Journal of Fluorine Chemistry最新文献

{"title":"Morphological control of bicontinuous phase-separated patterns by preparing mixed monolayers using non-amphiphilic s-triazine derivatives with three fluorinated chains","authors":"Yoshiki Shioda ,&nbsp;Itsuki Fujii ,&nbsp;Atsuhiro Fujimori","doi":"10.1016/j.jfluchem.2024.110351","DOIUrl":"10.1016/j.jfluchem.2024.110351","url":null,"abstract":"<div><div>In this study, the morphogenesis of the bicontinuous phase separation in mixed monolayers of a non-amphiphilic fluorocarbon derivative without a hydrophilic group and long-chain fatty acids is discussed. These fluorocarbon derivatives contain an <em>s</em>-triazine ring and three fluorocarbon chains. The corresponding fluorocarbon derivatives exhibit high crystallinity in the monolayers, allowing them to maintain crystalline regularity even in the \"sea\" region of the mixed monolayer that exhibits phase separation. In controlling the bicontinuous pattern, the formation of complex phase-separated morphology in the mixed system of fluorine-based derivatives and comb polymers, along with the high concentration and low diffusion conditions in the mixed hydrocarbon/fluorocarbon system, were examined. It was observed that the condensed phase domains became angular shape at a low temperature (5 °C), and the surface approached a bicontinuous feature at a high temperature (40 °C). With the formation of hydrogenated condensed domains, the \"sea\" region of fluorocarbon chains lost its order. At this point, the shape of the nanodomains tended to become more circular.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110351"},"PeriodicalIF":1.7,"publicationDate":"2024-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142319857","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":"Electrochemical radiofluorination using a split-bipolar electrode","authors":"Tomoyuki Kurioka ,&nbsp;Yingqing Lu ,&nbsp;Jason Jones ,&nbsp;Xueyi Wang ,&nbsp;Daniel Hernández-Valdés ,&nbsp;Afaf Genady ,&nbsp;R. Michael van Dam ,&nbsp;Shinsuke Inagi ,&nbsp;Saman Sadeghi","doi":"10.1016/j.jfluchem.2024.110350","DOIUrl":"10.1016/j.jfluchem.2024.110350","url":null,"abstract":"<div><div>Electrochemical (radio)fluorination (ECF) is a versatile approach for nucleophilic radiofluorination of electron-rich compounds such as thioether derivatives. However, ECF generally requires high concentrations of supporting salts, which leads to low molar activity (<em>A</em>_m) of the final product due to undesired contamination with [¹⁹F]F^– ions. Here, we demonstrate the first example of radiofluorination using a split bipolar electrode (s-BPE) platform with low concentration of supporting salt. Under optimal reaction conditions, the ECF of methyl (methylthio)acetate (MMTA) using s-BPEs provided [¹⁸F]F-MMTA with radiochemical conversion of up to 70 % and high molar activities (28–43 GBq/μmol; 0.74–1.1 Ci/μmol), with approximately 5 mM of tetrabutylammonium perchlorate as supporting electrolyte.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110350"},"PeriodicalIF":1.7,"publicationDate":"2024-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113924001106/pdfft?md5=3d701264dae2fafcf65bc4d0b4123a44&pid=1-s2.0-S0022113924001106-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142311151","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":"Dimerization of perfluoropropyl vinyl ether during the pyrolysis of hexafluoropropylene oxide dimer","authors":"Jiangkun Hou ,&nbsp;Shuanggen Wu ,&nbsp;Weifeng Chen ,&nbsp;Jianting Yang ,&nbsp;Xunqiu Wang","doi":"10.1016/j.jfluchem.2024.110352","DOIUrl":"10.1016/j.jfluchem.2024.110352","url":null,"abstract":"<div><div>Dimerization of perfluoropropyl vinyl ether (PPVE) generally reduces its yield and selectivity during the pyrolysis of hexafluoropropylene oxide dimer ((HFPO)₂). However, the mechanism of PPVE dimerization is not well understood. In this paper, the PPVE dimer was obtained during the pyrolysis of (HFPO)_2. Subsequently, the chemical structure of PPVE dimer was further determined by gas chromatography-mass spectrometry (GC–MS) and nuclear magnetic resonance (NMR). The results showed that the concentration of PPVE dimer rises in proportion to the extended reflux time of PPVE in the reaction system. Based on the experimental phenomenon, a possible generation mechanism of PPVE dimer was then proposed, and the possibility of the generation pathway was further verified in combination with density functional theory (DFT). In addition, to effectively reduce the production of PPVE dimer, crown ethers and quaternary ammonium salts were added to the reaction system as phase transfer catalysts. Among them, the phase transfer catalyst (15-crown-5) was more effective and reduced the PPVE dimer content from 1.34 % to 0.31 %. This work provides an idea to inhibit the dimerization of PPVE and increase the yield and selectivity of PPVE.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110352"},"PeriodicalIF":1.7,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142311150","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":"Recent advances in fluorine chemistry using flow technology","authors":"Kensuke Muta ,&nbsp;Hiroki Soutome ,&nbsp;Aiichiro Nagaki","doi":"10.1016/j.jfluchem.2024.110349","DOIUrl":"10.1016/j.jfluchem.2024.110349","url":null,"abstract":"<div><p>Organofluorine compounds have proven to play an important role in pharmaceutical, agrochemical, and functional materials owing to their unique properties. However, the synthesis of these compounds is often challenging due to the difficulties in handling fluorinating agents and controlling their reactivity precisely. Recently, flow microreactor systems have attracted significant attention from chemists as a highly efficient synthetic methodology. In this review, we summarize recent advances in fluorine chemistry facilitated by continuous flow technology, highlighting its advantages and potential applications in streamlined synthesis of organofluorine compounds.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110349"},"PeriodicalIF":1.7,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142233033","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":"Hydrothermal transformations of hydrated cerium(IV) fluoride in NaOH or HF media. The first crystal structure in the cerium tetrafluoride hydrate family","authors":"Evgeny Il'in ,&nbsp;Artemy Parshakov ,&nbsp;Andrei Churakov ,&nbsp;Ludmila Iskhakova ,&nbsp;Arina Filippova ,&nbsp;Sergei Kottsov ,&nbsp;Liudmila Demina ,&nbsp;Lyudmila Goeva ,&nbsp;Nikolai Simonenko ,&nbsp;Victor Privalov ,&nbsp;Alexander Baranchikov ,&nbsp;Vladimir Ivanov","doi":"10.1016/j.jfluchem.2024.110337","DOIUrl":"10.1016/j.jfluchem.2024.110337","url":null,"abstract":"<div><p>In order to synthesize new nanocrystalline compounds of cerium fluorides, the transformations of hydrated cerium(IV) fluoride with the composition CeF₄⋅H₂O under mild hydrothermal conditions were studied, in aqueous alkaline (1 M NaOH) or acidic (1 M HF) media. In alkaline medium, at 130 °С and 220 °C, hydrated cerium(IV) fluoride hydrolyses to form CeO₂, while in 1 M hydrofluoric acid at 130 °C, a mixture of crystalline Ce₃F₁₀⋅3H₂O and CeF₃ is formed. Hydrothermal treatment of cerium(IV) fluoride hydrate in 1 M HF at 220 °C yielded a new cerium(IV) fluoride hydrate (CeF₄)₃<strong>^.</strong>H₂O (Ce₃F₁₂^.H₂O). The new compound was studied by chemical analysis, powder and single crystal X-ray diffraction, scanning electron microscopy, ¹⁹F{¹H} and ¹H NMR, IR- and Raman spectroscopy. The noncentrosymmetric crystal structure of Ce₃F₁₂^.H₂O was found to be monoclinic (sp. gr. <em>C</em>m, <em>Z</em> = 4) being isomorphic to uranium or neptunium tetrafluoride hydrates (U₃F₁₂^.H₂O or Np₃F₁₂^.H₂O). The structure of this compound exhibits a three-dimensional network of corner- and edge-shared [CeF₉], [CeF₇(OH₂)], [CeF₈(OH₂)] and [CeF₈] polyhedra. The influence of the cerium(IV) cations coordination sphere composition on the relative lengths of Ce-O bonds and F…H<img>O hydrogen bonds discussed. The temperature behavior of the Ce₃F₁₂^.H₂O powder up to 500 °C was studied by thermogravimetry and differential scanning calorimetry.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110337"},"PeriodicalIF":1.7,"publicationDate":"2024-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142136091","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":"Improved conditions for the synthesis of tertiary fluorides using a KF/H2SO4 combination","authors":"Xavier Bertrand ,&nbsp;Doria Aissaoui ,&nbsp;Océane Meryem Col ,&nbsp;Mathieu Pucheault ,&nbsp;Laurent Chabaud ,&nbsp;Jean-François Paquin","doi":"10.1016/j.jfluchem.2024.110338","DOIUrl":"10.1016/j.jfluchem.2024.110338","url":null,"abstract":"<div><p>In this paper, we report the deoxyfluorination of tertiary alcohol using a simple combination of potassium fluoride and sulfuric acid. These cheap and widely available reagents allow for the synthesis of tertiary fluorides in good to excellent yields. Extension of the reaction to other functional groups such as alkenes, acetates and ethers have also been studied.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110338"},"PeriodicalIF":1.7,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113924000988/pdfft?md5=4199be9dabdf8f182cc63da6af843aba&pid=1-s2.0-S0022113924000988-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142128740","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":"Construction of new quaternary carbon center of fluorinated isoxazolines at C5 position via C-F bond cleavage","authors":"Kazuyuki Sato,&nbsp;Kazuki Nakano,&nbsp;Takahiro Ueda,&nbsp;Yukine Kitamura,&nbsp;Yuna Tanaka,&nbsp;Yukiko Karuo,&nbsp;Atsushi Tarui,&nbsp;Kentaro Kawai,&nbsp;Masaaki Omote","doi":"10.1016/j.jfluchem.2024.110335","DOIUrl":"10.1016/j.jfluchem.2024.110335","url":null,"abstract":"<div><p>A substitution reaction of <em>O</em>-, <em>S</em>-, or <em>N</em>-nucleophiles onto fluorinated isoxazolines via carbon–fluorine (C-F) bond cleavage was achieved. The C-F bond at the C5 position of fluorinated isoxazolines was dissociated by using SnCl₄ for the generation of a carbocation intermediate in this reaction. Subsequently, various nucleophiles such as alcohols, thiols, and amines were introduced, enabling the conversion to C<img>O, C-S, or C<img>N bonds and the formation of a new quaternary carbon center.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110335"},"PeriodicalIF":1.7,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142147587","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":"Dimethyl sulfoxide-mediated dibromination of gem-difluoroalkenes with hydrobromic acid as reagent","authors":"Xiaoying Wang,&nbsp;Jiaxi Cai,&nbsp;Xin Liu,&nbsp;Xin-Hua Duan,&nbsp;Mingyou Hu","doi":"10.1016/j.jfluchem.2024.110336","DOIUrl":"10.1016/j.jfluchem.2024.110336","url":null,"abstract":"<div><p>A method for the oxidative dibromination of <em>gem</em>-difluoroalkenes has been devised, employing HBr as the brominating agent and utilizing DMSO as both a mild oxidant and solvent. These uncomplicated conditions provide a high bromide atom economy, coupled with the accessibility and cost-effectiveness of DMSO and HBr. This approach notably expands the scope of <em>gem</em>-difluoroalkenes amenable to dibromination and furnishes a valuable precursor for ¹⁸F radiolabeling applications.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"279 ","pages":"Article 110336"},"PeriodicalIF":1.7,"publicationDate":"2024-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142096834","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":"Corrigendum to “Fabrication and characteristic of Fe3O4@MOR@CuO core-shell for investigation antibacterial properties” [Journal of Fluorine Chemistry, Volume 206, 2018, 36–42]","authors":"S.K. Rajabi,&nbsp;Sh. Sohrabnezhad","doi":"10.1016/j.jfluchem.2024.110314","DOIUrl":"10.1016/j.jfluchem.2024.110314","url":null,"abstract":"","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"278 ","pages":"Article 110314"},"PeriodicalIF":1.7,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0022113924000745/pdfft?md5=50d7bbb4984a41f4edd246a6ad0ab766&pid=1-s2.0-S0022113924000745-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141708238","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":"Thermal decomposition characteristics of C6F12O/CO2 gas mixtures under trace water conditions","authors":"Shuangshuang Tian ,&nbsp;Yingyu Wu ,&nbsp;Yilin Jin ,&nbsp;Jiahao Wang ,&nbsp;Benli Liu ,&nbsp;Feng Hu ,&nbsp;Xiaoping Jin","doi":"10.1016/j.jfluchem.2024.110331","DOIUrl":"10.1016/j.jfluchem.2024.110331","url":null,"abstract":"<div><p>In recent years, C₆F₁₂O gas mixtures has shown extensive prospects for application in medium and low-voltage gas-insulated equipment due to its superior electrical performance and environmental friendliness. The presence of trace water may promote overheating decomposition of gas mixtures_. Therefore, studying the thermal decomposition characteristics of C₆F₁₂O in a trace water condition is of significant importance for the industrial application, operation, and maintenance of gas equipment. In this paper, the thermal decomposition characteristics of C₆F₁₂O/CO₂ gas mixtures under trace water conditions are investigated both experimentally and theoretically. The analysis of decomposition products is conducted using gas chromatography-mass spectrometry (GC–MS) on a constructed experimental platform for C₆F₁₂O/CO₂ gas mixtures overheating. Based on ReaxFF molecular dynamics (ReaxFF-MD), the decomposition characteristics of the gas mixtures over time and the concentration of trace water are observed. The main decomposition reaction paths of C₆F₁₂O/CO₂ gas mixtures under trace water conditions are analyzed at a microscopic level. Experiment results indicate that the main thermal decomposition products include CF₄, C₂F₆, C₃F₆, C₃F₈, CF₂O, C₃F₇H, C₄F₁₀, C₆F₁₄, C₅F₁₂, and CF₃H. Additionally, trace water facilitates the thermal decomposition of the C₆F₁₂O/CO₂ gas mixtures. Theoretical results indicate that multi-step decomposition occurs in the C₆F₁₂O component of the gas mixtures, with main generated intermediates including CO, F, CF₃, C₂F₅, C₃F₇, CFO₂, CF₂, C₂, CF, C₄F₇O, CF₃O, CFO, O, C₃F₅O, CF₂O, C, C₂O, H, and OH. The findings of this study provide a foundation for further exploration of trace water content values in C₆F₁₂O gas mixtures at a microscopic level in subsequent research.</p></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"278 ","pages":"Article 110331"},"PeriodicalIF":1.7,"publicationDate":"2024-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141990306","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}