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Lighting up nonbenzenoid acepleiadylene with ultra-narrowband emission through aromaticity modulation

science China Chemistry 2023年第12期66卷 3506-3510页

作者： Pengcai Liu Xiao-Yu Tang Cheng-Zhuo Du Rui Xue Xing-Yu Chen Jiawen Cao Xiao-Ye Wang State Key Laboratory of Elemento-organic Chemistry Frontiers Science Center for New Organic MatterCollege of ChemistryNankai UniversityTianjin 300071China

Nonbenzenoid polycyclic arenes have attracted great attention because of their unique topological structures and appealing properties;however,they are generally considered as poor luminescent materials due to the ring puckering behavior of the nonhexagons.Acepleiadylene(APD),a nonbenzenoid isomer of pyrene,has been demonstrated as an excellent building block for optoelectronic applications,but its poor photoluminescence quantum yield(PLQY)has hampered its application in luminescent materials.Considering that the ring puckering character can be suppressed by increasing the rigidity of the nonhexagon rings,herein,we propose a novel strategy for enhancing the aromaticity of the nonhexagons to improve the PLQYs of APD derivatives.Electron-withdrawing cyano groups are introduced on the five-membered ring of APD to enhance the chargeseparated character and thus the aromaticity of the nonhexagons,endowing the cyano-substituted APDs(CNAPD and 2CNAPD)with better rigidity.Therefore,the cyano substitution successfully suppresses the nonradiative energy dissipation caused by the ring puckering,improving the PLQY from 2.4%for APD to 14%for CNAPD,and to 63%for 2CNAPD.In addition,the enhanced rigidity also suppresses the vibration sideband of the photoluminescence spectra,leading to an ultra-narrowband emission from 2CNAPD with a full-width at half-maximum(FWHM)of 13 nm(47 me V),which is a new record in organic molecules.These results demonstrate that APD derivatives have great potential in highly efficient luminescent materials with high color purity via the aromaticity regulation strategy,which provides a novel concept for designing nonbenzenoid luminescent materials.

关键词： nonbenzenoid arenes luminescence narrowband emission acepleiadylene

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Iron-Catalyzed Alkenylzincation of Internal Alkynes

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Chinese Journal of Chemistry 2023年第24期41卷 3547-3552页

作者： Wei-Na Wang Qiang Huang Ye Jin Qi-Lin Zhou Shou-Fei Zhu Frontiers Science Center for New Organic Matter State Key Laboratory and Institute of Elemento-Organic ChemistryCollege of ChemistryNankai UniversityTianjin300071 China

The alkenylzincation of internal alkynes is an effective method for the synthesis of multi-substituted conjugated dienes;however,the current catalytic systems for this reaction are limited in terms of substrate scope and selectivity control,which restricts its practical applications.Herein,we report the first iron-catalyzed alkenylzincation of internal alkynes,which features mild conditions,simple operation,broad substrate scope (including aryl/alkyl,diaryl,and dialkyl acetylenes),excellent functional group tolerance (tolerating highly active functional groups such as ester,methylthio,amide,sulfonyl,cyano,etc.),and high activity (with a turnover number of up to 11500,the highest record for carbometallation reactions).Notably,the catalytic system described in this article also realized the highly selective vinylzincation of unfunctionalized internal alkynes as well as the alkenylzincation of unsymmetrical diarylacetylenes and dialkyl acetylenes,which have not been achieved with other catalytic systems reported in the literatures.The current study provides a highly selective access to synthetically important multi-substituted conjugated dienes.

关键词： Iron catalysis Internal alkynes Alkenylzincation Conjugated dienes

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A silylene-stabilized distannavinylidene with a highly labile substituent

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science China Chemistry 2023年第12期66卷 3555-3561页

作者： Zihao Qiao Ming Chen Zhenbo Mo State Key Laboratory and Institute of Elemento-organic Chemistry Frontiers Science Center for New Organic MatterCollege of ChemistryNankai UniversityTianjin 300071China

Vinylidene and its heavier analogues are fundamentally important in synthetic chemistry,but their stabilization and structural characterization remains extremely challenging.Herein we describe that the reduction of an NHSi-stabilized stannyl-stannylene(2)with one molar equivalent of[(^(Mes)Nacnac)Mg]_(2)affords an NHSi-stabilized distannavinylidene(3).Single-crystal X-ray crystallography and density functional theory(DFT)calculations show that compound 3 features a pronounced Sn=Sn double bond and one lone pair of electrons at the two-coordinate Sn atom.Most strikingly,3 undergoes an interconversion with distannyne(4)upon the addition and removal of one molar equivalent of N-heterocyclic carbene.Compound 3 readily reacts with Ph_(2)C=C=O,Ad C≡P and(Al Cp^(*))_(4)to give the structurally interesting stannacycles(5,6)and an aluminyl distannyne(7),demonstrating its unique reactivity derived from the high substituent lability.

关键词： distannavinylidene silylenes stannacycles distannyne carboranes

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Recent Advances in Boron-Containing Acenes:Synthesis,Properties,and Optoelectronic Applications

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Chinese Journal of Chemistry 2023年第11期41卷 1355-1373页

作者： Yongkang Guo Cheng Chen Xiao-Ye Wang State Key Laboratory of Elemento-organic Chemistry Frontiers Science Center for New Organic MatterCollege of ChemistryNankai UniversityTianjin300071 China

Acenes with linearly fused benzene rings have attracted much attention due to their intriguing optical and electronic properties.Nevertheless,the poor ambient stability of longer acenes has hampered the investigation of their physicochemical properties and potential applications.The incorporation of main group elements into the acene backbones provides a viable strategy to enhance the stability,and meanwhile,generates a new family of heteroatom-doped acenes(namely heteroacenes)with modified properties and functions.In particular,boron-containing acenes represent an attractive class of heteroacenes owing to the existence of vacant p orbital of boron,which endows theπ-conjugated systems with appealing features,such as Lewis acidity,electron-accepting capability,stimuli-responsivity,and adjustable photophysical properties.During the past decade,significant progress has been achieved in the synthesis and applications of boron-containing acenes,but a focused review on this topic has been elusive.Here,we summarize the recent advances in the studies on boron-containing acenes,covering their synthesis,intriguing properties,and various applications in electroluminescence and electronic devices,as well as in biosensors,etc.We hope that this timely review will stimulate new research interest in this unique family of materials and promote their optoelectronic applications.

关键词： Acenes Boron Heteroacenes Luminophores Multi-color emission Light-emitting devices organic optoelectronics organicsemiconductors

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

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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 State Key Laboratory and Institute of Elemento-organic Chemistry Frontiers Science Center for New Organic Matter 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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Electro-reductive C-H cyanoalkylation of quinoxalin-2(1H)-ones

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Chinese Chemical Letters 2022年第8期33卷 4057-4060页

作者： Ling Ding Kaikai Niu Yuxiu Liu Qingmin Wang State Key Laboratory of Elemento-organic Chemistry Research Institute of Elemento-Organic ChemistryCollege of ChemistryFrontiers Science Center for New Organic MatterNankai UniversityTianjin 300071China

Herein,we report a practical electro-reductive protocol for the direct C-H cyanoalkylation of quinoxalin-2(1 H)-ones via iminyl radical-mediated ring opening.These mild reactions proceed under metal-,reductant-,and re... 详细信息

关键词： Electro-reductive C-H cyanoalkylation Reductant-free Quinoxalin-2(1H)-ones Ring-opening

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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 materials.However,their applications in traditional rechargeable batteries with nonaqueous electrolytes suffer from the premature failure and safety concerns.In 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 safety.This review aims to provide a comprehensive summary on the recent progress in advanced organic electrode materials for aqueous rechargeable batteries.We start from the overview of working principles and general design strategies of organic electrode materials in aqueous rechargeable batteries.Then 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 carriers.Finally,the critical challenges and future efforts of aqueous organic rechargeable batteries are discussed.More 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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Synthesis of a class of oxocarbons(C_(4)O_(4),C_(5)O_(5))and the application as high-capacity cathode materials for lithium-ion batteries

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science China Chemistry 2023年第10期66卷 2780-2784页

作者： Xuesen Hou Yong Lu Youxuan Ni Dongmei Zhang 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

Oxocarbons(C_(n)O_(n),n=3,4,5,6,...)are a series of compounds that are only composed of carbonyl groups.The highly electrophilic carbon atoms in C_(n)O_(n)make their poor stability toward H_(2)O,and thus the synthesis of C_(n)O_(n)is very challenging.Here an oxidation-dehydration method is developed to successfully synthesize C_(4)O_(4)and C_(5)O_(5).The combination of nuclear magnetic resonance(^(13)C NMR,^(1)H NMR),mass spectra,and infrared spectra unambiguously proves the exact chemical structure of C_(4)O_(4)and C_(5)O_(5).When used as a cathode material in lithium-ion batteries(LIBs),C_(5)O_(5)could deliver a high discharge capacity of 698m Ah g-1(corresponding to an energy density of 1,256 Wh kg-1C_(5)O_(5)).Furthermore,ex-situ infrared spectra and density functional theory(DFT)calculations demonstrate that the carbonyl groups are redox active sites during discharge and charge processes.This work paves the way to achieve the synthesis and battery application of oxocarbons.

关键词： oxocarbons C_(4)O_(4) C_(5)O_(5) organic cathode lithium-ion batteries

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Bimetallic anchoring catalysis for C–H and C–C activation

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science China Chemistry 2021年第11期64卷 1923-1937页

作者： Jiang-Fei Li Yu-Xin Luan Mengchun Ye State Key Laboratory and Institute of Elemento-organic Chemistry College of ChemistryFrontiers Science Center for New Organic MatterNankai UniversityTianjin300071China

Following the age of directing group,anchoring catalysis starts coming to the center of the stage.Different from the directinggroup strategy that needs a preinstalled directing group in substrates,anchoring catalysis relies on a reversible interaction between a substrate and a catalyst,which then directs metal to activate inert chemical bonds.Such reversible directing effect not only generates good site-and stereo-selectivity as traditional directing groups do but also eliminates the requirement of stoichiometric amounts of directing groups.Among variously reported anchoring catalysis,coordinative bimetallic anchoring catalysis in general displays superior reactivity than others because coordinative bonding not only affords strong interaction of catalysts with substrates but also displays good compatibility with substrates and reaction conditions.In recent years,big progress has been achieved for coordinative bimetallic anchoring catalysis.This review gave a detailed summary of this field,including catalyst development,catalyst types,reaction types and reaction mechanisms.

关键词： C–H activation C–C activation bimetallic catalysis enantioselective anchoring catalysis

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