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Advanced charge transfer technology for highly efficient and long-lived TADF-type organic afterglow with near-infrared light-excitable property

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Science China chemistry 2023年第4期66卷 1120-1131页

作者： Guangming Wang Xuefeng Chen Jiahui Liu Shuhui Ding Kaka Zhang Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China

Heavy atom effects and n-π*transitions have been frequently reported to enhance room-temperature organic phosphorescence efficiency but lead to shortage of phosphorescence lifetimes.Unlike these reported studies,we conceive the incorporation of advanced charge transfer(CT)technology to boost room-temperature organic afterglow efficiency and simultaneously maintain afterglow lifetimes.Here we design difluoroboronβ-diketonate(BF2bdk)CT compounds with moderate singlet-triplet splitting energy(ΔEST)of around 0.4 e V,and relatively large spin-orbit coupling matrix elements(SOCME(S_(1)-T_(1)),1–10 cm^(-1))to achieve efficient intersystem crossing(ISC)and moderate rates of reverse intersystem crossing(kRISC,1–10 s^(-1)).The advanced CT technology,which includes multiple electron-donating groups and orthogonal donor-acceptor arrangement,have been found to narrowΔESTand enhance both ISC and RISC.Meanwhile,the organic matrices suppress nonradiative decay of BF2bdk’s T1states by their rigid microenvironment.Consequently,thermally activated delayed fluorescence(TADF)-type organic afterglow materials can be achieved with afterglow efficiency up to 83.0%,long lifetimes of 433 ms,excellent processablility,as well as advanced anti-counterfeiting and information encryption.Furthermore,with the aid of up-conversion materials and through radiative energy transfer,TADF-type afterglow materials with aqueous dispersity and near-infrared light-excitable property have been achieved,which paves the way for biomedical applications.

关键词： afterglow charge transfer phosphorescence TADF triplet excited states

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1,2,5,6-Naphthalene Diimides:A Class of Promising Building Blocks for organic Semiconductors

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Chinese Journal of chemistry 2023年第10期41卷 1226-1234页

作者： Zheng Zhao Congwu Ge Xueqian Zhao Jintao Huang Xike Gao Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China

organic semiconductors have drawn extensive atten-tion due to their optoelectronic properties and wide applications in organic optoelectronics.In comparison with the popular 1,4,5,8-naphthalene diimides(1,4,5,8-NDIs),the angular-shaped 1,2,5,6-NDIs have exhibited tunable photophysical properties,self-as-sembly behaviors and charge transporting properties.Due to these unique features,1,2,5,6-NDIs show great potential for construction of high performance n-func-tional materials.In this review,we highlight the recent advances and future prospects of 1,2,5,6-NDI-basedπ-systems in the field of organic optoelectronics,in-cluding molecular design,synthesis,structure-prop-erty relationships as well as the applications in high performance organic field-effect transistors,organic photovoltaics,perovskite solar cells,and so on.

关键词： organic semiconductors Electron acceptors Design and synthesis 1,2,5,6-NDI Structural isomerism Polymer acceptors organic electronics

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Soluble Two-dimensional Supramolecular organic Frameworks(SOFs):An Emerging Class of 2D Supramolecular Polymers with Internal Longrange Orders

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Chinese Journal of Polymer Science 2019年第1期37卷 1-10页

作者： Shu-Yan Jiang Xin Zhao CAS Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

Two-dimensional(2D) materials have been demonstrated to exhibit unique properties originating from its 2D nature. In recent years, the construction of 2D materials has become a topic of great interest. This article summarizes the recent advance of 2D supramolecular organic frameworks(SOFs) which are homogeneously constructed in solution phase through self-assembly of rationally designed building blocks. These 2D SOFs are soluble and still maintain stable network structures in solutions, which exhibit uniqueness not only in structures but also in properties. In this concise review, the SOFs-related background is briefly introduced firstly, followed by outlining the research progress of soluble 2D SOFs from the perspective of monomer design, assembly, and structural characterization.The article ends with a personal outlook on the future development of this new class of supramolecular polymers.

关键词： Supramolecular organic frameworks(SOFs) self-assembly Two-dimensional Supramolecular polymers

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Fiber-like micelle with a p-conjugated polymer core: a potential building block for organic electronics

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Science Bulletin 2017年第18期62卷 1229-1230页

作者： Xian Yang Yinan Cui Chun Feng Daliao Tao Xiaoyu Huang Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

The self-assembly of block copolymer in solution are constantly expanding,in part because of the increasing degree of control over the size,morphology and functionality of self-assembled nanostructures that can be exerted by the introduction of additional driven force such as hydrogen-bonding,halogen bonding,p-p stacking,host-guest complexation,metal-coordination,electrostatic interaction and crystalline[1].Among these,the

关键词：纳米胶束共轭聚合物电子学纤维状主客体相互作用嵌段共聚物自组装控制程度

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The role of halogen bonding in improving OFET performance of a naphthalenediimide derivative

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Chinese Chemical Letters 2018年第3期29卷 423-428页

作者： Jing Li Yong-Hui Hu Cong-Wu Ge He-Gui Gong Xi-Ke Gao Department of chemistry College of Science Shanghai University Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

Controlling microstructure and thin film morphology of organic semiconductors by supramolecular arrangement is critical to improving their device performance. To realize well-controlling supramolecular assembly, a core-expanded naphthalene diimides derivative （1） was designed and synthesized as an n-type organic semiconductor and also as a halogen bonding （XB） donor that could form complementary XBs with 2,2-dipyridine or 2,2-bipyrimidine acceptor. The XB interactions in the solid state of 1/2,2- dipyridine and 1/2,2-bipyrimidine were confirmed by a series of characterization methods, such as thermal gravimetric analysis （TGA）, X-ray photoelectron spectroscopy （XPS）, nuclear magnetic resonance （NMR） involving 13F NMR and solid-state 13C NMR. organic field-effect transistors （OFETs） based on XB complexes 1/2,2-dipyridine or 1/2,2-bipyrimidine showed better device performance than that of devices based on pure 1, with the average electron mobility increased more than doubled （from 0.027cm2V-1 s-1 to 0.070cm2V-1 s-1）.

关键词： Supramolecular assembly Halogen bond Naphthalene diimide organic semiconductor organic field-effect transistor

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Adsorption properties of the double-imprinted electrospun crosslinked chitosan nanofibers

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Chinese Chemical Letters 2019年第3期30卷 762-766页

作者： Yan Li Mengqi Li Jie Zhang Xiaoyan Xu School of Materials Science and Engineering Tongji University Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

The adsorption properties of the Pb(Ⅱ)-Cd(Ⅱ) double-imprinted electrospun crosslinked chitosan nanofibers(Pd/Cd-DIECCNs) prepared by electropspinning and imprinting process for the removal of Pb(Ⅱ) and Cd(Ⅱ) from aqueous solutions were investigated. The prepared nanofibers were characterized by scanning electron microscope(SEM) analysis. Under the optimum experimental conditions, the minimum fiber average diameter was obtained 110 nm. Then the adsorption experiments were carried out to study the effect of different adsorption parameters, such as pH, the ratio between Pb(Ⅱ) and Cd(Ⅱ)in the mixed solutions, contact time, the Pd/Cd-DIECCNs dose and temperature in a batch system. The Extended Langmuir model was applied to describe the equilibrium data of Pb(Ⅱ) and Cd(Ⅱ). The maximum adsorption capacities of the Pd/Cd-DIECCNs arrived at 567 mg/g for Pb(Ⅱ) and 341 mg/g for Cd(Ⅱ), respectively.

关键词： Chitosan Double imprinted Crosslinked Electrospun Adsorption

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A Study on Constitutional Isomerism in Covalent organic Frameworks:Controllable Synthesis,Transformation,and Distinct Difference in Properties

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CCS chemistry 2020年第2期2卷 139-145页

作者： Rong-Ran Liang Fu-Zhi Cui Ru-Han A Qiao-Yan Qi Xin Zhao Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

Isomerism is an essential and widespread phenomenon in organic chemistry but rarely observed in covalent organic frameworks(COFs),a novel class of crystalline porous organic polymers with versatile applications.Herein,we give an account of the first example of a controllable synthesis of constitutional isomers of a COF.The two isomers exhibited marked differences in their gas/vapor adsorption behaviors and chemical stability in various solvents.Furthermore,structure transformation from one isomer to the other was realized.This work not only paves the way for rational design and synthesis of COF isomers but also provides a vivid example of structure–property relationship in crystalline porous polymers.

关键词： covalent organic framework constitutional isomer controllable synthesis isomeric transformation adsorption behavior

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Cascade Synthesis of Luminescent Difluoroboron Diketonate Compounds for Room-Temperature organic Afterglow Materials

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Chinese Journal of chemistry 2022年第21期40卷 2507-2515页

作者： Junbo Li Xuepu Wang Xiaoya Zhao Xuefeng Chen Shuhui Ding Minjian Wu Kaka Zhang College of chemistry and Materials Science Sichuan Normal UniversityChengduSichuan 610068China Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling RoadShanghai 200032China

Difluoroboronβ-diketonate(BF2bdk)compounds represent an important class of luminescent materials,whereas their synthesis requires multiple steps,which restrict their application in diverse fields.Here we report a cascade reaction to prepare BF2bdk from aromatic ketones,carboxylic acids,trifluoroacetic anhydride and boron trifluoride diethyl etherate.The cascade reaction is very simple and straightforward to produce BF2bdk with desired functional groups in reasonable isolation yields.Further,when some specific BF2bdk compounds are used as luminescent dopants,organic room-temperature phosphorescence with lifetimes>1.0 s and intense afterglow under ambient conditions can be achieved with the assistance by suitable organic matrices.The dopant-matrix materials exhibit excellent processability into desired patterns and large-area panels,and function as efficient donors of excited state energy transfer for the fabrication of red afterglow materials.

关键词： Afterglow Boron Luminescence Phosphorescence Photophysics

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A two-step solvothermal procedure to improve crystallinity of covalent organic frameworks and achieve scale-up preparation

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Chinese Chemical Letters 2022年第5期33卷 2464-2468页

作者： Xiang-Hao Han Jia-Qi Chu Wen-Zhuang Wang Qiao-Yan Qi Xin Zhao Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China Shanghai Normal University Shanghai 200234China

Covalent organic frameworks(COFs),as a novel class of functional polymers,exhibit versatile applica-tions due to their crystalline porous structures and conjugated skeletons.However,synthesis of COFs with high crystallinity still faces great challenges,especially for scale-up preparation.Herein we report a two-step solvothermal process to improve crystallinity of COFs.The first step focuses on polycondensa-tion of monomers with no need for optimizing crystallization conditions.In the second step,appropriate solvothermal conditions are used to facilitate crystallization of the COFs through defects correction and structural repairing.Furthermore,this strategy could also be applicable to scale-up synthesis of high qual-ity COFs,which lays a foundation for their practical applications.

关键词： Covalent organic frameworks Synthesis Solvothermal condensation High crystallinity Scale-up preparation

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Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline:Synthesis and semiconducting properties

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Chinese Chemical Letters 2023年第2期34卷 563-566页

作者： Fangwei Ding Debin Xia Xiping Ding Ruibin Deng Congwu Ge Yulin Yang Ruiqing Fan Kaifeng Lin Xike Gao MIIT key laboratory of Critical Materials Technology for New Energy Conversion and Storage School of Chemistry and Chemical EngineeringHarbin Institute of TechnologyHarbin 150001China Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic Chemistry Chinese Academy of SciencesShanghai 200032China

A novel air-stable n-type benzothiaphene endcapped azaarene(BTPQ) and its sulfonated derivative(BSPQ) were prepared via two pathways and characterized by NMR, UV–vis, fluorescence and cyclic voltammetry spectroscopy. Symmetrically introducing four nitrogen atoms into acenes, the semiconductor properties could be changed from p-type to n-type detected through the space charge limited current(SCLC) method. After sulfonation of BTPQ, BSPQ is with deeper frontier orbital energy levels and enhanced the electron mobility.

关键词： Azaarenes Deep LUMO levels n-type organic semiconductor Polycyclic aromatic hydrocarbons

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