
Herein, we present an efficient strategy for the synthesis of spiro(indenyl)cyclohexadienones through radical-promoted reaction of 2-alkynyl biaryls with sodium sulfinates under electrochemical conditions. The reaction involves sulfonylation and dearomative ipso-cyclisation in a domino fashion. This approach features the use of readily accessible precursors, wide functional group tolerance and external oxidant-free reaction conditions. The practicality of the method was also illustrated by scale-up reaction and further diversification of the product
{"title":"Electrochemical domino sulfonylation/dearomative ipso-annulation of 2-alkynyl biaryls to access spiro(indenyl)cyclohexadienones","authors":"Chada Raji Reddy, Karna Nair, Puthiya P Vinaya, Uprety Ajaykumar, Rene Gree","doi":"10.1002/ejoc.202400990","DOIUrl":"https://doi.org/10.1002/ejoc.202400990","url":null,"abstract":"Herein, we present an efficient strategy for the synthesis of spiro(indenyl)cyclohexadienones through radical-promoted reaction of 2-alkynyl biaryls with sodium sulfinates under electrochemical conditions. The reaction involves sulfonylation and dearomative ipso-cyclisation in a domino fashion. This approach features the use of readily accessible precursors, wide functional group tolerance and external oxidant-free reaction conditions. The practicality of the method was also illustrated by scale-up reaction and further diversification of the product","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142362724","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}
An efficient transition metal‐free approach for the synthesis of chroman‐4‐ones via double conjugate additions of 2‐hydroxyacetophenones on alkynyl nitriles utilizing NaH as a base has been realized. This operationally simple protocol offers library of 4‐chromanones in moderate to good yields.
利用 NaH 作为碱，通过 2-hydroxyacetophenones 与炔基腈纶的双共轭加成，实现了一种合成 4-色满酮的高效无过渡金属方法。该方法操作简单，能以中等至良好的收率合成 4-色满酮。
{"title":"Tetrasubstituted Chromanone Synthesis by a Tandem Oxa‐Michael/Michael Addition Reaction of 2‐Hydroxyacetophenones and Alkynyl Nitriles","authors":"Chandresh Kumari, Narendra Prasad Sahoo, Madan Kumar, Avijit Goswami","doi":"10.1002/ejoc.202401061","DOIUrl":"https://doi.org/10.1002/ejoc.202401061","url":null,"abstract":"An efficient transition metal‐free approach for the synthesis of chroman‐4‐ones via double conjugate additions of 2‐hydroxyacetophenones on alkynyl nitriles utilizing NaH as a base has been realized. This operationally simple protocol offers library of 4‐chromanones in moderate to good yields.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142369184","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}
Fei Pan, Qiao-Lin Xu, Yi Zhao, Xia-Ling Liu, Na Jin, Ke-Han He
Fluorinated motifs are commonly found in drugs and agrochemicals. The inclusion of fluorine-containing motifs in drug candidates during lead optimization has become a valuable strategy in pharmaceutical research and development. Significant research efforts have been dedicated to synthesizing molecules with a trifluoromethyl (CF3−) group on a stereogenic carbon. Herein, we disclose a mild and efficient nickel-catalyzed reductive cross-coupling between α-trifluoromethyl alkyl bromides and allylic sulfones, enabling the efficient synthesis of α-trifluoromethyl homoallylic alkanes. This reaction featuring base-free, mild conditions, a broad substrate scope, and high functional group tolerance. The synthetic versatility of this approach is further underscored by its successful application in the late-stage functionalization of a range of drug molecules. Our preliminary mechanistic study suggests that this allylation process operates through a radical intermediate.
{"title":"Nickel-Catalyzed Reductive Cross-Coupling of α-Trifluoromethylated Alkyl Electrophiles and Allylic Sulfones","authors":"Fei Pan, Qiao-Lin Xu, Yi Zhao, Xia-Ling Liu, Na Jin, Ke-Han He","doi":"10.1002/ejoc.202400986","DOIUrl":"https://doi.org/10.1002/ejoc.202400986","url":null,"abstract":"Fluorinated motifs are commonly found in drugs and agrochemicals. The inclusion of fluorine-containing motifs in drug candidates during lead optimization has become a valuable strategy in pharmaceutical research and development. Significant research efforts have been dedicated to synthesizing molecules with a trifluoromethyl (CF3−) group on a stereogenic carbon. Herein, we disclose a mild and efficient nickel-catalyzed reductive cross-coupling between α-trifluoromethyl alkyl bromides and allylic sulfones, enabling the efficient synthesis of α-trifluoromethyl homoallylic alkanes. This reaction featuring base-free, mild conditions, a broad substrate scope, and high functional group tolerance. The synthetic versatility of this approach is further underscored by its successful application in the late-stage functionalization of a range of drug molecules. Our preliminary mechanistic study suggests that this allylation process operates through a radical intermediate.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360501","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}
α-Galactosylceramide (αGalCer) is a synthetic glycolipid that, when loaded into the CD1d receptor of antigen presenting cells, activates iNKT cells to coordinate the generation of both innate and adaptive immune responses. In vaccines, the αGalCer adjuvant is generally delivered in liposomes, but interestingly, little is known about the intracellular fate of αGalCer–antigen conjugates resulting in the absence of clear “design rules” for this type of compounds and their formulations. To unravel the uptake mechanism of liposomal αGalCer conjugates and understand the fate of its components, we synthesized sulfoCy7–αGalCer 1 and sulfoCy5–αGalCer 2. The fluorescent probes were obtained from a linker–functionalized αGalCer, which was then modified with sulfoCy7/sulfoCy5. After formulation in liposomes, the cellular presentation was studied in a murine dendritic cell line using fluorescence imaging and flow cytometry. Imaging indicates that liposomes loaded with sulfoCy5–αGalCer are taken up by DC2.4 cells in a heterogeneous and concentration-dependent manner. Additionally, fluorescence antibody staining confirms that αGalCer is ultimately presented by CD1d receptors, but importantly is cleaved from sulfoCy5 before reaching the cell surface. These results validate our synthetic probes as useful in mechanistic studies of the uptake of αGalCer–antigen conjugates as shown here for DC2.4 cells.
{"title":"Synthesis of sulfoCy5- and sulfoCy7-αGalCer Probes as Chemical Tools for Investigating the Uptake of Liposomal αGalCer Conjugates by Antigen Presenting Cells","authors":"Cecilia Romanò, Philip Lund, Peng Wei, Hao Jiang, Chloé Stoll, Mads Hartvig Clausen","doi":"10.1002/ejoc.202400998","DOIUrl":"https://doi.org/10.1002/ejoc.202400998","url":null,"abstract":"α-Galactosylceramide (αGalCer) is a synthetic glycolipid that, when loaded into the CD1d receptor of antigen presenting cells, activates iNKT cells to coordinate the generation of both innate and adaptive immune responses. In vaccines, the αGalCer adjuvant is generally delivered in liposomes, but interestingly, little is known about the intracellular fate of αGalCer–antigen conjugates resulting in the absence of clear “design rules” for this type of compounds and their formulations. To unravel the uptake mechanism of liposomal αGalCer conjugates and understand the fate of its components, we synthesized sulfoCy7–αGalCer 1 and sulfoCy5–αGalCer 2. The fluorescent probes were obtained from a linker–functionalized αGalCer, which was then modified with sulfoCy7/sulfoCy5. After formulation in liposomes, the cellular presentation was studied in a murine dendritic cell line using fluorescence imaging and flow cytometry. Imaging indicates that liposomes loaded with sulfoCy5–αGalCer are taken up by DC2.4 cells in a heterogeneous and concentration-dependent manner. Additionally, fluorescence antibody staining confirms that αGalCer is ultimately presented by CD1d receptors, but importantly is cleaved from sulfoCy5 before reaching the cell surface. These results validate our synthetic probes as useful in mechanistic studies of the uptake of αGalCer–antigen conjugates as shown here for DC2.4 cells.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142330307","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}
Visible-light photocatalysis has emerged as a prominent research area in modern organic synthesis and environmental science. As an important transition metal, chromium has garnered widespread attention in the field of visible-light photocatalysis in recent years, primarily manifested in the following aspects: a) the unique photochemical properties of chromium(III) complexes endow them with longer excited-state lifetimes and higher reactivities; b) by harnessing visible light to induce single-electron transfer or hydrogen atom transfer to generate radicals, which subsequently form alkyl-chromium(III) intermediates with chromium(II) ligands, these intermediates can selectively attack electron-deficient carbonyl compounds, enabling the construction of target products; c) following metals like cerium, copper, iron, nickel, cobalt, titanium, and bismuth, the ligand-to-metal charge transfer (LMCT) reaction pathways in chromium photocatalysis have also been extensively investigated.This review will provide a comprehensive summary of recent research on chromium-mediated photocatalytic reactions, offering an in-depth exploration of their unique reactivity, mechanisms, and future directions.
{"title":"Chromium in Visible-Light Photocatalysis: Unique Reactivity, Mechanisms and Future Directions","authors":"Zhengjia Shen, Jia-Lin Tu","doi":"10.1002/ejoc.202401016","DOIUrl":"https://doi.org/10.1002/ejoc.202401016","url":null,"abstract":"Visible-light photocatalysis has emerged as a prominent research area in modern organic synthesis and environmental science. As an important transition metal, chromium has garnered widespread attention in the field of visible-light photocatalysis in recent years, primarily manifested in the following aspects: a) the unique photochemical properties of chromium(III) complexes endow them with longer excited-state lifetimes and higher reactivities; b) by harnessing visible light to induce single-electron transfer or hydrogen atom transfer to generate radicals, which subsequently form alkyl-chromium(III) intermediates with chromium(II) ligands, these intermediates can selectively attack electron-deficient carbonyl compounds, enabling the construction of target products; c) following metals like cerium, copper, iron, nickel, cobalt, titanium, and bismuth, the ligand-to-metal charge transfer (LMCT) reaction pathways in chromium photocatalysis have also been extensively investigated.This review will provide a comprehensive summary of recent research on chromium-mediated photocatalytic reactions, offering an in-depth exploration of their unique reactivity, mechanisms, and future directions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142330308","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}
Rohan Kumar Meher, Ravi Kumar, Abhijit Sau, Tarun K. Panda
We report here the use of amidophosphine borane {(BH₃)₂(PPh)₂N(CH₂)C₆H₅} as a competent reducing agent for the hydroboration of ketones and imines, yielding the corresponding secondary alcohols and secondary amines under mild and catalyst-free reaction conditions. Solid amidophosphine boranes, which are easy to synthesize, and easy to handle demonstrated excellent reactivity and functional group tolerance toward a wide variety of ketones and imines, including aromatic, heteroaromatic, and aliphatic derivatives with electron-withdrawing and electron-donating substitutions, thus showing excellent chemoselectivity.
{"title":"Efficient Hydroboration of Ketones and Imines Using Amidophosphine-borane under Catalyst-Free Conditions","authors":"Rohan Kumar Meher, Ravi Kumar, Abhijit Sau, Tarun K. Panda","doi":"10.1002/ejoc.202400985","DOIUrl":"https://doi.org/10.1002/ejoc.202400985","url":null,"abstract":"We report here the use of amidophosphine borane {(BH₃)₂(PPh)₂N(CH₂)C₆H₅} as a competent reducing agent for the hydroboration of ketones and imines, yielding the corresponding secondary alcohols and secondary amines under mild and catalyst-free reaction conditions. Solid amidophosphine boranes, which are easy to synthesize, and easy to handle demonstrated excellent reactivity and functional group tolerance toward a wide variety of ketones and imines, including aromatic, heteroaromatic, and aliphatic derivatives with electron-withdrawing and electron-donating substitutions, thus showing excellent chemoselectivity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142329598","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}
An exceptionally brilliant strategy to miniaturize electronic devices is to employ a single‐molecule between two electrodes for carrier conduction at single‐molecule break junctions (SMBJ). To understand the intrinsic mechanisms of operation at these junctions, extremely crucial is to study physical, chemical, and electrochemical properties employing single‐molecules at SMBJs. Further, redox‐based transformations at the nano‐junction could be achieved electrochemically to allow efficient switching between different redox states of a single‐molecule, showcasing the possibility of maneuvering transport properties with on‐off states of the molecule. Herein, are presented the fundamentals of SMBJs, and the electrochemically influenced transformations or switching of organic molecules pursued at SMBJs. Such an understanding of electrochemical phenomena at the nanoscale dimension could bridge the knowledge gap between macroscopic electronic circuits and single‐molecule electronic circuits, whereby the feasibility of switching between the states could maneuver the electronic properties as well as other photophysical parameters.
{"title":"Molecular Break Junction: A Stage for Redox Transformations","authors":"Ishita Neogi, Haritha S, Anjitha Sebastian, Simi Achankunju, Gourab Mohanty, Keshaba Nanda Parida","doi":"10.1002/ejoc.202400980","DOIUrl":"https://doi.org/10.1002/ejoc.202400980","url":null,"abstract":"An exceptionally brilliant strategy to miniaturize electronic devices is to employ a single‐molecule between two electrodes for carrier conduction at single‐molecule break junctions (SMBJ). To understand the intrinsic mechanisms of operation at these junctions, extremely crucial is to study physical, chemical, and electrochemical properties employing single‐molecules at SMBJs. Further, redox‐based transformations at the nano‐junction could be achieved electrochemically to allow efficient switching between different redox states of a single‐molecule, showcasing the possibility of maneuvering transport properties with on‐off states of the molecule. Herein, are presented the fundamentals of SMBJs, and the electrochemically influenced transformations or switching of organic molecules pursued at SMBJs. Such an understanding of electrochemical phenomena at the nanoscale dimension could bridge the knowledge gap between macroscopic electronic circuits and single‐molecule electronic circuits, whereby the feasibility of switching between the states could maneuver the electronic properties as well as other photophysical parameters.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142328877","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}
Gábor Berecz, Dávid Szabó, András Dancsó, Mária Tóthné Lauritz, Loránd Kiss, Gyula Simig, Balázs Volk
In continuation of our commitment to the synthesis of new ring systems based on the 6,11-dihydrodibenzo[c,f][1,2]thiazepin 5,5-dioxide core of the antidepressant drug tianeptine, we have incorporated two- and/or three-carbon bridges between the nitrogen atom of the sulfonamide moiety and the N-, O- or S-substituent at position 11 of the tricycle. The synthesis of 5 new ring systems is described and demonstrated with several target compounds.
{"title":"Synthesis of New Tetracyclic Ring Systems: Bridged Derivatives of Hydroxy-, Sulfanyl- and Amino-Substituted Dibenzo[c,f][1,2]thiazepine S,S-Dioxides","authors":"Gábor Berecz, Dávid Szabó, András Dancsó, Mária Tóthné Lauritz, Loránd Kiss, Gyula Simig, Balázs Volk","doi":"10.1002/ejoc.202400835","DOIUrl":"https://doi.org/10.1002/ejoc.202400835","url":null,"abstract":"In continuation of our commitment to the synthesis of new ring systems based on the 6,11-dihydrodibenzo[c,f][1,2]thiazepin 5,5-dioxide core of the antidepressant drug tianeptine, we have incorporated two- and/or three-carbon bridges between the nitrogen atom of the sulfonamide moiety and the N-, O- or S-substituent at position 11 of the tricycle. The synthesis of 5 new ring systems is described and demonstrated with several target compounds.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.8,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142325861","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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