A highly efficient catalytic enantioselective double annulation protocol has been developed for the asymmetric synthesis of hetero[7]helicenes. This method involves a sequential chiral phosphoric acid (CPA)-catalyzed three-component double Povarov reaction with a pentacyclic diamine followed by aromatization, which yielded various bispyridine-containing hetero[7]helicenes with good yields and excellent enantioselectivity. Notably, two distinct oxidative aromatization methods have been developed to selectively afford hetero[7]helicenes with either mono-amido or bis-amido substitutions at the peri-positions. Extensive derivatizations of these chiral heterohelicene products, along with detailed studies of their photophysical and chiroptical properties, underscore the significance of this method.
{"title":"Diverse enantioselective synthesis of hetero[7]helicenes via an organocatalyzed double annulation strategy†","authors":"Tianren Qin , Wansen Xie , Wei Liu , Xiaoyu Yang","doi":"10.1039/d4qo02188f","DOIUrl":"10.1039/d4qo02188f","url":null,"abstract":"<div><div>A highly efficient catalytic enantioselective double annulation protocol has been developed for the asymmetric synthesis of hetero[7]helicenes. This method involves a sequential chiral phosphoric acid (CPA)-catalyzed three-component double Povarov reaction with a pentacyclic diamine followed by aromatization, which yielded various bispyridine-containing hetero[7]helicenes with good yields and excellent enantioselectivity. Notably, two distinct oxidative aromatization methods have been developed to selectively afford hetero[7]helicenes with either mono-amido or bis-amido substitutions at the <em>peri</em>-positions. Extensive derivatizations of these chiral heterohelicene products, along with detailed studies of their photophysical and chiroptical properties, underscore the significance of this method.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1417-1424"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142879897","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Qiping He , Wenxin Yan , Xianglin Yu , Xinxiang Huang , Chang Liu , Yinchun Jiao , Yi Jin
Herein, we report a method for metal-catalyzed para-Csp2–H functionalization of arylamines through photoinduced ligand-to-metal charge transfer (LMCT) for prospective application. The photo-LMCT–homolysis mode allows Sc–N complexes to form nitrogen radical intermediates, which are then isomerized into aryl radicals and prepared for subsequent radical coupling. A selective construction of C–O, C–S, C–Se, and C–C bonds has been achieved, and these reactions offer operationally simple, low-catalyst, and highly regioselective procedures for accessing valuable arylamine functionalization in a single step.
{"title":"LMCT–homolysis-enabled C–H functionalization of arylamines†","authors":"Qiping He , Wenxin Yan , Xianglin Yu , Xinxiang Huang , Chang Liu , Yinchun Jiao , Yi Jin","doi":"10.1039/d4qo02146k","DOIUrl":"10.1039/d4qo02146k","url":null,"abstract":"<div><div>Herein, we report a method for metal-catalyzed <em>para</em>-Csp<sup>2</sup>–H functionalization of arylamines through photoinduced ligand-to-metal charge transfer (LMCT) for prospective application. The photo-LMCT–homolysis mode allows Sc–N complexes to form nitrogen radical intermediates, which are then isomerized into aryl radicals and prepared for subsequent radical coupling. A selective construction of C–O, C–S, C–Se, and C–C bonds has been achieved, and these reactions offer operationally simple, low-catalyst, and highly regioselective procedures for accessing valuable arylamine functionalization in a single step.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1521-1527"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142905509","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Meijia Zheng , Xiaotian Zhang , Xinran Zhang , Yingjie Liu , Qin Li , Lidan Mao , Weiguang Sun , Chunmei Chen , Yonghui Zhang , Hucheng Zhu
Bipolarsterols A–H (), eight undescribed steroids, were isolated from Bipolaris oryzae, along with nine known congeners. Their structures and absolute configurations were elucidated by comprehensive spectroscopic techniques, including NMR and ECD calculations. Compound represents the first example of a 19(l0 → 5)-abeo-7(8 → 9)-abeo-ergostane, featuring an unusual spiro[4.5]decan-6-one system, and compound is a new member of the rare steroid-phenylpropanoid hybrid class. Compound showed remarkable cytotoxicity against HT29 cells with an IC50 value of 5.8 μM. Compound showed a significant inhibitory effect on NO production in RAW264.7 with an IC50 value of 2.7 μM, through the inhibition of iNOS levels at the transcriptional and protein levels as well as the NF-κB pathway.
{"title":"Bipolarsterol A, a steroid with an unprecedented 6/5/6/5 carbon skeleton from the phytopathogenic fungus Bipolaris oryzae†","authors":"Meijia Zheng , Xiaotian Zhang , Xinran Zhang , Yingjie Liu , Qin Li , Lidan Mao , Weiguang Sun , Chunmei Chen , Yonghui Zhang , Hucheng Zhu","doi":"10.1039/d4qo02057j","DOIUrl":"10.1039/d4qo02057j","url":null,"abstract":"<div><div>Bipolarsterols A–H (), eight undescribed steroids, were isolated from <em>Bipolaris oryzae</em>, along with nine known congeners. Their structures and absolute configurations were elucidated by comprehensive spectroscopic techniques, including NMR and ECD calculations. Compound represents the first example of a 19(l0 → 5)-<em>abeo</em>-7(8 → 9)-<em>abeo</em>-ergostane, featuring an unusual spiro[4.5]decan-6-one system, and compound is a new member of the rare steroid-phenylpropanoid hybrid class. Compound showed remarkable cytotoxicity against HT29 cells with an IC<sub>50</sub> value of 5.8 μM. Compound showed a significant inhibitory effect on NO production in RAW264.7 with an IC<sub>50</sub> value of 2.7 μM, through the inhibition of iNOS levels at the transcriptional and protein levels as well as the NF-κB pathway.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1474-1484"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xun Yang , Yuxuan Xiao , Ying Yin , Haiyan Li , Jiahui Du , Xin Li , Wengui Duan , Lin Yu
With increasing concerns regarding the energy crisis and environmental changes, the development of sunlight-based methods for organic synthesis has become imperative. We present a masking enone strategy that effectively suppresses side reactions associated with enone products, enabling the β-selective acylation of alkenes catalyzed by excited-state copper under sunlight or visible light. This reaction yields highly valuable α,β-unsaturated ketones, which can be readily transformed into important building blocks through various conversions. Notably, this method is characterized by its sustainable and eco-friendly energy source, mild reaction conditions, high compatibility with functional groups, and suitability for gram-scale synthesis, making it promising for late-stage modifications of complex molecules. Mechanistic studies indicate that the reaction proceeds via a free radical pathway.
{"title":"Visible-light or sunlight photoredox-catalyzed β-selective acylation of alkenes to access α,β-unsaturated ketones†","authors":"Xun Yang , Yuxuan Xiao , Ying Yin , Haiyan Li , Jiahui Du , Xin Li , Wengui Duan , Lin Yu","doi":"10.1039/d4qo02101k","DOIUrl":"10.1039/d4qo02101k","url":null,"abstract":"<div><div>With increasing concerns regarding the energy crisis and environmental changes, the development of sunlight-based methods for organic synthesis has become imperative. We present a masking enone strategy that effectively suppresses side reactions associated with enone products, enabling the β-selective acylation of alkenes catalyzed by excited-state copper under sunlight or visible light. This reaction yields highly valuable α,β-unsaturated ketones, which can be readily transformed into important building blocks through various conversions. Notably, this method is characterized by its sustainable and eco-friendly energy source, mild reaction conditions, high compatibility with functional groups, and suitability for gram-scale synthesis, making it promising for late-stage modifications of complex molecules. Mechanistic studies indicate that the reaction proceeds via a free radical pathway.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1543-1549"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142917794","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hao-Yuan Li , Xiu-Long Yang , Fantao Zhou , Jun-Li Li , Qing-Yuan Meng , Xiaoying Niu
In this work, we present a UV-induced 6π-cyclization protocol enabling the synthesis of polysubstituted naphthol skeletons using a single cobaloxime catalyst. In addition, the dual-function photosensitizer 4CzIPN served as both an energy transfer (EnT) photosensitizer and a single electron transfer (SET) photocatalyst within the reaction, leading to the synthesis of the same skeleton under visible light irradiation. The sole by-product of the two strategies was hydrogen, offering potential utility.
{"title":"Photoinduced Co-catalyzed dehydrogenative cyclization of 2-alkenylphenyl carbonyl compounds and mechanistic insights†","authors":"Hao-Yuan Li , Xiu-Long Yang , Fantao Zhou , Jun-Li Li , Qing-Yuan Meng , Xiaoying Niu","doi":"10.1039/d4qo02132k","DOIUrl":"10.1039/d4qo02132k","url":null,"abstract":"<div><div>In this work, we present a UV-induced 6π-cyclization protocol enabling the synthesis of polysubstituted naphthol skeletons using a single cobaloxime catalyst. In addition, the dual-function photosensitizer 4CzIPN served as both an energy transfer (EnT) photosensitizer and a single electron transfer (SET) photocatalyst within the reaction, leading to the synthesis of the same skeleton under visible light irradiation. The sole by-product of the two strategies was hydrogen, offering potential utility.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1626-1632"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142936537","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Jiaxu Feng , Luca Nicchio , Liting Liu , Yingying Wu , Kui Lu , Stefano Protti , Xia Zhao
The literature on the use of trivalent phosphines in the activation of electrophilic unsaturated reagents is large. However, the application of such derivatives for the generation of radical intermediates has received attention only in the past decade. This review provides a detailed description of the phosphine-mediated-photocatalyzed and photoredox-catalyzed protocols for the formation of carbon–carbon and carbon–heteroatom bonds proposed in the last decade.
{"title":"Recent advances in visible light-driven phosphine-mediated transformations","authors":"Jiaxu Feng , Luca Nicchio , Liting Liu , Yingying Wu , Kui Lu , Stefano Protti , Xia Zhao","doi":"10.1039/d4qo02079k","DOIUrl":"10.1039/d4qo02079k","url":null,"abstract":"<div><div>The literature on the use of trivalent phosphines in the activation of electrophilic unsaturated reagents is large. However, the application of such derivatives for the generation of radical intermediates has received attention only in the past decade. This review provides a detailed description of the phosphine-mediated-photocatalyzed and photoredox-catalyzed protocols for the formation of carbon–carbon and carbon–heteroatom bonds proposed in the last decade.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1695-1707"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/qo/d4qo02079k?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142905508","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xincheng Zhou , Zhichao Chang , Yongchun Hu , Jianming Zhong , Jiaying Liao , Chunying Rong , Wang Zhou
The photochromic behaviors of spiropyrans that are fused with an aromatic ring adjacent to the spirocarbon have not been well studied. A series of benzofuranone-based spiropyrans containing a thiophene, benzothiophene, selenophene, or indole ring close to the spirocarbon center were synthesized through rhodium(iii)-catalyzed annulation of hydroxyl 1,2-diarylethane-1,2-diones with internal alkynes. Their temperature-dependent photochromic properties were observed experimentally and explained by density functional theory (DFT) calculations.
{"title":"Benzofuranone-based spiropyrans: synthesis, temperature-dependent photochromic properties, and DFT calculations†","authors":"Xincheng Zhou , Zhichao Chang , Yongchun Hu , Jianming Zhong , Jiaying Liao , Chunying Rong , Wang Zhou","doi":"10.1039/d4qo02123a","DOIUrl":"10.1039/d4qo02123a","url":null,"abstract":"<div><div>The photochromic behaviors of spiropyrans that are fused with an aromatic ring adjacent to the spirocarbon have not been well studied. A series of benzofuranone-based spiropyrans containing a thiophene, benzothiophene, selenophene, or indole ring close to the spirocarbon center were synthesized through rhodium(<span>iii</span>)-catalyzed annulation of hydroxyl 1,2-diarylethane-1,2-diones with internal alkynes. Their temperature-dependent photochromic properties were observed experimentally and explained by density functional theory (DFT) calculations.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1619-1625"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142968530","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Rubal Sharma , Mitsuhiro Arisawa , Shinobu Takizawa , Mohamed S. H. Salem
Skeletal editing is an emerging approach in synthetic chemistry that enables precise atom-level modifications within molecular cores, facilitating complex transformations and minimizing resource-intensive synthesis. This review provides a comprehensive overview of the most recent advancements in skeletal editing, with a particular focus on single atom modifications. While skeletal editing can be applied to both cyclic and acyclic compounds, this review centers on carbo- and heterocyclic systems exclusively. By integrating historical context and categorizing key developments, it highlights the major achievements in insertion, deletion, and transmutation, connecting related works and delving into mechanistic insights.
{"title":"Remodelling molecular frameworks via atom-level surgery: recent advances in skeletal editing of (hetero)cycles","authors":"Rubal Sharma , Mitsuhiro Arisawa , Shinobu Takizawa , Mohamed S. H. Salem","doi":"10.1039/d4qo02157f","DOIUrl":"10.1039/d4qo02157f","url":null,"abstract":"<div><div>Skeletal editing is an emerging approach in synthetic chemistry that enables precise atom-level modifications within molecular cores, facilitating complex transformations and minimizing resource-intensive synthesis. This review provides a comprehensive overview of the most recent advancements in skeletal editing, with a particular focus on single atom modifications. While skeletal editing can be applied to both cyclic and acyclic compounds, this review centers on carbo- and heterocyclic systems exclusively. By integrating historical context and categorizing key developments, it highlights the major achievements in insertion, deletion, and transmutation, connecting related works and delving into mechanistic insights.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1633-1670"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/qo/d4qo02157f?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142936510","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Manuel Buendía , Anton J. Stasyuk , Salvatore Filippone , Miquel Solà , Nazario Martín
Supramolecular chemistry of carbon-based materials provides a variety of chemical structures with potential applications in materials science and biomedicine. Here, we explore the supramolecular complexation of fullerenes C60 and C70, highlighting the ability of molecular nanographene tweezers to capture these structures. The binding constant for the complex was significantly higher than for , showing a clear selectivity for the more π-extended C70. DFT calculations confirmed these experimental results by showing that the interaction energy of C70 with is more than 5 kcal mol−1 higher than that of C60. Theoretical calculations predict that the dispersion interaction provides about 58–59% of the total interaction energy, followed by electrostatic attraction with 26% and orbital interactions, which contribute 15–16%. The racemic nanographene tweezers effectively recognize fullerene molecules and hold promise for future applications in chiral molecule recognition.
{"title":"All-carbon supramolecular complexation of a bilayer molecular nanographene with [60] and [70]fullerenes†","authors":"Manuel Buendía , Anton J. Stasyuk , Salvatore Filippone , Miquel Solà , Nazario Martín","doi":"10.1039/d4qo02071e","DOIUrl":"10.1039/d4qo02071e","url":null,"abstract":"<div><div>Supramolecular chemistry of carbon-based materials provides a variety of chemical structures with potential applications in materials science and biomedicine. Here, we explore the supramolecular complexation of fullerenes C<sub>60</sub> and C<sub>70</sub>, highlighting the ability of molecular nanographene tweezers to capture these structures. The binding constant for the complex was significantly higher than for , showing a clear selectivity for the more π-extended C<sub>70</sub>. DFT calculations confirmed these experimental results by showing that the interaction energy of C<sub>70</sub> with is more than 5 kcal mol<sup>−1</sup> higher than that of C<sub>60</sub>. Theoretical calculations predict that the dispersion interaction provides about 58–59% of the total interaction energy, followed by electrostatic attraction with 26% and orbital interactions, which contribute 15–16%. The racemic nanographene tweezers effectively recognize fullerene molecules and hold promise for future applications in chiral molecule recognition.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1438-1443"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/qo/d4qo02071e?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142879845","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Jiaxin Wang , Xuelong Zhang , Aichen Li , Rui He , Surong Zhang , Xiangyue Li , Lanlan Zhang , Guodong Ju , Chao Wang
The transition-metal-catalyzed intermolecular three-component dearomative difunctionalization of indoles in a one-pot fashion remains largely unexplored. Herein, we present a novel Ni-catalyzed dearomative alkylborylation of indoles utilizing a ligand-enabled, directing group-assisted strategy. This regio- and diastereoselective reaction efficiently converts readily accessible indoles into valuable C3-borylated and C2-alkylated indolines. Additionally, we established a practical one-pot procedure for accessing valuable 2,3-disubstituted indoles with boron retained by combining this protocol with the subsequent oxidation of the resulting indolines. The robustness of this protocol is demonstrated through gram-scale reactions, facile late-stage decoration of complex drug-like molecules, and various downstream diversifications.
{"title":"Amino alcohol ligand-enabled Ni-catalyzed regio- and diastereoselective dearomative borylalkylation of indoles†","authors":"Jiaxin Wang , Xuelong Zhang , Aichen Li , Rui He , Surong Zhang , Xiangyue Li , Lanlan Zhang , Guodong Ju , Chao Wang","doi":"10.1039/d4qo02187h","DOIUrl":"10.1039/d4qo02187h","url":null,"abstract":"<div><div>The transition-metal-catalyzed intermolecular three-component dearomative difunctionalization of indoles in a one-pot fashion remains largely unexplored. Herein, we present a novel Ni-catalyzed dearomative alkylborylation of indoles utilizing a ligand-enabled, directing group-assisted strategy. This regio- and diastereoselective reaction efficiently converts readily accessible indoles into valuable C3-borylated and C2-alkylated indolines. Additionally, we established a practical one-pot procedure for accessing valuable 2,3-disubstituted indoles with boron retained by combining this protocol with the subsequent oxidation of the resulting indolines. The robustness of this protocol is demonstrated through gram-scale reactions, facile late-stage decoration of complex drug-like molecules, and various downstream diversifications.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1513-1520"},"PeriodicalIF":0.0,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142879896","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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