Pub Date : 2025-04-01Epub Date: 2025-03-07DOI: 10.1016/j.jfluchem.2025.110416
Jie Yang, Yan Zhou, Liqin Kang, Hua Zhang, Chuanxiang Liu
A new naphthalimide-derived chemosensor (R) was developed for the detection of fluoride through F--driven desilylation-decyanation cascade. The probe exhibited significant "naked-eye" changes in UV–visible absorption (red shift of 300 nm), and a fluorescent turn-off response to fluoride (LOD = 27.2 nM). The sensing mechanism was confirmed by spectral comparison, NMR titration, and MS analysis. Accordingly, R-loaded test paper was prepared and used to detect fluoride in aqueous solutions.
{"title":"A fluoride-responsive naphthalimide-derived chemosensor: Mechanistic insights into F--driven desilylation-decyanation cascade","authors":"Jie Yang, Yan Zhou, Liqin Kang, Hua Zhang, Chuanxiang Liu","doi":"10.1016/j.jfluchem.2025.110416","DOIUrl":"10.1016/j.jfluchem.2025.110416","url":null,"abstract":"<div><div>A new naphthalimide-derived chemosensor (<strong>R</strong>) was developed for the detection of fluoride through F<sup>-</sup>-driven desilylation-decyanation cascade. The probe exhibited significant \"naked-eye\" changes in UV–visible absorption (red shift of 300 nm), and a fluorescent turn-off response to fluoride (LOD = 27.2 <em>n</em>M). The sensing mechanism was confirmed by spectral comparison, NMR titration, and MS analysis. Accordingly, <strong>R</strong>-loaded test paper was prepared and used to detect fluoride in aqueous solutions.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110416"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143563366","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-04-30DOI: 10.1016/j.jfluchem.2025.110425
Zhou Yu , Sheng Wang , Wenbo Chen , Lele Wen , Long Lu
An efficient method for synthesizing sulfonyl fluorides by fluorinating sulfonyl hydrazides with 10 % F2/N2 was developed. This transformation demonstrated a broad substrate scope, yielding a series of sulfonyl fluorides in moderate to good yields. Additionally, a 10 g scale experiment was conducted, demonstrating the practicality of this method.
{"title":"Fluorination of sulfonyl hydrazides with fluorine gas for the synthesis of sulfonyl fluorides","authors":"Zhou Yu , Sheng Wang , Wenbo Chen , Lele Wen , Long Lu","doi":"10.1016/j.jfluchem.2025.110425","DOIUrl":"10.1016/j.jfluchem.2025.110425","url":null,"abstract":"<div><div>An efficient method for synthesizing sulfonyl fluorides by fluorinating sulfonyl hydrazides with 10 % F<sub>2</sub>/N<sub>2</sub> was developed. This transformation demonstrated a broad substrate scope, yielding a series of sulfonyl fluorides in moderate to good yields. Additionally, a 10 g scale experiment was conducted, demonstrating the practicality of this method.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110425"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143887151","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-05-05DOI: 10.1016/j.jfluchem.2025.110429
Hai-Han Liu, Zhong-Min Su, Hong-Liang Xu
Due to its toxicity and hazard, the experimental observation of the structure and characteristics of hydrogen fluoride (HF) clusters poses significant challenges. In this work, by integrating theoretical analysis with prior experimental findings, we determined that the stable chair-like hexamer structure (HF)6 can be transformed into a planar cyclic anion (HF)6@e upon the addition of a single electron. Excitingly, there is a larger interaction (Eint = -9.92 kcal/mol) between the two (HF)6 layers in [(HF)6]2@e: an innovative one electron sigma bond (σ1e) emerges. Further, the geometry of σ1e can be adjusted by varying the strength of the additional electric field. This study offers new insights into the HF clusters and demands further explorations in this field.
{"title":"One electron into the multilayer cyclic hexamer of hydrogen fluoride","authors":"Hai-Han Liu, Zhong-Min Su, Hong-Liang Xu","doi":"10.1016/j.jfluchem.2025.110429","DOIUrl":"10.1016/j.jfluchem.2025.110429","url":null,"abstract":"<div><div>Due to its toxicity and hazard, the experimental observation of the structure and characteristics of hydrogen fluoride (HF) clusters poses significant challenges. In this work, by integrating theoretical analysis with prior experimental findings, we determined that the stable chair-like hexamer structure (HF)<sub>6</sub> can be transformed into a planar cyclic anion (HF)<sub>6</sub>@e upon the addition of a single electron. Excitingly, there is a larger interaction (<em>E</em><sub>int</sub> = -9.92 kcal/mol) between the two (HF)<sub>6</sub> layers in [(HF)<sub>6</sub>]<sub>2</sub>@e: an innovative <em>one electron sigma bond</em> (<em>σ</em><sub>1e</sub>) emerges. Further, the geometry of <em>σ</em><sub>1e</sub> can be adjusted by varying the strength of the additional electric field. This study offers new insights into the HF clusters and demands further explorations in this field.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110429"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143903519","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-02-21DOI: 10.1016/j.jfluchem.2025.110406
Shankar Gairhe, Mason Ferrie, Haoran Sun
Under light irradiation, carbonyl compounds interact with molecular oxygen, a common excited state quencher, resulting in the formation of either triplet state-oxygen adducts or singlet oxygen via energy transfer. With phenanthrene-9,10-o-quinones, molecular oxygen usually adds on molecular structures forming triplet state-oxygen adducts which then convert to different final products, often complex mixtures. Here, we report that perfluoroalkylated phenanthrene-9,10-o-quinones exclusively undergo light mediated transformation into diphenic anhydride derivatives.
{"title":"Clean photochemical conversion of perfluoroalkylated phenanthrene-9,10-o-quinones to perfluoroalkylated diphenic anhydrides","authors":"Shankar Gairhe, Mason Ferrie, Haoran Sun","doi":"10.1016/j.jfluchem.2025.110406","DOIUrl":"10.1016/j.jfluchem.2025.110406","url":null,"abstract":"<div><div>Under light irradiation, carbonyl compounds interact with molecular oxygen, a common excited state quencher, resulting in the formation of either triplet state-oxygen adducts or singlet oxygen via energy transfer. With phenanthrene-9,10-o-quinones, molecular oxygen usually adds on molecular structures forming triplet state-oxygen adducts which then convert to different final products, often complex mixtures. Here, we report that perfluoroalkylated phenanthrene-9,10-o-quinones exclusively undergo light mediated transformation into diphenic anhydride derivatives.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110406"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143521298","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-05-29DOI: 10.1016/j.jfluchem.2025.110435
Syed Muzzamil Hussain Shah , Ebrahim Al-Qadami , Ismail Abdulazeez , Mohamed A. Yassin , Sani I. Abba , Dahiru U. Lawal , Isam H. Aljundi
Emerging pollutants (EPs), a diverse group of organic contaminants including pharmaceuticals, personal care products, and industrial chemicals such as per- and polyfluoroalkyl substances (PFAS), pose a significant threat to global water quality, human health, and ecological systems. These persistent and often unregulated compounds necessitate effective removal strategies. To better understand the range of available PFAS treatment methods in water and their reported efficiency, a literature-based systematic review was conducted in multiple phases, ensuring a thorough and structured analysis. In the first phase, a comprehensive search of Scopus and Web of Science (WoS) was performed, employing specific keywords to identify the relevant research. As this study prioritized experimental research on PFAS degradation and removal, the selection process involved excluding duplicates, non-English publications, modeling studies, book chapters, PFAS monitoring and characterization studies, and the review articles. After a thorough screening, the technical papers specifically investigating the treatment methods were selected for an in-depth analysis, focusing on the several parameters, including the medium type, target PFAS, treatment type, treatment method and the treatment efficacy. This review critically synthesizes key information on effective treatment technologies and experimental procedures, presenting a year-wise analysis of advancements and trends. Therefore, the findings presented herein provide a comprehensive overview of the progress in PFAS degradation technologies, highlighting key advancements, challenges, and research gaps. Thus, this review serves as a valuable resource to guide future research and the development of more efficient and sustainable PFAS treatment strategies.
新兴污染物（EPs）是一组不同的有机污染物，包括药品、个人护理产品和工业化学品，如全氟烷基和多氟烷基物质（PFAS），对全球水质、人类健康和生态系统构成重大威胁。这些持久性和不受管制的化合物需要有效的去除策略。为了更好地了解水中可用的PFAS处理方法的范围及其报道的效率，我们分多个阶段进行了基于文献的系统综述，以确保进行全面和结构化的分析。第一阶段，综合检索Scopus和Web of Science (WoS)，使用特定关键词识别相关研究。由于本研究优先考虑PFAS降解和去除的实验研究，因此选择过程包括排除重复、非英文出版物、建模研究、书籍章节、PFAS监测和表征研究以及综述文章。经过全面筛选，选择专门研究处理方法的技术论文进行深入分析，重点关注介质类型、靶PFAS、处理类型、处理方法、处理效果等几个参数。本综述批判性地综合了有关有效治疗技术和实验程序的关键信息，提出了对进展和趋势的年度分析。因此，本文的研究结果提供了PFAS降解技术进展的全面概述，突出了关键进展、挑战和研究差距。因此，本综述为指导未来研究和开发更有效和可持续的PFAS治疗策略提供了宝贵的资源。
{"title":"Per- and polyfluoroalkyl substances (PFASs) in water-based environments: A systematic review of treatment technologies and research trends (2017–2024)","authors":"Syed Muzzamil Hussain Shah , Ebrahim Al-Qadami , Ismail Abdulazeez , Mohamed A. Yassin , Sani I. Abba , Dahiru U. Lawal , Isam H. Aljundi","doi":"10.1016/j.jfluchem.2025.110435","DOIUrl":"10.1016/j.jfluchem.2025.110435","url":null,"abstract":"<div><div>Emerging pollutants (EPs), a diverse group of organic contaminants including pharmaceuticals, personal care products, and industrial chemicals such as per- and polyfluoroalkyl substances (PFAS), pose a significant threat to global water quality, human health, and ecological systems. These persistent and often unregulated compounds necessitate effective removal strategies. To better understand the range of available PFAS treatment methods in water and their reported efficiency, a literature-based systematic review was conducted in multiple phases, ensuring a thorough and structured analysis. In the first phase, a comprehensive search of Scopus and Web of Science (WoS) was performed, employing specific keywords to identify the relevant research. As this study prioritized experimental research on PFAS degradation and removal, the selection process involved excluding duplicates, non-English publications, modeling studies, book chapters, PFAS monitoring and characterization studies, and the review articles. After a thorough screening, the technical papers specifically investigating the treatment methods were selected for an in-depth analysis, focusing on the several parameters, including the medium type, target PFAS, treatment type, treatment method and the treatment efficacy. This review critically synthesizes key information on effective treatment technologies and experimental procedures, presenting a year-wise analysis of advancements and trends. Therefore, the findings presented herein provide a comprehensive overview of the progress in PFAS degradation technologies, highlighting key advancements, challenges, and research gaps. Thus, this review serves as a valuable resource to guide future research and the development of more efficient and sustainable PFAS treatment strategies.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110435"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144168688","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-05-07DOI: 10.1016/j.jfluchem.2025.110428
Sheng Wang , Zhou Yu , Wenbo Chen , Yaming Wu , Chun-Hui Xing , Long Lu
An efficient and mild approach was developed for the difluoroamination of diaryl gem‑dichlorides. This transformation was achieved using the ferric chloride as a Lewis acid and difluorosulfamate tetramethylammonium salt as the difluoroamination reagent. The method exhibited moderate functional group tolerance, highlighting its versatility for introducing difluoroamino groups. And the retention of the CCl bond in the product offers the potential possibilities for subsequent modifications.
{"title":"Difluoroamination of diaryl gem-dichlorides with difluorosulfamate tetramethylammonium salts","authors":"Sheng Wang , Zhou Yu , Wenbo Chen , Yaming Wu , Chun-Hui Xing , Long Lu","doi":"10.1016/j.jfluchem.2025.110428","DOIUrl":"10.1016/j.jfluchem.2025.110428","url":null,"abstract":"<div><div>An efficient and mild approach was developed for the difluoroamination of diaryl gem‑dichlorides. This transformation was achieved using the ferric chloride as a Lewis acid and difluorosulfamate tetramethylammonium salt as the difluoroamination reagent. The method exhibited moderate functional group tolerance, highlighting its versatility for introducing difluoroamino groups. And the retention of the C<img>Cl bond in the product offers the potential possibilities for subsequent modifications.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110428"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143912819","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-03-30DOI: 10.1016/j.jfluchem.2025.110423
Noora A. Rajala , Edla K. Kerminen , Simo A. Salo , Melina J.J. Väkiparta , Anna K. Kirjavainen
Ruthenium-mediated 18F-deoxyfluorination of phenols is a fairly new, but highly underutilized, labeling method option of tracers for positron emission tomography (PET). Most of the published methods are directed toward peptide syntheses and include extensive preparation steps. This study aimed to simplify ruthenium-mediated 18F-deoxyfluorination of [18F]FPATPP by using the TRASIS AllinOne synthesis platform. This protocol takes minimal preparation time (1 h) and applies a straightforward synthesis that can be used to produce tracers from their electron-rich phenolic precursors bearing protic functional groups such as alcohols and amines. The new simplified cassette method afforded a novel cannabinoid receptor 1 specific tracer [18F]FPATPP with a radiochemical yield of 34 ± 2 %, radiochemical purity of ≥ 97 %, and a molar activity of 620 ± 75 GBq/µmol. The total synthesis time was 55 min. In addition, we developed an attachable accessory compatible with TRASIS AllinOne to enable needle movement to enhance the synthesis yield. Our results broaden the possibilities of a cassette based synthesis development for 18F-labeled molecules and bridge the gap between research and GMP compatible synthesis methods.
{"title":"A simplified GMP-compliant cassette synthesis for ruthenium-mediated 18F-deoxyfluorination of [18F]FPATPP from a phenolic precursor","authors":"Noora A. Rajala , Edla K. Kerminen , Simo A. Salo , Melina J.J. Väkiparta , Anna K. Kirjavainen","doi":"10.1016/j.jfluchem.2025.110423","DOIUrl":"10.1016/j.jfluchem.2025.110423","url":null,"abstract":"<div><div>Ruthenium-mediated <sup>18</sup>F-deoxyfluorination of phenols is a fairly new, but highly underutilized, labeling method option of tracers for positron emission tomography (PET). Most of the published methods are directed toward peptide syntheses and include extensive preparation steps. This study aimed to simplify ruthenium-mediated <sup>18</sup>F-deoxyfluorination of [<sup>18</sup>F]FPATPP by using the TRASIS AllinOne synthesis platform. This protocol takes minimal preparation time (1 h) and applies a straightforward synthesis that can be used to produce tracers from their electron-rich phenolic precursors bearing protic functional groups such as alcohols and amines. The new simplified cassette method afforded a novel cannabinoid receptor 1 specific tracer [<sup>18</sup>F]FPATPP with a radiochemical yield of 34 ± 2 %, radiochemical purity of ≥ 97 %, and a molar activity of 620 ± 75 GBq/µmol. The total synthesis time was 55 min. In addition, we developed an attachable accessory compatible with TRASIS AllinOne to enable needle movement to enhance the synthesis yield. Our results broaden the possibilities of a cassette based synthesis development for <sup>18</sup>F-labeled molecules and bridge the gap between research and GMP compatible synthesis methods.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110423"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143735255","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-05-03DOI: 10.1016/j.jfluchem.2025.110431
Matheus P. Freitas
Cyclobutane, a key cycloalkane in various functional compounds, including pharmaceuticals, exhibits significant property modifications upon fluorination, such as altered conformation, polarity, and lipophilicity. This quantum-chemical study, performed at the G3MP2B3 level, investigates the effects of mono- and difluorination of cyclobutane. It examines the energetics of incorporating axial and equatorial fluorines at geminal, vicinal, and 1,3-relative positions. Isodesmic reaction analysis reveals that fluorination of cyclobutane is thermodynamically favorable overall. However, introducing axial fluorine is less energetically favorable, rendering diaxial trans-1,2- and cis-1,3-cyclobutanes unstable. Among the isomers, 1,1-difluorocyclobutane achieves notable stabilization via an anomeric-like interaction (nF → σ*CF), whereas other isomers experience greater destabilization due to Lewis-type interactions compared to electron delocalization. Axial and equatorial C − F bonds can be distinguished by their 1JCF coupling constants. These insights are valuable for the rational design of fluorinated cyclobutane derivatives with properties influenced by the stereochemical arrangement and relative positioning of fluorine atoms.
{"title":"Energetic insights into the fluorination of Cyclobutane: Mono- and Difluorocyclobutanes","authors":"Matheus P. Freitas","doi":"10.1016/j.jfluchem.2025.110431","DOIUrl":"10.1016/j.jfluchem.2025.110431","url":null,"abstract":"<div><div>Cyclobutane, a key cycloalkane in various functional compounds, including pharmaceuticals, exhibits significant property modifications upon fluorination, such as altered conformation, polarity, and lipophilicity. This quantum-chemical study, performed at the G3MP2B3 level, investigates the effects of mono- and difluorination of cyclobutane. It examines the energetics of incorporating axial and equatorial fluorines at geminal, vicinal, and 1,3-relative positions. Isodesmic reaction analysis reveals that fluorination of cyclobutane is thermodynamically favorable overall. However, introducing axial fluorine is less energetically favorable, rendering diaxial <em>trans</em>-1,2- and <em>cis</em>-1,3-cyclobutanes unstable. Among the isomers, 1,1-difluorocyclobutane achieves notable stabilization via an anomeric-like interaction (<em>n</em><sub>F</sub> → σ*<sub>CF</sub>), whereas other isomers experience greater destabilization due to Lewis-type interactions compared to electron delocalization. Axial and equatorial <em>C</em> − <em>F</em> bonds can be distinguished by their <sup>1</sup><em>J</em><sub>CF</sub> coupling constants. These insights are valuable for the rational design of fluorinated cyclobutane derivatives with properties influenced by the stereochemical arrangement and relative positioning of fluorine atoms.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110431"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143903518","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-05-17DOI: 10.1016/j.jfluchem.2025.110433
Sergiy S. Mykhaylychenko , Svitlana V. Shishkina , Eduard B. Rusanov , Yuriy G. Shermolovich
The synthesis of new fluorinated thiazolidine-, thiazoline- and thiazole-5-carboxylic acid esters was performed via a one-pot cascade heterocyclization reaction of N-monosubstituted perfluoroalkanethioamides with methyl bromoacetate in the presence of 1,8-diazabicyclo[5.4.0]undec‑7-ene. The structures of fluorine-containing 1,3-thiazolidine and 1,3-thiazole derivatives have been determined by X-ray diffraction analysis. The plausible reaction pathways leading to the formation of various products are discussed. It was shown that the nature of the substituent at the nitrogen atom of thioamides, perfluoroalkyl chain length and the amount of the base significantly affect the reaction outcome.
{"title":"One-pot cascade synthesis of fluorinated thiazolidine-, thiazoline- and thiazole-5-carboxylic acid esters from N-monosubstituted perfluoroalkanethioamides","authors":"Sergiy S. Mykhaylychenko , Svitlana V. Shishkina , Eduard B. Rusanov , Yuriy G. Shermolovich","doi":"10.1016/j.jfluchem.2025.110433","DOIUrl":"10.1016/j.jfluchem.2025.110433","url":null,"abstract":"<div><div>The synthesis of new fluorinated thiazolidine-, thiazoline- and thiazole-5-carboxylic acid esters was performed via a one-pot cascade heterocyclization reaction of <em>N</em>-monosubstituted perfluoroalkanethioamides with methyl bromoacetate in the presence of 1,8-diazabicyclo[5.4.0]undec‑7-ene. The structures of fluorine-containing 1,3-thiazolidine and 1,3-thiazole derivatives have been determined by X-ray diffraction analysis. The plausible reaction pathways leading to the formation of various products are discussed. It was shown that the nature of the substituent at the nitrogen atom of thioamides, perfluoroalkyl chain length and the amount of the base significantly affect the reaction outcome.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110433"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144071843","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-04-01Epub Date: 2025-04-24DOI: 10.1016/j.jfluchem.2025.110426
Weican Hu , Xingxing Wang , Wu Hao, Pu Li, Wenfang Feng, Zhibin Zhou, Heng Zhang
To expediate the development of ionic liquids (ILs) as electrolyte materials for battery application, an adequate correlation between chemical structures of ILs and their inherent properties is essential. Herein, a series of ILs containing sulfinyl-functionalized fluorinated imide anions with a lower valence state sulfur [i.e., S(IV)] are synthesized and suggested as electrolyte candidates for battery use. Our results show that structural modifications of the sulfinyl-functionalized fluorinated imide anions allow precise control of the physical and electrochemical properties of the corresponding ILs, including thermal properties, transport behaviors, and electrochemical stability. Replacing classic sulfonyl group (–SO2–) with sulfinyl moiety (–SO–) affords ILs with higher structural flexibility, and stronger resistance towards crystallization. The incorporation of longer perfluoroalkyl functionalities slightly increases the oxidative tolerance of the ILs with sulfinyl-functionalized fluorinated imide anions, which may allow more positive participation in building the electrode-electrolyte interface. The present work brings new opportunities for customizing IL-based electrolytes for the conversion-type electrode materials with lower working potentials.
为了加速离子液体作为电池电解质材料的发展，离子液体的化学结构与其固有性质之间的充分关联是至关重要的。本文合成了一系列含有低价态硫（即S(IV)）的亚砜基功能化氟亚胺阴离子的il，并建议将其作为电池使用的电解质候选物。我们的研究结果表明，对亚酰基功能化氟化亚胺阴离子的结构修饰可以精确控制相应il的物理和电化学性能，包括热性能、输运行为和电化学稳定性。用亚砜基部分（- so -）取代传统的磺酰基（- so2 -），使il具有更高的结构柔韧性和更强的抗结晶性。长全氟烷基官能团的加入略微增加了具有亚砜基官能团的氟亚胺阴离子的il的氧化耐受性，这可能允许更积极地参与建立电极-电解质界面。本研究为低功电位转换型电极材料定制基于il的电解质提供了新的机会。
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