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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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Amine-catalyzed polycyclotrimerization of arylene bipropiolate:A metal-free and regioselective route to hyperbranched polymer

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Science China Chemistry 2008年第8期51卷 705-708页

作者： JIM Cathy K w lam jacky w y HAEUSSLER Matthias Department of Chemistry The Hong Kong University of Science & TechnologyClear Water BayKowloonHong KongChina

This paper presents a new synthetic route to hyperbranched polymer. An arylene bipropiolate monomer,dimethylmethylenebis(1,4-phenylene) bipropiolate,was prepared by a one-step esterification reaction of bisphenol A with propiolic acid. Polycyclotrimrtization of the monomer was effected by reflux in dimethylformamide(DMF),producing a soluble hyperbranched poly(aroxycarbonylphenylene) in a good yield. The polymer was perfectly branched with a degree of branching of 100%.

关键词： cyclotrimerization regioselectivity hyperbranched polymer

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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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Restriction of Intramolecular Motion(RIM):Investigating AIE Mechanism from Experimental and Theoretical Studies

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Chemical Research in Chinese Universities 2021年第1期37卷 1-15页

作者： ZHANG Jianyu ZHANG Haoke lam jacky w.y. TANG Ben Zhong Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration and ReconstructionInstitute for Advanced Studyand Department of Chemical and Biological EngineeringThe Hong Kong University of Science&TechnologyClear Water BayKowloonHong KongP.R.China MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang UniversityHangzhou310027P.R.China Center for Aggregation-Induced Emission SCUT-HKUST Joint Research InstituteState Key Laboratory of Luminescent Materials and DevicesSouth China University of TechnologyGuangzhou510640P.R.China Guangzhou Development District AIE InstituteGuangzhou510530P.R.China

Mechanistic studies promote scientific development from phenomena to ***-induced emission(AIE),as an unusual photophysical phenomenon,builds the bridge between molecular science and aggregate *** the twenty-year development of AIE,restriction of intramolecular motion(RIM)has been verified as the working mechanism of AIE *** this review,these mechanistic works about RIM are summarized from experimental and theoretical ***,the experimental studies are introduced from three parts:external rigidification,structural modification and structural *** the theoretical part,calculations on the low-frequency motion of AIEgens have been performed to prove the RIM *** virtue of the theoretical calculations,some new mechanisms are proposed to supplement the RIM,such as restriction of access to conical intersection,suppression of Kasha transition,restriction of access to dark state,*** is foreseeable that the RIM mechanism will unify the photophysical theories for both molecules and aggregates,and inspire more progress in aggregate science.

关键词： Aggregation-induced emission(AIE) Restriction of intramolecular motion Photophysical mechanism Aggregate science

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Synthesis and properties of poly(1-phenyl-1-octyne)s containing stereogenic and chromophoric pendant groups

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Science China Chemistry 2009年第10期52卷 1691-1702页

作者： lam jacky w.y. JIM Cathy K.w. KwOK Hoi Sing Department of Chemistry The Hong Kong University of Science & Technology Center for Display Research The Hong Kong University of Science & Technology

Poly(1-phenyl-1-octyne)s containing different stereogenic and chromophoric pendants {-[(C6H13)C= C(C6H4-p-CO2-R)] n -R = [(1S)-endo]-(?)-borneyl (P3), (1R,2S,5R)-(?)-menthyl (P4), -C6H4-p-(1R,2S,5R)-(?)-menthyl (P5), 2-napthyl (P6), 4-biphenylyl (P7)} have been designed and synthesized. The polymers are prepared in moderate yields by wCl6-Ph4Sn and possess high molecular weights (M w up to 64000). The structures and properties of the polymers are characterized and evaluated by NMR, TGA, UV, CD, PL, and EL analyses. All the polymers are thermally stable and their temperatures for 5% weight loss locate in the range of 300 to 416°C under nitrogen. The energy band gaps of all the polymers are ～3.0 eV. Polymers P4 and P5 show CD absorptions associated with the helicity of the polymer segments. Excitation of the THF solutions of P3–P7 by UV irradiation gives strong blue lights of ～485 nm with quantum yields higher than 20%. The thin films of the polymers also emit in the same spectral region, indicative of little aggregation-caused quenching of light emission. Multilayer EL devices with a configuration of ITO/Polymer:PVK/BCP/Alq3/LiF/Al are constructed, which emit blue lights of ～487 nm. The maximum luminance and external quantum efficiency vary with the pendant groups, with P6 exhibiting the highest external quantum efficiency of 0.16%. The spectra stability of the EL devices is outstanding and the EL peak maximum experiences little change with the applied voltage.

关键词： chiral photoluminescence polyacetylene electroluminescence helicity

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CARBAZOLE-CONTAINING HyPERBRANCHED POLy(ARyLENEETHyNyLENE)S:SyNTHESIS,CHARACTERIZATION,ANDPROPERTIES

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Chinese Journal of Polymer Science 2007年第6期25卷 641-649页

作者： Han Peng Xiu-wen Zheng jacky w. y. lam Ben-zhong Tang Institute of Material Science and Engineering South China University of Technology Guangzhou 510640 China Department of Chemistry Hong Kong University of Science ＆ Technology Clear Water Bay Kowloon Hong Kong China

New hyperbranched poly（aryleneethynylene）s containing carbazole moieties are synthesized in high yields （up to 87%） by polycyclotrimerization of 3,6-bis（4-ethynylphenyl）-9-octylcarbazole and its copolymerization with 1-octyne catalyzed by CpCo（CO）2 in THF. The structures and properties of the polymers are characterized and evaluated by IR, NMR, TGA, UV, photoluminescence, and cyclic voltammetry analyses. All the polymers are soluble in common organic solvents and show outstanding thermal stability （≥ 430℃）. They graphitize in high yields （up to 79%） when pyrolyzed at 800℃. Upon photoexcitation, the polymers emit a strong deep blue light of ca. 400 nm with quantum yields larger than 60%.

关键词： Acetylenes Carbazole Cyclopolymerization Hyperbranched Luminescence.

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Theoretical study of substituent effect on the charge mobility of 2,5-bis(trialkylsilylethynyl)-1,1,3,4-tetraphenylsiloles

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Science China Chemistry 2010年第11期53卷 2311-2317页

作者： lam jacky wing yip Department of Chemistry The Hong Kong University of Science & Technology

The theoretical calculation of the charge mobility of 2,5-bis(trialkylsilylethynyl)-1,1,3,4-tetraphenylsiloles is presented.B3LyP/6-31* calculations demonstrated that these silole molecules possessed large coupling matrix elements and reorganization energies for electron and hole transfers and high electron *** bulkiness of the trialkyl substituents influenced the charge mobility of the silole molecules,with the smaller trimethyl group imparting higher charge mobility than triethyl and triisopropyl substituents.

关键词： silole theoretical calculation substitution effect electronic structure charge mobility

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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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