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A fluoride-responsive naphthalimide-derived chemosensor: Mechanistic insights into F--driven desilylation-decyanation cascade
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-03-07 DOI: 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,&nbsp;Yan Zhou,&nbsp;Liqin Kang,&nbsp;Hua Zhang,&nbsp;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":"2025-03-07","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}
引用次数: 0
Electrochemical reduction behavior of Si(IV) ions in LiF-SiO2 and KF-SiO2 melts at 1173 K
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-03-04 DOI: 10.1016/j.jfluchem.2025.110420
Yuta Suzuki , Takuya Goto
Metal electrodeposition from metal oxides is beneficial not only in the terrestrial metal smelting process but also in the process of recovering metals from minerals on the Moon and Mars. In the electrochemical process, a binary melt of metal oxide and metal fluoride can be a promising reaction media for constructing a practical electrolytic system that allows metal recovery directly from metal oxide at lower temperatures. In this study, the electrochemical reduction behavior of Si(IV) ions in LiF-SiO2 and KF-SiO2 melts at 1173 K, which included 10 mol% SiO2, was studied toward controlling the electrodeposition process of crystalline Si in high-temperature melts with higher SiO2 composition ratios. The dissolution behavior of SiO2 was investigated by high-temperature Raman spectroscopy and density functional theory calculation, revealing that Si(IV) complex ions such as Si3F7–2 K are formed in the KF-SiO2 system, whereas Si(IV) ion was not easily bonded to constituent ions of the LiF-SiO2 melt. It was demonstrated that polycrystalline Si could be obtained by potentiostatic electrolysis in both melts, and the reduction rate of Si(IV) ions was faster in the LiF-SiO2 system. The Raman spectroscopy and XRD analysis revealed that the electrodeposits were the polycrystalline Si and the alloys such as Li-Si and K-Si. The reported data on the interaction between fluoride ions and Si(IV) ions in the binary melt of metal fluoride and SiO2 will contribute to realizing an in-situ resource utilization process that enables one-step Si recovery from SiO2.
{"title":"Electrochemical reduction behavior of Si(IV) ions in LiF-SiO2 and KF-SiO2 melts at 1173 K","authors":"Yuta Suzuki ,&nbsp;Takuya Goto","doi":"10.1016/j.jfluchem.2025.110420","DOIUrl":"10.1016/j.jfluchem.2025.110420","url":null,"abstract":"<div><div>Metal electrodeposition from metal oxides is beneficial not only in the terrestrial metal smelting process but also in the process of recovering metals from minerals on the Moon and Mars. In the electrochemical process, a binary melt of metal oxide and metal fluoride can be a promising reaction media for constructing a practical electrolytic system that allows metal recovery directly from metal oxide at lower temperatures. In this study, the electrochemical reduction behavior of Si(IV) ions in LiF-SiO<sub>2</sub> and KF-SiO<sub>2</sub> melts at 1173 K, which included 10 mol% SiO<sub>2</sub>, was studied toward controlling the electrodeposition process of crystalline Si in high-temperature melts with higher SiO<sub>2</sub> composition ratios. The dissolution behavior of SiO<sub>2</sub> was investigated by high-temperature Raman spectroscopy and density functional theory calculation, revealing that Si(IV) complex ions such as Si<sub>3</sub>F<sub>7</sub>–2 K are formed in the KF-SiO<sub>2</sub> system, whereas Si(IV) ion was not easily bonded to constituent ions of the LiF-SiO<sub>2</sub> melt. It was demonstrated that polycrystalline Si could be obtained by potentiostatic electrolysis in both melts, and the reduction rate of Si(IV) ions was faster in the LiF-SiO<sub>2</sub> system. The Raman spectroscopy and XRD analysis revealed that the electrodeposits were the polycrystalline Si and the alloys such as Li-Si and K-Si. The reported data on the interaction between fluoride ions and Si(IV) ions in the binary melt of metal fluoride and SiO<sub>2</sub> will contribute to realizing an in-situ resource utilization process that enables one-step Si recovery from SiO<sub>2</sub>.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110420"},"PeriodicalIF":1.7,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552015","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}
引用次数: 0
Theoretical study on the compatibility of C4F7N decomposition products with metal oxides: First-principles
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-03-04 DOI: 10.1016/j.jfluchem.2025.110417
Gang Peng , Xiajin Rao , Dajian Li , Benli Liu , Yingyu Wu
The compatibility between the gas and solid materials within the gas chamber is key to ensuring the safe operation of electrical equipment. Current research primarily focuses on the compatibility between the C4F7N (Heptafluoroisobutyronitrile) and the solid materials used in equipment. However, C4F7N decomposes under electrical and thermal fault conditions, while metal materials are also prone to oxidation during the manufacturing and operation processes. In this paper, the interaction systems between the main decomposition products of C4F7N (CO, CF4 and C3F6(perfluoropropene)) and typical metal surface oxides (Al2O3, CuO) are established. Based on first-principles, the interaction energy, charge transfer, electronic density of states, differential charge density, and weak interaction forces are evaluated as five microscopic parameters. The interaction mechanisms between the decomposition products of C4F7N and the surface oxides of typical metal materials are analyzed at the microscopic level, further assessing their compatibility. The results show that both CO and CF4 exhibit weak interactions with the Al2O3(0 0 0 1) interface, demonstrating good compatibility. However, the interaction energy between C3F6 and the Al2O3(0 0 0 1) interface reaches -3.13 eV with a charge transfer of 0.336e, showing significant charge accumulation, as well as stronger interactions, and the apparent overlap between the 2p orbitals of F atoms and the 3p orbitals of Al atoms between 0eV-6eV. This suggests the potential formation of chemical bonds, leading to poor compatibility. The interactions between CO, CF4 and C3F6 with the CuO(1 1 1) interface are all weak, indicating good compatibility. In conclusion, to ensure the safe operation of C4F7N/CO2 environmentally friendly gas-insulated equipment, it is recommended to maximize the use of copper materials in metal equipment and avoid prolonged exposure of the equipment to environments prone to oxidation, thereby further enhancing the stability and reliability of the equipment.
{"title":"Theoretical study on the compatibility of C4F7N decomposition products with metal oxides: First-principles","authors":"Gang Peng ,&nbsp;Xiajin Rao ,&nbsp;Dajian Li ,&nbsp;Benli Liu ,&nbsp;Yingyu Wu","doi":"10.1016/j.jfluchem.2025.110417","DOIUrl":"10.1016/j.jfluchem.2025.110417","url":null,"abstract":"<div><div>The compatibility between the gas and solid materials within the gas chamber is key to ensuring the safe operation of electrical equipment. Current research primarily focuses on the compatibility between the C<sub>4</sub>F<sub>7</sub>N (Heptafluoroisobutyronitrile) and the solid materials used in equipment. However, C<sub>4</sub>F<sub>7</sub>N decomposes under electrical and thermal fault conditions, while metal materials are also prone to oxidation during the manufacturing and operation processes. In this paper, the interaction systems between the main decomposition products of C<sub>4</sub>F<sub>7</sub>N (CO, CF<sub>4</sub> and C<sub>3</sub>F<sub>6</sub>(perfluoropropene)) and typical metal surface oxides (Al<sub>2</sub>O<sub>3</sub>, CuO) are established. Based on first-principles, the interaction energy, charge transfer, electronic density of states, differential charge density, and weak interaction forces are evaluated as five microscopic parameters. The interaction mechanisms between the decomposition products of C<sub>4</sub>F<sub>7</sub>N and the surface oxides of typical metal materials are analyzed at the microscopic level, further assessing their compatibility. The results show that both CO and CF<sub>4</sub> exhibit weak interactions with the Al<sub>2</sub>O<sub>3</sub>(0 0 0 1) interface, demonstrating good compatibility. However, the interaction energy between C<sub>3</sub>F<sub>6</sub> and the Al<sub>2</sub>O<sub>3</sub>(0 0 0 1) interface reaches -3.13 eV with a charge transfer of 0.336e, showing significant charge accumulation, as well as stronger interactions, and the apparent overlap between the 2p orbitals of F atoms and the 3p orbitals of Al atoms between 0eV-6eV. This suggests the potential formation of chemical bonds, leading to poor compatibility. The interactions between CO, CF<sub>4</sub> and C<sub>3</sub>F<sub>6</sub> with the CuO(1 1 1) interface are all weak, indicating good compatibility. In conclusion, to ensure the safe operation of C<sub>4</sub>F<sub>7</sub>N/CO<sub>2</sub> environmentally friendly gas-insulated equipment, it is recommended to maximize the use of copper materials in metal equipment and avoid prolonged exposure of the equipment to environments prone to oxidation, thereby further enhancing the stability and reliability of the equipment.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110417"},"PeriodicalIF":1.7,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552017","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}
引用次数: 0
Fluorinated vs. non-fluorinated 1,3-dimethoxypropane: A comparative analysis for lithium metal battery applications
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-02-27 DOI: 10.1016/j.jfluchem.2025.110418
Alexander A. Hizbullin, Irina V. Kutovaya, Olga I. Shmatova
{"title":"Fluorinated vs. non-fluorinated 1,3-dimethoxypropane: A comparative analysis for lithium metal battery applications","authors":"Alexander A. Hizbullin,&nbsp;Irina V. Kutovaya,&nbsp;Olga I. Shmatova","doi":"10.1016/j.jfluchem.2025.110418","DOIUrl":"10.1016/j.jfluchem.2025.110418","url":null,"abstract":"","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110418"},"PeriodicalIF":1.7,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552016","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}
引用次数: 0
Retro-favorskii reaction employing fluoride sources and its use as immobilization strategy
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-02-24 DOI: 10.1016/j.jfluchem.2025.110405
Andrea Giovanelli , Marco Carlotti
In this study, we developed a novel and simple approach to perform retro-Favorskii type reactions comprising the use of a readily available fluoride source. Compared to the methods usually employed – which rely on the use of strong basic systems, such as KOH in toluene, at high temperatures and a reaction time of several hours – the one we propose employs milder conditions, shorter reaction times, is compatible with more solvents, and produces no appreciable amount of byproducts, thus allowing simple workup procedures. The reaction we describe is enabled by the strong basic character of the fluoride ion in absence of water. However, we observed that the reaction is remarkably tolerant to humidity and no anhydrous conditions are needed, making the reaction extremely straightforward to perform. The possibility of performing such reactions in a fast and reliable manner, without the appreciable formation of byproducts, can offer new interesting opportunities to efficiently employ propargyl alcohols derivatives as a masking group for carbonyls. The latter approach can be particularly interesting for the synthesis and derivatization of carbonyl-rich compounds – such as large, conjugated, electron-deficient systems or quinoid-based pigments – for which the limited solubility often precludes the synthesis of certain derivatives or their application in functional devices.
{"title":"Retro-favorskii reaction employing fluoride sources and its use as immobilization strategy","authors":"Andrea Giovanelli ,&nbsp;Marco Carlotti","doi":"10.1016/j.jfluchem.2025.110405","DOIUrl":"10.1016/j.jfluchem.2025.110405","url":null,"abstract":"<div><div>In this study, we developed a novel and simple approach to perform retro-Favorskii type reactions comprising the use of a readily available fluoride source. Compared to the methods usually employed – which rely on the use of strong basic systems, such as KOH in toluene, at high temperatures and a reaction time of several hours – the one we propose employs milder conditions, shorter reaction times, is compatible with more solvents, and produces no appreciable amount of byproducts, thus allowing simple workup procedures. The reaction we describe is enabled by the strong basic character of the fluoride ion in absence of water. However, we observed that the reaction is remarkably tolerant to humidity and no anhydrous conditions are needed, making the reaction extremely straightforward to perform. The possibility of performing such reactions in a fast and reliable manner, without the appreciable formation of byproducts, can offer new interesting opportunities to efficiently employ propargyl alcohols derivatives as a masking group for carbonyls. The latter approach can be particularly interesting for the synthesis and derivatization of carbonyl-rich compounds – such as large, conjugated, electron-deficient systems or quinoid-based pigments – for which the limited solubility often precludes the synthesis of certain derivatives or their application in functional devices.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"283 ","pages":"Article 110405"},"PeriodicalIF":1.7,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143473934","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}
引用次数: 0
Clean photochemical conversion of perfluoroalkylated phenanthrene-9,10-o-quinones to perfluoroalkylated diphenic anhydrides
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-02-21 DOI: 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,&nbsp;Mason Ferrie,&nbsp;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":"2025-02-21","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}
引用次数: 0
Fluorine-containing isosteres enable a structure-activity relationship study of gingerol derivatives
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-02-01 DOI: 10.1016/j.jfluchem.2025.110400
Shelby E. Cooper, Diarta Kabashi, Marlin E. Yacoub, Jessica A. Molen, Osman Farhan, Christina Farley, Samantha Yencha, Michelle M. Figueiredo, Nidheesh Phadnis, Wynter Henry, Julian A. Harris, Frank Wilkinson, John A. Milligan
A series of fluorinated and non-fluorinated [6]-gingerol, [6]-paradol, [6]-shogaol and ferulate derivatives were synthesized. Testing these analogs in anti-proliferation assays with MCF-7, A549, HCT-116 and HEK-293 cell lines provided insight into the structural features that contribute to the anti-proliferative activity of naturally occurring ginger constituents. In particular, the use of both vinyl and alkyl trifluoromethyl isosteres allowed us to evaluate the structure-activity impact of the enone motif found in shogaols. Our results indicate that enone-containing derivatives have a higher potency, suggesting the conjugated enone motif characteristic of shogaols may be primarily responsible for the anti-cancer activity of the broader natural product family.
{"title":"Fluorine-containing isosteres enable a structure-activity relationship study of gingerol derivatives","authors":"Shelby E. Cooper,&nbsp;Diarta Kabashi,&nbsp;Marlin E. Yacoub,&nbsp;Jessica A. Molen,&nbsp;Osman Farhan,&nbsp;Christina Farley,&nbsp;Samantha Yencha,&nbsp;Michelle M. Figueiredo,&nbsp;Nidheesh Phadnis,&nbsp;Wynter Henry,&nbsp;Julian A. Harris,&nbsp;Frank Wilkinson,&nbsp;John A. Milligan","doi":"10.1016/j.jfluchem.2025.110400","DOIUrl":"10.1016/j.jfluchem.2025.110400","url":null,"abstract":"<div><div>A series of fluorinated and non-fluorinated [6]-gingerol, [6]-paradol, [6]-shogaol and ferulate derivatives were synthesized. Testing these analogs in anti-proliferation assays with MCF-7, A549, HCT-116 and HEK-293 cell lines provided insight into the structural features that contribute to the anti-proliferative activity of naturally occurring ginger constituents. In particular, the use of both vinyl and alkyl trifluoromethyl isosteres allowed us to evaluate the structure-activity impact of the enone motif found in shogaols. Our results indicate that enone-containing derivatives have a higher potency, suggesting the conjugated enone motif characteristic of shogaols may be primarily responsible for the anti-cancer activity of the broader natural product family.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"282 ","pages":"Article 110400"},"PeriodicalIF":1.7,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143386313","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}
引用次数: 0
2-Trifluoromethoxyacetic acid – Synthesis and characterization
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-02-01 DOI: 10.1016/j.jfluchem.2025.110396
Thorsten Meier , Sabine Lorenzen , Tanja Knuplez , Tobias Preitschopf , Karsten Koppe , Peter Barthen , Rüdiger Bertermann , Michael Schulte , Nikolai Ignat‘ev , Maik Finze
A straightforward and high-yield synthesis of 2-trifluoromethoxyacetic acid CF3OCH2C(O)OH starting from trifluoromethyl triflate CF3SO2OCF3 is described. The trifluoromethoxide anion was generated from trifluoromethyl triflate and a fluoride source followed by a nucleophilic substitution reaction with the {OCF3} ion to yield CF3OCH2C(O)OC2H5. The ester was converted into M{CF3OCH2CO2} (M = Na, K) and the acid CF3OCH2C(O)OH was obtained from the sodium salt and HCl. In addition, the silver(I) salt of the {CF3OCH2CO2} anion was synthesized from CF3OCH2C(O)OH and silver(I) oxide. The study includes a new synthesis for the starting compound CF3SO2OCF3 and a detailed description for the preparation of [N(CH3)4]{OCF3}. Furthermore, the crystal structures of CF3OCH2C(O)OH, CF3OCH2C(O)OC2H5, M{CF3OCH2CO2} (M = K, Ag), and [N(CH3)4]{OCF3} are reported.
{"title":"2-Trifluoromethoxyacetic acid – Synthesis and characterization","authors":"Thorsten Meier ,&nbsp;Sabine Lorenzen ,&nbsp;Tanja Knuplez ,&nbsp;Tobias Preitschopf ,&nbsp;Karsten Koppe ,&nbsp;Peter Barthen ,&nbsp;Rüdiger Bertermann ,&nbsp;Michael Schulte ,&nbsp;Nikolai Ignat‘ev ,&nbsp;Maik Finze","doi":"10.1016/j.jfluchem.2025.110396","DOIUrl":"10.1016/j.jfluchem.2025.110396","url":null,"abstract":"<div><div>A straightforward and high-yield synthesis of 2-trifluoromethoxyacetic acid CF<sub>3</sub>OCH<sub>2</sub>C(O)OH starting from trifluoromethyl triflate CF<sub>3</sub>SO<sub>2</sub>OCF<sub>3</sub> is described. The trifluoromethoxide anion was generated from trifluoromethyl triflate and a fluoride source followed by a nucleophilic substitution reaction with the {OCF<sub>3</sub>}<sup>–</sup> ion to yield CF<sub>3</sub>OCH<sub>2</sub>C(O)OC<sub>2</sub>H<sub>5</sub>. The ester was converted into M{CF<sub>3</sub>OCH<sub>2</sub>CO<sub>2</sub>} (M = Na, K) and the acid CF<sub>3</sub>OCH<sub>2</sub>C(O)OH was obtained from the sodium salt and HCl. In addition, the silver(I) salt of the {CF<sub>3</sub>OCH<sub>2</sub>CO<sub>2</sub>}<sup>–</sup> anion was synthesized from CF<sub>3</sub>OCH<sub>2</sub>C(O)OH and silver(I) oxide. The study includes a new synthesis for the starting compound CF<sub>3</sub>SO<sub>2</sub>OCF<sub>3</sub> and a detailed description for the preparation of [N(CH<sub>3</sub>)<sub>4</sub>]{OCF<sub>3</sub>}. Furthermore, the crystal structures of CF<sub>3</sub>OCH<sub>2</sub>C(O)OH, CF<sub>3</sub>OCH<sub>2</sub>C(O)OC<sub>2</sub>H<sub>5</sub>, M{CF<sub>3</sub>OCH<sub>2</sub>CO<sub>2</sub>} (M = K, Ag), and [N(CH<sub>3</sub>)<sub>4</sub>]{OCF<sub>3</sub>} are reported.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"282 ","pages":"Article 110396"},"PeriodicalIF":1.7,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143152572","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}
引用次数: 0
Novel synthetic method of 1,1,2,2-tetrafluoro-2-[(1,2,2-trifluoroethenyl)oxy]ethanesulfonyl fluoride
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-02-01 DOI: 10.1016/j.jfluchem.2025.110399
Nobuyuki Uematsu , Yasuhiro Nagato , Ken-ichi Yakigaya , Kaishi Hori , Hideki Date , Akitake Nakamura , Kazuki Maeda
A novel synthetic method of 1,1,2,2-tetrafluoro-2-[(1,2,2-trifluoroethenyl)oxy]ethanesulfonyl fluoride, the raw material for perfluorinated polymer electrolyte membranes, was developed from the starting material CF3CF(COF)O(CF2)2SO2F via the ring-opening reaction of cyclic compound and the cleavage reaction of vinyl sulfonic anhydride using commercially available reagents.
{"title":"Novel synthetic method of 1,1,2,2-tetrafluoro-2-[(1,2,2-trifluoroethenyl)oxy]ethanesulfonyl fluoride","authors":"Nobuyuki Uematsu ,&nbsp;Yasuhiro Nagato ,&nbsp;Ken-ichi Yakigaya ,&nbsp;Kaishi Hori ,&nbsp;Hideki Date ,&nbsp;Akitake Nakamura ,&nbsp;Kazuki Maeda","doi":"10.1016/j.jfluchem.2025.110399","DOIUrl":"10.1016/j.jfluchem.2025.110399","url":null,"abstract":"<div><div>A novel synthetic method of 1,1,2,2-tetrafluoro-2-[(1,2,2-trifluoroethenyl)oxy]ethanesulfonyl fluoride, the raw material for perfluorinated polymer electrolyte membranes, was developed from the starting material CF<sub>3</sub>CF(COF)O(CF<sub>2</sub>)<sub>2</sub>SO<sub>2</sub>F via the ring-opening reaction of cyclic compound and the cleavage reaction of vinyl sulfonic anhydride using commercially available reagents.</div></div>","PeriodicalId":357,"journal":{"name":"Journal of Fluorine Chemistry","volume":"282 ","pages":"Article 110399"},"PeriodicalIF":1.7,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143152573","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}
引用次数: 0
Synthesis of poly [2,3,5,6-tetrafluoro-4-(trifluoromethyl) phenylaminophosphazene]/LiNbO3 nanocomposites and characterization of their morphological, mechanical, and piezoelectric behavior for energy harvesting applications
IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Pub Date : 2025-02-01 DOI: 10.1016/j.jfluchem.2025.110404
Nand Kumar , Nagmani Manikpuri , Atanu Giri , Om Prakash Gautam
The use of polymer nanocomposites for piezoelectric energy harvesting applications has created exciting opportunities in flexible electronics. In this research, we synthesized poly [2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenylaminophosphazene (PTPP)]/LiNbO₃ nanocomposites by incorporating trigonal crystalline lithium niobate nanoparticles (average particle size ∼ 45 nm) into PTPP via solution casting method. Further, we investigated the effects of different concentrations of lithium niobate (LiNbO₃) nanoparticles on the thermal, mechanical, and piezoelectric performance of the PTPP nanocomposites. The synthesized nanocomposites exhibited strong interfacial interactions between the organic and inorganic phases, resulting in a uniform morphology across all compositions, except for the 8 % loading, which showed some agglomeration. Additionally, both PTPP and its nanocomposites demonstrated high thermal stability, with the highest char yield of 64.1 % observed at 8 % LiNbO₃ loading. Mechanical testing revealed a significant improvement in tensile strength (224 %) and a reduction in elongation at break (34.4 %) with 8 % LiNbO₃ loading. These enhancements in thermal and mechanical properties were attributed to the presence of strong C-F bonds and LiNbO₃ content in the nanocomposites. Besides this, dynamic mechanical analysis indicated that 8 % LiNbO₃-loaded PTPP nanocomposite also exhibited the lowest tan δ value of 0.68 and the highest energy storage capacity with minimal loss over a high-temperature range due to the restricted mobility of polymer chain with the addition of nanoparticles. PTPP also exhibited a piezoelectric effect with a coefficient of 26.4 pC/N, which was further enhanced by the incorporation of LiNbO₃, reaching a maximum increase of 6.4 %. These novel nanocomposites show great potential for energy-harvesting applications in electronic devices.
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Journal of Fluorine Chemistry
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