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Recent Progress in AIE-active Polymers

Chinese Journal of Polymer Science 2019年第4期37卷 289-301,I0004页

作者： yu Bing Hu Jacky w.y.lam Ben Zhong Tang HKUST-Shenzhen Research Institute Department of Chemistry The Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction and Institute for Advanced StudyThe Hong Kong University of Science and Technology Center for Aggregation-Induced Emission SCUT-HKUST Joint Research InstituteState Key Laboratory of Luminescent Materials and DevicesSouth China University of Technology

The demand for highly efficient solid-state luminophores is continuously growing due to their potential applications in optoelectrical devices, chemosensors, and biological applications. The discovery of luminogens with aggregation-induced emission(AIE)by Tang et al. in 2001 provides a good reponse to this demand. Among the exploited AIE luminogens, AIE-active polymers possess many advantages such as simple synthesis, convenient structrue modifications, and good processability, which offer an extensive platform for scientists and engineers. Herein, the design principles and latest synthetic advancement of AIE-active polymers are summarized, including click polymerization and multicomponent polymerization. Non-conjugated heteroatom-rich polymers were in situ generated and demonstated non-conventional clusteroluminoscence. Advanced applications including fluorescent sensors, stimuli-responsive materials,biological applications, circularly polarized luminescence, and electroluminescence are then introduced in detail. AIE-active polymers display the signal-amplification effect for sensitive and selective response to chemo/bioanalytes or stimuli and enhanced photosensitization effect for cancer theranostics. Retrospecting the expansion of this field can further strengthen our belief that AIE-active polymers are promising for conceptual innovation and technological breakthroughs in the near future.

关键词： Aggregation-induced emission Polymer synthesis High-tech application

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Conjugated polymers developed from alkynes

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National Science Review 2015年第4期2卷 493-509页

作者： yajing Liu Jacky w.y.lam Ben Zhong Tang HKUST-Shenzhen Research Institute Department of Chemistry Division of Life Science State Key Laboratory of Molecular NeuroscienceInstitute for Advanced Study Institute of Molecular Functional Materials and Division of Biomedical Engineering The Hong Kong University of Science and Technology Guangdong Innovative Research Team SCUT-HKUST Joint Research Laboratory State Key Laboratory of Luminescent Materials and Devices South China University of Technology

The numerous merits of conjugated polymers(CPs) have encouraged scientists to develop a variety of synthetic routes to CPs with diverse structures and functionalities. Among the large scope of substrates,alkyne plays an important role in constructing polymers with conjugated backbones. In addition to some well-developed reactions including Glaser–Hay and Sonogashira coupling, azide/thiol-yne click reaction and cyclotrimerization, some novel alkyne-based reactions have also been explored such as oxidative polycoupling, decarbonylative polycoupling and multicomponent tandem polymerizations. his review focuses on the recent progress on the synthetic methodology of CPs in the last ive years using monomers with two or more triple bonds and some of their high-technological applications. Selected examples of materials properties of these CPs are given in this review, such as luorescence response to chemical or physical stimuli, magnetism, white light emission, cell imaging and bioprobing. Finally, a short perspective is raised in regard to the outlook of the preparation methodologies, functionalities as well as potential applications of CPs in the future.

关键词： conjugated polymer alkyne synthetic methodology functional polymer

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Mechanistic connotations of restriction of intramolecular motions(RIM)

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National Science Review 2021年第6期8卷 10-13页

作者： yujie Tu Zheng Zhao Jacky w.y.lam Ben Zhong Tang Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionInstitute for Advanced Study and Department of Chemical and Biological EngineeringThe Hong Kong University of Science and Technology Center for Aggregation-Induced Emission SCUT-HKUST Joint Research InstituteState Key Laboratory of Luminescent Materials and DevicesSouth China University of Technology AIE Institute Guangzhou Development District Ming wai Lau Centre for Reparative Medicine Karolinska Institutet

Molecules are all in constant motions,which influence their properties. For example, in photophysics, the light emission behavior of a luminogen is determined by its electronic and nuclear motions in the excited state. Flexible molecular motions usually favor nonradiative decay along with the transformation of excited-state energy to other forms such as thermal energy. Therefore,the restriction of intramolecular motions(RIM) is commonly adopted to achieve luminescent materials with high emission brightness.

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SyNTHESIS OF A HyPERBRANCHED POLy(AROyLARyLENE) CONTAINING TRIAZOLE AND FLUORENE FUNCTIONALITIES By CLICK CHEMISTRy AND METAL-FREE,REGIOSELECTIVE POLyCyCLOTRIMERIZATION

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Chinese Journal of Polymer Science 2009年第2期27卷 145-148页

作者： Cathy K.w.Jim Jacky w.y.lam 唐本忠 Department of Chemistry The Hong Kong University of Science & TechnologyClear Water BayKowloonHong KongChina Department of Polymer Science and Engineering Key Laboratory of Macromolecular Synthesis and Functionalization of Ministry of EducationZhejiang University

A new bis(aroylacetylene) containing tfiazole and fluorene moieties is synthesized by click chemistry. Polycyclotrimerization of the monomer is catalyzed by piperidine in refluxed dioxane,furnishing a regioregular poly(aroylarylene) in a satisfactory *** hyperbranched structure of the polymer is characterized spectroscopically with satisfactory *** polymer enjoys no metal detriment and is soluble in common organic solvents such as tetrahydrofuran (THF),chloroform,dichloromethane (DCM),and N,N-...

关键词： Regioregular Click chemistry Polycyclotrimerization Hyperbranched polymer.

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Metal-free multicomponent polymerization of activated diyne,electrophilic styrene and isocyanide towards highly substituted and functional poly(cyclopentadiene)

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Science China Chemistry 2023年第3期66卷 863-869页

作者： Xinyue Liu Xueqin yang Xin Li Jianwei Sun Benzhao He Jacky w.y.lam Ben Zhong Tang Department of Chemistry and Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction Guangdong-Hong Kong-Macao Joint Laboratory of Optoelectronic and Magnetic Functional MaterialsThe Hong Kong University of Science and TechnologyHong Kong 999077China Center for Advanced Materials Research Beijing Normal University at ZhuhaiZhuhai 519085China School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhen 518172China Center for Aggregation-Induced Emission South China University of TechnologyGuangzhou 510640China

The development of a facile and efficient polymerization to prepare cyclopentadiene-containing polymers is of vital importance and highly desired. In this work, a metal-free multicomponent polymerization of activated diyne, electrophilic styrene and isocyanide for the preparation of highly substituted poly(cyclopentadiene) was established. Soluble and thermally stable polymers with high molecular weights are obtained in high yields under mild conditions. By introducing the tetraphenylethene or triphenylamine moiety into polymer backbones, the resultant polymers show unique aggregation-induced emission(AIE)characteristics. Interestingly, AIE polymers can also be generated in situ from non-AIE monomers. Moreover, the prepared polymers can generate photopatterns to function as photoresists and can also serve as visualizing agents to selectively stain the lipid droplets in live cells. This efficient polymerization will open up enormous opportunities for preparing functional cyclopentadiene-containing polymers applicable in diverse areas.

关键词： multicomponent polymerization activated alkynes highly substituted poly(cyclopentadiene)

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A mitochondria-targeted AIE photosensitizer for enhancing specificity and efficacy of ferroptosis inducer

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Science China Chemistry 2022年第5期65卷 870-876页

作者： Shan wang Chao Chen Jianmin wu Jianyu Zhang Jacky w.y.lam Hongyang wang Lei Chen Ben Zhong Tang Fudan University Shanghai Cancer Center Shanghai Medical CollegeFudan UniversityShanghai 200032China Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionInstitute for Advanced StudyState Key Laboratory of Molecular NanoscienceDivision of Life Scienceand Department of Chemical and Biological EngineeringThe Hong Kong University of Science and TechnologyHong Kong 999077China Institute of Metabolism and Integrative Biology Fudan UniversityShanghai 200433China The International Cooperation Laboratory on Signal Transduction Eastern Hepatobiliary Surgery HospitalSecond Military Medical UniversityShanghai 200438China National Center for Liver Cancer Shanghai 200441China Shenzhen Institute of Aggregate Science and Technology School of Science and EngineeringThe Chinese University of Hong KongShenzhen 518172China AIE Institute Guangzhou Development DistrictGuangzhou 510530China

Ferroptosis is a form of regulated cell death characterized by iron-dependent accumulation of lipid peroxidation and lethal reactive oxygen species(ROS).To date,misregulated ferroptosis has been implicated in several types of cancers,and ferroptosis inducers can be used to promote ferroptosis in tumor cells and play an anti-tumor ***,the specificity and efficacy of ferroptosis inducers remain ***,a new mitochondria-targeted photosensitizer(PS)with aggregation-induced emission(AIE)characteristic named TCSVP was designed,which efficiently generates ROS in mitochondria after light *** administration significantly sensitizes tumor cells to ferroptosis inducer(RSL3)-mediated cell death by specifically and light-dependently triggering a moderate ROS generation in vitro and in ***,the expression levels of ferroptosis related proteins Acyl-CoA synthetase long-chain family member 4(FACL4/ACSL4)and cyclooxygenase-2(COX2)were increased in TCSVP/RSL3-treated cells after light exposure,coupled with decreased Glutathione peroxidase 4(GPX4)activity and excessive malondialdehyde(MDA)*** study declared that light-induced moderate ROS generation within mitochondria in cancer cells by AIE-PS can be used to enhance the specificity and efficacy of ferroptosis inducers,bringing a new synergistic strategy for tumor intervention.

关键词： controlling ROS generation high-performance AIE-PS lipid peroxidation ferroptosis

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New carbazole-substituted siloles for the fabrication of efficient non-doped OLEDs

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Chinese Chemical Letters 2019年第3期30卷 592-596页

作者： yi Xiong Jiajie Zeng Bin Chen Jacky w.y.lam Zujin Zhao Shuming Chen Ben Zhong Tang State Key Laboratory of Luminescent Materials and Devices Center for Aggregation-Induced Emission South China University of Technology Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction The Hong Kong University of Science & Technology Department of Electrical and Electronic Engineering South University of Science and Technology of China

Luminogenic molecules with aggregation-induced emission(AIE) property are free of aggregationcaused quenching and thus have great potential in the fabrication of efficient non-doped OLEDs. Herein, a series of new carbazole-substituted siloles have been synthesized and characterized. Their crystal and electronic structures, thermal stabilities, electrochemical behaviors, and photophysical properties are thoroughly investigated. These silole derivatives exhibit prominent AIE characteristics with high emission efficiencies in solid films. They can function as light-emitting layers in non-doped OLEDs,affording eminent electroluminescence efficiencies of 17.59 cd/A, 12.55 Im/w and 5.63%, amongst the most efficient non-doped OLEDs based on fluorescent emitters, indicating their promising applications in OLEDs.

关键词： Aggregation-induced emission Silole Photoluminescence Electroluminescence Organic light-emitting diode

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A general powder dusting method for latent fingerprint development based on AIEgens

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Science China Chemistry 2018年第8期61卷 966-970页

作者： Zijie Qiu Bin Hao Xinggui Gu Zhaoyu wang Ni Xie Jacky w.y.lam Hongxia Hao Ben Zhong Tang Key Laboratory of Evidence Science (China University of Political Science and Law) Ministry of Education Beijing 100088 China Collaborative Innovation Center of Judicial Civilization China Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction Division of Life Science State Key Laboratory of Molecular Neuroscienee Institute for Advanced Study Institute of Molecular Functional Materials Division of Biomedical Engineering the Hong Kong University of Science and Technology Clear Water Bay Kowloon China NSFC Center for Luminescence from Molecular Aggregates SCUT-HKUST Joint Research Institute State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou 510640 China

Powder dusting method is the most practically useful approach for latent fingerprint development in the crime scene. Herein, a general powder dusting method has been explored for latent fingerprint development based on aggregation-induced emission luminogens(AIEgens). A series of tetraphenylethene(TPE) derivatives with multiple diphenylamine(DPA), namely, TPE-DPA,TPE-2 DPA and TPE-4 DPA, were selected as candidates to dope with magnetic powders and applied for latent fingerprint development. After screening, the magnetic powder 3 doped with TPE-4 DPA proves to be the best, in terms of fluorescent intensity, resolution and adhesiveness. Afterwards, the magnetic powder 3 was applied for visualization of latent fingerprint on various smooth and porous substrates, including glass, stainless steel, leaf, ceram, plastic bag, lime wall, wood and paper *** details, such as island, core, termination and bifurcation, can be clearly observed for the fluorescent fingerprint images.

关键词： latent fingerprint development powder dusting aggregation-induced emission

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Red-emitting salicylaldehyde Schiff base with AIE behaviour and large Stokes shift

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Chinese Chemical Letters 2018年第10期29卷 1493-1496页

作者： Junyi Gong Peifa wei yuanan Su ying Li Xing Feng Jacky w.y.lam Dongzhou Zhang Xiangzhi Song Ben Zhong Tang College of Chemistry and Chemical Engineering Central South University Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and ReconstructionDivision of Life Science and Division of Biomedical EngineeringThe Hong Kong University of Science and Technology Partnership for Extreme Crystallography Hawaii Institute of Geophysiscs and PlanetologyUniversity of Hawaii at Manoa

Three salicylaldehyde Schiff base（SSB）, iso-PBP, PBP and EPB, were facilely synthesized and exhibited aggregation-induced emission. The introduction of C= N-N = C moiety in these SSB dyes largely extend the conjugation system and push their emission to yellow to red spectral region. These SSB dyes were negligibly fluorescent in dilute THF solution. In THF/water mixtures with high water fractions, they displayed strong yellow to red fluorescence（up to 617nm） and large Stokes shifts（up to 152 nm）. Single crystal analysis on EBP showed the longer emission of in aggregated state was attributed to the molecular packing effect as compared with that in dilute solution. The bio-imaging application indicated EBP could specifically accumulate in lipid droplets in living cells.

关键词： Aggregation-induced emission Salicylaldehyde Schiff base Red-emitting ESIPT Aldehyde-amine condensation

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In-situ generation of poly(quinolizine)s via catalyst-free polyannulations of activated diyne and pyridines

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Science China Chemistry 2022年第4期65卷 789-795页

作者： Benzhao He Jiachang Huang Jing Zhang Xinyue Liu Dong wang Herman H.y.Sung yajun Liu Anjun Qin Jacky w.y.lam Ben Zhong Tang Center for Advanced Materials Research Science and Technology Experimental PlatformAdvanced Institute of Natural SciencesBeijing Normal University at ZhuhaiZhuhai 519085China Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstructionand Guangdong-Hong Kong-Macao Joint Laboratory of Optoelectronic and Magnetic Functional MaterialsThe Hong Kong University of Science&TechnologyKowloonHong KongChina Center for AIE Research College of Materials Science and EngineeringShenzhen UniversityShenzhen 518060China Department of Laboratory Medicine Nanfang HospitalSouthern Medical UniversityGuangzhou 510515China State Key Laboratory of Luminescent Materials and Devices Guangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesCenter for Aggregation-Induced EmissionSouth China University of TechnologyGuangzhou 510640China HKUST-Shenzhen Research Institute Shenzhen 518057China Shenzhen Institute of Aggregate Science and Technology School of Science and EngineeringThe Chinese University of Hong KongShenzhen 518172China

The development of new polymerization routes to afford N-heterocyclic polymers is of vital importance and highly desired for various practical applications. Herein, a facile and efficient polyannulation reaction of dual-activated alkyne and pyridines was developed to construct novel N-heterocyclic poly(quinolizine)s. This polymerization can proceed smoothly under catalystfree conditions with 100% atom utilization to furnish poly(quinolizine)s with high molecular weights(up to 34,100) and welldefined structures in acceptable yields. The resulting polymers show good solubility, high thermal stability and strong red emission. Moreover, the prepared poly(quinolizine)s exhibit low cytotoxicity and can selectively label lysosomes in live *** the remarkable advantages of readily available raw materials, mild polymerization conditions, atom economy, and excellent product performance, this new and efficient polymerization tool will open up enormous opportunities for preparing functional N-heterocyclic polymers.

关键词： polyannulation activated alkyne N-heterocyclic polymers poly(quinolizine)s bioimaging

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