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Visible-Light-Driven Four-Component Radical Relay Aminocarbonylation of Unactivated Alkenes

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Chinese Journal of Chemistry 2024年第9期42卷 990-996页

作者： Bin Lu Feng-Shuo Bao Zi-Wei He Wen-Jing Xiao Jia-Rong Chen Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction College of ChemistryCentralChina Normal University152 Luoyu RoadWuhanHubei 430079China Wuhan Institute of photochemistry and Technology 7North Bingang RoadWuhanHubei 430083China key {1. of Organo-Pharmaceutical Chemistry of Jiangxi Province Gannan Normal UniversityGanzhouJiangxi 341000China

Catalytic four-component radical carbonylation of unactivated alkenes has recently been recognized as a robust protocol for rapid construction of various structurally diverse carbonyl *** the significance of fluorine-containing groups,this reaction class has been extensively applied to assembly of a variety of perfluoroalkyl carboxylic acid derivatives by transition metal ***,we report a visible-light-driven radical relay 1.2-perfluoroalkylation aminocarbonylation of unactivated alkenes using CO gas as carbonyl source and 4CzIPN as organic photocatalyst.A wide range of alkenes and amines were well tolerated,providing the valuableβ-perfluoroalkylated amides with generally good yields and high chemoselectivity.

关键词： Visible light Photoredox catalysis Radical aminocarbonylation Multicomponent reaction Carbon monoxide Unactivated alkenes AmidesIReactionmechanisms

Luminescent metal-halide perovskites:fundamentals,synthesis,and light-emitting devices

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Science China Chemistry 2024年第6期67卷 1776-1838页

作者： Kang Wang Jeong Hui Kim Jie Yang Xiaoke Liu Yixuan Dou Yuxuan Li Weijian Tao Haiyun Dong Haiming Zhu Kaifeng Wu Li Na Quan Feng Gao Jianpu Wang Letian Dou Yong Sheng Zhao Beijing National laboratory for Molecular Sciences(BNLMS) Key Laboratory of PhotochemistryInstitute of ChemistryChinese Academy of SciencesBeijing100190China Davidson School of Chemical Engineering Purdue UniversityWest LafayetteIN47907USA School of Chemical Sciences University of Chinese Academy of SciencesBeijing100049China key {1. of Flexible Electronics(KLOFE) Institute of Advanced Materials(IAM)&School of Flexible Electronics(Future Technologies)Nanjing Tech University(NanjingTech)Nanjing211816China Department of Physics Linköping UniversityLinköping58183Sweden Department of Chemistry Virginia TechBlacksburgVA24060USA State key {1. of Molecular Reaction Dynamics Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian116023China Department of Chemistry Zhejiang UniversityHangzhou310058China Changzhou University Changzhou213164China Department of Chemistry Purdue UniversityWest LafayetteIN47907USA

Metal-halide perovskites have garnered considerable research attention as highly efficient light emitters in recent years due to their outstanding optoelectronic properties with remarkable tunability and excellent solution *** advancements have been achieved in the development of novel halide perovskites,and the exploitations of these materials in lightemitting *** review comprehensively outlines recent breakthroughs in metal-halide perovskites,encompassing the rational design of perovskite materials with tunable light emission properties,the controllable growth of single crystal for a deeper understanding of their structure-property relationships,as well as the fundamental insights into the photophysics and carrier dynamics in perovskite ***,it provides an overview of recent applications of perovskite materials in high-performance light-emitting diodes(LEDs)and lasers.

关键词： metal-halide perovskites perovskite luminescent materials perovskite synthesis excited-state processes perovskite light-emitting diodes perovskite lasers

Dynamic steric confinement effect expands the frontier of Cu-catalyzed asymmetric propargylic aminations

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Science China Chemistry 2024年第10期67卷 3181-3183页

作者： Peng Chen Mao-Mao Zhang Wen-Jing Xiao Liang-Qiu Lu Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction Ministry of EducationCollege of ChemistryCentral China Normal UniversityWuhan 430079China Wuhan Institute of photochemistry and Technology Wuhan 430082China State key {1. for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical Physics(LICP)Chinese Academy of SciencesLanzhou 730000China School of Chemistry and Chemical Engineering Henan Normal UniversityXinxiang 453007China

Chiralα-tertiary amines and related azacycles are commonly found in many natural products,pharmaceuticals and agrochemicals[1..Copper-catalyzed asymmetric propargylic amination(APA)reactions have been established as a reliable method to access enantio-enriched propargylic amines,largely due to the seminal contribution of Nishibayashi et al.[2]and van Maarseveen et al.[3]in 2008.

关键词： catalyzed asymmetric amines

Metallaphotoredox-Catalyzed Three-Component Couplings for Practical Synthesis of Ureas and Carbamates

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Chinese Journal of Chemistry 2024年第3期42卷 264-270页

作者： Ernest Koranteng Zhen-Cao Shu Yi-Yin Liu Qian Yang Bin Shi Qiang-Xian Wu Fen Tan Liang-Qiu Lu Wen-Jing Xiao Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction Ministry of EducationCollege of ChemistryCentral China Normal University152 Luoyu RoadWuhanHubei430079 China Wuhan Youji Industries Co. LtdNo.1 2nd Chemical Rd.WuhanHubei430082 China Hubei key {1. of Purification and Application of Plant Anti-cancer Active Ingredients School of Chemistry and Life SciencesHubei University of EducationWuhanHubei430205 China State key {1. for Oxo Synthesis and Selective Oxidation Lanzhou Institute of Chemical PhysicsChinese Academy of SciencesLanzhouGansu730000 China School of Chemistry and Chemical Engineering Henan Normal UniversityXinxiangHenan453007 China Wuhan Institute of photochemistry and Technology WuhanHubei430082 China State key {1. of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032 China

Ureas are widely used in drugs,materials and catalysts because of their diamide structure,which can form strong hydrogen ***,it is of great scientific significance to develop efficient and green methods for the synthesis of urea compounds,especially unsymmetrical ***,we have disclosed novel and highly efficient three-component coupling reactions of organic halides,sodium cyanate and amines enabled by nickel/photoredox dual catalysis for the preparation of unsymmetrical *** reaction features simple and safe operations,broad substrate scopes,and product *** allows the facile synthesis of N-aryl/vinyl ureas from readily available,user-friendly feedstocks under mild conditions(27 examples,36%—98%yields).In addition,this method is further derived to alcohols as nucleophiles to synthesize a series of carbamates(1. examples,40%—95%yields).The mechanism experiment shows that the isocyanate produced by the coupling of halide and sodium cyanate may be the key intermediate in this reaction.

关键词： Cross-coupling Nickel Photoredox catalysis Three-component reaction Ureas Carbamates

Design of advanced porous silver powder with high-sintering activity to improve silicon solar cells

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Nano Research 2024年第4期17卷 3189-3197页

作者： Yongsheng Li Ziwei Chen Rui Zhou Wenguang Zhao Mu Li Jun Chen Zhongyuan Huang Jian Liu Yuhang Li Maolin Yang Minghan Yu Dong Zhou Yuan Lin Feng Pan School of Advanced Materials Peking UniversityShenzhen Graduate SchoolShenzhen 518055China Institute of Advanced Science Facilities Shenzhen 518107China Institute of Zhejiang University-Quzhou Quzhou 324000China key {1. of photochemistry Institute of ChemistryChinese Academy of SciencesBeijing 100190China Institute of Materials Research(IMR) Tsinghua UniversityTsinghua Shenzhen International Graduate SchoolShenzhen 518055China School of Materials Science and Engineering Harbin Institute of Technology(Shenzhen)Shenzhen 518055China

Silver(Ag)paste is widely used in semiconductor metallization,especially in silicon solar *** powder is the material with the highest proportion in Ag *** morphology and structure of Ag powder are crucial which determine its characteristics,especially for the sintering *** this work,a simple method was developed to synthesize a type of microcrystalline spherical Ag particles(SP-A)with internal pores and the structural changes and sintering behavior were thoroughly studied by combining ultra-small-angle X-ray scattering(USAXS),small-angle X-ray scattering(SAXS),in-situ heating X-ray diffraction(XRD),focused ion beam(FIB),and thermal analysis *** to the unique internal pores,the grain size of SP-A is smaller,and the coefficient of thermal expansion(CTE)is higher than that of traditional solid Ag *** a result,the sintering activity of SP-A is excellent,which can form a denser sintered body and form silver nanoparticles at the Ag–Si interface to improve silver silicon *** silicon solar cell built with SP-A obtained a low series resistance(Rs)and a high photoelectric conversion efficiency(PCE)of 1..26%.These fill a gap in Ag particle structure research,which is significant for the development of high-performance electronic Ag particles and efficient semiconductor devices.

关键词： silver particles small angle X-ray scattering(SAXS) pore size distribution in-situ heating X-ray diffraction(XRD) sintering silicon solar cells

Advances in self-assembly-based circularly polarized luminescent materials

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Science China Chemistry 2024年第10期67卷 3247-3257页

作者： Bing-Hao Liu Yang Zong Na Liu Zong-Quan Wu State key {1. of Supramolecular Structure and Materials College of ChemistryJilin UniversityChangchun 130012China The School of Pharmaceutical Sciences Jilin UniversityChangchun 130021China

Circularly polarized luminescent(CPL)materials have garnered attention for their diverse applications,including three-dimensional(3D)imaging,bio-imaging,chiral sensing,and other emerging ***,the fabrication of CPL-activated materials required the use of chiral luminescent small *** introduction of the idea of self-assembly has transformed the production of CPL-activated materials,providing new and promising opportunities for their *** utilizing self-assembly,it is now feasible to produce chiral nano-assemblies with CPL activity not only from chiral molecules but also from non-chiral substances and inorganic *** addition,self-assembly routes provide a way to increase the asymmetry factor,creating possibilities for additional refinement and adjustment of CPL material *** review offers a summary of the current progress and developments in the self-assembly of small molecules and polymers,with a specific emphasis on their capacity to create or enhance CPL in different *** aim of this review is to inspire interest in optical materials that are based on the principles of self-assembly.

关键词： circularly polarized luminescence photochemistry self-assembly chiral materials

Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor

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Chinese Chemical Letters 2024年第4期35卷 399-403页

作者： Zhixiang Li Zhirong Yang Chang Yao Bin Wu Gang Qian Xuezhi Duan Xinggui Zhou Jing Zhang State key {1. of Chemical Engineering East China University of Science and TechnologyShanghai 200237China School of Chemical Engineering Zhengzhou UniversityZhengzhou 450001China

2-Hydroxycarbazole and 4-hydroxycarbazole are important chemicals with extensive applications in optoelectronic materials and pharmaceutical *** of the art yield of 2-hydroxycarbazole is~30%and the reaction time is typically in hours or ***,we developed a green route for the continuous and high-throughput synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole via photochemical intramolecular cyclization of 3–hydroxy-2–chloro-diphenylamine using a self-designed millimeter scale photoreactor,which was designed based on sizing-up and numbering-up strategies for a decent liquid holdup(6.8 m L)and fabricated via femtosecond laser engraving *** photochemical synthesis was carried out continuously under the illumination of 365 nm UV-LED with dimethyl sulfoxide as solvent and potassium t-butoxide as *** was found that under optimized conditions a 2-hydroxycarbazole yield of 31.6%and a 4-hydroxycarbazole yield of 1..1.were obtained with a residence time of 1.*** to semibatch operations,the reaction time was shortened by 1.2 orders of *** a result,a throughput of 1..3 g/day 2-hydroxycarbazole and 4.0 g/day 4-hydroxycarbazole can be achieved from the *** was proposed that the short reaction time and high product yield are resulted from higher photon transfer rates and more uniform photon distribution provided by the millimeter scale photoreactor,which enhances the reaction rates and mitigates overreaction.

关键词： Millimeter scale reactor 2-Hydroxycarbazole photochemistry UV-LED Process intensification

Designing Tough,Printable,and Adaptable Eutectogels with Multinetworks via Synergy of Rapid Orthogonal Photopolymerizations and Solvent Effect in Seconds

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CCS Chemistry 2024年第2期6卷 390-402页

作者： Jupen Liu Lijun Zhou Ping Zhang Yanxia Zhao Hongqiu Wei You Yu key {1. of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education College of Chemistry and Materials ScienceNorthwest UniversityXi’an 710069

Achieving a straightforward design of tough,printable,and adaptable polymeric eutectogels is still challenging in related fields due to the uncontrollable polymerization and solvent-exchanging processes,and inherent contrasting multiple ***,we report a one-step synergistic strategy based on ruthenium chemistry-catalyzed photopolymerization and solvent effect for preparing high-performance *** orthogonal ruthenium photochemistry helps multinetworks formation via phenol-coupling of gelatin and copolymerization of acrylamide(AAm)and[2-(methacryloyloxy)ethyl]trimethylammonium tetrafluoroborate(META)monomers in *** obvious difference in the supramolecular interactions of free AAm monomers and polymerized units in P(AAm-co-META)with deep eutectic solvents(DESs)significantly promotes the microphase-separation behavior in ***,the in situ polymerization and microphase-separation behavior enable the as-prepared eutectogel materials to have excellent mechanical properties(stress of∼1.2 MPa),toughness(∼4.0 MJ m^(−3)),elasticity,adaptivity,and conductivity(∼0.5 S m^(−1.at room temperature).Also,the critical strength of the resultant eutectogels can be modulated by varying the DES *** rapid and well-controlled synergistic approach is compatible with extrusion printing techniques to make flexible sensors with high sensitivities and response times to detect pressure in a range of 0–500 *** a general and simple strategy has application potential in biological,engineering,and material sciences.

关键词： orthogonal chemistry visible-light photopolymerization solvent effect microphase separation adaptable polymers printable eutectogels

Photoinduced transposed Paternò-Büchi reaction for effective synthesis of high-performance jet fuel

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Chinese Journal of Chemical Engineering 2024年第3期67卷 39-48页

作者： Jinxiu Hu Xianlong Liu Yi Liu Kang Xue Chengxiang Shi Xiangwen Zhang Li Wang Ji-Jun Zou Lun Pan key {1. for Green Chemical Technology of the Ministry of Education School of Chemical Engineering and TechnologyTianjin UniversityTianjin 300072China Haihe laboratory of Sustainable Chemical Transformations Tianjin 300192China Zhejiang Institute of Tianjin University Ningbo 315201China Collaborative Innovative Center of Chemical Science and Engineering(Tianjin) Tianjin 300072China

High-energy-density fuels are important for volume-limited aerospace vehicles,but the increase in fuel energy density always leads to poor cryogenic ***,we investigated the transposed Paternò-Büchi reaction of biomass cyclic ketone and cyclic alkene to synthesize a new kind of alkyl-substituted polycyclic hydrocarbon fuel with high energy density and good cryogenic *** triplet-energy-quenching results and phosphorescent emission spectra reveal the sensitization mechanism of the reaction,including photosensitizer excitation,triplettriplet energy transfer,cyclization,and relaxation,and the possible reaction path was revealed by the density functional theory(DFT)*** reaction conditions of photosensitizer type and addition,molar ratio of substrates,reaction temperature,and incident light intensity were optimized,with the target product yield achieving 65.5%.Moreover,the reaction dynamics of the reaction rate versus the light intensity are *** the hydrogenation-deoxygenation reaction,three fuels with a high density of 0.864-0.938 g·ml^(-1. and a low freezing point of<-55℃ are *** work provides a benign and effective approach to synthesize high-performance fuels.

关键词： High-energy-density fuel Transposed Patern-oeBüchi reaction Kinetics Bioenergy photochemistry