Journal of Fluorine Chemistry最新文献

{"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 ,&nbsp;Ebrahim Al-Qadami ,&nbsp;Ismail Abdulazeez ,&nbsp;Mohamed A. Yassin ,&nbsp;Sani I. Abba ,&nbsp;Dahiru U. Lawal ,&nbsp;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}

{"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>_F → σ*_CF), 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 ¹<em>J</em>_CF 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}

{"title":"One-pot cascade synthesis of fluorinated thiazolidine-, thiazoline- and thiazole-5-carboxylic acid esters from N-monosubstituted perfluoroalkanethioamides","authors":"Sergiy S. Mykhaylychenko ,&nbsp;Svitlana V. Shishkina ,&nbsp;Eduard B. Rusanov ,&nbsp;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}

{"title":"Sulfinyl-functionalized fluorinated imide anions for ionic liquids and battery electrolytes","authors":"Weican Hu ,&nbsp;Xingxing Wang ,&nbsp;Wu Hao,&nbsp;Pu Li,&nbsp;Wenfang Feng,&nbsp;Zhibin Zhou,&nbsp;Heng Zhang","doi":"10.1016/j.jfluchem.2025.110426","DOIUrl":"10.1016/j.jfluchem.2025.110426","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110426"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143899510","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}

{"title":"Structural characterization of new Tl+ and Pb2+ oxyfluoridozirconates deriving from hexagonal layer structures of M’xM3×9–13 general formula","authors":"Jean-Paul Laval","doi":"10.1016/j.jfluchem.2025.110424","DOIUrl":"10.1016/j.jfluchem.2025.110424","url":null,"abstract":"<div><div>A new series of Tl⁺ and Pb²⁺ oxyfluoridozirconates is isolated and structurally described in hexagonal symmetry, P6₃/mmc space group and close lattice parameters (<em>a</em> = 7.649 Å and <em>c</em> = 15.797 Å for Tl_0.69Zr₃O_1.91F_8.87; <em>a</em> = 7.647(2) Å and <em>c</em> = 15.835(4) Å for Pb_0.714Zr₃O_2.90F_7.62). The refined Tl content varies from 0.69/1 to 0.90/1 (0.71 to 0.76 for Pb) and is never stoichiometric. Their structure corresponds to a stacking of hexagonal layers containing a strong framework of ZrOF₇ bicapped trigonal prisms and ZrO₂F₅ pentagonal bipyramids sharing edges and vertices and forming triangular clusters of formula comprised between Zr₃OF₁₈ and Zr₃O₄F₁₂. These units are all centered on one O anion and interconnected <em>via</em> F corners with three other triangular units forming layers delimiting holes of distorted hexagonal section partly occupied by Tl⁺ or Pb²⁺ cations.</div><div>This new type is compared to many structures presenting various stackings of similar hexagonal or pseudo-hexagonal layers with M³⁺ or M⁴⁺ cations of high size coordinated by 6, 7, 7 + 8, 8, 8 + 9, 9 F and/or O anions. All belong to a same family of phases of M’_xM₃X_9–13 general formula.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110424"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143854383","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}

{"title":"Enantioselective isothiourea-catalysed α-fluorination of C1-ammonium enolates generated from arylesters","authors":"Nicole Stanek ,&nbsp;Lotte Stockhammer ,&nbsp;Anja Moser,&nbsp;Mario Waser","doi":"10.1016/j.jfluchem.2025.110434","DOIUrl":"10.1016/j.jfluchem.2025.110434","url":null,"abstract":"<div><div>We herein report the chiral isothiourea-catalyzed α-fluorination of electron-deficient arylesters. This transformation proceeds via the in situ formation of chiral C1-ammonium enolates, which then undergo the α-fluorination with high levels of enantioselectivities, followed by addition of alcohols, such as MeOH, to give the final chiral α-F-esters.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110434"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144168689","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}

{"title":"A simplified GMP-compliant cassette synthesis for ruthenium-mediated 18F-deoxyfluorination of [18F]FPATPP from a phenolic precursor","authors":"Noora A. Rajala ,&nbsp;Edla K. Kerminen ,&nbsp;Simo A. Salo ,&nbsp;Melina J.J. Väkiparta ,&nbsp;Anna K. Kirjavainen","doi":"10.1016/j.jfluchem.2025.110423","DOIUrl":"10.1016/j.jfluchem.2025.110423","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110423"},"PeriodicalIF":1.7,"publicationDate":"2025-03-30","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}

{"title":"Radical 1,2-fluoroalkylation/stannylation of terminal alkynes","authors":"Vyacheslav I. Supranovich,&nbsp;Alexander D. Dilman","doi":"10.1016/j.jfluchem.2025.110422","DOIUrl":"10.1016/j.jfluchem.2025.110422","url":null,"abstract":"<div><div>A method for the radical 1,2-fluoroalkylation/stannylation of terminal alkynes using fluorinated bromides and a tin(II) salt is described. The reaction is performed under photocatalytic conditions and involves radical addition at the triple bond followed by interaction of the vinyl radical with tin(II). Treatment of the reaction mixture with butylzinc bromide leads to vinyl tributylstannanes, which can be involved in the Stille cross-coupling or subjected to iododestannylation.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110422"},"PeriodicalIF":1.7,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143684634","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}

{"title":"Synthesis of fluorinated 4H-chromen-4-ones from 2-hydroxyacetophenones and in vitro evaluation of their anticancer and antiviral activity","authors":"Larisa Politanskaya ,&nbsp;Jiaying Wang ,&nbsp;Yulia Meshkova ,&nbsp;Mariya Marenina ,&nbsp;Tatyana Tolstikova ,&nbsp;Maria Niukalova ,&nbsp;Iana Esaulkova ,&nbsp;Alexandrina Volobueva ,&nbsp;Vladimir Zarubaev","doi":"10.1016/j.jfluchem.2025.110421","DOIUrl":"10.1016/j.jfluchem.2025.110421","url":null,"abstract":"<div><div>Simple and useful approaches to the synthesis of a large series of 2-X-substituted 4<em>H</em>-chromen-4-one derivatives (X = Me, CF₃, SH, COOMe, COOEt), fluorinated on benzene ring, are reported. Firstly a series of 2-hydroxyacetophenones – the versatile building blocks – was synthesized <em>via</em> Fries rearrangement of acylphenols or by the Sonogashira reaction of polyfluorinated <em>o</em>-iodophenols with TIPS-acetylene, followed by the hydration of the triple bond. Then the transformations of the obtained fluorinated 2-hydroxyacetophenones with ethyl acetate, diethyl oxalate, carbon disulfide and anhydrides of carboxylic acids in the presence of base were investigated. The synthesis of 8-aryl substituted 4<em>H</em>-chromen-4-ones was achieved through the electrophilic iodination of phenolic compounds, followed by the Suzuki coupling of the resulting iodine-containing substrates (2-hydroxyacetophenones or chromene derivatives) with arylboric acids. In this way less reactive biologically important fluorinated 2-hydroxyacetophenones were successfully used extending the scope of the 4<em>H</em>-chromen-4-one family having potential biological activity. Some of the obtained fluorinated chromones were evaluated for cytotoxicity in MCF-7, HepG2, HeLa human cancer cells and in normal human foreskin fibroblast cells (hT'ER B'j1). It has been established that compound <strong>33</strong> has the most pronounced anticancer activity. Screening of all synthesized compounds (35 examples) for their inhibitory activity against influenza A virus A/Puerto Rico/8/34 (H1N1) in the MDCK cell culture revealed that a number of heterocycles (<strong>32, 41, 31, 11, 3, 35</strong>) differing both in the degree of fluorination and the nature of the substituents exhibit a significant antiviral effect (SI = 12 – 24). Among the studied compounds 2-methyl-4<em>H</em>-chromen-4-ones <strong>31, 35</strong> and <strong>3</strong> showed pronounced antiviral inhibitory activity (IC₅₀ = 2 – 5 μM). The most promising compound <strong>32</strong>, containing 6,7,8-trifluorosubstituted scaffold demonstrated low toxicity (CC₅₀ = 823 μM) and high virus inhibition activity (IC₅₀ = 35 μM) caused SI = 24, which allows it to be considered as potential drug-candidate in further in-depth studies.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110421"},"PeriodicalIF":1.7,"publicationDate":"2025-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143641788","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}

{"title":"Addition reaction of 1,6-diiodoperfluorohexane with ethylene: Process optimization and kinetic study","authors":"Zihan Ai,&nbsp;Baohe Wang,&nbsp;Zhaobang Zhang,&nbsp;Bangxing Yin,&nbsp;Jing Zhu,&nbsp;Jing Ma","doi":"10.1016/j.jfluchem.2025.110419","DOIUrl":"10.1016/j.jfluchem.2025.110419","url":null,"abstract":"<div><div>The fluorine-containing compound with symmetrical structure (I-C₂H₄-(CF₂)_n-C₂H₄-I) is a widely used the intermediate of fluorine-containing copolymer having various applications in the organic fluorine chemical industry. Herein, the addition reaction of 1,6-diiodoperfluorohexane (I-C₆F₁₂-I) with ethylene was studied at different temperatures (130 to 170 °C), reaction time (4 to 12 h), solvents (acetonitrile, DMF, Py, n-hexane) and initiators (AIBN, DTBP, CuI, CuCl). The yield of the product (I-C₂H_4<img>C₆F_12<img>C₂H₄-I) was up to 73 % under optimal reaction conditions (150 °C, 10 h, CuI, acetonitrile). The kinetic equation of the reaction was derived through further studies on the reaction kinetics. The addition reaction is a consecutive reaction, the reaction order and the activation energy of the first step (I-C₆F₁₂-I to I-C₆F_12<img>C₂H₄-I) are 1.131 and 56.53 kJ mol^-1, and the reaction order and the activation energy of the second step (I-C₆F_12<img>C₂H₄-I to I-C₂H_4<img>C₆F_12<img>C₂H₄-I) are 0.479 and 49.81 kJ mol^-1. These are important results that allows for further process intensification and designing of reactor.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110419"},"PeriodicalIF":1.7,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143641787","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}