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Spin effect on redox acceleration and regioselectivity in Fe-catalyzed alkyne hydrosilylation

National Science Review 2024年第2期11卷 155-167页

作者： Peng He Meng-Yang Hu Jin-Hong Li Tian-Zhang Qiao Yi-Lin Lu Shou-Fei Zhu Frontiers Science center for New organic Matter State Key Laboratory and Institute of Elemento-Organic Chemistry Nankai University

Iron catalysts are ideal transition metal catalysts because of the Earths abundant, cheap, biocompatible features of iron salts. Iron catalysts often have unique open-shell structures that easily undergo spin crossover in chemical transformations, a feature rarely found in noble metal catalysts. Unfortunately, little is known currently about how the open-shell structure and spin crossover affect the reactivity and selectivity of iron catalysts, which makes the development of iron catalysts a low efficient trial-and-error program. In this paper, a combination of experiments and theoretical calculations revealed that the iron-catalyzed hydrosilylation of alkynes is typical spin-crossover catalysis. Deep insight into the electronic structures of a set of well-defined open-shell active formal Fe(0) catalysts revealed that the spin-delocalization between the iron center and the 1,10-phenanthroline ligand effectively regulates the iron center's spin and oxidation state to meet the opposite electrostatic requirements of oxidative addition and reductive elimination, respectively,and the spin crossover is essential for this electron transfer process. The triplet transition state was essential for achieving high regioselectivity through tuning the nonbonding interactions. These findings provide an important reference for understanding the effect of catalyst spin state on reaction. It is inspiring for the development of iron catalysts and other Earth-abundant metal catalysts, especially from the point of view of ligand development.

关键词： spin effect spin-delocalization spin crossover iron-catalysis alkyne hydrosilylation

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Enhanced organic degradation and microbial community cooperation by inoculating Bacillus licheniformis in low temperature composting

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Journal of Environmental Sciences 2024年第9期143卷 189-200页

作者： Jing Su Kaiyun Zhou Wenjie Chen Shaoqi Xu Ziwei Feng Yuan Chang Xiaoyan Ding Yi Zheng Xingling Tao Ake Zhang Yue Wang Ji Li Guochun Ding Yuquan Wei Nanjing Institute of Environmental Sciences Ministry of Ecology and EnvironmentNanjing 210042China College of Resources and Environmental Science Beijing Key Laboratory of Biodiversity and Organic FarmingChina Agricultural UniversityBeijing 100193China organic Recycling Institute(Suzhou)of China Agricultural University Wuzhong DistrictSuzhou 215128China Fuyang Academy of Agricultural Sciences Fuyang 236065China

Microbial activity and interaction are the important driving factors in the start-up phase of food waste composting at low *** aim of this study was to explore the effect of inoculating Bacillus licheniformis on the degradation of organic components and the potential microbe-driven mechanism from the aspects of organic matter degradation,enzyme activity,microbial community interaction,and microbial metabolic *** results showed that after inoculating ***,temperature increased to 47.8℃ on day2,and the degradation of readily degraded carbohydrates(RDC)increased by 31.2%,and the bioheat production increased by 16.5%.There was an obvious enhancement of extracellular enzymes activities after inoculation,especially amylase activity,which increased by 7.68 times on day *** inoculated *** colonized in composting as key genus in the start-up *** network analysis and Mantel test indicated that inoculation drove the cooperation between microbial network modules who were responsible for various organic components(RDC,lipid,protein,and lignocellulose)degradation in the start-up *** function prediction suggested that carbohydrate metabolisms including starch and sucrose metabolism,glycolysis/gluconeogenesis,pyruvate metabolism,etc.,were improved by increasing the abundance of related functional genes after *** conclusion,inoculating *** accelerated organic degradation by driving the cooperation between microbial network modules and enhancing microbial metabolism in the start-up phase of composting.

关键词： Microbial agent organic matter degradation Microbial interaction Food waste Low temperature composting

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Selective nickel-electrocatalyzed benzylic C-H oxygenation of functionalized alkyl arenes

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Chinese Chemical Letters 2024年第2期35卷 396-401页

作者： Shunyao Tang Siyi Wang Dongmei Zhang Xinxing Zhang Guang Yang Yanwei Wang Youai Qiu State Key Laboratory of Elemento-organic Chemistry Frontiers Science Center for New Organic MatterCollege of ChemistryNankai UniversityTianjin 300071China College of Chemistry Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education)Renewable Energy Conversion and Storage Center (RECAST)Frontiers Science Center for New Organic MatterNankai UniversityTianjin 300071China

Herein, a site-selective paired electrochemical C–H oxidation of functionalized alkyl arenes promoted by nickel catalyst is disclosed. A Ni(Ⅱ)-dioxygen species formed in situ efficiently enable the oxidation process under mild conditions with a broad substrate scope with excellent functional group compatibilities,such as free carboxylic acid, aldehyde, halogen(including aryl iodide), amide and amino acid. The use of the nickel catalyst in combination with water provides a safe, green and economical method for oxidation of a range of molecules varying in complexity and drug derivatives, demonstrating its potential application in organic synthesis and the pharmaceutical industry. Reaction outcomes and mechanistic studies revealed the key role of the in situ Ni(Ⅱ)-dioxygen species for the subsequent oxidation of C(sp^(3))–H bonds,and short-lived reactive intermediates(aryl radical cation) was rapidly captured by the combination of a bipolar ultramicroelectrode(BUME) with nano-electrospray ionization mass spectrometry.

关键词： Electrochemical C-H oxidation Functionalized alkyl arenes Paired nickel-electrocatalysis H_(2)O oxidation Ketones

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Azocalixarenes: a scaffold of universal excipients with high efficiency

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Science China Chemistry 2024年第5期67卷 1697-1706页

作者： Yu-Xin Yue Yi-Lin Lin Meng-Meng Chen Han-Wen Tian Rong Ma Ze-Han Wang Fang-Yuan Chen Yu-Chen Pan Dong-Sheng Guo College of Chemistry State Key Laboratory of Elemento-Organic ChemistryKey Laboratory of Functional Polymer Materials(Ministry of Education)Frontiers Science Center for New Organic MatterCollaborative Innovation Center of Chemical Science and Engineering(Tianjin)Nankai UniversityTianjin 300071China

Excipients are important components of pharmaceutical preparations that affect their quality, safety, and efficacy. Macrocyclic receptors are a family of supramolecular excipients with several advantages, including molecular-level protection, small sizes,fast kinetics of host-guest recognition, and modular construction. With the continuous advances in the medical field, personalized and precision medicine requires the development of excipients with low dosages, integrated modifying effects, universality,and controlled release. To meet these requirements, we have developed a new family of macrocyclic excipients based on calixarenes by integrating their covalent(broad chemical design space) and noncovalent(wide range of substrates) ***, azocalixarenes(Azo CAs) were designed, showing high binding affinities to a broad spectrum of active pharmaceutical ingredients(APIs), selectivity to interferents, and responsiveness to hypoxic microenvironments. Due to their highly efficient and controllable recognition, Azo CAs serve as low-dose excipients for 30 APIs. Molecular encapsulation by Azo CAs results in the integrated modification of the physicochemical properties of APIs, including solubility, stability, bioavailability,and biocompatibility. Moreover, Azo CAs can be reduced by azoreductases overexpressed in hypoxic microenvironments,leading to the controlled release of APIs. Collectively, Azo CA excipients have broad application prospects for a series of diseases such as enteritis, arthritis, stroke, cancer, bacterial infection and kidney injury, with diverse therapeutic modalities,including chemotherapy, photodynamic therapy, photothermal therapy, immunotherapy, boron neutron capture therapy, radiotherapy, fluorescence imaging, and their combinations.

关键词： supramolecular chemistry host-guest systems excipient calixarene molecular recognition

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Iridium-Catalyzed Asymmetric Hydrogenation of Dialkyl Imines

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CCS Chemistry 2024年第4期6卷 905-911页

作者： Zheng Wang Xin-Yi Yang Yue Xu Qi-Lin Zhou State Key Laboratory and Institute of Elemento-organic Chemistry College of ChemistryFrontiers Science Center for New Organic MatterNankai UniversityTianjin 300071

Asymmetric hydrogenation of dialkyl imines to chiral amines is difficult because the two alkyls of imines are so similar in spatial and electronic structure that chiral catalysts are difficult to distinguish between *** this study,we described an asymmetric hydrogenation of dialkyl imines by a chiral iridium catalyst containing spiro phosphine-amine-phosphine *** precisely adjusting the chiral pocket of catalyst,a highly efficient catalyst was *** this catalyst,a variety of dialkyl imines were hydrogenated to chiral amines with high yield and enantioselectivity.

关键词： spiro PNP ligand iridium catalyst enantioselective hydrogenation dialkyl imines chiral amines

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Low-density polyethylene microplastics partially alleviate the ecotoxicological effects induced by cadmium exposure on the earthworm Eisenia fetida

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Soil Ecology Letters 2024年第1期6卷 47-60页

作者： Song Zhang Yating Du Guangshen Shang Kejiao Hu Xing Wang College of Resources and Environmental Sciences China Agricultural UniversityBeijing 100193China Beijing Key Laboratory of Biodiversity and organic farming Beijing 100193China organic Cycle Research Institute(Suzhou) China Agricultural UniversitySuzhou 215100China Key Laboratory of Plant-Soil Interactions Ministry of EducationBeijing 100193China

LDPE had no effect on the mortality,growth,and reproduction of *** did not alter the mortality,growth,and reproduction of earth-worm caused by *** alleviated histopathological damage to earthworms caused by *** alleviated DNA damage in earthworm coelomocytes caused by *** did not affect the accumulation of Cd in ***(Cd)can accumulate in the food chain,with serious impacts on human health and ***(MPs)such as low-density polyethylene(LDPE)should be considered not only as a single pollutant but also as a carrier of other *** this study,we investigated the joint effects of 30%LDPE and 313 mg kg-1 Cd on mortality,growth,reproduction,microstructure,DNA damage,oxidative stress,and mRNA levels in the earthworm Eisenia *** found that 313 mg kg-1 Cd inhibited growth and reproduction and damaged the microstructures of the skin and ***,LDPE had no effect on the mortality,growth,or cocoon production of ***,it did not increase the mortality,growth,or inhibition of cocoon production caused by Cd and instead alleviated the DNA damage in coelomocytes caused by Cd ***,it did not alter the accumulation of Cd in the *** indicators can be used for toxicity safety assessment and soil ecological risk assessment of LDPE and Cd cooccurrence in soil.

关键词： microplastics Eisenia fetida DNA damage histopathological damage heavy metals

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Synergistic effects of chemical additives and mature compost on reducing H_2S emission during kitchen waste composting

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Journal of Environmental Sciences 2024年第5期139卷 84-92页

作者： Yongdi Liu Haihou Wang Hao Zhang Yueyue Tao Rui Chen Sheng Hang Xiaoyan Ding Meidi Cheng Guochun Ding Yuquan Wei Ting Xu Ji Li College of Resources and Environmental Science Beijing Key Laboratory of Biodiversity and Organic FarmingChina Agricultural UniversityBeijing 100193China organic Recycling Institute(Suzhou)of China Agricultural University Wuzhong DistrictSuzhou 215128China Suzhou Academy of Agricultural Sciences Institute of Agricultural Sciences in Taihu Lake DistrictSuzhou 215155China Technical Centre for Soil Agriculture and Rural Ecology and EnvironmentMinistry of Ecology and EnvironmentBeijing 100012China College of Chemistry and Chemical Engineering Yantai UniversityYantai 264005China

Additives could improve composting performance and reduce gaseous emission,but few studies have explored the synergistic of additives on H_(2)S emission and compost *** research aims to make an investigation about the effects of chemical additives and mature compost on H_(2)S emission and compost maturity of kitchen waste *** results showed that additives increased the germination index value and H_(2)S emission reduction over 15 days and the treatment with both chemical additives and mature compost achieved highest germination index value and H_(2)S emission reduction(85%).Except for the treatment with only chemical additives,the total sulfur content increased during the kitchen waste *** proportion of effective sulfur was higher with the addition of chemical additives,compared with other *** relative abundance of H_(2)S-formation bacterial(Desulfovibrio)was reduced and the relative abundance of bacterial(Pseudomonas and Paracoccus),which could convert sulfur-containing substances and H_(2)S to sulfate was improved with *** the composting process with both chemical additives and mature compost,the relative abundance of Desulfovibrio was lowest,while the relative abundance of Pseudomonas and Paracoccus was *** together,the chemical additives and mature compost achieved H_(2)S emission reduction by regulating the dynamics of microbial community.

关键词： Kitchen waste composting Sulfur conversion Chemical additives Mature compost Microbial community

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Molecular recognition of cyclophanes in water

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Chinese Chemical Letters 2024年第5期35卷 32-44页

作者： Fang-Yuan Chen Wen-Chao Geng Kang Cai Dong-Sheng Guo College of Chemistry State Key Laboratory of Elemento-Organic ChemistryKey Laboratory of Functional Polymer Materials(Ministry of Education)Frontiers Science Center for New Organic MatterCollaborative Innovation Center of Chemical Science and Engineering(Tianjin)Nankai UniversityTianjin 300071China College of Chemistry Nankai UniversityTianjin 300071China

Molecular recognition in water,the biological solvent,always receives significant research focus in supramolecular *** mechanisms of molecular recognition in water is key to comprehending biological processes at the molecular *** the past five decades,supramolecular chemists have developed a vast array of synthetic receptors with highly diverse structures and recognition *** them,cyclophanes represent an important family of macrocyclic receptors that have been extensively *** aromatic moieties in cyclophanes not only facilitate chemical modifications to impart water solubility but also enable forming hydrophobic cavities for guest inclusion in aqueous *** by Koga et al.,who reported the first inclusion complex of cyclophanes in water and solid state,numerous water-soluble cyclophanes,including derivatives of blue box,calixarenes,resorcinarenes,pillararenes,octopusarenes,biphenarenes,coronarenes,and naphthotubes,etc.,have been synthesized and subjected to investigation of the recognition capabilities in aqueous *** review provides an overview of cyclophane receptors designed to bind organic guests in *** categorize them into two classes based on the modifications made to their hydrophobic cavities:those with“exo-functionalized hydrophobic cavities”and those with“endo-functionalized hydrophobic cavities”.We introduce their distinctive features and discuss strategies to enhance recognition affinity and *** review aims to inspire the development of novel synthetic receptors with intriguing properties and foster practical applications of cyclophanes.

关键词： Biomimetic receptor Cyclophane Molecular recognition Hydrophobic effect High-affinity Macrocycles

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Advanced organic electrode materials for aqueous rechargeable batteries

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Science China Chemistry 2024年第1期67卷 137-164页

作者： Gaojing Yang Yaxun Zhu Qi Zhao Zhimeng Hao Yong Lu Qing Zhao Jun Chen Frontiers Science center for New organic Matter Key Laboratory of Advanced Energy Materials Chemistry(Ministry of Education)College of ChemistryNankai UniversityTianjin 300071China

organic electrode materials take advantages of potentially sustainable production and structural tunability compared with present commercial inorganic electrode ***,their applications in traditional rechargeable batteries with nonaqueous electrolytes suffer from the premature failure and safety *** comparison,aqueous rechargeable batteries based on organic electrode materials have received extensive attentions in recent years for low-cost and sustainable energy storage systems due to their inherent *** review aims to provide a comprehensive summary on the recent progress in advanced organic electrode materials for aqueous rechargeable *** start from the overview of working principles and general design strategies of organic electrode materials in aqueous rechargeable *** the research advances of organic electrode materials in various aqueous rechargeable batteries are highlighted in terms of charge carriers(monovalent ions,multivalent ions,and anions).We emphasized the characteristics of organic electrode materials in various charge ***,the critical challenges and future efforts of aqueous organic rechargeable batteries are *** organic electrode materials with better electronic conductivity and fast reaction kinetics are still needed to build advanced aqueous batteries for commercial applications.

关键词： organic electrode materials aqueous batteries organic batteries rechargeable batteries

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Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C_(6)F_(5))_(3)/chiral phosphoric acid

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Chinese Chemical Letters 2024年第5期35卷 135-140页

作者： Zhen Liu Zhi-Yuan Ren Chen Yang Xiangyi Shao Li Chen Xin Li State Key Laboratory of Elemento-organic Chemistry Frontiers Science Center for New Organic MatterCollege of ChemistryNankai UniversityTianjin 300071China Haihe Laboratory of Sustainable Chemical Transformations Tianjin 300192China Zhenhai High School of Zhejiang Ningbo 315299China

Catalytic enantioselective alkenylation is an efficient method to construct chiral alkene molecules,but the asymmetric alkenylation of simple alkenes catalyzed by metal-free catalysts remains an elusive ***,we reported an asymmetric alkenylation of benzoxazinones with diarylethylenes by utilizing a B(C_(6)F_(5))_(3)/chiral phosphoric acid catalyst.A broad of benzoxazinones and diarylethylenes with electron-withdrawing and electron-donating groups were tolerated(up to 95%yield and 97.5:2.5 e.r.)in the methodology under mild reaction ***,the synthetic utility was confirmed by the scaled-up reaction and transformations of the *** mechanism was preliminarily explored by control reactions,nonlinear effect experiment and DFT calculations.

关键词： Asymmetric alkenylation Simple alkenes Benzoxazinones B(C_(6)F_(5))_(3)/chiral phosphoric acid Theoretical calculations

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