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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

Anion-induced differential assembly and structural transformation of supramolecular coordination cages

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Chinese Chemical Letters 2024年第3期35卷 268-272页

作者： Shao-Ping Zheng Yao-Wei Xu Pei-Yang Su Chen-Hui Liu Yin-Hui Huang Yu-Lin Lu Zhang-Wen Wei Zhiwei Jiao Hai-Sen Xu Cheng-Yong Su MOE Laboratory of Bioinorganic and Synthetic chemistry Lehn Institute of Functional MaterialsSchool of ChemistrySun Yat-sen UniversityGuangzhou 510006China institute of Environmental Research at Greater Bay Area Guangzhou UniversityGuangzhou 510006China State Key Laboratory of Organometallic chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

The intimate host-anion interactions will regulate thermodynamics and kinetics in the self-assembly of cationic cages mimicking biological counterparts.Herein,we report construction and transformation of three Pd(Ⅱ)-based metal-organic cages(MOCs)depending on different anions.Stoichiometric conversions of the lantern-shaped MOC-34 into either octahedral MOC-35 or tricapped trigonal prism MOC-36 are induced by BF_(4)^(–)or NO_(3)^(–),respectively.MOC-36 is kinetically favored and can undergo quantitative conversion to the thermodynamically preferred MOC-35 upon heating,accelerated by excess BF_(4)^(–)to motivate dissociative dynamics of Pd-vertices and lower activation barrier of cage transformation.The guest encapsulation behaviors of MOC-35 and MOC-36 have also been tested.These results manifest a significance of host-anion dynamics beyond complementary anion template,shedding light on the understanding of intricate anion recognition in nature.

关键词： Supramolecular coordination cage Dynamic host-anion interactions Structural transformation Anion receptor Guest inclusion

Synthesis and Modulation of Low-Dimensional Transition Metal Chalcogenide Materials via Atomic Substitution

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Nano-Micro Letters 2024年第9期16卷 49-94页

作者： Xuan Wang Akang Chen XinLei Wu Jiatao Zhang Jichen Dong Leining Zhang Key Laboratory of Cluster Science Ministry of Education of ChinaBeijing Key Laboratory of Photoelectronic and Electrophonic Conversion MaterialsSchool of Chemistry and Chemical EngineeringBeijing Institute of TechnologyBeijing 100081People’s Republic of China Beijing National Laboratory for Molecular Sciences Key Laboratory of Organic SolidsInstitute of Chemistry Chinese Academy of SciencesBeijing 100190People’s Republic of China

In recent years,low-dimensional transition metal chalcogenide(TMC)materials have garnered growing research attention due to their superior electronic,optical,and catalytic properties compared to their bulk counterparts.The controllable synthesis and manipulation of these materials are crucial for tailoring their properties and unlocking their full potential in various applications.In this context,the atomic substitution method has emerged as a favorable approach.It involves the replacement of specific atoms within TMC structures with other elements and possesses the capability to regulate the compositions finely,crystal structures,and inherent properties of the resulting materials.In this review,we present a comprehensive overview on various strategies of atomic substitution employed in the synthesis of zero-dimensional,one-dimensional and two-dimensional TMC materials.The effects of substituting elements,substitution ratios,and substitution positions on the structures and morphologies of resulting material are discussed.The enhanced electrocatalytic performance and photovoltaic properties of the obtained materials are also provided,emphasizing the role of atomic substitution in achieving these advancements.Finally,challenges and future prospects in the field of atomic substitution for fabricating low-dimensional TMC materials are summarized.

关键词： Transition metal chalcogenides Atomic substitution Ion exchange Low-dimensional materials Controllable synthesis

Copper-catalyzed asymmetric dearomatizing amination of 2-naphthols: Csp2–N coupling via 1,3-reductive elimination

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Science China chemistry 2024年第8期 2694-2700页

作者： Aying Yihuo Maoping Pu Zheng Tan Jibang Liao Jiuqi Tan Qi-Lin Zhou Xiaohua Liu Xiaoming Feng Key Laboratory of Green chemistry & Technology Ministry of Education College of Chemistry Sichuan University Key Laboratory and institute of Elemento-organic chemistry College of Chemistry Frontiers Science Center for New Organic Matter Nankai University

An efficient catalytic asymmetric dearomatizing amination of 2-naphthols and phenols catalyzed by N,N′-dioxide-copper（I）complex as a chiral catalyst was presented. A variety of optically active β-naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained with high yield and enantioselectivity under mild reaction conditions. Mechanistic studies indicated that this Csp2–N dearomatizing coupling proceeds via 1,3-reductive elimination of phenolate-CuⅢ-amino intermediate in five-membered ring transition states. The origin of enantioselectivity has also been elucidated based on density functional theory calculations.

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Denitration of Nitroarenes Under Ambient Physiological Conditions Catalyzed by Graphdiyne-Supported Palladium

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CCS chemistry 2024年第3期6卷 641-651页

作者： Endong Zhang Yanyan Chen Fengting Lv Zicheng Zuo Feng He Yongjun Li Yiming Huang Yuliang Li Shu Wang Beijing National Laboratory for Molecular Sciences Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing 100190 College of chemistry University of Chinese Academy of SciencesBeijing 100049

The direct cleavage of C–NO_(2)bonds for reductive denitration of nitroarenes remains a challenging transformation in synthetic organic chemistry.Herein,we report a biocompatible palladium-deposited graphdiyne nanocatalyst(Pd@GDY/DSPE-PEG)that can catalyze reductive denitration of nitroarenes under ambient physiological conditions.Mechanistic studies support this transformation via the oxidative addition of nitroarenes with Pd(0)and subsequent ligand exchange to form arylpalladium hydride.This one-step reductive denitration via Pd@GDY/DSPE-PEG successfully facilitates the repair of the nitrated proteins arising from endogenic ONOO−and restores their physiological function,including blocking the apoptosis pathway in living cells.Moreover,Pd@GDY/DSPE-PEG was further successfully applied for catalytic denitration to reduce the level of 3-nitrotyrosine residues of proteins located in the mouse brain hippocampus in vivo.This study provides an ideal strategy for designing highly active enzymatic mimicking synthetic catalysts for the regulation of the nitrated protein level and the detoxification of nitrative damage of living cells and tissues.

关键词： 3-nitrotyrosine artificial nanaocatalysts reductive denitration palladium-deposited graphdiyne repairing nitrated protein

Polyimide covalent organic frameworks as efficient solid-state Li^(+) electrolytes

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Science China chemistry 2024年第5期67卷 1647-1652页

作者： Xu Liu Shi Wang Siqi Liu Chengfang Liu Xiangchun Li Jian Wu Dazhi Li Shihao Xu Chongyang Liu Wen-Yong Lai State Key Laboratory of organic Electronics and Information Displays(SKLOEID) Institute of Advanced Materials(IAM)School of Chemistry and Life SciencesNanjing University of Posts&TelecommunicationsNanjing 210023China

Covalent organic frameworks(COFs) are attractive porous crystalline materials with extremely high stability, easy functionalization, and open channels, which are expected to be unique ion conductors/transporters in lithium ion batteries(LIBs). Despite recent advances, low ion conductivity and low transference number, resulting in low charging/discharging rate, low energy density, and short battery life, are the main issues that limit their direct application as solid electrolytes in LIBs. Here, we designed and synthesized a novel polyimide COF, namely, TAPA-PDI-COF, with abundant C=O groups, which has been successfully employed as high-performance solid electrolytes by doping TAPA-PDI-COF and succinonitrile(SN). Both the well-defined nanochannels of COFs and SN confined in the well-aligned channels restricted the free migration of anions, while C=O on COFs and CN groups of SN enhanced Li^(+) transport, thus achieving a high ion conductivity of 0.102 m S cm^(-1)at 80 °C and a high lithium-ion transference number of 0.855 at room temperature. According to density functional theory(DFT)calculations, Li-ion migration mainly adopted in-plane transport rather than the axial pathway, which may be due to the shorter hopping distances in the planar pathway. The results suggest an effective strategy for the design and development of all-solidstate ionic conductors for achieving high-performance LIBs.

关键词： lithium ion batteries(LIBs) covalent organic frameworks(COFs) solid-state ion conductors solid-state electrolytes ion conductivity

Recovery and in-situ reduction of precious metals by graphdiyne and graphdiyne oxide for antibacterial use

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Rare Metals 2024年第4期43卷 1747-1757页

作者： Ming-Ji Jiang Ya-Na Zhang Ling-Shen Meng Jing Kang Yong-Jun Li Alideertu Dong College of chemistry and Chemical Engineering Inner Mongolia University Engineering Research Center of Dairy Quality and Safety Control Technology Ministry of EducationInner Mongolia University Department of chemistry University of Zurich Laboratory of organic Solids and Beijing National Laboratory for Molecular Sciences Institute of ChemistryChinese Academy of Sciences

Based on the in-situ self-reduction and chemical stability,graphdiyne（GDY） and graphdiyne oxide（GDYO） are used as trapping agents to investigate the ability for recovering Au3+,Ag+,and Pd2+under different pH values and interfering ions.Under strong acidity at pH=1,these two agents demonstrate high select recovery towards the three precious metal ions,which could be insitu reduced to nanoparticles（NPs）.In addition,superparamagnetic Fe3O4NPs are deposited on the surfaces of GDY and GDYO.The magnetic responses enable GDYFe3O4to recover precious metals conveniently and efficiently by the aid of an external magnetic field.This study also confirms the antibacterial activity of the as-recovered NPs deposited on GDY and GDYO against Escherichia coli and Staphylococcus aureus(1 × 10～5 colony-forming unit（CFU）·ml-1),and the antibacterial rates are 100%.This strategy of recovering precious metals and subsequently reusing to combat pathogens will be of great significance for environmental remediation and biomedical applications.

关键词： Graphdiyne In-situ reduction Recovery Precious metals Antibacterial

Asymmetric reversible structural switching of a diene coordination polymer promoted by UV-visible light

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Science China chemistry 2024年第2期67卷 536-541页

作者： Yong Wang Qiaoqiao Zhang Yong-Yong Cao Qi Liu Brendan F.Abrahams Jian-Ping Lang College of chemistry Chemical Engineering and MaterialsSoochow UniversitySuzhou215123China State Key Laboratory of Organometallic chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032China College of Biological Chemical Science and EngineeringJiaxing UniversityJiaxing314001China School of chemistry University of MelbourneVictoria3010Australia

In natural and artificial systems,reversible reactions are commonly asymmetric with respect to the time scale and nature of the stimuli which drive the forward and backward processes.In applications for which switching behavior is required,it is desirable that the reversible reaction goes as close to symmetric as possible;however,such systems are uncommon.Herein,we report an example of ultraviolet(UV)-visible light-regulated asymmetric reversible structural switching involving a diene-based coordination polymer,CP1 and its monocyclobutane product,CP1a.It is possible to cycle at least ten times through a forward [2+2] photocycloaddition reaction and the reverse,photocleavage reaction.A single cycle can be completed within a few minutes.The transformation is accompanied by fast and distinct fluorescence changes,arising from optimisation of the reaction conditions.Density functional theory calculations allow rationalisation of the asymmetric reversible transformation between CP1 and CP1a rather than between CP1 and its dicyclobutane product CP1b.This work provides a clear illustration of reversible structural switching which approaches symmetric behaviour with respect to reaction rate and stimuli.The insights gained from this work also assist in the design of fast,reversible switching materials.

关键词： asymmetrical reversible structural switching coordination polymer photocycloaddition UV-visible light-controlled fluorescence switching

Advances of Electrochemical and Electrochemiluminescent Sensors Based on Covalent organic Frameworks

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Nano-Micro Letters 2024年第2期16卷 395-422页

作者： Yue Cao Ru Wu Yan‑Yan Gao Yang Zhou Jun‑Jie Zhu Key Laboratory for organic Electronics and Information Displays(KLOEID)and institute of Advanced Materials(IAM) Nanjing University of Posts and Telecommunications(NJUPT)Nanjing 210023People’s Republic of China State Key Laboratory of Analytical chemistry for Life Science School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023People’s Republic of China

Covalent organic frameworks(COFs),a rapidly developing category of crystalline conjugated organic polymers,possess highly ordered structures,large specific surface areas,stable chemical properties,and tunable pore microenvironments.Since the first report of boroxine/boronate ester-linked COFs in 2005,COFs have rapidly gained popularity,showing important application prospects in various fields,such as sensing,catalysis,separation,and energy storage.Among them,COFs-based electrochemical(EC)sensors with upgraded analytical performance are arousing extensive interest.In this review,therefore,we summarize the basic properties and the general synthesis methods of COFs used in the field of electroanalytical chemistry,with special emphasis on their usages in the fabrication of chemical sensors,ions sensors,immunosensors,and aptasensors.Notably,the emerged COFs in the electrochemiluminescence(ECL)realm are thoroughly covered along with their preliminary applications.Additionally,final conclusions on state-of-the-art COFs are provided in terms of EC and ECL sensors,as well as challenges and prospects for extending and improving the research and applications of COFs in electroanalytical chemistry.

关键词： Covalent organic frameworks Electrochemistry Electrochemiluminescence Sensors