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Asymmetric side-chain engineering of organic semiconductor for ultrasensitive gas sensing

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Chinese Chemical Letters 2024年第3期35卷 428-433页

作者： Xiaoying Ma Xiaojuan Dai Lanyi Xiang Jiajun Chang Danfeng Zhi Haozhen Zhao Zhenjie Ni Ye Zou Xike Gao Fengjiao Zhang School of Chemical Sciences University of Chinese Academy of SciencesBeijing 100049China laboratory of organic Solids Institute of ChemistryChinese Academy of SciencesBeijing 100190China Key laboratory of Synthetic and Self-Assembly Chemistry for organic Functional Molecules Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China Binzhou Institute of Technology Binzhou 256606China

Molecular structure of organic semiconductor plays a critical role in determining the performance and functionality of organic electronic devices,by optimizing the electrical,optical and physicochemical *** alkyl chains are fundamental units in tailering the solubility and assemblability,among which the asymmetric properties have been reported as key element for controlling the packing motifs and intrinsic charge ***,we expanded the scope of molecular asymmetry dependent sensing features based on a new series of naphthalene diimides(NDI)-based derivatives substituted with a same branching alkyl chain but various linear-shaped alkyl chains(Cn-).A clear molecular stacking change,from head-to-head bilayer to head-to-tail monolayer packing model,is observed based on the features of anisotropic molecular interactions with the change in the chain *** importantly,a unique LUMO level shift of 0.17 eV is validated for NDI-PhC4,providing a record sensitivity up to 150%to 0.01 ppb ammonia,due to the desired molecular reactivity and device amplification *** results indicate that asymmetric side-chain engineering opens a route for breath healthcare.

关键词： organic thin film transistor Asymmetric side chain Gas sensing Molecular stacking Energy level manipulating

Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis

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Chinese Chemical Letters 2024年第4期35卷 106-123页

作者： Wei Zhou Xi Chen Lin Lu Xian-Rong Song Mu-Jia Luo Qiang Xiao Key laboratory of organic Chemistry of Jiangxi Province Jiangxi Science&Technology Normal UniversityNanchang 330013China

Indole-derived radical cations, open-shell reactive species, display distinctive dual reactivity due to the carbon-centered radical and more electrophilic carbocation, which frequently appear in a variety of single electron oxidation reactions for synthesizing structurally diverse functionalized indoles and indolines. Electrocatalysis is considered as a synthetically attractive and environmentally friendly alternative for driving the single electron oxidation of indoles. Remarkable achievements in electrocatalytic indolederived radical cation-mediated indole functionalization have been realized so far. This review comprehensively summarizes the recent progresses in the applications of electrocatalytic indole radical cations,including C(sp~2)–H functionalization, dearomative 2,3-difunctionalization, and ring-opening reaction, emphasizing the vital single electron oxidation steps of indoles, the substrates scope and limitations, and the reaction mechanisms.

关键词： Electrocatalysis Indole radical cation C-H functionalizatin Dearomative 2 3-difunctionalization

High-performance ultrathin Ag electrodes by chemical bond anchoring Ag atoms for stretchable organic light-emitting devices

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Nano Research 2024年第8期17卷 7614-7620页

作者： Yue Qin Yawei Wang Xinxin Wang Yaqi Zhang Jiahao Xu Kanchi Dong Yuehua Chen Wenyong Lai Xinwen Zhang State Key laboratory of organic Electronics and Information Displays and Institute of Advanced Materials(IAM) Nanjing University of Posts and TelecommunicationsNanjing 210023China

The progress of stretchable organic light-emitting devices(OLEDs)has brought about new possibilities for highly functional wearable ***,the efficiency and durability of stretchable OLEDs have been limited by the performance of stretchable transparent ***,we proposed an interface engineering strategy that involves anchoring the growth of silver(Ag)atoms with amine-enriched biomaterials for high-quality stretchable transparent *** strong interactions between the Ag atom and the amine group enable the uniform Ag electrodes at an ultralow thickness of 7 nm,and provide remarkable mechanical flexibility and strain endurance to the Ag *** distinct effects of different amino acids were investigated,and a deep understanding of their unique contributions to the film formation process was *** resulting ultrathin Ag electrodes exhibit outstanding optoelectrical properties(transmittance of~98% and sheet resistance of~8.7Ω/sq)and excellent stretchability during 500 stretching cycles at 100%*** green phosphorescent OLEDs based on the Ag electrodes have been demonstrated with a current efficiency of up to~70.4 cd/***,the devices show excellent stretching stability,retaining~89% of the original luminance and~78% of the original current efficiency after 200 stretching cycles at 100%*** work opens up new possibilities for stretchable transparent electrodes,fostering advancements in wearable displays and other innovative flexible devices.

关键词： transparent flexible electrodes ultrathin metal film interface mechanical stability

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

Chiral thermally activated delayed fluorescence materials for circularly polarized organic light-emitting diodes

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Science China Chemistry 2024年第4期67卷 1097-1116页

作者： Li Yuan Yi-Pin Zhang You-Xuan Zheng State Key laboratory of Coordination Chemistry Collaborative Innovation Center of Advanced MicrostructuresJiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

Chirality is an important natural characteristic of organic molecules,and chiral organic molecules have shown extensive application in areas such as pharmaceutical development and material *** from the ability to achieve circularly polarized luminescence(CPL),chiral luminescent materials have shown potential applications in anti-glare display,optical communication and,3D display,*** to the ability to harvest both singlet and triplet excitons by a fast reverse intersystem crossing process without involving noble metals,chiral thermally activated delayed fluorescence(TADF)materials with point chirality,axial chirality,planar chirality and helical chirality are regarded as the state-of-the-art materials for circularly polarized organic light-emitting diodes(CP-OLEDs).In recent years,the chiral TADF materials and CP-OLEDs have rapidly developed,but unfortunately,the dissymmetry factors(g)are far from the requirement of practical *** ideal emitters and devices should have both high efficiency and a g factor,or at least a balance between these two *** review gives an overview of recent progress in chiral TADF materials,with a particular focus on the chiral skeleton,CPL property and device ***,the molecular design concept,device structure and methods to improve the g factors of chiral materials and CP-OLEDs are also discussed.

关键词： chiral thermally activated delayed fluorescence material chiral skeleton circularly polarized luminescence circularly polarized organic light-emitting diodes dissymmetry factor

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High-speed flexible near-infrared organic photodiode for optical communication

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National Science Review 2024年第3期11卷 227-238页

作者： Yu Zhu Hongbin Chen Ruiman Han Hao Qin Zhaoyang Yao Hang Liu Yanfeng Ma Xiangjian Wan Guanghui Li Yongsheng Chen The Centre of Nanoscale Science and Technology and Key laboratory of Functional Polymer Materials Institute of Polymer ChemistryTianjin Key Laboratory of Functional Polymer Materials College of Chemistry and Renewable Energy Conversion and Storage Center(RECAST) Nankai University State Key laboratory of Elemento-organic Chemistry Nankai University

Optical communication is a particularly compelling technology for tackling the speed and capacity bottlenecks in data communication in modern society. Currently, the silicon photodetector plays a dominant role in high-speed optical communication across the visible-near-infrared spectrum. However, its intrinsic rigid structure, high working bias and low responsivity essentially limit its application in next-generation flexible optoelectronic devices. Herein, we report a narrow-bandgap non-fullerene acceptor（NFA） with a remarkable π-extension in the direction of both central and end units（CH17） with respect to the Y6 series, which demonstrates a more effective and compact 3D molecular packing, leading to lower trap states and energetic disorders in the photoactive film. Consequently, the optimized solution-processed organic photodetector（OPD） with CH17 exhibits a remarkable response time of 91 ns（λ = 880 nm） due to the high charge mobility and low parasitic capacitance, exceeding the values of most commercial Si photodiodes and all NFA-based OPDs operating in self-powered mode. More significantly, the flexible OPD exhibits negligible performance attenuation（<1%） after bending for 500 cycles, and maintains 96% of its initial performance even after 550 h of indoor exposure. Furthermore, the high-speed OPD demonstrates a high data transmission rate of 80 MHz with a bit error rate of 3.5 × 10-4, meaning it has great potential in next-generation high-speed flexible optical communication systems.

关键词： flexible organic photodetector high-speed NIR organic photodetector optical communication light fidelity narrow-bandgap non-fullerene acceptors

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 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

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

Electric-Induced Cycloelimination for Simulating Structural Plasticity in organic Nociceptors

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CCS Chemistry 2024年第6期6卷 1466-1476页

作者： Zhiheng Zhu Kai Liu Haojie Huang Yangshuang Bian Mingcong Qin Chengyu Wang Wei Wen Mingliang Zhu Wenkang Shi Yanwei Liu Zhiyuan Zhao Huijuan Yan Hanlin Wang Yunqi Liu Yunlong Guo Beijing National laboratory for Molecular Sciences Key Laboratory of Organic SolidsInstitute of ChemistryChinese Academy of SciencesBeijing 100190 University of Chinese Academy of Sciences Beijing 100190

Continuous lifelong acquisition,updating,and finetuning of knowledge and skills is of crucial significance for the survival of ***,current neuromorphic devices exhibit obvious catastrophic forgetting when restimulated by new *** remains a challenge for neuromorphic devices and artificial intelligence to achieve continuous ***,we propose an electric-induced cycloelimination strategy to realize an organic transistor nociceptor that can simulate synaptic and structural *** system benefits from the ring-opening characteristics of cross-linked poly(vinyl cinnamate)under a strong pulse voltage,during which new energy-level trap states are *** prepared organic transistor nociceptors exhibit both structural and synaptic *** simulate the characteristics of human nociceptors,including threshold,relaxation,sensitization,and maladaptation *** the first time,we have simulated and explored the structural plasticity behavior in organisms based on electronic *** remarkably,the transistor nociceptors realize the reinput of information without forgetting the initial informa *** strategy developed for the preparation of organic transistor nociceptors provides insights for addressing the catastrophic forgetting in the lifelong learning of intelligent neuromorphic devices.

关键词： electric-induced cycloelimination structural plasticity organic nociceptors organic transistors metaplasticity