{"title":"Highly diversified fluorinated chromane-thiadiazol-saturated cyclic amine hybrids: Design, synthesis, single crystal XRD and MCF-7 Cell-line Study","authors":"Bhavika Mohite , Bhadreshkumar K. Chabhadiya , Nishith Teraiya , Khushal Kapadiya , Ramavatar Meena , Aniruddhasinh Rana , Smita Jauhari","doi":"10.1016/j.jfluchem.2025.110448","DOIUrl":"10.1016/j.jfluchem.2025.110448","url":null,"abstract":"<div><div>The current study focuses on the synthesis and characterization of novel fluorinated chromane derivatives, aiming to explore their structural and biological potential. The molecular framework integrates fluorine for enhanced physicochemical properties, employing nucleophilic substitution and cyclization strategies. The synthesized derivatives <strong>(4a–4j)</strong> were characterized using advanced spectroscopic methods (<sup>1</sup>H NMR, <sup>19</sup>F NMR, <sup>13</sup>C NMR, and mass spectrometry) and crystallographic analysis, confirming their structural core. Biological evaluations against MCF-7 breast cancer cells revealed significant cytotoxicity, with compounds <strong>4 g</strong> and <strong>4f</strong> demonstrating superior activity (IC<sub>50</sub>: 2.73 µM and 3.81 µM, respectively) compared to the standard sunitinib (IC<sub>50</sub>: 5.00 µM). SAR analysis highlights the role of specific cycloaliphatic and polar substituents in enhancing activity. Additionally, docking studies targeting VEGFR2 elucidated key binding interactions, corroborating the compounds' potential as anticancer agents. This work showed the incorporation of fluorine and the rational design of fluorinated scaffolds for drug development.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110448"},"PeriodicalIF":1.7,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144366915","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 and properties of energetic N-fluorodinitromethyl heterocyclic salts","authors":"Andrei A. Gakh , Victor V. Semenov","doi":"10.1016/j.jfluchem.2025.110436","DOIUrl":"10.1016/j.jfluchem.2025.110436","url":null,"abstract":"<div><div>The synthesis of a new class of energetic salts, <em>N</em>-fluorodinitromethyl heterocyclic salts, was accomplished by electrophilic fluorination of corresponding heterocyclic <em>N-</em>dinitromethyl ylides with diluted fluorine. These salts represent rare examples of compounds containing a fluorodinitromethyl moiety directly attached to a positively charged nitrogen atom. Further improvements can be achieved in combination with explosophoric anions, such as the cyanodinitromethanide anion. Despite their unusual structural features, <em>N</em>-fluorodinitromethyl heterocyclic salts have good thermal and chemical stability under ambient conditions.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110436"},"PeriodicalIF":1.7,"publicationDate":"2025-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144212474","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 1,1,2,2,3,3,4,4-octafluoro-4-[(1,2,2-trifluoroethenyl)oxy]butanesulfonyl fluoride","authors":"Nobuyuki Uematsu , Hideo Saito , Masa-aki Sasayama , Sayuri Aoki , Mikihiko Nakamura , Nobuto Hoshi , Masanori Ikeda","doi":"10.1016/j.jfluchem.2025.110432","DOIUrl":"10.1016/j.jfluchem.2025.110432","url":null,"abstract":"<div><div>We investigated two synthetic routes (Route A: first synthesis of the CF<sub>2</sub><img>CFO group and then the SO<sub>2</sub>F group, Route B: first synthesis of the SO<sub>2</sub>F group and then the CF<sub>2</sub><img>CFO group) to synthesize CF<sub>2</sub><img>CFO(CF<sub>2</sub>)<sub>4</sub>SO<sub>2</sub>F (SSC monomer), the raw material for the short-side-chain perfluorinated polymer electrolyte membrane, from I(CF<sub>2</sub>)<sub>4</sub>I using the same commercially available reagents but in different order of use. In Route A, by-products [CF<sub>2</sub><img>CFO(CF<sub>2</sub>)<sub>4</sub>I and the compound presumed to have the structure of CF<sub>2</sub>SO<sub>2</sub>F] were formed in the second half of the synthesis of SSC monomer, but they were difficult to remove from SSC monomer. On the other hand, in Route B, by-product I(CF<sub>2</sub>)<sub>4</sub>I formed in the first half of the synthesis of SSC monomer was easily removed by the conversion with oleum. In addition, the reaction of I(CF<sub>2</sub>)<sub>4</sub>I with Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub> produced I(CF<sub>2</sub>)<sub>4</sub>SO<sub>2</sub>Na and NaO<sub>2</sub>S(CF<sub>2</sub>)<sub>4</sub>SO<sub>2</sub>Na, which were separated by the extraction operation with ethyl acetate, and NaO<sub>2</sub>S(CF<sub>2</sub>)<sub>4</sub>SO<sub>2</sub>Na was converted to I(CF<sub>2</sub>)<sub>4</sub>I by chlorine gas in the presence of NaI. We chose Route B and obtained high-purity SSC monomer.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"285 ","pages":"Article 110432"},"PeriodicalIF":1.7,"publicationDate":"2025-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144205051","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}
Larisa Politanskaya , Bulat Khasanov , Irina Bagryanskaya , Maria Niukalova , Sergey Aksakov , Irina Balashova , Vladimir Zarubaev
{"title":"Efficient synthesis, structure and anti-influenza virus activity of fluorinated pyrido[4,3-b][1,4]thiazine 1,1-dioxide derivatives","authors":"Larisa Politanskaya , Bulat Khasanov , Irina Bagryanskaya , Maria Niukalova , Sergey Aksakov , Irina Balashova , Vladimir Zarubaev","doi":"10.1016/j.jfluchem.2025.110430","DOIUrl":"10.1016/j.jfluchem.2025.110430","url":null,"abstract":"<div><div>A series of fluorinated bicyclic fused compounds, containing fragments of pyridine and 3,4-dihydro-2<em>H</em>-1,4-thiazine 1,1-dioxide were synthesized via one-pot substitution of halogen atoms by N-nucleophiles in polyfluorinated precursor. Formation of the heterocyclic moiety was proceed as a two-stage process starting from Br replacement at the side chain followed by intramolecular aminodefluorination. The structures of some of the obtained heterocycles were confirmed using X-ray diffraction analysis. In addition, their inhibitory activity against influenza A/Puerto Rico/8/34 (H1N1) virus in MDCK cell culture was evaluated and compound-leader was found.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110430"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143916887","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}
Jiawen Deng , Lukang Lin , Yahan Zhang , Xu Yao , Jun Zhang , Jin-Hong Lin , Wenbin Yi , Xing Zheng , Ji-Chang Xiao
{"title":"Synthesis and characterization of 5-(trifluoromethyl)tetrazol-based energetic salts","authors":"Jiawen Deng , Lukang Lin , Yahan Zhang , Xu Yao , Jun Zhang , Jin-Hong Lin , Wenbin Yi , Xing Zheng , Ji-Chang Xiao","doi":"10.1016/j.jfluchem.2025.110427","DOIUrl":"10.1016/j.jfluchem.2025.110427","url":null,"abstract":"<div><div>Two types of 5-trifluoromethyl tetrazole-based energetic salts were successfully synthesized from trifluoroacetamide and sodium azide. The synthetic approach is characterized by its simplicity and safety. The X-ray diffraction analysis reveals the presence of both intermolecular and intramolecular hydrogen bonding within the crystal lattice of energetic salts. The synthesized compound <strong>4</strong> demonstrated notable physical properties, including high densities (1.64 g cm<sup>-3</sup>), great thermal stability (with decomposition temperatures of 167 °C), and excellent insensitivity (impact sensitivity exceeding 40 J). These attributes suggest that the compound <strong>4</strong> possess promising energetic performance and is potential candidates for use as insensitive high-energy materials.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110427"},"PeriodicalIF":1.7,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143912818","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}
Zhou Yu , Sheng Wang , Wenbo Chen , Lele Wen , Long Lu
{"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}
{"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}
Sheng Wang , Zhou Yu , Wenbo Chen , Yaming Wu , Chun-Hui Xing , Long Lu
{"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}
Syed Muzzamil Hussain Shah , Ebrahim Al-Qadami , Ismail Abdulazeez , Mohamed A. Yassin , Sani I. Abba , Dahiru U. Lawal , Isam H. Aljundi
{"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}
{"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}