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Unusual Single Electron Transfer Reactions between Alkenes and Iodine Electrophiles

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Chinese Journal of Chemistry 2024年第5期42卷 471-477页

作者： Zhengzhao Lou Jingyu Hu Chuanfa Ni Xiu Wang Jinbo Hu Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Ling Ling RoadShanghai200032 China School of Physical Science and Technology ShanghaiTech University100 Haike RoadShanghai201210 China

The electrophilic addition to an alkene with an electrophile has been widely studied and applied in organic synthesis.The organic chemistry textbook describes the classical reaction between an alkene and an iodine electrophile(such as elemental iodine and N-iodosuccinimide(NIS))as a typical ionic reaction,in which an iodonium ion is formed and then attacked by a nucleophile.However,in this article,we report a new and unusual reaction mode between an alkene and NIS;that is,a single electron transfer(SET)process occurs between these two reactants by forming an electron-donor acceptor complex.Not only does this unusual single electron transfer reaction between an alkene and NIS add fundamentally important knowledge to organic chemistry,it also provides a valuable synthetic method as the new SET reaction mode with opposite regioselectivity as compared with the traditional ionic mode.

关键词： Electrophilic addition Radical ions Reaction mechanisms Alkenes fluorine

Mulberry Biomass-Derived Nanomedicines Mitigate Colitis through Improved Inflamed Mucosa Accumulation and Intestinal Microenvironment Modulation

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Research 2024年第1期6卷 791-807页

作者： Wenjing Yang Ya Ma Haiting Xu Zhenhua Zhu Jiaxue Wu Cheng Xu Wei Sun Erhu Zhao Min Wang Rui L.Reis Subhas C.Kundu Xiaoxiao Shi Bo Xiao State Key Laboratory of Silkworm Genome Biology College of SericultureTextileand Biomass SciencesSouthwest UniversityChongqing 400715China Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing Faculty of Materials and EnergySouthwest UniversityChongqing 400715China Department of Gastroenterology The First Affiliated Hospital of Nanchang UniversityNanchang 330006China Bs Research Group I3Bs—Research Institute on BiomaterialsBiodegradables and BiomimeticsUniversity of MinhoHeadquarters of the European Institute of Excellence on Tissue Engineering and Regenerative MedicineAveParkBarco 4805-017GuimaraesPortugal ICVS/3B’s-PT Government Associate Laboratory BragaGuimarãesPortugal

The therapeutic outcomes of conventional oral medications against ulcerative colitis(UC)are restricted by inefficient drug delivery to the colitis mucosa and weak capacity to modulate the inflammatory microenvironment.Herein,a fluorinated pluronic(FP127)was synthesized and employed to functionalize the surface of mulberry leaf-derived nanoparticles(MLNs)loading with resveratrol nanocrystals(RNs).The obtained FP127@RN-MLNs possessed exosome-like morphologies,desirable particle sizes(around 171.4 nm),and negatively charged surfaces(−14.8 mV).The introduction of FP127 to RN-MLNs greatly improved their stability in the colon and promoted their mucus infiltration and mucosal penetration capacities due to the unique fluorine effect.

关键词： fluorine sizes Biomass

Access to Versatile Functionalized Cu(Ⅲ) Complexes Enabled by Direct Transmetalation to Well-Defined Copper(Ⅲ) Fluoride Complex Me_(4)N^(+)[Cu(CF_(3))_(3)F]^(-)

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Chinese Journal of Chemistry 2024年第10期42卷 1107-1113页

作者： Guangyu Wang Huaiyuan Li Xuebing Leng Long Lu Qilong Shen Key Laboratory of fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling LuShanghai 200032China

The invention of a well-defined Cu(Ⅲ)fluoride complex Me_(4)N^(+)[Cu(CF_(3))_(3)(F)]^(-)1 enabled to access a versatile of functionalized Cu(Ⅲ)complexes[Me_(4)N]^(+)[Cu(X)(CF_(3))_(3)]^(-)(X=C_(6)F_(5),C_(6)F_(5)C≡C,CN,Cl,N_(3),^(t)BuOO,SCN,OAc,SAr),many of them for the first time.The availability of these complexes allowed us to evaluate the trans-influence order of ligand in Cu(Ⅲ)complexes:Bn>CF_(3)^(-)>C_(6)F_(5)^(-)>N_(3)^(-)>py~CH_(3)^(-)~C_(6)F_(5)C≡C>NO_(2)PhO^(-)~^(t)BuOO^(-)~CH_(3)COO^(-)>F^(-).

关键词： fluorine Copper Cu(Ⅲ) Cu(Ⅲ)fluoride Trifluoromethyl

Recent Advances in C-F Bond Formation from Carbon-Centered Radicals

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Chinese Journal of Chemistry 2024年第9期42卷 1009-1031页

作者： Jihua Zhang Juanjuan Wang Qiang Cheng College of Chemistry and Molecular Sciences Wuhan UniversityWuhanHubei 430072China

Construction of C-F bonds is a direct and efficient method for introducing fluorine into pharmaceuticals,agrochemicals,and materials.Strategies such as nucleophilic,electrophilic,radical,and transition-metal catalyzed fluorination have been developed to meet the demand of diverse C-F bond formation.Among them,radical fluorination has been witnessed with substantial advancement in a recent decade.Herein,we reviewed methods for formation of C-F bonds with carbon-centered radicals as key intermediates,especially in recent five years.We introduce in the paper with different fluorinating reagents,strategies for radical generation,and application in late-stage functionalization and synthesis of PET tracers.We also indicate the current limitations and propose the direction of the field for the future development.

关键词： fluorine Fluorinating reagents Late-stage fluorination [^(18)F]jfluorination Radical reactions Synthetic methods

Significant Lifetime Enhancement in QLEDs by Reducing Interfacial Charge Accumulation via fluorine Incorporation in the ZnO Electron Transport Layer

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Nano-Micro Letters 2022年第12期14卷 432-446页

作者： Dong Seob Chung Tyler Davidson-Hall Giovanni Cotella Quan Lyu Peter Chun Hany Aziz Department of Electrical and Computer Engineering Waterloo Institute for NanotechnologyUniversity of Waterloo200 University Avenue WestWaterlooON N2L 3G1Canada Ipswich Research Centre Huawei Technologies Research&Development(UK)Ltd.Phoenix House(B55)Adastral ParkIpswich IP53REUK Ottawa IC Laboratory Huawei Canada19 Allstate ParkwayMarkhamON L3R 5B4Canada

ZnO nanoparticles are widely used for the electron transport layers(ETLs)of quantum dots light emitting devices(QLEDs).In this work we show that incorporating fluorine(F)into the ZnO ETL results in significant enhancement in device electroluminescence stability,leading to LT50 at 100 cd m^(−2) of 2,370,000 h in red QLED,47X longer than the control devices.X-ray photo-electron spectroscopy,time-of-flight secondary ion mass spectroscopy,photoluminescence and electrical measurements show that the F passivates oxygen vacancies and reduces electron traps in ZnO.Transient photoluminescence versus bias measurements and capacitance-voltage-luminance measurements reveal that the CF4 plasma-treated ETLs lead to increased electron concentration in the QD and the QD/hole transport layer interface,subsequently decreasing hole accumulation,and hence the higher stability.The findings provide new insights into the critical roles that optimizing charge distribution across the layers play in influencing stability and present a novel and simple approach for extending QLED lifetimes.

关键词： Colloidal quantum dots Quantum dots light emitting device Device stability Zinc oxide nanoparticles fluorine

Multifunctional high-fluorine-content molecule with high dipole moment as electrolyte additive for high performance lithium metal batteries

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Rare Metals 2022年第3期41卷 726-729页

作者： Xi Tang Wen-Chao Zhang Liu-Yue Cao Institute of Environmental Engineering School of Metallurgy and EnvironmentCentral South UniversityChangsha 410083China School of Chemical and Biomolecular Engineering the University of SydneyDarlingtonNSW 2006Australia

Lithium metal batteries (LMBs) have been regarded as the most promising technology beyond lithium-ion batteries to meet the ever-increasing demand for high-energy and highpower secondary battery technologies. Challenges such as poor electrochemical stability of electrolytes, dendritic Li plating, gradual cathode structure degradation.

关键词： battery lithium fluorine

Study on the resource utilization of high fluorine-containing organic waste through fluidized incineration

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Waste Disposal and Sustainable Energy 2022年第2期4卷 117-129页

作者： Wenhan Li Zengyi Ma Jianhua Yan Qianming Huang Xingjian Wen Zian Zhai Bochen Huang Shuang Wang Yongqiang Chen Science and Technology on Reactor System Design Technology Laboratory Nuclear Power Institute of ChinaChengdu610213China State Key Laboratory of Clean Energy Utilization Institute for Thermal Power EngineeringZhejiang UniversityHangzhou310027China Zhejiang Xianchuang Energy&Technology Co.Ltd Jinhua321000China

In this study,the method of fluidized incineration and water washing to recover hydrogen fluoride(HF)was proposed to dispose of high fluorine-containing organic waste.The resource utilization of the waste was investigated in a fluidized bed incinerator with a disposal capability of 10 t/d.The evolution characteristics of fluorine,operation conditions of the incineration system,absorption coefficient for HF by water washing,and HF corrosion during combustion were assessed.The results showed that HF and fluorocarbons were detected as the initial gaseous fluorides released during combustion.The release of HF could be divided into three stages,in which HF was generated from the volatilization of HF in the waste and the hydrolysis of fluorine in water-soluble salts(60–220℃),oxidative decomposition of fluorinated organic components and residual carbon(220–800℃),and hydrolysis of insoluble fluorinated inorganic minerals(800–1000℃).Fluorocarbons could be destroyed through reactions with free radicals H,O,and OH or through single-molecule decomposition.Enhancing the temperature in the furnace and increasing the content of oxygen and hydrogen in the incineration materials were conducive to reducing the generation of fluorocarbons.By sampling and analyzing the bottom slag,bag filter ash and exhaust gas during the field test,the relevant pollutant discharge could meet the national emission standards.The waste heat utilization of high-temperature flue gas and the recovery of hydrofluoric acid and hydrochloric acid were realized.In the recovery of HF by water washing,the total absorption coefficients for 1#to 4#packed absorbers were 52.38 kg/(h m^(2)),39.96 kg/(h m^(2)),5.98 kg/(h m^(2))and 3.89 kg/(h m^(2)),respectively.In the actual operation,alumina showed good corrosion resistance to high-temperature HF and could be used as bed materials or refractory materials.Low-temperature corrosion of HF occurred in the quenching heat exchanger,which was damaged after 6 months of continuous operation.High-temperature corrosion of HF o

关键词： Organic waste fluorine Fluidized incineration Resource utilization

Chloro-free synthesis of LiPF_(6)using the fluorine-oxygen exchange technique

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Chinese Chemical Letters 2022年第8期33卷 4061-4063页

作者： Jian Liu Yuanli Cai Huan Pang Bin Cao Chengzhi Luo Zhenghao Hu Chaoqun Xiao Hu Zhang Fulu Lv Yitao Cao Lei Yu School of Chemistry and Chemical Engineering Yangzhou UniversityYangzhou 225002China Tianzhu Hongfu Lithium Industry Technology Development Company Limited Wuwei 733200China Royal Holloway University of LondonEgham TW200QRUnited Kingdom

A hydrogen fluoride-free and chloro-free method for synthesizing LiPF_(6) was developed.Employing CaF_(2) as the direct fluorinating reagent instead of hydrogen fluoride made it much safer and more environmentfriendly than conventional methods and reduced the metal residues in product owing to the relatively low-acid reaction conditions less corrosive to equipments.The use of P_(2)O_(5) as phosphorus source instead of traditionally employed PCl_(5) significantly reduced the chloro residue in product.Ca(H_(2)PO_(4))_(2),the only by-product of the process,could be easily converted into Ca_(3)(PO_(4))_(2),a best-selling chemical.The above advantages not only reduce the production costs by ca.20%,but also significantly improve the product purity.The fluorine-oxygen exchange reaction is a completely new technique for LiPF_(6) production and may bring about technological revolution in the related industry.

关键词： Lithium fluorine Electrolyte High purity Green chemistry Process

fluorine doping for improved thermoelectric properties of spark plasma sintered bismuth telluride

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Journal of Materials Science & Technology 2021年第31期90卷 225-235页

作者： Jinseo Kim Le Thai Duy Hyunwoo Kang Byungmin Ahn Hyungtak Seo Department of Energy Systems Research Ajou UniversitySuwon 16499South Korea Department of Materials Science and Engineering Ajou UniversitySuwon 16499South Korea

Bismuth-telluride(Bi_(2)Te_(3))is considered to have the best thermoelectric properties at room temperature(ca.300 K).Thus,synthesis and improvement of Bi_(2)Te_(3)and its derivatives quickly and cost-effectively at favorite temperatures are of interests.Recently,doping fluorine(F)into electronic materials(e.g.,FTO)has gained attention;however,it is not applied to Bi_(2)Te_(3)till now.Here,our synthesis of F-doped Bi_(2)Te_(3)for thermoelectric application is introduced using spark plasma sintering(SPS)for Bi_(2)Te_(3)preparation and reactive ion etching(RIE,with SF_6 gas)for F-doping.The exposure time of SF_6 plasma is adjusted to evaluate F-doping effect on the thermoelectric properties of the samples.During characterizations,the increased electrical conductivity and the improved Seebeck coefficient of F-doped Bi_(2)Te_(3)are observed.Through spectroscopic studies and DFT calculations,the main mechanism behind that improvement is unveiled.It also emphasizes the essential role of the F-doping(optimum treatment time of 40 s)in increasing the carrier concentrations as well as electrical conductivity.With increasing measurement temperature(300-510 K),F-doping raises the figure of merit of electron rich Bi_(2)Te_(3)from 1.0 to 1.11(peaked at 390 K).

关键词： Bismuth-telluride fluorine Doping Thermoelectric Spark plasma sintering