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Rapid access to diverse indoles by addition/S_NAr with Grignard reagents and 2-fluorophenyl acetonitriles

Green Synthesis and Catalysis 2024年

作者： Gu, Yuanyun Feng, Yaxin Huang, Baotong Wang, Yan-En Yuan, Yaqi Xiong, Dan Hu, Yonghong Xu, Xiufang Walsh, Patrick J. Mao, Jianyou Technical Institute of Fluorochemistry (TIF) State Key Laboratory of Materials Oriented Chemical Engineering (MCE) School of Chemistry and Molecular Engineering Nanjing Tech University 30 South Puzhu Road Nanjing 211816 China Department of Chemistry Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education) College of Chemistry Nankai University Tianjin 300071 China College of Science Hebei Agricultural University Baoding 071000 China College of Food Science and Light Industry Nanjing Tech University Nanjing 211800 China Roy and Diana Vagelos Laboratories Department of Chemistry University of Pennsylvania Philadelphia 19104-6323 United States

Indoles are essential heterocycles in natural products, biological chemistry, and medicinal chemistry. Efficient approaches to their synthesis, therefore, remain in demand. Herein is reported a novel and scalable method to produce a wide variety of indoles by combining Grignard reagents and 2-fluorobenzyl cyanides (59 examples, 45%–95% yields). The Grignard reagent adds to the nitrile to give a metalated imine that undergoes S_NAr with unactivated C–F bonds. This strategy installs the R group of RMgX at the indole 2-position, and it is noteworthy that a diverse array of Grignard reagents (aryl, alkyl, vinyl, and cyclopropyl) provide the desired heterocyclic products. The resulting N-magnesiated indole can be in situ functionalized at the 3-position with alkyl halides or functionalized on the nitrogen with silyl chlorides. This method enables the synthesis of indoles with functional groups at each position of the indole backbone (C4–C7), providing handles for further functionalization. © 2024 Fudan University

关键词： 2-Aryl indoles 2-Fluorobenzyl cyanides Grignard reagents Indomethacin SNAr

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The effect of ligands on the size distribution of copper nanoclusters: insights from molecular dynamics simulations

arXiv

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arXiv 2024年

作者： Elishav, Oren Blumer, Ofir Vanderlick, T. Kyle Hirshberg, Barak Department of Chemical and Environmental Engineering Yale University New HavenCT06520 United States School of Chemistry Tel Aviv University Tel Aviv6997801 Israel The Center for Computational Molecular and Materials Science Tel Aviv University Tel Aviv6997801 Israel The Ratner Center for Single Molecule Science Tel Aviv University Tel Aviv6997801 Israel The Center for Physics and Chemistry of Living Systems Tel Aviv University Tel Aviv6997801 Israel

Controlling the size distribution in the nucleation of copper particles is crucial for achieving nanocrystals with desired physical and chemical properties. However, their synthesis involves a complex system of solvents, ligands, and copper precursors with intertwining effects on the size of the nanoclusters. We combine molecular dynamics simulations and DFT calculations to provide insight into the nucleation mechanism in the presence of a triphenylphosphite ligand. We identify the crucial role of the strength of the metal-phosphine bond in inhibiting the cluster’s growth. We demonstrate computationally several practical routes to fine-tune the bond strength by modifying the side groups of the additive. Our work provides molecular insight into the complex nucleation process of protected copper nanocrystals, which can assist in controlling their size distribution and, eventually, their morphology. Copyright © 2024, The Authors. All rights reserved.

关键词： Ligands

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molecular interaction volume model of mixing enthalpy for molten salt system: An integrated calorimetry-model case study of LaCl3-(LiCl-KCl)

arXiv

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arXiv 2024年

作者： Goncharov, Vitaliy G. Smith, William Li, Jiahong Eakin, Jeffrey A. Reinhart, Erik D. Boncella, James Gibson, Luke D. Bryantsev, Vyacheslav S. Gong, Rushi Shang, Shun-Li Liu, Zi-Kui Xu, Hongwu Clark, Aurora Guo, Xiaofeng Department of Chemistry Washington State University PullmanWA99164 United States Materials Science and Engineering Program Washington State University PullmanWA99164 United States Computational Sciences and Engineering Division Oak Ridge National Laboratory P.O. Box 2008 Oak RidgeTN37831 United States Chemical Science Division Oak Ridge National Laboratory P.O. Box 2008 Oak RidgeTN37831 United States Department of Materials Science and Engineering Pennsylvania State University University ParkPA16802 United States Earth and Environmental Sciences Division Los Alamos National Laboratory Los Alamos New MexicoNM87545 United States Arizona State University TempeAZ United States Department of Chemistry The University of Utah Salt Lake CityUT84112 United States

Calorimetric determination of enthalpies of mixing (ΔHmix) of multicomponent molten salts often employs empirical models that lack parameters with clear physical interpretation (e.g., coordination numbers, molar volumes, and pair potentials). Although such physics informed models are not always needed, a thermodynamic understanding of the relationships between excess energies of mixing and local to intermediate solvation structures is particularly important for pyrochemical separation, as is the case for lanthanides (Ln), which are common neutron poisons and critical industrial elements found in spent nuclear fuels. Here we implement the molecular interaction volume model (MIVM) to synthesize information from experimentally measured ΔHmix (using high temperature melt drop calorimetry) and the distribution of solvation structures from ab initio molecular dynamics (AIMD) simulations. This was demonstrated by a case study of molten salt system consisted of LaCl3 mixing with a eutectic LiCl-KCl (58mol% - 42mol%) at 873 K and 1133 K. The parameters modelled from MIVM were used to extrapolate excess Gibbs energy (ΔGmix), and compositional dependence of La3+ activity in the LaCl3-(LiCl-KCl) system. In contrast, by AIMD or polarizable ion model (PIM) simulations, a significant deviation regarding the predicted ΔHmix was seen if computed directly from the molecular dynamic trajectories. The integrated experimental and simulation data within the MIVM formalism are generalizable to a wide variety of molten salts and demonstrate a significant improvement over currently employed methods to study molten salts for nuclear and separations sciences. Copyright © 2024, The Authors. All rights reserved.

关键词： Enthalpy

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Enhancing the Electron Pair Approximation with Measurements on Trapped Ion Quantum Computers

arXiv

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arXiv 2023年

作者： Zhao, Luning Goings, Joshua Wang, Qingfeng Shin, Kyujin Kyoung, Woomin Noh, Seunghyo Rhee, Young Min Kim, Kyungmin IonQ Inc College ParkMD20740 United States Chemical Physics Program Institute for Physical Science and Technology University of Maryland College ParkMD20742 United States Materials Research & Engineering Center CTO Division Hyundai Motor Company Uiwang16082 Korea Republic of Department of Chemistry KAIST Daejeon34141 Korea Republic of

The electron pair approximation offers a resource efficient variational quantum eigensolver (VQE) approach for quantum chemistry simulations on quantum computers. With the number of entangling gates scaling quadratically with system size and a constant energy measurement overhead, the orbital optimized unitary pair coupled cluster double (oo-upCCD) ansatz strikes a balance between accuracy and efficiency on today’s quantum computers. However, the electron pair approximation makes the method incapable of producing quantitatively accurate energy predictions. In order to improve the accuracy without increasing the circuit depth, we explore the idea of reduced density matrix (RDM) based second order perturbation theory (PT2) as an energetic correction to electron pair approximation. The new approach takes into account of the broken-pair energy contribution that is missing in pair-correlated electron simulations, while maintaining the computational advantages of oo-upCCD ansatz. In dissociations of N2, Li2O, and chemical reactions such as the unimolecular decomposition of CH2OH+ and the SN2 reaction of CH3I + Br−, the method significantly improves the accuracy of energy prediction. On two generations of the IonQ’s trapped ion quantum computers, Aria and Forte, we find that unlike the VQE energy, the PT2 energy correction is highly noise-resilient. By applying a simple error mitigation approach based on post-selection solely on the VQE energies, the predicted VQE-PT2 energy differences between reactants, transition state, and products are in excellent agreement with noise-free simulators. © 2023, CC BY.

关键词： Trapped ions

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Cation and anion topotactic transformations in cobaltite thin films leading to Ruddlesden-Popper phases

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Physical Review materials 2021年第6期5卷 064416-064416页

作者： I-Ting Chiu Min-Han Lee Shaobo Cheng Shenli Zhang Larry Heki Zhen Zhang Yahya Mohtashami Pavel N. Lapa Mingzhen Feng Padraic Shafer Alpha T. N'Diaye Apurva Mehta Jon A. Schuller Giulia Galli Shriram Ramanathan Yimei Zhu Ivan K. Schuller Yayoi Takamura Department of Chemical Engineering University of California Davis Davis California 95616 USA Materials Science and Engineering Program University of California San Diego La Jolla California 92093 USA Department of Physics and Center for Advanced Nanoscience University of California San Diego La Jolla California 92093 USA Condensed Matter Physics and Materials Science Division Brookhaven National Laboratory Upton New York 11973 USA Pritzker School of Molecular Engineering The University of Chicago Chicago Illinois 60637 USA Materials Department University of California Santa Barbara Santa Barbara California 93106 USA School of Materials Engineering Purdue University West Lafayette Indiana 47907 USA Department of Electrical and Computer Engineering University of California Santa Barbara Santa Barbara California 93106 USA Department of Materials Science and Engineering University of California Davis Davis California 95616 USA Advanced Light Source Lawrence Berkeley National Laboratory Berkeley California 94720 USA Stanford Synchrotron Radiation Lightsource SLAC National Accelerator Laboratory Menlo Park California 94025 USA Materials Science Division and Center for Molecular Engineering Argonne National Laboratory Lemont Illinois 60439 USA

Topotactic transformations involve structural changes between related crystal structures due to a loss or gain of material while retaining a crystallographic relationship. The perovskite oxide La0.7Sr0.3CoO3 (LSCO) is an ideal system for investigating phase transformations due to its high oxygen vacancy conductivity, relatively low oxygen vacancy formation energy, and strong coupling of the magnetic and electronic properties to the oxygen stoichiometry. While the transition between cobaltite perovskite and brownmillerite (BM) phases has been widely reported, further reduction beyond the BM phase lacks systematic studies. In this paper, we study the evolution of the physical properties of LSCO thin films upon exposure to highly reducing environments. We observe the rarely reported crystalline Ruddlesden-Popper phase, which involves the loss of both oxygen anions and cobalt cations upon annealing where the cobalt is found as isolated Co ions or Co nanoparticles. First-principles calculations confirm that the concurrent loss of oxygen and cobalt ions is thermodynamically possible through an intermediary BM phase. The strong correlation of the magnetic and electronic properties to the crystal structure highlights the potential of utilizing ion migration as a basis for emerging applications such as neuromorphic computing.

关键词： Crystal defects Electrical conductivity Electronic structure of atoms & molecules Epitaxial strain First-principles calculations Magnetism Phase transitions

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A bioinspired high-modulus mineral hydrogel binder for improving the cycling stability of microsized silicon particle-based lithium-ion battery

引用

Nano Research 2019年第5期12卷 1121-1127页

作者： Meng Tian Xiao Chen Shengtong Sun Dong Yang Peiyi Wu State Key Laboratory of Molecular Engineering of Polymers Department of Macromolecular ScienceLaboratory for Advanced MaterialsFudan UniversityShanghai 200433China State Key Laboratory for Modification of Chemical Fibers and Polymer Materials College of ChemistryChemical Engineering and BiotechnologyCenter for Advanced Low-dimension MaterialsDonghua UniversityShanghai 201620China

Silicon with high specific capacity is deemed an ideal anode material for lithium ion batteries,which,however suffers from low cycling life due to its dramatic volume ***-soluble polymer binders recently gain increasing attention by providing an eco-friendly and low-cost way in improving the cycling stability of Si-based ***,a novel bioinspired supramolecular mineral hydrogel binder consisting of polyacrylic acid (PAA) physically crosslinked with amorphous calcium carbonate (ACC) nanoparticles is designed for high-performance anodes made from low-cost microsized Si *** to its organic-inorganic hydrophilic nature,ACC-PAA hybrid binder exhibits the reported highest modulus (~22 GPa) for polymer binders in electrolyte,even higher than lithiated Si species (Li15Si4,~12 GPa).Together with its excellent adhesion and electrochemical stability,ACC-PAA binder can effectively suppress the pulverization of Si particles and maintain the mechanical integrity of electrodes during ***,even with a low binder content,the anode still shows an initial discharge capacity of 2,973 mAh·g^-1 and Coulombic efficiency of 81.5%,and retains 75% at a current density of 600 mA·g^-1 after 100 *** present organic-inorganic hybrid mineral binder may open a new approach for designing more effective polymer binders for Si-based lithium-ion batteries.

关键词： polymer binder mineral hydrogel microsized silicon particle lithium-ion battery

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Study of Ultrafast Photocarrier Dynamics in Polycrystalline Cdte Films Under Low Illumination

SSRN

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SSRN 2022年

作者： Hu, Gang Li, Bo-Han Li, Huang Cao, Hongyuan Ren, Zefeng Zhao, Dewei Li, Wei Zhang, Jingquan Institute of Solar Energy Materials and Devices College of Materials Science and Engineering Sichuan University No. 24 South Section 1 Yihuan Road Chengdu610065 China Engineering Research Center of Alternative Energy Materials & Devices Ministry of Education China State Key Laboratory of Molecular Reaction Dynamics and Dynamics Research Center for Energy and Environmental Materials Dalian Institute of Chemical Physics Chinese Academy of Sciences Dalian116023 China Hefei National Laboratory for Physical Sciences at the Microscale Department of Chemical Physics University of Science and Technology of China Hefei230026 China

The photocarrier dynamics in polycrystalline CdTe films is closely related to device performance. However, the test results obtained at different illumination intensity may be different, and even significantly deviate from the ones in practical application environments. Here, the photocarrier dynamics in polycrystalline CdTe films deposited by thermal evaporation was studied through time-resolved transient absorption (TA) under different pump intensity. It was found that the behaviors of photocarriers in CdTe films is strongly dependent on the pump intensity. Under low pump intensity that close to operating environments, the lifetime of free carriers becomes extremely short compared to high intensity, which is interpreted as a rapid trapping of free carriers by defects. For low pump intensity, numerical fitting by a physical model with one defect level shows that the free carriers in band-edge can be rapidly trapped by defects within tens of picoseconds and then slowly recover to the ground state within several nanoseconds. Our results renewed the knowledge of photocarrier dynamics in polycrystalline CdTe films and develops a new characterization method for the preparation of high-quality films. © 2022, The Authors. All rights reserved.

关键词： Cadmium telluride

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Emerging contaminants:A One Health perspective

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The Innovation 2024年第4期5卷 140-170,139页

作者： Fang Wang Leilei Xiang Kelvin Sze-Yin Leung Martin Elsner Ying Zhang Yuming Guo Bo Pan Hongwen Sun Taicheng An Guangguo Ying Bryan WBrooks Deyi Hou Damian EHelbling Jianqiang Sun Hao Qiu Timothy MVogel Wei Zhang Yanzheng Gao Myrna JSimpson Yi Luo Scott XChang Guanyong Su Bryan MWong Tzung-May Fu Dong Zhu Karl JJobst Chengjun Ge Frederic Coulon Jean Damascene Harindintwali Xiankui Zeng Haijun Wang Yuhao Fu Zhong Wei Rainer Lohmann Changer Chen Yang Song Concepcion Sanchez-Cid Yu Wang Ali El-Naggar Yiming Yao Yanran Huang Japhet Cheuk-Fung Law Chenggang Gu Huizhong Shen Yanpeng Gao Chao Qin Hao Li Tong Zhang Natàlia Corcoll Min Liu Daniel SAlessi Hui Li Kristian KBrandt Yolanda Pico Cheng Gu Jianhua Guo Jianqiang Su Philippe Corvini Mao Ye Teresa Rocha-Santos Huan He Yi Yang Meiping Tong Weina Zhang Fidèle Suanon Ferdi Brahushi Zhenyu Wang Syed AHashsham Marko Virta Qingbin Yuan Gaofei Jiang Louis A.Tremblay Qingwei Bu Jichun Wu Willie Peijnenburg Edward Topp Xinde Cao Xin Jiang Minghui Zheng Taolin Zhang Yongming Luo Lizhong Zhu Xiangdong Li DamiàBarceló Jianmin Chen Baoshan Xing Wulf Amelung Zongwei Cai Ravi Naidu Qirong Shen Janusz Pawliszyn Yong-guan Zhu Andreas Schaeffer Matthias C.Rillig Fengchang Wu Gang Yu James M.Tiedje State Key Laboratory of Soil and Sustainable Agriculture Institute of Soil ScienceChinese Academy of SciencesNanjing 210008China University of Chinese Academy of Sciences Beijing 100049China Department of Chemistry Hong Kong Baptist UniversityHong KongChina HKBU Institute of Research and Continuing Education Shenzhen Virtual University ParkShenzhenChina Technical University of Munich TUM School of Natural SciencesInstitute of Hydrochemistry85748 GarchingGermany School of Resources&Environment Northeast Agricultural UniversityHarbin 150030China Climate Air Quality Research UnitSchool of Public Health and Preventive MedicineMonash UniversityMelbourneVICAustralia Faculty of Environmental Science&Engineering Kunming University of Science&TechnologyKunming 650500China Ministry of Education Key Laboratory of Pollution Processes and Environmental Criteria College of Environmental Science and EngineeringNankai UniversityTianjin 300350China Guangdong Key Laboratory of Environmental Catalysis and Health Risk Control School of Environmental Science and EngineeringInstitute of Environmental Health and Pollution ControlGuangdong University of TechnologyGuangzhou 510006China Ministry of Education Key Laboratory of Environmental Theoretical Chemistry South China Normal UniversityGuangzhouGuangdong 510006China Department of Environmental Science Baylor UniversityWacoTXUSA Center for Reservoir and Aquatic Systems Research(CRASR) Baylor UniversityWacoTXUSA School of Environment Tsinghua UniversityBeijing 100084China School of Civil and Environmental Engineering Cornell UniversityIthacaNY 14853USA Key Laboratory of Microbial Technology for Industrial Pollution Control of Zhejiang Province Zhejiang University of TechnologyHangzhou 310014China School of Environmental Science and Engineering Shanghai Jiao Tong UniversityShanghai 200240China Laboratoire d’Ecologie Microbienne Universite Claude Bernard Lyon 1UMR CNRS 5557UMR INRAE 1418VetAgro Sup69622 VilleurbanneFrance Department of Pla

Environmental pollution is escalating due to rapid global development that often prioritizes human needs over planetary *** global efforts to mitigate legacy pollutants,the continuous introduction of new substances remains a major threat to both people and the *** response,global initiatives are focusing on risk assessment and regulation of emerging contaminants,as demonstrated by the ongoing efforts to establish the UN’s Intergovernmental science-Policy Panel on chemicals,Waste,and Pollution *** review identifies the sources and impacts of emerging contaminants on planetary health,emphasizing the importance of adopting a One Health *** for monitoring and addressing these pollutants are discussed,underscoring the need for robust and socially equitable environmental policies at both regional and international *** actions are needed to transition toward sustainable pollution management practices to safeguard our planet for future generations.

关键词： pollution planet contaminants

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Deciphering the Oxygen Absorption Pre-edge: A Caveat on its Application for Probing Oxygen Redox Reactions in Batteries

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Energy & Environmental materials 2021年第2期4卷 246-254页

作者： Subhayan Roychoudhury Ruimin Qiao Zengqing Zhuo Qinghao Li Yingchun Lyu Jung-Hyun Kim Jun Liu Eungje Lee Bryant J.Polzin Jinghua Guo Shishen Yan Yongsheng Hu Hong Li David Prendergast Wanli Yang Advanced Light Source Lawrence Berkeley National Laboratory1 Cyclotron RoadBerkeley CA 94720USA School of Advanced Materials Shenzhen Graduate SchoolPeking UniversityShenzhen 518055China School of Physics National Key Laboratory of Crystal MaterialsShandong UniversityJinan 250100China Beijing National Laboratory for Condensed Matter Physics Institute of PhysicsChinese Academy of SciencesBeijing 100190China Mechanical and Aerospace Engineering The Ohio State UniversityColumbus OH 43210USA R&D department 2M LLC193 Thompson DrHockessin DE 19707USA Chemical Science and Engineering Division Argonne National LaboratoryArgonne IL 60439 USA The Molecular Foundry Lawrence Berkeley National Laboratory1 Cyclotron Road Berkeley CA 94720 USA

The pre-edges of oxygen-K X-ray absorption spectra have been ubiquitous in transition metal(TM)oxide studies in various fields,especially on the fervent topic of oxygen redox states in battery ***,critical debates remain on the use of the O-K pre-edge variations upon electrochemical cycling as evidences of oxygen redox reactions,which has been a popular practice in the battery *** study presents an investigation of the O-K pre-edge of 55 oxides covering all 3d TMs with different elements,structures,and electrochemical states through combined experimental and theoretical *** is shown unambiguously that the O-K pre-edge variation in battery cathodes is dominated by changing TM-d ***,the pre-edge enables a unique opportunity to project the lowest unoccupied TM-d states onto one common energy window,leading to a summary map of the relative energy positions of the low-lying TM states,with higher TM oxidation states at lower energies,corresponding to higher electrochemical *** results naturally clarify some unusual redox reactions,such as Cr^(3+/6+).This work provides a critical clarification on O-K pre-edge interpretation and more importantly a benchmark database of O-K pre-edge for characterizing redox reactions in batteries and other energy materials.

关键词： battery oxygen redox x-ray absorption spectroscopy cathode material redox reaction

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Photothermal conversion of CO 2 to fuel with nickel-based catalysts: A review

Environmental Functional Materials

引用

Environmental Functional materials 2022年第2期1卷 204-217页

作者： Yiling He Yi Zhou Ji Feng Mingyang Xing State Environmental Protection Key Lab of Environmental Risk Assessment and Control on Chemical Processes. School of Resources & Environmental Engineering East China University of Science and Technology Shanghai 200237 China Department of Mechanical Engineering University of California Riverside Riverside CA 92521 USA Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center Frontiers Science Center for Materiobiology and Dynamic Chemistry Institute of Fine Chemicals School of Chemistry & Molecular Engineering East China University of Science & Technology 130 Meilong Road Shanghai 200237 China

Converting CO 2 to fuel is a promising strategy to mitigate the greenhouse effect and achieve ‘carbon neutrality’. Photothermal catalysis has been widely used for CO 2 reduction because it effectively reduces the apparent activation energy of the reaction and provides milder catalytic conditions as well as higher catalytic efficiency than conventional catalytic methods. In this review, the basic principles of photothermal catalytic CO 2 reduction and the factors used to evaluate photothermal catalytic conversion efficiency are introduced. Then, the common types of Ni-based catalysts and their design strategies are summarized and discussed. Among these catalysts, metal oxides have been extensively studied and developed. Accordingly, they currently achieve product yields up to the mmol/(g·h) level. Strategies such as elemental doping and morphology control are often adopted for the modification of photothermal catalysts as a means to improve catalytic performance. Finally, future trends in the field of photothermal catalytic CO 2 reduction are proposed, including mechanistic studies, practical applications, and coupling with other carbon-neutral technologies.

关键词： CO 2 reduction Photothermal catalysis: Ni-based catalyst Selectivity Metal complex

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